🕷️ Crawler Inspector

URL Lookup

Direct Parameter Lookup

Raw Queries and Responses

1. Shard Calculation

Query:

Response:

Calculated Shard: 93 (from laksa056)

2. Crawled Status Check

Query:

curl -X POST \
  'http://laksa093.int.ahrefs:8124/' \
  -H 'Content-Type: text/plain' \
  -H 'X-ClickHouse-Database: crawler3' \
  -H 'Authorization: Basic YXBpOg==' \
  -d 'SELECT getAhrefsURLFromUnparsed(src_unparsed) AS found_url, ifNull(toUnixTimestamp(download_stamp), 0) AS crawl_time, ifNull(toUnixTimestamp(props_url_first_seen), 0) AS first_indexed_time, download_http_code AS http_code, src_unparsed AS src_unparsed, src_root_hash AS src_root_hash, history_drop_reason AS history_drop_reason, meta_title AS meta_title, meta_descriptions AS meta_descriptions, attrs_boilerpipe_text AS attrs_boilerpipe_text, attrs_markdown AS attrs_markdown, attrs_readable_markdown AS attrs_readable_markdown, meta_canonical AS meta_canonical FROM crawler3.page_info_local FINAL PREWHERE (src_root_hash, src_unparsed) IN ((getAhrefsRootHashFromUnparsed(getAhrefsUnparsedNoserviceFromURL(\'https://go.drugbank.com/drugs/DB01065\')), getAhrefsUnparsedNoserviceFromURL(\'https://go.drugbank.com/drugs/DB01065\'))) FORMAT JSONEachRow'

Response:

{"found_url":"https:\/\/go.drugbank.com\/drugs\/DB01065","crawl_time":1772681132,"first_indexed_time":1600397263,"http_code":200,"src_unparsed":"com,drugbank!go,\/drugs\/DB01065 s443","src_root_hash":"15397128513976815493","history_drop_reason":null,"meta_title":"Melatonin: Uses, Interactions, Mechanism of Action | DrugBank","meta_descriptions":["Melatonin is an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement."],"attrs_boilerpipe_text":"Description\nA naturally occurring hormone that promotes sleep.\nDescription\nA naturally occurring hormone that promotes sleep.\nDrugBank ID\nDB01065\nModality\nSmall Molecule\nClinical Trials\nPhase 0\n8\nPhase 1\n62\nPhase 2\n141\nPhase 3\n80\nPhase 4\n59\nSummary\nMelatonin\nis an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement.\nBrand Names\nCircadin, Melatonin Neurim, Slenyto\nGeneric Name\nMelatonin\nDrugBank Accession Number\nDB01065\nBackground\nMelatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958.  In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and lowering the body temperature.  Melatonin is also implicated in the regulation of mood, learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant.  Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders (ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.\nModality\nSmall Molecule\nGroups\nApproved, Investigational, Nutraceutical, Vet approved\nStructure\nWeight\nAverage: 232.2783\nMonoisotopic: 232.121177766\nChemical Formula\nC\n13\nH\n16\nN\n2\nO\n2\nSynonyms\n5-methoxy-N-acetyl tryptamine\n5-methoxy-N-acetyltryptamine\nMelatonin\nMelatonina\nMélatonine\nN-[2-(5-methoxyindol-3-yl)ethyl]acetamide\nN-Acetyl-5-methoxytryptamine\nExternal IDs\nBCI-049\nJ5.258B\nNPC-15\nNSC-113928\nNSC-56423\nIndication\nUsed orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. Evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. It has received FDA orphan drug status as an oral medication for this use. A number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. It appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. It may also improve secondary insomnia associated with various sleep-wake cycle disturbances. Other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (DSPS), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with IL-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders.\nReduce drug development failure rates\nBuild, train, & validate machine-learning models\nwith evidence-based and structured datasets.\nSee how\nBuild, train, & validate predictive machine-learning models with structured datasets.\nSee how\nAssociated Conditions\nIndication Type\nIndication\nCombined Product Details\nApproval Level\nAge Group\nPatient Characteristics\nDose Form\nManagement of\nInsomnia\n••••••••••••\nUsed in combination to manage\nInsomnia\nCombination Product in combination with:\nValerian (DB13196)\n,\ngamma-Aminobutyric acid (DB02530)\n••••••••••••\nPharmacodynamics\nMelatonin is a hormone normally produced in the pineal gland and released into the blood. The essential amino acid L-tryptophan is a precursor in the synthesis of melatonin. It helps regulate sleep-wake cycles or the circadian rhythm. Production of melatonin is stimulated by darkness and inhibited by light. High levels of melatonin induce sleep and so consumption of the drug can be used to combat insomnia and jet lag.\nMT1 and MT2 receptors may be a target for the treatment of circadian and non circadian sleep disorders because of their differences in pharmacology and function within the SCN. SCN is responsible for maintaining the 24 hour cycle which regulates many different body functions ranging from sleep to immune functions\nMechanism of action\nMelatonin is a derivative of tryptophan. It binds to melatonin receptor type 1A, which then acts on adenylate cylcase and the inhibition of a cAMP signal transduction pathway. Melatonin not only inhibits adenylate cyclase, but it also activates phosphilpase C. This potentiates the release of arachidonate. By binding to melatonin receptors 1 and 2, the downstream signallling cascades have various effects in the body. The melatonin receptors are G protein-coupled receptors and are expressed in various tissues of the body. There are two subtypes of the receptor in humans, melatonin receptor 1 (MT1) and melatonin receptor 2 (MT2). Melatonin and melatonin receptor agonists, on market or in clinical trials, all bind to and activate both receptor types.The binding of the agonists to the receptors has been investigated for over two decades or since 1986. It is somewhat known, but still not fully understood. When melatonin receptor agonists bind to and activate their receptors it causes numerous physiological processes.\nMT1 receptors are expressed in many regions of the central nervous system (CNS): suprachiasmatic nucleus of the hypothalamus (SNC), hippocampus, substantia nigra, cerebellum, central dopaminergic pathways, ventral tegmental area and nucleus accumbens. MT1 is also expressed in the retina, ovary, testis, mammary gland, coronary circulation and aorta, gallbladder, liver, kidney, skin and the immune system. MT2 receptors are expressed mainly in the CNS, also in the lung, cardiac, coronary and aortic tissue, myometrium and granulosa cells, immune cells, duodenum and adipocytes.\nThe binding of melatonin to melatonin receptors activates a few signaling pathways. MT1 receptor activation inhibits the adenylyl cyclase and its inhibition causes a rippling effect of non activation; starting with decreasing formation of cyclic adenosine monophosphate (cAMP), and then progressing to less protein kinase A (PKA) activity, which in turn hinders the phosphorilation of cAMP responsive element-binding protein (CREB binding protein) into P-CREB. MT1 receptors also activate phospholipase C (PLC), affect ion channels and regulate ion flux inside the cell. The binding of melatonin to MT2 receptors inhibits adenylyl cyclase which decreases the formation of cAMP.[4] As well it hinders guanylyl cyclase and therefore the forming of cyclic guanosine monophosphate (cGMP). Binding to MT2 receptors probably affects PLC which increases protein kinase C (PKC) activity. Activation of the receptor can lead to ion flux inside the cell.\nTarget\nActions\nOrganism\nA\nMelatonin receptor type 1A\nagonist\nHumans\nA\nMelatonin receptor type 1B\nagonist\nHumans\nA\nRibosyldihydronicotinamide dehydrogenase [quinone]\ninhibitor\nHumans\nU\nEstrogen receptor\nantagonist\nHumans\nU\nNuclear receptor ROR-beta\nagonist\nHumans\nU\nMyeloperoxidase\ninhibitor\nHumans\nU\nEosinophil peroxidase\ninhibitor\nHumans\nU\nCalreticulin\nmodulator\nHumans\nU\nCalmodulin\nantagonist\nHumans\nAbsorption\nThe absorption and bioavailability of melatonin varies widely.\nVolume of distribution\nNot Available\nProtein binding\nn\/a\nMetabolism\nHepatically metabolized to at least 14 identified metabolites (identified in mouse urine): 6-hydroxymelatonin glucuronide, 6-hydroxymelatonin sulfate, N-acetylserotonin glucuronide, N-acetylserotonin sulfate, 6-hydroxymelatonin, 2-oxomelatonin, 3-hydroxymelatonin, melatonin glucuronide, cyclic melatonin, cyclic N-acetylserotonin glucuronide, cyclic 6-hydroxymelatonin, 5-hydroxyindole-3-acetaldehyde, di-hydroxymelatonin and its glucuronide conjugate. 6-Hydroxymelatonin glucuronide is the major metabolite found in mouse urine (65-88% of total melatonin metabolites in urine).\nHover over products below to view reaction partners\nRoute of elimination\nNot Available\nHalf-life\n35 to 50 minutes\nClearance\nNot Available\nToxicity\nGenerally well-tolerated when taken orally. The most common side effects, day-time drowsiness, headache and dizziness, appear to occur at the same frequency as with placebo. Other reported side effects include transient depressive symptoms, mild tremor, mild anxiety, abdominal cramps, irritability, reduced alertness, confusion, nausea, vomiting, and hypotension. Safety in Adults: Evidence indicates that it is likely safe to use in oral and parenteral forms for up to two months when used appropriately. Some evidence indicates that it can be safely used orally for up to 9 months in some patients. It is also likely safe to use topically when used appropriately. Safety in Children: Melatonin appeared to be used safely in small numbers of children enrolled in short-term clinical trials. However, concerns regarding safety in children have arisen based on their developmental state. Compared to adults over 20 years of age, people under 20 produce high levels of melatonin. Melatonin levels are inversely related to gonadal development and it is thought that exogenous administration of melatonin may adversely affect gonadal development. Safety during Pregnancy: High doses of melatonin administered orally or parenterally may inhibit ovulation. Not advised for use in individuals who are pregnant or trying to become pregnant. Safety during Lactation: Not recommended as safety has not be established.\nOral, rat: LD\n50\n≥3200 mg\/kg\nPathways\nPathway\nCategory\nTryptophan Metabolism\nMetabolic\nPharmacogenomic Effects\/ADRs\nNot Available\nDrug Interactions\nThis information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.\nApproved\nVet approved\nNutraceutical\nIllicit\nWithdrawn\nInvestigational\nExperimental\nAll Drugs\nDrug\nInteraction\nIntegrate drug-drug\ninteractions in your software\n1,2-Benzodiazepine\nThe risk or severity of CNS depression can be increased when Melatonin is combined with 1,2-Benzodiazepine.\nAbametapir\nThe serum concentration of Melatonin can be increased when it is combined with Abametapir.\nAbatacept\nThe metabolism of Melatonin can be increased when combined with Abatacept.\nAbiraterone\nThe serum concentration of Melatonin can be increased when it is combined with Abiraterone.\nAcenocoumarol\nThe metabolism of Acenocoumarol can be decreased when combined with Melatonin.\nFood Interactions\nAvoid alcohol. Ingesting alcohol may reduce the effects of melatonin.\nTake after a meal. Administration of melatonin after eating slows the absorption and reduces the Cmax of melatonin.\nInternational\/Other Brands\nMela-T (Alacer Corp. (Canada))\n\/\nMelatol (Elisium (Argentina))\n\/\nMelatonin (Biomed International Products Corp., Nutravite Pharmaceuticals (2008) Inc., Viva Pharmaceutical Inc., Kripps Pharmacy Ltd., SunOpta Inc.)\n\/\nNature'S Harmony (SunOpta Inc. (Canada))\n\/\nRevital Melatonin (Chin Tai Ginseng Co., Ltd (Canada))\n\/\nRx Balance (SunOpta Inc. (Canada))\n\/\nSleep Right (SunOpta Inc. (Canada))\n\/\nVivitas (SunOpta Inc. (Canada))\nBrand Name Prescription Products\nName\nDosage\nStrength\nRoute\nLabeller\nMarketing Start\nMarketing End\nRegion\nImage\nMelatol\nLiquid\n1 mg\/30mL\nOral\nPureTek Corporation\n2024-10-17\nNot applicable\nCircadin\nTablet, extended release\n2 mg\nOral\nRad Neurim Pharmaceuticals Eec Sarl\n2016-09-08\nNot applicable\nCircadin\nTablet, extended release\n2 mg\nOral\nRad Neurim Pharmaceuticals Eec Sarl\n2016-09-08\nNot applicable\nCircadin\nTablet, extended release\n2 mg\nOral\nRad Neurim Pharmaceuticals Eec Sarl\n2016-09-08\nNot applicable\nCircadin\nTablet, extended release\n2 mg\nOral\nRad Neurim Pharmaceuticals Eec Sarl\n2016-09-08\nNot applicable\nOver the Counter Products\nName\nDosage\nStrength\nRoute\nLabeller\nMarketing Start\nMarketing End\nRegion\nImage\nEssential Oil\nOil\n2.5 mg\/10mL\nCutaneous\nShantou Youjia E-Commerce Co., Ltd.\n2024-02-01\n2024-12-31\nUnapproved\/Other Products\nName\nIngredients\nDosage\nRoute\nLabeller\nMarketing Start\nMarketing End\nRegion\nImage\nMedi-doze Rx Sleep Aid\nMelatonin\n(6 mg\/1)\n+\nValerian\n(50 mg\/1)\n+\ngamma-Aminobutyric acid\n(30 mg\/1)\nTablet\nOral\nTwo Hip Consulting, Llc\n2013-02-20\n2016-04-11\nMelatol\nMelatonin\n(1 mg\/30mL)\nLiquid\nOral\nPureTek Corporation\n2024-10-17\nNot applicable\nDrug Categories\nAmines\nAntioxidants\nBiogenic Amines\nBiogenic Monoamines\nBiological Factors\nCentral Nervous System Agents\nCentral Nervous System Depressants\nCompounds used in a research, industrial, or household setting\nCytochrome P-450 CYP1A1 Substrates\nCytochrome P-450 CYP1A2 Substrates\nCytochrome P-450 CYP2C19 Substrates\nCytochrome P-450 CYP2C9 Substrates\nCytochrome P-450 Substrates\nHeterocyclic Compounds, Fused-Ring\nHormones\nHormones, Hormone Substitutes, and Hormone Antagonists\nHypnotics and Sedatives\nIndoles\nMelatonin Receptor Agonists\nMelatonin, agonists\nNervous System\nOAT3\/SLC22A8 Inhibitors\nProtective Agents\nPsycholeptics\nTryptamines\nAffected organisms\nHumans and other mammals\nUNII\nJL5DK93RCL\nCAS number\n73-31-4\nInChI Key\nDRLFMBDRBRZALE-UHFFFAOYSA-N\nInChI\nInChI=1S\/C13H16N2O2\/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13\/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)\nIUPAC Name\nN-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide\nSMILES\nCOC1=CC2=C(NC=C2CCNC(C)=O)C=C1\nSynthesis Reference\nRobert A. S. Welch, Keith Betteridge, \"Method of stimulating cashmere growth on cashmere-producing goats using melatonin.\" U.S. Patent US4855313, issued August, 1986.\nUS4855313\nGeneral References\nBoutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [\nArticle\n]\nCaniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. [\nArticle\n]\nHardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. [\nArticle\n]\nHattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. [\nArticle\n]\nMa X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210\/en.2007-1412. Epub 2008 Jan  10. [\nArticle\n]\nReiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. [\nArticle\n]\nPDB Entries\n2qwx\n\/\n2qx4\n\/\n2qx6\n\/\n4qog\n\/\n4qoi\n\/\n5i8f\n\/\n5mxb\n\/\n5mxw\n\/\n6tr5\nClinical Trials\nClinical Trial & Rare Diseases  Add-on Data Package\nExplore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more.\nPreview package\nPhase\nStatus\nPurpose\nConditions\nCount\nStart Date\nWhy Stopped\n100+ additional columns\nUnlock 175K+ rows when you subscribe.\nView sample data\nNot Available\nActive Not Recruiting\nPrevention\nOral Lichen Planus\n1\nsomestatus\nstop reason\njust information to hide\nNot Available\nActive Not Recruiting\nTreatment\nPsychosis\n\/\nSchizophrenia Disorders\n\/\nSchizophrenias\n1\nsomestatus\nstop reason\njust information to hide\nNot Available\nCompleted\nNot Available\nInsomnia\n1\nsomestatus\nstop reason\njust information to hide\nNot Available\nCompleted\nNot Available\nPostoperative Delirium (POD)\n1\nsomestatus\nstop reason\njust information to hide\nNot Available\nCompleted\nNot Available\nPostoperative pain\n1\nsomestatus\nstop reason\njust information to hide\nManufacturers\nNot Available\nPackagers\nMason Distributors\nMedisca Inc.\nNational Vitamin Company\nPhysiologics\nRugby Laboratories\nDosage Forms\nForm\nRoute\nStrength\nCapsule\nNot applicable\n10 mg\/1\nCapsule\nOral\n5.00000 mg\nCapsule, coated\nOral\n3 mg\nCapsule, liquid filled\nOral\n3 mg\nChewable gel\nOral\n2.5 mg\/1\nLiquid\nOral\n1 mg\/4mL\nLiquid\nOral\n1 mg\/30mL\nOil\nCutaneous\n2.5 mg\/10mL\nSolution\nOral\n1 mg\/ml\nSolution \/ drops\nOral\n1 mg\/1mL\nTablet\nNot applicable\n10 mg\/1\nTablet\nOral\nTablet\nOral\n0.5 mg\nTablet\nOral\n1 mg\nTablet\nOral\n1.500 mg\nTablet\nOral\n2 mg\nTablet\nOral\n3 mg\/1\nTablet\nOral\n3 MG\nTablet\nOral\n4 mg\nTablet\nOral\n5 MG\nTablet\nOral\n5 mg\/1\nTablet\nSublingual\n3.000 mg\nTablet, chewable\nOral\n2.5 mg\/1\nTablet, extended release\nOral\n1 MG\nTablet, extended release\nOral\n2 mg\nTablet, extended release\nOral\n5 MG\nTablet, film coated\nOral\n3 mg\nTablet, film coated\nOral\n5 mg\nPrices\nUnit description\nCost\nUnit\nMelatonin powder\n45.6USD\ng\nMelatonin 3 mg tablet\n0.22USD\ntablet\nMelatonin 5 mg tablet\n0.12USD\ntablet\nMelatonin 5 mg tablet sl\n0.1USD\ntablet\nMelatonin sublingual tablet\n0.09USD\ntablet\nMelatonin 1 mg tablet\n0.03USD\ntablet\nDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.\nPatents\nNot Available\nState\nSolid\nExperimental Properties\nProperty\nValue\nSource\nmelting point (°C)\n117 °C\nPhysProp\nlogP\n1.6\nNot Available\nPredicted Properties\nProperty\nValue\nSource\nWater Solubility\n0.143 mg\/mL\nALOGPS\nlogP\n1.42\nALOGPS\nlogP\n1.15\nChemaxon\nlogS\n-3.2\nALOGPS\npKa (Strongest Acidic)\n15.8\nChemaxon\npKa (Strongest Basic)\n-1.6\nChemaxon\nPhysiological Charge\n0\nChemaxon\nHydrogen Acceptor Count\n2\nChemaxon\nHydrogen Donor Count\n2\nChemaxon\nPolar Surface Area\n54.12 Å\n2\nChemaxon\nRotatable Bond Count\n4\nChemaxon\nRefractivity\n66.28 m\n3\n·mol\n-1\nChemaxon\nPolarizability\n25.65 Å\n3\nChemaxon\nNumber of Rings\n2\nChemaxon\nBioavailability\n1\nChemaxon\nRule of Five\nYes\nChemaxon\nGhose Filter\nYes\nChemaxon\nVeber's Rule\nNo\nChemaxon\nMDDR-like Rule\nNo\nChemaxon\nPredicted ADMET Features\nProperty\nValue\nProbability\nHuman Intestinal Absorption\n+\n1.0\nBlood Brain Barrier\n+\n0.9928\nCaco-2 permeable\n-\n0.5536\nP-glycoprotein substrate\nSubstrate\n0.6188\nP-glycoprotein inhibitor I\nNon-inhibitor\n0.9569\nP-glycoprotein inhibitor II\nNon-inhibitor\n0.6838\nRenal organic cation transporter\nNon-inhibitor\n0.542\nCYP450 2C9 substrate\nNon-substrate\n0.8231\nCYP450 2D6 substrate\nSubstrate\n0.5062\nCYP450 3A4 substrate\nSubstrate\n0.6505\nCYP450 1A2 substrate\nInhibitor\n0.9304\nCYP450 2C9 inhibitor\nNon-inhibitor\n0.9071\nCYP450 2D6 inhibitor\nInhibitor\n0.8084\nCYP450 2C19 inhibitor\nNon-inhibitor\n0.9025\nCYP450 3A4 inhibitor\nNon-inhibitor\n0.7194\nCYP450 inhibitory promiscuity\nHigh CYP Inhibitory Promiscuity\n0.6803\nAmes test\nNon AMES toxic\n0.9132\nCarcinogenicity\nNon-carcinogens\n0.9498\nBiodegradation\nNot ready biodegradable\n0.8764\nRat acute toxicity\n1.8922 LD50, mol\/kg\nNot applicable\nhERG inhibition (predictor I)\nWeak inhibitor\n0.9631\nhERG inhibition (predictor II)\nNon-inhibitor\n0.5124\nADMET data is predicted using\nadmetSAR\n, a free tool for evaluating chemical ADMET properties. (\n23092397\n)\nMass Spec (NIST)\nDownload\n(8.2 KB)\nSpectra\nSpectrum\nSpectrum Type\nSplash Key\nGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)\nGC-MS\nsplash10-001i-0490000000-aa93967315af900a76ce\nGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)\nGC-MS\nsplash10-03k9-0900000000-a15ee6def3f8d75b1231\nGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)\nGC-MS\nsplash10-001j-0490000000-94ef1be9ab930060778a\nGC-MS Spectrum - GC-MS (2 TMS)\nGC-MS\nsplash10-001i-1490000000-03e24298c7bd1ed4066a\nPredicted GC-MS Spectrum - GC-MS\nPredicted GC-MS\nsplash10-0076-4920000000-a8d9d614e9f8769a1359\nGC-MS Spectrum - GC-MS\nGC-MS\nsplash10-001i-1490000000-03e24298c7bd1ed4066a\nGC-MS Spectrum - GC-EI-TOF\nGC-MS\nsplash10-001j-0590000000-63d5e32dd5f7877a4402\nGC-MS Spectrum - GC-EI-TOF\nGC-MS\nsplash10-001i-0590000000-52b3a733f8b49582d3fb\nGC-MS Spectrum - GC-EI-TOF\nGC-MS\nsplash10-0229-1900000000-d81c6f617bc486066136\nMass Spectrum (Electron Ionization)\nMS\nsplash10-03k9-1900000000-45ee4fdc7acdb33dad3b\nMS\/MS Spectrum - Quattro_QQQ 10V, Positive\nLC-MS\/MS\nsplash10-00di-0920000000-f90ec9b77e1a245e35a8\nMS\/MS Spectrum - Quattro_QQQ 25V, Positive\nLC-MS\/MS\nsplash10-05fr-0900000000-49e4482c65e82ac64b66\nMS\/MS Spectrum - Quattro_QQQ 40V, Positive\nLC-MS\/MS\nsplash10-003r-0900000000-8a4ae0fd610cca992d74\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative\nLC-MS\/MS\nsplash10-0159-0090000000-939a1caf5760c0ba189c\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative\nLC-MS\/MS\nsplash10-0006-0930000000-9e6fcea2c634ac9d85a0\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative\nLC-MS\/MS\nsplash10-0006-0900000000-ddd29e731a7de56c1808\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative\nLC-MS\/MS\nsplash10-0006-0900000000-34b4fb52810a15ea5bd6\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative\nLC-MS\/MS\nsplash10-001i-0090000000-5ca2df63ec2baefdae8c\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive\nLC-MS\/MS\nsplash10-001i-0190000000-5bae6e63e9b40e60e0a4\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive\nLC-MS\/MS\nsplash10-00di-0900000000-529bf6d5c2091993f865\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive\nLC-MS\/MS\nsplash10-00di-0900000000-158a60fe696120b23b41\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive\nLC-MS\/MS\nsplash10-0a5c-0900000000-5e86b2de659ce47762c0\nLC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive\nLC-MS\/MS\nsplash10-001i-0900000000-881c0d57239d56c46f2d\nLC-MS\/MS Spectrum - LC-ESI-IT (LC\/MSD Trap XCT, Agilent Technologies) , Positive\nLC-MS\/MS\nsplash10-00di-0910000000-f256f78adbcbeb2464de\nLC-MS\/MS Spectrum - LC-ESI-IT (LC\/MSD Trap XCT, Agilent Technologies) , Positive\nLC-MS\/MS\nsplash10-0a4i-0900000000-bd15d952a2fc6c5cbb23\nMS\/MS Spectrum - DI-ESI-qTof , Positive\nLC-MS\/MS\nsplash10-05fr-0900000000-7acf9405f4beeb34566c\nMS\/MS Spectrum - DI-ESI-qTof , Positive\nLC-MS\/MS\nsplash10-00di-0900000000-13245183cd8c8cd511c3\nLC-MS\/MS Spectrum - LC-ESI-qTof , Positive\nLC-MS\/MS\nsplash10-05ai-2900000000-07b3d32f002dba733c10\nLC-MS\/MS Spectrum - LC-ESI-QQ , negative\nLC-MS\/MS\nsplash10-0159-0090000000-939a1caf5760c0ba189c\nLC-MS\/MS Spectrum - LC-ESI-QQ , negative\nLC-MS\/MS\nsplash10-0006-0930000000-9e6fcea2c634ac9d85a0\nLC-MS\/MS Spectrum - LC-ESI-QQ , negative\nLC-MS\/MS\nsplash10-0006-0900000000-ddd29e731a7de56c1808\nLC-MS\/MS Spectrum - LC-ESI-QQ , negative\nLC-MS\/MS\nsplash10-0006-0900000000-34b4fb52810a15ea5bd6\nLC-MS\/MS Spectrum - LC-ESI-QQ , negative\nLC-MS\/MS\nsplash10-001i-0090000000-5ca2df63ec2baefdae8c\nLC-MS\/MS Spectrum - LC-ESI-QTOF , negative\nLC-MS\/MS\nsplash10-00lr-0090000000-3c42f6997539afb44682\nLC-MS\/MS Spectrum - LC-ESI-QTOF , negative\nLC-MS\/MS\nsplash10-014m-0960000000-7991e64dacb3c7f5cf32\nLC-MS\/MS Spectrum - LC-ESI-QTOF , negative\nLC-MS\/MS\nsplash10-0006-0900000000-882be43bc196e928a3cf\nMS\/MS Spectrum - , negative\nLC-MS\/MS\nsplash10-014i-0190000000-ddda9232f0e8e1b402f7\nLC-MS\/MS Spectrum - LC-ESI-QQ , positive\nLC-MS\/MS\nsplash10-001i-0190000000-5bae6e63e9b40e60e0a4\nLC-MS\/MS Spectrum - LC-ESI-QQ , positive\nLC-MS\/MS\nsplash10-00di-0900000000-529bf6d5c2091993f865\nLC-MS\/MS Spectrum - LC-ESI-QQ , positive\nLC-MS\/MS\nsplash10-00di-0900000000-158a60fe696120b23b41\nLC-MS\/MS Spectrum - LC-ESI-QQ , positive\nLC-MS\/MS\nsplash10-0a5c-0900000000-5e86b2de659ce47762c0\nLC-MS\/MS Spectrum - LC-ESI-QQ , positive\nLC-MS\/MS\nsplash10-001i-0900000000-881c0d57239d56c46f2d\nLC-MS\/MS Spectrum - LC-ESI-IT , positive\nLC-MS\/MS\nsplash10-00di-0910000000-d659c749adcab685e8bb\nLC-MS\/MS Spectrum - LC-ESI-QTOF , positive\nLC-MS\/MS\nsplash10-00di-0900000000-6817d8039761a9058337\nLC-MS\/MS Spectrum - LC-ESI-QTOF , positive\nLC-MS\/MS\nsplash10-00di-0900000000-349d5a97e2406d0db910\nLC-MS\/MS Spectrum - LC-ESI-QTOF , positive\nLC-MS\/MS\nsplash10-001i-0900000000-9e30dcf47c9eca14650e\nMS\/MS Spectrum - , positive\nLC-MS\/MS\nsplash10-00di-1900000000-73dc69b26b1fba60f253\nMS\/MS Spectrum - , positive\nLC-MS\/MS\nsplash10-05ai-2900000000-07b3d32f002dba733c10\nMS\/MS Spectrum - , positive\nLC-MS\/MS\nsplash10-00di-0900000000-2e847095e37f4ffe7c8b\nPredicted MS\/MS Spectrum - 10V, Positive (Annotated)\nPredicted LC-MS\/MS\nsplash10-0089-0960000000-9acd48062f28a100f9da\nPredicted MS\/MS Spectrum - 10V, Negative (Annotated)\nPredicted LC-MS\/MS\nsplash10-03di-5790000000-571ee430d2b0391822e3\nPredicted MS\/MS Spectrum - 20V, Positive (Annotated)\nPredicted LC-MS\/MS\nsplash10-00di-0900000000-1a38178248f05cf91e65\nPredicted MS\/MS Spectrum - 20V, Negative (Annotated)\nPredicted LC-MS\/MS\nsplash10-052f-9000000000-9950a9dee5e36e935714\nPredicted MS\/MS Spectrum - 40V, Positive (Annotated)\nPredicted LC-MS\/MS\nsplash10-006x-0900000000-5d47768c1bb474f51f38\nPredicted MS\/MS Spectrum - 40V, Negative (Annotated)\nPredicted LC-MS\/MS\nsplash10-0006-4900000000-9374ee5bf5eb87317f56\n1H NMR Spectrum\n1D NMR\nNot Applicable\n1H NMR Spectrum\n1D NMR\nNot Applicable\n13C NMR Spectrum\n1D NMR\nNot Applicable\nPredicted 1H NMR Spectrum\n1D NMR\nNot Applicable\nPredicted 13C NMR Spectrum\n1D NMR\nNot Applicable\n[1H,13C] 2D NMR Spectrum\n2D NMR\nNot Applicable\nChromatographic Properties\nCollision Cross Sections (CCS)\nAdduct\nCCS Value (Å\n2\n)\nSource type\nSource\n[M-H]-\n159.6858961\npredicted\nDarkChem Lite v0.1.0\n[M-H]-\n152.8346632\npredicted\nDarkChem Standard v0.1.0\n[M-H]-\n152.9149983\npredicted\nDarkChem Lite v0.1.0\n[M-H]-\n165.2831961\npredicted\nDarkChem Lite v0.1.0\n[M-H]-\n159.7026961\npredicted\nDarkChem Lite v0.1.0\n[M-H]-\n150.02837\npredicted\nDeepCCS 1.0 (2019)\n[M+H]+\n159.1911961\npredicted\nDarkChem Lite v0.1.0\n[M+H]+\n157.166152\npredicted\nDarkChem Standard v0.1.0\n[M+H]+\n157.1763686\npredicted\nDarkChem Lite v0.1.0\n[M+H]+\n166.2821961\npredicted\nDarkChem Lite v0.1.0\n[M+H]+\n159.7927961\npredicted\nDarkChem Lite v0.1.0\n[M+H]+\n152.38637\npredicted\nDeepCCS 1.0 (2019)\n[M+Na]+\n158.6747961\npredicted\nDarkChem Lite v0.1.0\n[M+Na]+\n165.6858961\npredicted\nDarkChem Lite v0.1.0\n[M+Na]+\n167.0242025\npredicted\nDarkChem Lite v0.1.0\n[M+Na]+\n165.6891961\npredicted\nDarkChem Lite v0.1.0\n[M+Na]+\n159.5635961\npredicted\nDarkChem Lite v0.1.0\n[M+Na]+\n158.4795\npredicted\nDeepCCS 1.0 (2019)\nTargets\nBuild, predict & validate machine-learning models\nUse our structured and evidence-based datasets to\nunlock newinsights and accelerate drug research.\nLearn more\nUse our structured and evidence-based datasets to unlock new insights and accelerate drug research.\nLearn more\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nYes\nActions\nAgonist\nGeneral Function\nHigh affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity. Possibly involved in sleep induction, by melatonin activation of the potassium channel KCNMA1\/BK and the dissociation of G-beta and G-gamma subunits, thereby decreasing synaptic transmission (By similarity)\nSpecific Function\nG protein-coupled receptor activity\nGene Name\nMTNR1A\nUniprot ID\nP48039\nUniprot Name\nMelatonin receptor type 1A\nMolecular Weight\n39374.315 Da\nReferences\nRadogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. [\nArticle\n]\nChen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [\nArticle\n]\nBoutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [\nArticle\n]\nHardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. [\nArticle\n]\nSrinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007\/s12325-010-0065-y. Epub 2010 Sep  6. [\nArticle\n]\nCarocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016\/j.bmc.2010.06.100. Epub 2010 Jul 3. [\nArticle\n]\nPrendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210\/en.2009-0710. Epub 2009 Dec 4. [\nArticle\n]\nWitt-Enderby PA, Chu GH, Gillen ML, Li PK: Development of a high-affinity ligand that binds irreversibly to Mel1b melatonin receptors. J Med Chem. 1997 Dec 19;40(26):4195-8. [\nArticle\n]\nLiu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. [\nArticle\n]\nHoashi Y, Takai T, Kosugi Y, Nakashima M, Nakayama M, Hirai K, Uchikawa O, Koike T: Discovery of a Potent and Orally Bioavailable Melatonin Receptor Agonist. J Med Chem. 2021 Mar 25;64(6):3059-3074. doi: 10.1021\/acs.jmedchem.0c01836. Epub 2021 Mar 7. [\nArticle\n]\nGunia-Krzyzak A, Zelaszczyk D, Rapacz A, Zeslawska E, Waszkielewicz AM, Panczyk K, Sloczynska K, Pekala E, Nitek W, Filipek B, Marona H: Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH(3) or 2-CH(3). Bioorg Med Chem. 2017 Jan 15;25(2):471-482. doi: 10.1016\/j.bmc.2016.11.014. Epub 2016 Nov 11. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nYes\nActions\nAgonist\nGeneral Function\nHigh affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity\nSpecific Function\nG protein-coupled receptor activity\nGene Name\nMTNR1B\nUniprot ID\nP49286\nUniprot Name\nMelatonin receptor type 1B\nMolecular Weight\n40187.895 Da\nReferences\nRadogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. [\nArticle\n]\nBoutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [\nArticle\n]\nHardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. [\nArticle\n]\nSrinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007\/s12325-010-0065-y. Epub 2010 Sep  6. [\nArticle\n]\nCarocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016\/j.bmc.2010.06.100. Epub 2010 Jul 3. [\nArticle\n]\nPrendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210\/en.2009-0710. Epub 2009 Dec 4. [\nArticle\n]\nMattson RJ, Catt JD, Keavy D, Sloan CP, Epperson J, Gao Q, Hodges DB, Iben L, Mahle CD, Ryan E, Yocca FD: Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett. 2003 Mar 24;13(6):1199-202. [\nArticle\n]\nLiu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. [\nArticle\n]\nFerreira MA Jr, Azevedo H, Mascarello A, Segretti ND, Russo E, Russo V, Guimaraes CRW: Discovery of ACH-000143: A Novel Potent and Peripherally Preferred Melatonin Receptor Agonist that Reduces Liver Triglycerides and Steatosis in Diet-Induced Obese Rats. J Med Chem. 2021 Feb 25;64(4):1904-1929. doi: 10.1021\/acs.jmedchem.0c00627. Epub 2021 Feb 8. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nYes\nActions\nInhibitor\nGeneral Function\nThe enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis\nSpecific Function\nchloride ion binding\nGene Name\nNQO2\nUniprot ID\nP16083\nUniprot Name\nRibosyldihydronicotinamide dehydrogenase [quinone]\nMolecular Weight\n25918.4 Da\nReferences\nRadogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. [\nArticle\n]\nZhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093\/nar\/gkad751. [\nArticle\n]\nFukatsu K, Uchikawa O, Kawada M, Yamano T, Yamashita M, Kato K, Hirai K, Hinuma S, Miyamoto M, Ohkawa S: Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists. J Med Chem. 2002 Sep 12;45(19):4212-21. doi: 10.1021\/jm020114g. [\nArticle\n]\nLiu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. [\nArticle\n]\nDu H, Wang J, Zhang X, Hu Z: A novel quantitative structure-activity relationship method to predict the affinities of MT3 melatonin binding site. Eur J Med Chem. 2008 Dec;43(12):2861-9. doi: 10.1016\/j.ejmech.2008.02.012. Epub 2008 Feb 29. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nAntagonist\nGeneral Function\nNuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1\/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA\/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA\/p65 and NFKB1\/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol\/E2) (By similarity)\nSpecific Function\n14-3-3 protein binding\nGene Name\nESR1\nUniprot ID\nP03372\nUniprot Name\nEstrogen receptor\nMolecular Weight\n66215.45 Da\nReferences\ndel Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. [\nArticle\n]\nYoo YM, Jeung EB: Melatonin-induced estrogen receptor alpha-mediated calbindin-D9k expression plays a role in H2O2-mediated cell death in rat pituitary GH3 cells. J Pineal Res. 2009 Nov;47(4):301-7. doi: 10.1111\/j.1600-079X.2009.00714.x. Epub 2009 Oct 1. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nAgonist\nGeneral Function\nNuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity)\nSpecific Function\nDNA-binding transcription activator activity, RNA polymerase II-specific\nGene Name\nRORB\nUniprot ID\nQ92753\nUniprot Name\nNuclear receptor ROR-beta\nMolecular Weight\n53219.385 Da\nReferences\nBecker-Andre M, Wiesenberg I, Schaeren-Wiemers N, Andre E, Missbach M, Saurat JH, Carlberg C: Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily. J Biol Chem. 1994 Nov 18;269(46):28531-4. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nInhibitor\nGeneral Function\nPart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971)\nSpecific Function\nchromatin binding\nGene Name\nMPO\nUniprot ID\nP05164\nUniprot Name\nMyeloperoxidase\nMolecular Weight\n83867.71 Da\nReferences\nGalijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021\/bi702016q. Epub 2008 Feb 1. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nInhibitor\nGeneral Function\nMediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis\nSpecific Function\nheme binding\nGene Name\nEPX\nUniprot ID\nP11678\nUniprot Name\nEosinophil peroxidase\nMolecular Weight\n81039.5 Da\nReferences\nLu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038\/bjp.2008.173. Epub 2008 Jun 2. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nModulator\nGeneral Function\nCalcium-binding chaperone that promotes folding, oligomeric assembly and quality control in the endoplasmic reticulum (ER) via the calreticulin\/calnexin cycle. This lectin interacts transiently with almost all of the monoglucosylated glycoproteins that are synthesized in the ER (PubMed:7876246). Interacts with the DNA-binding domain of NR3C1 and mediates its nuclear export (PubMed:11149926). Involved in maternal gene expression regulation. May participate in oocyte maturation via the regulation of calcium homeostasis (By similarity). Present in the cortical granules of non-activated oocytes, is exocytosed during the cortical reaction in response to oocyte activation and might participate in the block to polyspermy (By similarity)\nSpecific Function\ncalcium ion binding\nGene Name\nCALR\nUniprot ID\nP27797\nUniprot Name\nCalreticulin\nMolecular Weight\n48141.2 Da\nReferences\nHardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. [\nArticle\n]\nMacias M, Escames G, Leon J, Coto A, Sbihi Y, Osuna A, Acuna-Castroviejo D: Calreticulin-melatonin. An unexpected relationship. Eur J Biochem. 2003 Mar;270(5):832-40. [\nArticle\n]\nKind\nProtein group\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nAntagonist\nGeneral Function\nCalmodulin acts as part of a calcium signal transduction pathway by mediating the control of a large number of enzymes, ion channels, aquaporins and other proteins through calcium-binding (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Calcium-binding is required for the activation of calmodulin (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Among the enzymes to be stimulated by the calmodulin-calcium complex are a number of protein kinases, such as myosin light-chain kinases and calmodulin-dependent protein kinase type II (CaMK2), and phosphatases (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis (PubMed:16760425). Is a regulator of voltage-dependent L-type calcium channels (PubMed:31454269). Mediates calcium-dependent inactivation of CACNA1C (PubMed:26969752). Positively regulates calcium-activated potassium channel activity of KCNN2 (PubMed:27165696). Forms a potassium channel complex with KCNQ1 and regulates electrophysiological activity of the channel via calcium-binding (PubMed:25441029). Acts as a sensor to modulate the endoplasmic reticulum contacts with other organelles mediated by VMP1:ATP2A2 (PubMed:28890335)\nSpecific Function\nadenylate cyclase activator activity\nComponents:\nName\nUniProt ID\nCalmodulin-1\nP0DP23\nCalmodulin-2\nP0DP24\nCalmodulin-3\nP0DP25\nReferences\ndel Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. [\nArticle\n]\nRadogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. [\nArticle\n]\nEnzymes\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nSubstrate\nInhibitor\nGeneral Function\nA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195)\nSpecific Function\narachidonate monooxygenase activity\nGene Name\nCYP1A1\nUniprot ID\nP04798\nUniprot Name\nCytochrome P450 1A1\nMolecular Weight\n58164.815 Da\nReferences\nChang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [\nArticle\n]\nMa X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [\nArticle\n]\nDutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. [\nArticle\n]\nLiu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nSubstrate\nGeneral Function\nA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)\nSpecific Function\ncaffeine oxidase activity\nGene Name\nCYP1A2\nUniprot ID\nP05177\nUniprot Name\nCytochrome P450 1A2\nMolecular Weight\n58406.915 Da\nReferences\nChang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [\nArticle\n]\nMa X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [\nArticle\n]\nTurpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. [\nArticle\n]\nHartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. [\nArticle\n]\nHartter S, Wang X, Weigmann H, Friedberg T, Arand M, Oesch F, Hiemke C: Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin. J Clin Psychopharmacol. 2001 Apr;21(2):167-74. [\nArticle\n]\nDutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. [\nArticle\n]\nLiu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nSubstrate\nInhibitor\nGeneral Function\nA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity)\nSpecific Function\nestrogen 16-alpha-hydroxylase activity\nGene Name\nCYP1B1\nUniprot ID\nQ16678\nUniprot Name\nCytochrome P450 1B1\nMolecular Weight\n60845.33 Da\nReferences\nChang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [\nArticle\n]\nMa X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [\nArticle\n]\nYu Z, Tian X, Peng Y, Sun Z, Wang C, Tang N, Li B, Jian Y, Wang W, Huo X, Ma X: Mitochondrial cytochrome P450 (CYP) 1B1 is responsible for melatonin-induced apoptosis in neural cancer cells. J Pineal Res. 2018 Aug;65(1):e12478. doi: 10.1111\/jpi.12478. Epub 2018 Mar 25. [\nArticle\n]\nDutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. [\nArticle\n]\nLiu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nSubstrate\nGeneral Function\nA cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)\nSpecific Function\n(R)-limonene 6-monooxygenase activity\nGene Name\nCYP2C19\nUniprot ID\nP33261\nUniprot Name\nCytochrome P450 2C19\nMolecular Weight\n55944.565 Da\nReferences\nHuuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. [\nArticle\n]\nFacciola G, Hidestrand M, von Bahr C, Tybring G: Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes. Eur J Clin Pharmacol. 2001 Mar;56(12):881-8. doi: 10.1007\/s002280000245. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nSubstrate\nGeneral Function\nA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)\nSpecific Function\n(R)-limonene 6-monooxygenase activity\nGene Name\nCYP2C9\nUniprot ID\nP11712\nUniprot Name\nCytochrome P450 2C9\nMolecular Weight\n55627.365 Da\nReferences\nMo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nSubstrate\nGeneral Function\nCatalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine)\nSpecific Function\nacetylserotonin O-methyltransferase activity\nGene Name\nASMT\nUniprot ID\nP46597\nUniprot Name\nAcetylserotonin O-methyltransferase\nMolecular Weight\n38452.51 Da\nReferences\nMinneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nSubstrate\nGeneral Function\nCatalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, contributing to maintain homeostasis by preventing autoimmunity or immunopathology that would result from uncontrolled and overreacting immune responses (PubMed:25691885). Tryptophan shortage inhibits T lymphocytes division and accumulation of tryptophan catabolites induces T-cell apoptosis and differentiation of regulatory T-cells (PubMed:25691885). Acts as a suppressor of anti-tumor immunity (PubMed:14502282, PubMed:23103127, PubMed:25157255, PubMed:25691885). Limits the growth of intracellular pathogens by depriving tryptophan (PubMed:25691885). Protects the fetus from maternal immune rejection (PubMed:25691885)\nSpecific Function\nelectron transfer activity\nGene Name\nIDO1\nUniprot ID\nP14902\nUniprot Name\nIndoleamine 2,3-dioxygenase 1\nMolecular Weight\n45325.89 Da\nReferences\nFerry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nSubstrate\nInhibitor\nGeneral Function\nPart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971)\nSpecific Function\nchromatin binding\nGene Name\nMPO\nUniprot ID\nP05164\nUniprot Name\nMyeloperoxidase\nMolecular Weight\n83867.71 Da\nReferences\nFerry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [\nArticle\n]\nGalijasevic S: The development of myeloperoxidase inhibitors. Bioorg Med Chem Lett. 2019 Jan 1;29(1):1-7. doi: 10.1016\/j.bmcl.2018.11.031. Epub 2018 Nov 15. [\nArticle\n]\nLiu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. [\nArticle\n]\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nInhibitor\nGeneral Function\nA cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo\/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874)\nSpecific Function\naromatase activity\nGene Name\nCYP19A1\nUniprot ID\nP11511\nUniprot Name\nAromatase\nMolecular Weight\n57882.48 Da\nReferences\nGonzalez A, Martinez-Campa C, Mediavilla MD, Alonso-Gonzalez C, Sanchez-Mateos S, Hill SM, Sanchez-Barcelo EJ, Cos S: Effects of MT1 melatonin receptor overexpression on the aromatase-suppressive effect of melatonin in MCF-7 human breast cancer cells. Oncol Rep. 2007 Apr;17(4):947-53. doi: 10.3892\/or.17.4.947. [\nArticle\n]\nTransporters\nKind\nProtein\nOrganism\nHumans\nPharmacological action\nUnknown\nActions\nInhibitor\nGeneral Function\nFunctions as an organic anion\/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S\/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification\/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate\/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)\nSpecific Function\norganic anion transmembrane transporter activity\nGene Name\nSLC22A8\nUniprot ID\nQ8TCC7\nUniprot Name\nOrganic anion transporter 3\nMolecular Weight\n59855.585 Da\nReferences\nOhtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [\nArticle\n]\nKusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [\nArticle\n]","attrs_markdown":"[Accelerate decision confidence with proactive biopharma intelligence Discover How](https:\/\/go.drugbank.com\/product_tour)\n\n[Log in](https:\/\/go.drugbank.com\/public_users\/log_in)\n\n- [Explore](https:\/\/go.drugbank.com\/drugs\/DB01065)\n  [Drug Knowledgebase Start here! Dig into essential drug information](https:\/\/go.drugbank.com\/drugs)\n  \n  [Interaction Checker Check interactions in up to 5 drugs at a time](https:\/\/go.drugbank.com\/drug-interaction-checker)\n  \n  Advanced Exploration\n  \n  - [Categories & ATC Classifications](https:\/\/go.drugbank.com\/categories)\n  - [Pathways](https:\/\/go.drugbank.com\/pathways)\n  - [Drug Reactions](https:\/\/go.drugbank.com\/reactions)\n  - [Drug Classification](https:\/\/go.drugbank.com\/classyfication)\n  - [Drug Targets](https:\/\/go.drugbank.com\/targets)\n  \n  - [Advanced Search](https:\/\/go.drugbank.com\/unearth\/advanced\/drugs)\n  - [Target Sequence](https:\/\/go.drugbank.com\/structures\/search\/bonds\/sequence)\n  - [Spectra Search](https:\/\/go.drugbank.com\/spectra\/ms\/search)\n  - [Pharmaco-omics](https:\/\/go.drugbank.com\/pharmaco\/search)\n  - [Chemical Structure](https:\/\/go.drugbank.com\/structures\/search\/small_molecule_drugs\/structure)\n- [For Drug Discovery](https:\/\/go.drugbank.com\/drugs\/DB01065)\n  [Products Biopharma Intelligence Operating System Enable critical research decisions using AI‑powered intelligence.](https:\/\/go.drugbank.com\/product_tour)\n  \n  [Use Case Drug Discovery & Repurposing Access detailed drug and target data for your pharmaceutical research.](https:\/\/go.drugbank.com\/use_cases\/ml_drug_discovery_repurposing)\n  \n  [Products Data Library Explore detailed drug information packages to support your research & drug discovery.](https:\/\/go.drugbank.com\/data_packages)\n  \n  [![Snowflake](https:\/\/go.drugbank.com\/assets\/snowflake-64d406433cc6454a57e1fbb945b310dbe7ed1bc795123729e029c38b072854ed.svg)Products Data access in Snowflake Increase scalability & security by streamlining data sharing & analysis in the cloud.](https:\/\/app.snowflake.com\/marketplace\/providers\/GZTYZJ6Q7UU\/DrugBank)\n- [For Clinical Software](https:\/\/go.drugbank.com\/drugs\/DB01065)\n  [Products Clinical Intelligence API Learn about our seamless integration into healthcare software.](https:\/\/go.drugbank.com\/clinical)\n  \n  [Use Case Telehealth Power your remote care software.](https:\/\/go.drugbank.com\/use_cases\/telehealth)\n  \n  [Use Case Electronic Medical Records Empower providers with reliable drug information.](https:\/\/go.drugbank.com\/use_cases\/electronic_medical_records)\n  \n  Learn more about API Features\n  \n  - [Drug Search](https:\/\/go.drugbank.com\/clinical\/drug_search)\n  - [Drug-Drug Interaction Checker](https:\/\/go.drugbank.com\/clinical\/drug_drug_interaction_checker)\n  - [Drug Allergy](https:\/\/go.drugbank.com\/clinical\/drug_allergy)\n  - [US Drug Labels](https:\/\/go.drugbank.com\/clinical\/us_drug_labels)\n- [For Academic Research](https:\/\/go.drugbank.com\/releases\/latest)\n- [Resources](https:\/\/go.drugbank.com\/drugs\/DB01065)\n  Company\n  \n  - [About Us](https:\/\/go.drugbank.com\/about)\n  - [Newsroom](https:\/\/go.drugbank.com\/press)\n  - [Careers](https:\/\/drugbank.bamboohr.com\/careers)\n  \n  Learn More\n  \n  - [Help Center](https:\/\/dev.drugbank.com\/guides\/index)\n  - [Blog](https:\/\/blog.drugbank.com\/)\n  - [E-Books & Webinars](https:\/\/go.drugbank.com\/resources)\n  - [Customer Stories](https:\/\/go.drugbank.com\/customers)\n- [Book a Demo](https:\/\/go.drugbank.com\/contact\/sales)\n- [Log in](https:\/\/go.drugbank.com\/public_users\/log_in)\n\n[Ask AI](https:\/\/go.drugbank.com\/product_tour)\n\nLog in or create an account for full access to this data.\n\n[Create Account](https:\/\/go.drugbank.com\/public_users\/sign_up)\n\n[Log in](https:\/\/go.drugbank.com\/public_users\/log_in)\n\n[NAV](https:\/\/go.drugbank.com\/drugs\/DB01065)\n\n[Identification](https:\/\/go.drugbank.com\/drugs\/DB01065#identification-header)\n\n[Summary](https:\/\/go.drugbank.com\/drugs\/DB01065#summary)[Brand Names](https:\/\/go.drugbank.com\/drugs\/DB01065#brand-names)[Name](https:\/\/go.drugbank.com\/drugs\/DB01065#name)[Accession Number](https:\/\/go.drugbank.com\/drugs\/DB01065#accession-number)[Background](https:\/\/go.drugbank.com\/drugs\/DB01065#background)[Modality](https:\/\/go.drugbank.com\/drugs\/DB01065#modality)[Groups](https:\/\/go.drugbank.com\/drugs\/DB01065#groups)[Structure](https:\/\/go.drugbank.com\/drugs\/DB01065#structure)[Weight](https:\/\/go.drugbank.com\/drugs\/DB01065#weight)[Chemical Formula](https:\/\/go.drugbank.com\/drugs\/DB01065#chemical-formula)[Synonyms](https:\/\/go.drugbank.com\/drugs\/DB01065#synonyms)[External IDs](https:\/\/go.drugbank.com\/drugs\/DB01065#external-ids)\n\n[Pharmacology](https:\/\/go.drugbank.com\/drugs\/DB01065#pharmacology-header)\n\n[Indication](https:\/\/go.drugbank.com\/drugs\/DB01065#indication)[Associated Conditions](https:\/\/go.drugbank.com\/drugs\/DB01065#associated-conditions)[Contraindications & Blackbox Warnings](https:\/\/go.drugbank.com\/drugs\/DB01065#contraindications-blackbox-warnings)[Pharmacodynamics](https:\/\/go.drugbank.com\/drugs\/DB01065#pharmacodynamics)[Mechanism of action](https:\/\/go.drugbank.com\/drugs\/DB01065#mechanism-of-action)[Absorption](https:\/\/go.drugbank.com\/drugs\/DB01065#absorption)[Volume of distribution](https:\/\/go.drugbank.com\/drugs\/DB01065#volume-of-distribution)[Protein binding](https:\/\/go.drugbank.com\/drugs\/DB01065#protein-binding)[Metabolism](https:\/\/go.drugbank.com\/drugs\/DB01065#metabolism)[Route of elimination](https:\/\/go.drugbank.com\/drugs\/DB01065#route-of-elimination)[Half-life](https:\/\/go.drugbank.com\/drugs\/DB01065#half-life)[Clearance](https:\/\/go.drugbank.com\/drugs\/DB01065#clearance)[Adverse Effects](https:\/\/go.drugbank.com\/drugs\/DB01065#adverse-effects)[Toxicity](https:\/\/go.drugbank.com\/drugs\/DB01065#toxicity)[Pathways](https:\/\/go.drugbank.com\/drugs\/DB01065#pathways)[Pharmacogenomic Effects\/ADRs](https:\/\/go.drugbank.com\/drugs\/DB01065#pharmacogenomic-effects-adrs)\n\n[Interactions](https:\/\/go.drugbank.com\/drugs\/DB01065#interactions-header)\n\n[Drug Interactions](https:\/\/go.drugbank.com\/drugs\/DB01065#drug-interactions)[Food Interactions](https:\/\/go.drugbank.com\/drugs\/DB01065#food-interactions)\n\n[Products](https:\/\/go.drugbank.com\/drugs\/DB01065#products-header)\n\n[International\/Other Brands](https:\/\/go.drugbank.com\/drugs\/DB01065#international-other-brands)[Brand Name Prescription Products](https:\/\/go.drugbank.com\/drugs\/DB01065#brand-name-prescription-products)[Over the Counter Products](https:\/\/go.drugbank.com\/drugs\/DB01065#over-the-counter-products)[Unapproved\/Other Products](https:\/\/go.drugbank.com\/drugs\/DB01065#unapproved-other-products)\n\n[Categories](https:\/\/go.drugbank.com\/drugs\/DB01065#categories-header)\n\n[ATC Codes](https:\/\/go.drugbank.com\/drugs\/DB01065#atc-codes)[Drug Categories](https:\/\/go.drugbank.com\/drugs\/DB01065#drug-categories)[Chemical Taxonomy](https:\/\/go.drugbank.com\/drugs\/DB01065#chemical-taxonomy)[Affected organisms](https:\/\/go.drugbank.com\/drugs\/DB01065#affected-organisms)\n\n[Chemical Identifiers](https:\/\/go.drugbank.com\/drugs\/DB01065#chemical-identifiers-header)\n\n[UNII](https:\/\/go.drugbank.com\/drugs\/DB01065#unii)[CAS number](https:\/\/go.drugbank.com\/drugs\/DB01065#cas-number)[InChI Key](https:\/\/go.drugbank.com\/drugs\/DB01065#inchi-key)[InChI](https:\/\/go.drugbank.com\/drugs\/DB01065#inchi)[IUPAC Name](https:\/\/go.drugbank.com\/drugs\/DB01065#iupac-name)[SMILES](https:\/\/go.drugbank.com\/drugs\/DB01065#smiles)\n\n[References](https:\/\/go.drugbank.com\/drugs\/DB01065#references-header)\n\n[Synthesis Reference](https:\/\/go.drugbank.com\/drugs\/DB01065#synthesis-reference)[General References](https:\/\/go.drugbank.com\/drugs\/DB01065#general-references)[External Links](https:\/\/go.drugbank.com\/drugs\/DB01065#external-links)[PDB Entries](https:\/\/go.drugbank.com\/drugs\/DB01065#pdb-entries)[MSDS](https:\/\/go.drugbank.com\/drugs\/DB01065#msds)\n\n[Clinical Trials](https:\/\/go.drugbank.com\/drugs\/DB01065#clinical-trials-header)\n\n[Pharmacoeconomics](https:\/\/go.drugbank.com\/drugs\/DB01065#pharmacoeconomics-header)\n\n[Manufacturers](https:\/\/go.drugbank.com\/drugs\/DB01065#manufacturers)[Packagers](https:\/\/go.drugbank.com\/drugs\/DB01065#packagers)[Dosage Forms](https:\/\/go.drugbank.com\/drugs\/DB01065#dosage-forms)[Prices](https:\/\/go.drugbank.com\/drugs\/DB01065#prices)[Patents](https:\/\/go.drugbank.com\/drugs\/DB01065#patents)\n\n[Properties](https:\/\/go.drugbank.com\/drugs\/DB01065#properties-header)\n\n[State](https:\/\/go.drugbank.com\/drugs\/DB01065#state)[Experimental Properties](https:\/\/go.drugbank.com\/drugs\/DB01065#experimental-properties)[Predicted Properties](https:\/\/go.drugbank.com\/drugs\/DB01065#predicted-properties)[Predicted ADMET Features](https:\/\/go.drugbank.com\/drugs\/DB01065#predicted-admet-features)\n\n[Spectra](https:\/\/go.drugbank.com\/drugs\/DB01065#spectra-header)\n\n[Mass Spec](https:\/\/go.drugbank.com\/drugs\/DB01065#mass-spec)[Spectra](https:\/\/go.drugbank.com\/drugs\/DB01065#spectra)\n\n[Targets (9)](https:\/\/go.drugbank.com\/drugs\/DB01065#targets)\n\n[Enzymes (9)](https:\/\/go.drugbank.com\/drugs\/DB01065#enzymes)\n\n[Transporters (1)](https:\/\/go.drugbank.com\/drugs\/DB01065#transporters)\n\n# Melatonin\n[**Star**](https:\/\/go.drugbank.com\/public_users\/log_in?record_star_accession=DB01065 \"You must be signed in to star an entry\")\n\n[**31**](https:\/\/go.drugbank.com\/drugs\/DB01065)\n\n[![](https:\/\/go.drugbank.com\/assets\/locked\/AI-Chat-a64a3de153fd7ca4457e73bcec8b2358868da6c4dda160f9b4693e2d85af5a37.png) **The AI Assistant built for biopharma intelligence.** Access detailed, actionable insights to your most complex research questions. Leverage validated reasoning and citable data to power your critical research decisions.Learn More](https:\/\/go.drugbank.com\/product_tour)\n\n[**The AI Assistant built for biopharma intelligence.**Learn More](https:\/\/go.drugbank.com\/product_tour)\n## Overview\nDescription\n\nA naturally occurring hormone that promotes sleep.\n\n[Structure](https:\/\/go.drugbank.com\/drugs\/DB01065#structure)\n\n![](https:\/\/go.drugbank.com\/structures\/DB01065\/thumb.svg)\n\nDescription\n\nA naturally occurring hormone that promotes sleep.\n\nDrugBank ID\n\nDB01065\n\nModality\n\nSmall Molecule\n\n[Patents](https:\/\/go.drugbank.com\/drugs\/DB01065#patents)\n\n0\n\n[Indicated Conditions](https:\/\/go.drugbank.com\/drugs\/DB01065#indication)\n\n1\n\n[Clinical Trials](https:\/\/go.drugbank.com\/drugs\/DB01065#clinical-trials-header)\n\nPhase 0\n\n8\n\nPhase 1\n\n62\n\nPhase 2\n\n141\n\nPhase 3\n\n80\n\nPhase 4\n\n59\n\nMechanism of Action\n\n- [Melatonin receptor type 1A](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000515)\n  Agonist\n- [Melatonin receptor type 1B](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000327)\n  Agonist\n- [Ribosyldihydronicotinamide dehydrogenase \\[quinone\\]](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000220)\n  Inhibitor\n## Identification\nSummary\n\n**Melatonin** is an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement.\n\nBrand Names\n\n*Circadin, Melatonin Neurim, Slenyto*\n\nGeneric Name\n\nMelatonin\n\nDrugBank Accession Number\n\nDB01065\n\nBackground\n\nMelatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and lowering the body temperature. Melatonin is also implicated in the regulation of mood, learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders (ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.\n\nModality\n\nSmall Molecule\n\nGroups\n\nApproved, Investigational, Nutraceutical, Vet approved\n\nStructure\n\n[![](https:\/\/go.drugbank.com\/structures\/DB01065\/thumb.svg)](https:\/\/go.drugbank.com\/structures\/DB01065\/image.svg)\n\n[3D](https:\/\/go.drugbank.com\/structures\/small_molecule_drugs\/DB01065)\n\nDownload\n\n[MOL](https:\/\/go.drugbank.com\/structures\/small_molecule_drugs\/DB01065.mol)[SDF](https:\/\/go.drugbank.com\/structures\/small_molecule_drugs\/DB01065.sdf)[3D-SDF](https:\/\/go.drugbank.com\/structures\/small_molecule_drugs\/DB01065.sdf?type=3d)[PDB](https:\/\/go.drugbank.com\/structures\/small_molecule_drugs\/DB01065.pdb)[SMILES](https:\/\/go.drugbank.com\/structures\/small_molecule_drugs\/DB01065.smiles)[InChI](https:\/\/go.drugbank.com\/structures\/small_molecule_drugs\/DB01065.inchi)\n\n[Similar Structures](https:\/\/go.drugbank.com\/structures\/search\/small_molecule_drugs\/structure?database_id=DB01065&search_type=similarity#results)\n\n#### Structure for Melatonin (DB01065)\n×\n\n![](https:\/\/go.drugbank.com\/structures\/DB01065\/image.svg)\n\nClose\n\nWeight\n\nAverage: 232.2783   \nMonoisotopic: 232.121177766\n\nChemical Formula\n\nC13H16N2O2\n\nSynonyms\n\n- 5-methoxy-N-acetyl tryptamine\n- 5-methoxy-N-acetyltryptamine\n- Melatonin\n- Melatonina\n- Mélatonine\n- N-\\[2-(5-methoxyindol-3-yl)ethyl\\]acetamide\n- N-Acetyl-5-methoxytryptamine\n\nExternal IDs\n\n- BCI-049\n- J5.258B\n- NPC-15\n- NSC-113928\n- NSC-56423\n## Pharmacology\n[![](https:\/\/go.drugbank.com\/assets\/locked\/AI-Chat-a64a3de153fd7ca4457e73bcec8b2358868da6c4dda160f9b4693e2d85af5a37.png) **The AI Assistant built for biopharma intelligence.** Access detailed, actionable insights to your most complex research questions. Leverage validated reasoning and citable data to power your critical research decisions.Learn More](https:\/\/go.drugbank.com\/product_tour)\n\n[**The AI Assistant built for biopharma intelligence.**Learn More](https:\/\/go.drugbank.com\/product_tour)\n\nIndication\n\nUsed orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. Evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. It has received FDA orphan drug status as an oral medication for this use. A number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. It appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. It may also improve secondary insomnia associated with various sleep-wake cycle disturbances. Other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (DSPS), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with IL-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders.\n\n[![](https:\/\/go.drugbank.com\/assets\/locked\/Pharmacology-da701df37a1a51c9ee28326cbba45e6bdeef07bce6ddf5e2eb757439eea83e8e.png) **Reduce drug development failure rates** **Build, train, & validate machine-learning models**with evidence-based and structured datasets.See how](https:\/\/bit.ly\/3l5TIQu)\n\n[Build, train, & validate predictive machine-learning models with structured datasets.See how](https:\/\/bit.ly\/3yeDgkJ)\n\nAssociated Conditions\n\n| Indication Type | Indication | Combined Product Details | Approval Level | Age Group | Patient Characteristics | Dose Form |\n|---|---|---|---|---|---|---|\n| Management of | [Insomnia](https:\/\/go.drugbank.com\/conditions\/DBCOND0017531) |   | •••••••••••• |   |   |   |\n| Used in combination to manage | [Insomnia](https:\/\/go.drugbank.com\/conditions\/DBCOND0017531) | Combination Product in combination with: [Valerian (DB13196)](https:\/\/go.drugbank.com\/drugs\/DB13196), [gamma-Aminobutyric acid (DB02530)](https:\/\/go.drugbank.com\/drugs\/DB02530) | •••••••••••• |   |   |   |\n\n[Create Account](https:\/\/go.drugbank.com\/public_users\/sign_up)\n\nContraindications & Blackbox Warnings\n\n[![](https:\/\/go.drugbank.com\/assets\/locked\/Contraindications-32d728a7df37129e96c82b2461211bfec263a710b0cf8adcd77a85600db2d24b.png) **Prevent Adverse Drug Events Today** Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Learn more](https:\/\/www.drugbank.com\/clinical#add-on-modules)\n\n[Avoid life-threatening adverse drug events with our Clinical APILearn more](https:\/\/www.drugbank.com\/clinical#add-on-modules)\n\nPharmacodynamics\n\nMelatonin is a hormone normally produced in the pineal gland and released into the blood. The essential amino acid L-tryptophan is a precursor in the synthesis of melatonin. It helps regulate sleep-wake cycles or the circadian rhythm. Production of melatonin is stimulated by darkness and inhibited by light. High levels of melatonin induce sleep and so consumption of the drug can be used to combat insomnia and jet lag. MT1 and MT2 receptors may be a target for the treatment of circadian and non circadian sleep disorders because of their differences in pharmacology and function within the SCN. SCN is responsible for maintaining the 24 hour cycle which regulates many different body functions ranging from sleep to immune functions\n\nMechanism of action\n\nMelatonin is a derivative of tryptophan. It binds to melatonin receptor type 1A, which then acts on adenylate cylcase and the inhibition of a cAMP signal transduction pathway. Melatonin not only inhibits adenylate cyclase, but it also activates phosphilpase C. This potentiates the release of arachidonate. By binding to melatonin receptors 1 and 2, the downstream signallling cascades have various effects in the body. The melatonin receptors are G protein-coupled receptors and are expressed in various tissues of the body. There are two subtypes of the receptor in humans, melatonin receptor 1 (MT1) and melatonin receptor 2 (MT2). Melatonin and melatonin receptor agonists, on market or in clinical trials, all bind to and activate both receptor types.The binding of the agonists to the receptors has been investigated for over two decades or since 1986. It is somewhat known, but still not fully understood. When melatonin receptor agonists bind to and activate their receptors it causes numerous physiological processes. MT1 receptors are expressed in many regions of the central nervous system (CNS): suprachiasmatic nucleus of the hypothalamus (SNC), hippocampus, substantia nigra, cerebellum, central dopaminergic pathways, ventral tegmental area and nucleus accumbens. MT1 is also expressed in the retina, ovary, testis, mammary gland, coronary circulation and aorta, gallbladder, liver, kidney, skin and the immune system. MT2 receptors are expressed mainly in the CNS, also in the lung, cardiac, coronary and aortic tissue, myometrium and granulosa cells, immune cells, duodenum and adipocytes. The binding of melatonin to melatonin receptors activates a few signaling pathways. MT1 receptor activation inhibits the adenylyl cyclase and its inhibition causes a rippling effect of non activation; starting with decreasing formation of cyclic adenosine monophosphate (cAMP), and then progressing to less protein kinase A (PKA) activity, which in turn hinders the phosphorilation of cAMP responsive element-binding protein (CREB binding protein) into P-CREB. MT1 receptors also activate phospholipase C (PLC), affect ion channels and regulate ion flux inside the cell. The binding of melatonin to MT2 receptors inhibits adenylyl cyclase which decreases the formation of cAMP.\\[4\\] As well it hinders guanylyl cyclase and therefore the forming of cyclic guanosine monophosphate (cGMP). Binding to MT2 receptors probably affects PLC which increases protein kinase C (PKC) activity. Activation of the receptor can lead to ion flux inside the cell.\n\n| Target | Actions | Organism |\n|---|---|---|\n| A[Melatonin receptor type 1A](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000515) | agonist | Humans |\n| A[Melatonin receptor type 1B](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000327) | agonist | Humans |\n| A[Ribosyldihydronicotinamide dehydrogenase \\[quinone\\]](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000220) | inhibitor | Humans |\n| U[Estrogen receptor](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000123) | antagonist | Humans |\n| U[Nuclear receptor ROR-beta](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0003554) | agonist | Humans |\n| U[Myeloperoxidase](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0001075) | inhibitor | Humans |\n| U[Eosinophil peroxidase](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0003555) | inhibitor | Humans |\n| U[Calreticulin](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0002109) | modulator | Humans |\n| U[Calmodulin](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0027477) | antagonist | Humans |\n\nAbsorption\n\nThe absorption and bioavailability of melatonin varies widely.\n\nVolume of distribution\n\nNot Available\n\nProtein binding\n\nn\/a\n\nMetabolism\n\nHepatically metabolized to at least 14 identified metabolites (identified in mouse urine): 6-hydroxymelatonin glucuronide, 6-hydroxymelatonin sulfate, N-acetylserotonin glucuronide, N-acetylserotonin sulfate, 6-hydroxymelatonin, 2-oxomelatonin, 3-hydroxymelatonin, melatonin glucuronide, cyclic melatonin, cyclic N-acetylserotonin glucuronide, cyclic 6-hydroxymelatonin, 5-hydroxyindole-3-acetaldehyde, di-hydroxymelatonin and its glucuronide conjugate. 6-Hydroxymelatonin glucuronide is the major metabolite found in mouse urine (65-88% of total melatonin metabolites in urine).\n\n**Hover over products below to view reaction partners**\n\n- Melatonin\n  - [6-Hydroxymelatonin](https:\/\/go.drugbank.com\/reactions\/259)\n    - [6-Hydroxymelatonin glucuronide](https:\/\/go.drugbank.com\/reactions\/1547)\n    - [6-Hydroxymelatonin sulfate](https:\/\/go.drugbank.com\/reactions\/1544)\n  - [N-Acetyl-5-hydroxytryptamine](https:\/\/go.drugbank.com\/reactions\/414)\n    - [N-Acetyl-5-hydroxytryptamine glucuronide](https:\/\/go.drugbank.com\/reactions\/1546)\n    - [N-Acetyl-5-hydroxytryptamine sulfate](https:\/\/go.drugbank.com\/reactions\/1545)\n  - [5-Methoxytryptamine](https:\/\/go.drugbank.com\/reactions\/1548)\n    - [Bufotenine](https:\/\/go.drugbank.com\/reactions\/1551)\n      - [N,N-Dimethyltryptamine](https:\/\/go.drugbank.com\/reactions\/1552)\n    - [Pinoline](https:\/\/go.drugbank.com\/reactions\/1550)\n\nRoute of elimination\n\nNot Available\n\nHalf-life\n\n35 to 50 minutes\n\nClearance\n\nNot Available\n\nAdverse Effects\n\n[![](https:\/\/go.drugbank.com\/assets\/locked\/AdverseEffects-5c75088f6dd600a6c494e9851006309fd1e423f24e4beba13dd0171d4f511993.png) **Improve decision support & research outcomes** With structured adverse effects data, including: **blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library\\!**See the data](https:\/\/go.drugbank.com\/data_packages\/target\/data_modules\/structured_adverse_effects#adverse_effect_incidences)\n\n[Improve decision support & research outcomes with our structured adverse effects data.See a data sample](https:\/\/go.drugbank.com\/data_packages\/target\/data_modules\/structured_adverse_effects#adverse_effect_incidences)\n\nToxicity\n\nGenerally well-tolerated when taken orally. The most common side effects, day-time drowsiness, headache and dizziness, appear to occur at the same frequency as with placebo. Other reported side effects include transient depressive symptoms, mild tremor, mild anxiety, abdominal cramps, irritability, reduced alertness, confusion, nausea, vomiting, and hypotension. Safety in Adults: Evidence indicates that it is likely safe to use in oral and parenteral forms for up to two months when used appropriately. Some evidence indicates that it can be safely used orally for up to 9 months in some patients. It is also likely safe to use topically when used appropriately. Safety in Children: Melatonin appeared to be used safely in small numbers of children enrolled in short-term clinical trials. However, concerns regarding safety in children have arisen based on their developmental state. Compared to adults over 20 years of age, people under 20 produce high levels of melatonin. Melatonin levels are inversely related to gonadal development and it is thought that exogenous administration of melatonin may adversely affect gonadal development. Safety during Pregnancy: High doses of melatonin administered orally or parenterally may inhibit ovulation. Not advised for use in individuals who are pregnant or trying to become pregnant. Safety during Lactation: Not recommended as safety has not be established.\n\nOral, rat: LD50 ≥3200 mg\/kg\n\nPathways\n\n| Pathway | Category |\n|---|---|\n| [Tryptophan Metabolism](http:\/\/smpdb.ca\/view\/SMP0000063?highlight[compounds][]=DB01065&highlight[proteins][]=DB01065) | Metabolic |\n\nPharmacogenomic Effects\/ADRs\n\nNot Available\n## Interactions\n[![](https:\/\/go.drugbank.com\/assets\/locked\/AI-Chat-a64a3de153fd7ca4457e73bcec8b2358868da6c4dda160f9b4693e2d85af5a37.png) **The AI Assistant built for biopharma intelligence.** Access detailed, actionable insights to your most complex research questions. Leverage validated reasoning and citable data to power your critical research decisions.Learn More](https:\/\/go.drugbank.com\/product_tour)\n\n[**The AI Assistant built for biopharma intelligence.**Learn More](https:\/\/go.drugbank.com\/product_tour)\n\nDrug Interactions\n\nThis information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.\n\n- [Approved](https:\/\/go.drugbank.com\/drugs\/DB01065#show-approved)\n- [Vet approved](https:\/\/go.drugbank.com\/drugs\/DB01065#show-vet_approved)\n- [Nutraceutical](https:\/\/go.drugbank.com\/drugs\/DB01065#show-nutraceutical)\n- [Illicit](https:\/\/go.drugbank.com\/drugs\/DB01065#show-illicit)\n- [Withdrawn](https:\/\/go.drugbank.com\/drugs\/DB01065#show-withdrawn)\n- [Investigational](https:\/\/go.drugbank.com\/drugs\/DB01065#show-investigational)\n- [Experimental](https:\/\/go.drugbank.com\/drugs\/DB01065#show-experimental)\n- [All Drugs](https:\/\/go.drugbank.com\/drugs\/DB01065#show-all)\n\n| Drug | Interaction |\n|---|---|\n| Integrate drug-drug  interactions in your software |   |\n| [1,2-Benzodiazepine](https:\/\/go.drugbank.com\/drugs\/DB12537) | The risk or severity of CNS depression can be increased when Melatonin is combined with 1,2-Benzodiazepine. |\n| [Abametapir](https:\/\/go.drugbank.com\/drugs\/DB11932) | The serum concentration of Melatonin can be increased when it is combined with Abametapir. |\n| [Abatacept](https:\/\/go.drugbank.com\/drugs\/DB01281) | The metabolism of Melatonin can be increased when combined with Abatacept. |\n| [Abiraterone](https:\/\/go.drugbank.com\/drugs\/DB05812) | The serum concentration of Melatonin can be increased when it is combined with Abiraterone. |\n| [Acenocoumarol](https:\/\/go.drugbank.com\/drugs\/DB01418) | The metabolism of Acenocoumarol can be decreased when combined with Melatonin. |\n\nFood Interactions\n\n- Avoid alcohol. Ingesting alcohol may reduce the effects of melatonin.\n- Take after a meal. Administration of melatonin after eating slows the absorption and reduces the Cmax of melatonin.\n## Products\nInternational\/Other Brands\n\nMela-T (Alacer Corp. (Canada)) \/ Melatol (Elisium (Argentina)) \/ Melatonin (Biomed International Products Corp., Nutravite Pharmaceuticals (2008) Inc., Viva Pharmaceutical Inc., Kripps Pharmacy Ltd., SunOpta Inc.) \/ Nature'S Harmony (SunOpta Inc. (Canada)) \/ Revital Melatonin (Chin Tai Ginseng Co., Ltd (Canada)) \/ Rx Balance (SunOpta Inc. (Canada)) \/ Sleep Right (SunOpta Inc. (Canada)) \/ Vivitas (SunOpta Inc. (Canada))\n\nBrand Name Prescription Products\n\n| Name | Dosage | Strength | Route | Labeller | Marketing Start | Marketing End | Region | Image |\n|---|---|---|---|---|---|---|---|---|\n| Melatol | Liquid | 1 mg\/30mL | Oral | PureTek Corporation | 2024-10-17 | Not applicable | US![US flag](https:\/\/go.drugbank.com\/assets\/countries\/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) |   |\n| Circadin | Tablet, extended release | 2 mg | Oral | Rad Neurim Pharmaceuticals Eec Sarl | 2016-09-08 | Not applicable | EU![EU flag](https:\/\/go.drugbank.com\/assets\/countries\/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) |   |\n| Circadin | Tablet, extended release | 2 mg | Oral | Rad Neurim Pharmaceuticals Eec Sarl | 2016-09-08 | Not applicable | EU![EU flag](https:\/\/go.drugbank.com\/assets\/countries\/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) |   |\n| Circadin | Tablet, extended release | 2 mg | Oral | Rad Neurim Pharmaceuticals Eec Sarl | 2016-09-08 | Not applicable | EU![EU flag](https:\/\/go.drugbank.com\/assets\/countries\/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) |   |\n| Circadin | Tablet, extended release | 2 mg | Oral | Rad Neurim Pharmaceuticals Eec Sarl | 2016-09-08 | Not applicable | EU![EU flag](https:\/\/go.drugbank.com\/assets\/countries\/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) |   |\n\nOver the Counter Products\n\n| Name | Dosage | Strength | Route | Labeller | Marketing Start | Marketing End | Region | Image |\n|---|---|---|---|---|---|---|---|---|\n| Essential Oil | Oil | 2\\.5 mg\/10mL | Cutaneous | Shantou Youjia E-Commerce Co., Ltd. | 2024-02-01 | 2024-12-31 | US![US flag](https:\/\/go.drugbank.com\/assets\/countries\/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) |   |\n\nUnapproved\/Other Products\n\n| Name | Ingredients | Dosage | Route | Labeller | Marketing Start | Marketing End | Region | Image |\n|---|---|---|---|---|---|---|---|---|\n| Medi-doze Rx Sleep Aid | Melatonin (6 mg\/1) + [Valerian](https:\/\/go.drugbank.com\/drugs\/DB13196) (50 mg\/1) + [gamma-Aminobutyric acid](https:\/\/go.drugbank.com\/drugs\/DB02530) (30 mg\/1) | Tablet | Oral | Two Hip Consulting, Llc | 2013-02-20 | 2016-04-11 | US![US flag](https:\/\/go.drugbank.com\/assets\/countries\/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) |   |\n| Melatol | Melatonin (1 mg\/30mL) | Liquid | Oral | PureTek Corporation | 2024-10-17 | Not applicable | US![US flag](https:\/\/go.drugbank.com\/assets\/countries\/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) |   |\n## Categories\nATC Codes\n\n[N05CH01 — Melatonin](https:\/\/go.drugbank.com\/atc\/N05CH01)\n\n- [N05CH — Melatonin receptor agonists](https:\/\/go.drugbank.com\/atc\/N05CH)\n- [N05C — HYPNOTICS AND SEDATIVES](https:\/\/go.drugbank.com\/atc\/N05C)\n- [N05 — PSYCHOLEPTICS](https:\/\/go.drugbank.com\/atc\/N05)\n- [N — NERVOUS SYSTEM](https:\/\/go.drugbank.com\/atc\/N)\n\nDrug Categories\n\n- [Amines](https:\/\/go.drugbank.com\/categories\/DBCAT000266)\n- [Antioxidants](https:\/\/go.drugbank.com\/categories\/DBCAT000368)\n- [Biogenic Amines](https:\/\/go.drugbank.com\/categories\/DBCAT000285)\n- [Biogenic Monoamines](https:\/\/go.drugbank.com\/categories\/DBCAT000468)\n- [Biological Factors](https:\/\/go.drugbank.com\/categories\/DBCAT000036)\n- [Central Nervous System Agents](https:\/\/go.drugbank.com\/categories\/DBCAT000044)\n- [Central Nervous System Depressants](https:\/\/go.drugbank.com\/categories\/DBCAT000399)\n- [Compounds used in a research, industrial, or household setting](https:\/\/go.drugbank.com\/categories\/DBCAT000196)\n- [Cytochrome P-450 CYP1A1 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT006050)\n- [Cytochrome P-450 CYP1A2 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT002609)\n- [Cytochrome P-450 CYP2C19 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT002638)\n- [Cytochrome P-450 CYP2C9 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT002634)\n- [Cytochrome P-450 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT005101)\n- [Heterocyclic Compounds, Fused-Ring](https:\/\/go.drugbank.com\/categories\/DBCAT004973)\n- [Hormones](https:\/\/go.drugbank.com\/categories\/DBCAT000056)\n- [Hormones, Hormone Substitutes, and Hormone Antagonists](https:\/\/go.drugbank.com\/categories\/DBCAT000057)\n- [Hypnotics and Sedatives](https:\/\/go.drugbank.com\/categories\/DBCAT000452)\n- [Indoles](https:\/\/go.drugbank.com\/categories\/DBCAT000528)\n- [Melatonin Receptor Agonists](https:\/\/go.drugbank.com\/categories\/DBCAT002489)\n- [Melatonin, agonists](https:\/\/go.drugbank.com\/categories\/DBCAT001822)\n- [Nervous System](https:\/\/go.drugbank.com\/categories\/DBCAT002148)\n- [OAT3\/SLC22A8 Inhibitors](https:\/\/go.drugbank.com\/categories\/DBCAT003946)\n- [Protective Agents](https:\/\/go.drugbank.com\/categories\/DBCAT000367)\n- [Psycholeptics](https:\/\/go.drugbank.com\/categories\/DBCAT002185)\n- [Tryptamines](https:\/\/go.drugbank.com\/categories\/DBCAT001049)\n\nChemical TaxonomyProvided by [Classyfire](http:\/\/classyfire.wishartlab.com\/)\n\nDescription\n\nThis compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.\n\nKingdom\n\n[Organic compounds](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0000000)\n\nSuper Class\n\n[Organoheterocyclic compounds](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0000002)\n\nClass\n\n[Indoles and derivatives](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0000211)\n\nSub Class\n\n[Indoles](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0002497)\n\nDirect Parent\n\n[3-alkylindoles](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0004196)\n\nAlternative Parents\n\n[Anisoles](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0000138) \/ [Alkyl aryl ethers](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0000128) \/ [Substituted pyrroles](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0002257) \/ [Heteroaromatic compounds](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0004144) \/ [Propargyl-type 1,3-dipolar organic compounds](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0003633) \/ [Carboximidic acids](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0002484) \/ [Azacyclic compounds](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0004139) \/ [Organopnictogen compounds](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0004557) \/ [Organonitrogen compounds](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0000278) \/ [Hydrocarbon derivatives](http:\/\/classyfire.wishartlab.com\/tax_nodes\/C0004150)\n\nSubstituents\n\n3-alkylindole \/ Alkyl aryl ether \/ Anisole \/ Aromatic heteropolycyclic compound \/ Azacycle \/ Benzenoid \/ Carboximidic acid \/ Carboximidic acid derivative \/ Ether \/ Heteroaromatic compound\n\nMolecular Framework\n\nAromatic heteropolycyclic compounds\n\nExternal Descriptors\n\nacetamides, tryptamines ([CHEBI:16796](http:\/\/www.ebi.ac.uk\/chebi\/searchId.do?chebiId=CHEBI:16796))  \/ Indole alkaloids, Melatonin ([C01598](http:\/\/www.genome.jp\/dbget-bin\/www_bget?cpd:C01598))  \/ a small molecule ([N-ACETYL-5-METHOXY-TRYPTAMINE](http:\/\/metacyc.org\/META\/new-image?type=COMPOUND&object=N-ACETYL-5-METHOXY-TRYPTAMINE))\n\nAffected organisms\n\n- Humans and other mammals\n## Chemical Identifiers\nUNII\n\n[JL5DK93RCL](https:\/\/drugs.ncats.io\/drug\/JL5DK93RCL)\n\nCAS number\n\n73-31-4\n\nInChI Key\n\nDRLFMBDRBRZALE-UHFFFAOYSA-N\n\nInChI\n\nInChI=1S\/C13H16N2O2\/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13\/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)\n\nIUPAC Name\n\nN-\\[2-(5-methoxy-1H-indol-3-yl)ethyl\\]acetamide\n\nSMILES\n\nCOC1=CC2=C(NC=C2CCNC(C)=O)C=C1\n## References\nSynthesis Reference\n\nRobert A. S. Welch, Keith Betteridge, \"Method of stimulating cashmere growth on cashmere-producing goats using melatonin.\" U.S. Patent US4855313, issued August, 1986.\n\n[US4855313](https:\/\/www.google.com\/?tbm=pts#q=4855313&tbm=pts)\n\nGeneral References\n\n1. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1674)\\]\n2. Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1675)\\]\n3. Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1676)\\]\n4. Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1677)\\]\n5. Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210\/en.2007-1412. Epub 2008 Jan 10. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1678)\\]\n6. Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1679)\\]\n\nExternal Links\n\nHuman Metabolome Database\n\n[HMDB0001389](http:\/\/www.hmdb.ca\/metabolites\/HMDB0001389)\n\nKEGG Drug\n\n[D08170](http:\/\/www.genome.jp\/dbget-bin\/www_bget?drug:D08170)\n\nKEGG Compound\n\n[C01598](http:\/\/www.genome.jp\/dbget-bin\/www_bget?cpd:C01598)\n\nPubChem Compound\n\n[896](http:\/\/pubchem.ncbi.nlm.nih.gov\/summary\/summary.cgi?cid=896)\n\nPubChem Substance\n\n[46509101](http:\/\/pubchem.ncbi.nlm.nih.gov\/summary\/summary.cgi?sid=46509101)\n\nChemSpider\n\n[872](http:\/\/www.chemspider.com\/Chemical-Structure.872.html)\n\nBindingDB\n\n[53978](http:\/\/www.bindingdb.org\/bind\/chemsearch\/marvin\/MolStructure.jsp?monomerid=53978)\n\nRxNav\n\n[6711](https:\/\/mor.nlm.nih.gov\/RxNav\/search?searchBy=RXCUI&searchTerm=6711)\n\nChEBI\n\n[16796](http:\/\/www.ebi.ac.uk\/chebi\/searchId.do?chebiId=16796)\n\nChEMBL\n\n[CHEMBL45](http:\/\/www.ebi.ac.uk\/chembldb\/index.php\/compound\/inspect\/CHEMBL45)\n\nZINC\n\n[ZINC000000057060](https:\/\/zinc.docking.org\/substances\/ZINC000000057060)\n\nTherapeutic Targets Database\n\n[DAP000429](http:\/\/bidd.nus.edu.sg\/group\/cjttd\/ZFTTDDRUG.asp?ID=DAP000429)\n\nPharmGKB\n\n[PA164752558](http:\/\/www.pharmgkb.org\/drug\/PA164752558)\n\nGuide to Pharmacology\n\n[GtP Drug Page](http:\/\/www.guidetopharmacology.org\/GRAC\/LigandDisplayForward?ligandId=1357)\n\nPDBe Ligand\n\n[ML1](http:\/\/www.ebi.ac.uk\/pdbe-srv\/pdbechem\/chemicalCompound\/show\/ML1)\n\nDrugs.com\n\n[Drugs.com Drug Page](https:\/\/www.drugs.com\/melatonin.html)\n\nPDRhealth\n\n[PDRhealth Drug Page](http:\/\/www.pdrhealth.com\/drug_info\/nmdrugprofiles\/nutsupdrugs\/mel_0286.shtml)\n\nWikipedia\n\n[Melatonin](https:\/\/en.wikipedia.org\/wiki\/Melatonin)\n\nPDB Entries\n\n[2qwx](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=2qwx) \/ [2qx4](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=2qx4) \/ [2qx6](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=2qx6) \/ [4qog](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=4qog) \/ [4qoi](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=4qoi) \/ [5i8f](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=5i8f) \/ [5mxb](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=5mxb) \/ [5mxw](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=5mxw) \/ [6tr5](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=6tr5)\n\nMSDS\n\n[Download](https:\/\/s3-us-west-2.amazonaws.com\/drugbank\/msds\/DB01065.pdf?1265922741) (72 KB)\n## Clinical Trials\nClinical Trials\n\n###### Clinical Trial & Rare Diseases Add-on Data Package\nExplore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more.\n\n[Preview package](https:\/\/go.drugbank.com\/data_packages\/trial)\n\n| Phase | Status | Purpose | Conditions | Count | Start Date | Why Stopped | 100+ additional columns |\n|---|---|---|---|---|---|---|---|\n| Unlock 175K+ rows when you subscribe. [View sample data](https:\/\/go.drugbank.com\/data_packages\/trial\/data_modules\/clinical_trials) |   |   |   |   |   |   |   |\n| Not Available | Active Not Recruiting | Prevention | [Oral Lichen Planus](https:\/\/go.drugbank.com\/conditions\/DBCOND0030626) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0030626&phase=&purpose=prevention&status=active_not_recruiting) | somestatus | stop reason | just information to hide |\n| Not Available | Active Not Recruiting | Treatment | [Psychosis](https:\/\/go.drugbank.com\/conditions\/DBCOND0020753) \/ [Schizophrenia Disorders](https:\/\/go.drugbank.com\/conditions\/DBCOND0031361) \/ [Schizophrenias](https:\/\/go.drugbank.com\/conditions\/DBCOND0033618) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0020753%2CDBCOND0031361%2CDBCOND0033618&phase=&purpose=treatment&status=active_not_recruiting) | somestatus | stop reason | just information to hide |\n| Not Available | Completed | Not Available | [Insomnia](https:\/\/go.drugbank.com\/conditions\/DBCOND0017531) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0017531&phase=&status=completed) | somestatus | stop reason | just information to hide |\n| Not Available | Completed | Not Available | [Postoperative Delirium (POD)](https:\/\/go.drugbank.com\/conditions\/DBCOND0073043) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0073043&phase=&status=completed) | somestatus | stop reason | just information to hide |\n| Not Available | Completed | Not Available | [Postoperative pain](https:\/\/go.drugbank.com\/conditions\/DBCOND0022333) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0022333&phase=&status=completed) | somestatus | stop reason | just information to hide |\n\nUnlock 75,000+ rows when you subscribe\n\nExplore data packages curated & structured to speed up your pharmaceutical research\n\n[View Sample Data](https:\/\/go.drugbank.com\/data_packages\/trial\/data_modules\/clinical_trials)\n## Pharmacoeconomics\nManufacturers\n\nNot Available\n\nPackagers\n\n- Mason Distributors\n- Medisca Inc.\n- National Vitamin Company\n- Physiologics\n- Rugby Laboratories\n\nDosage Forms\n\n| Form | Route | Strength |\n|---|---|---|\n| Capsule | Not applicable | 10 mg\/1 |\n| Capsule | Oral | 5\\.00000 mg |\n| Capsule, coated | Oral | 3 mg |\n| Capsule, liquid filled | Oral | 3 mg |\n| Chewable gel | Oral | 2\\.5 mg\/1 |\n| Liquid | Oral | 1 mg\/4mL |\n| Liquid | Oral | 1 mg\/30mL |\n| Oil | Cutaneous | 2\\.5 mg\/10mL |\n| Solution | Oral | 1 mg\/ml |\n| Solution \/ drops | Oral | 1 mg\/1mL |\n| Tablet | Not applicable | 10 mg\/1 |\n| Tablet | Oral |   |\n| Tablet | Oral | 0\\.5 mg |\n| Tablet | Oral | 1 mg |\n| Tablet | Oral | 1\\.500 mg |\n| Tablet | Oral | 2 mg |\n| Tablet | Oral | 3 mg\/1 |\n| Tablet | Oral | 3 MG |\n| Tablet | Oral | 4 mg |\n| Tablet | Oral | 5 MG |\n| Tablet | Oral | 5 mg\/1 |\n| Tablet | Sublingual | 3\\.000 mg |\n| Tablet, chewable | Oral | 2\\.5 mg\/1 |\n| Tablet, extended release | Oral | 1 MG |\n| Tablet, extended release | Oral | 2 mg |\n| Tablet, extended release | Oral | 5 MG |\n| Tablet, film coated | Oral | 3 mg |\n| Tablet, film coated | Oral | 5 mg |\n\nPrices\n\n| Unit description | Cost | Unit |\n|---|---|---|\n| Melatonin powder | 45\\.6USD | g |\n| Melatonin 3 mg tablet | 0\\.22USD | tablet |\n| Melatonin 5 mg tablet | 0\\.12USD | tablet |\n| Melatonin 5 mg tablet sl | 0\\.1USD | tablet |\n| Melatonin sublingual tablet | 0\\.09USD | tablet |\n| Melatonin 1 mg tablet | 0\\.03USD | tablet |\n\nDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.\n\nPatents\n\nNot Available\n## Properties\nState\n\nSolid\n\nExperimental Properties\n\n| Property | Value | Source |\n|---|---|---|\n| melting point (°C) | 117 °C | PhysProp |\n| logP | 1\\.6 | Not Available |\n\nPredicted Properties\n\n| Property | Value | Source |\n|---|---|---|\n| Water Solubility | 0\\.143 mg\/mL | [ALOGPS](http:\/\/www.vcclab.org\/lab\/alogps\/) |\n| logP | 1\\.42 | [ALOGPS](http:\/\/www.vcclab.org\/lab\/alogps\/) |\n| logP | 1\\.15 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| logS | \\-3.2 | [ALOGPS](http:\/\/www.vcclab.org\/lab\/alogps\/) |\n| pKa (Strongest Acidic) | 15\\.8 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| pKa (Strongest Basic) | \\-1.6 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Physiological Charge | 0 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Hydrogen Acceptor Count | 2 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Hydrogen Donor Count | 2 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Polar Surface Area | 54\\.12 Å2 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Rotatable Bond Count | 4 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Refractivity | 66\\.28 m3·mol\\-1 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Polarizability | 25\\.65 Å3 | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| Number of Rings | 2 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Bioavailability | 1 | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| Rule of Five | Yes | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| Ghose Filter | Yes | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| Veber's Rule | No | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| MDDR-like Rule | No | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n\nPredicted ADMET Features\n\n| Property | Value | Probability |\n|---|---|---|\n| Human Intestinal Absorption | \\+ | 1\\.0 |\n| Blood Brain Barrier | \\+ | 0\\.9928 |\n| Caco-2 permeable | \\- | 0\\.5536 |\n| P-glycoprotein substrate | Substrate | 0\\.6188 |\n| P-glycoprotein inhibitor I | Non-inhibitor | 0\\.9569 |\n| P-glycoprotein inhibitor II | Non-inhibitor | 0\\.6838 |\n| Renal organic cation transporter | Non-inhibitor | 0\\.542 |\n| CYP450 2C9 substrate | Non-substrate | 0\\.8231 |\n| CYP450 2D6 substrate | Substrate | 0\\.5062 |\n| CYP450 3A4 substrate | Substrate | 0\\.6505 |\n| CYP450 1A2 substrate | Inhibitor | 0\\.9304 |\n| CYP450 2C9 inhibitor | Non-inhibitor | 0\\.9071 |\n| CYP450 2D6 inhibitor | Inhibitor | 0\\.8084 |\n| CYP450 2C19 inhibitor | Non-inhibitor | 0\\.9025 |\n| CYP450 3A4 inhibitor | Non-inhibitor | 0\\.7194 |\n| CYP450 inhibitory promiscuity | High CYP Inhibitory Promiscuity | 0\\.6803 |\n| Ames test | Non AMES toxic | 0\\.9132 |\n| Carcinogenicity | Non-carcinogens | 0\\.9498 |\n| Biodegradation | Not ready biodegradable | 0\\.8764 |\n| Rat acute toxicity | 1\\.8922 LD50, mol\/kg | Not applicable |\n| hERG inhibition (predictor I) | Weak inhibitor | 0\\.9631 |\n| hERG inhibition (predictor II) | Non-inhibitor | 0\\.5124 |\n\nADMET data is predicted using [admetSAR](http:\/\/lmmd.ecust.edu.cn:8000\/), a free tool for evaluating chemical ADMET properties. ([23092397](http:\/\/www.ncbi.nlm.nih.gov\/pubmed\/23092397))\n## Spectra\nMass Spec (NIST)\n\n[Download](https:\/\/s3-us-west-2.amazonaws.com\/drugbank\/mass_specs\/DB01065.gif?1265922774) (8.2 KB)\n\nSpectra\n\n| Spectrum | Spectrum Type | [Splash Key](http:\/\/splash.fiehnlab.ucdavis.edu\/) |\n|---|---|---|\n| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https:\/\/go.drugbank.com\/spectra\/c_ms\/735) | GC-MS | [splash10-001i-0490000000-aa93967315af900a76ce](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0490000000-aa93967315af900a76ce) |\n| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https:\/\/go.drugbank.com\/spectra\/c_ms\/736) | GC-MS | [splash10-03k9-0900000000-a15ee6def3f8d75b1231](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-03k9-0900000000-a15ee6def3f8d75b1231) |\n| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https:\/\/go.drugbank.com\/spectra\/c_ms\/737) | GC-MS | [splash10-001j-0490000000-94ef1be9ab930060778a](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001j-0490000000-94ef1be9ab930060778a) |\n| [GC-MS Spectrum - GC-MS (2 TMS)](https:\/\/go.drugbank.com\/spectra\/c_ms\/1945) | GC-MS | [splash10-001i-1490000000-03e24298c7bd1ed4066a](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-1490000000-03e24298c7bd1ed4066a) |\n| [Predicted GC-MS Spectrum - GC-MS](https:\/\/go.drugbank.com\/spectra\/c_ms\/7100) | Predicted GC-MS | [splash10-0076-4920000000-a8d9d614e9f8769a1359](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0076-4920000000-a8d9d614e9f8769a1359) |\n| [GC-MS Spectrum - GC-MS](https:\/\/go.drugbank.com\/spectra\/c_ms\/31319) | GC-MS | [splash10-001i-1490000000-03e24298c7bd1ed4066a](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-1490000000-03e24298c7bd1ed4066a) |\n| [GC-MS Spectrum - GC-EI-TOF](https:\/\/go.drugbank.com\/spectra\/c_ms\/32276) | GC-MS | [splash10-001j-0590000000-63d5e32dd5f7877a4402](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001j-0590000000-63d5e32dd5f7877a4402) |\n| [GC-MS Spectrum - GC-EI-TOF](https:\/\/go.drugbank.com\/spectra\/c_ms\/32277) | GC-MS | [splash10-001i-0590000000-52b3a733f8b49582d3fb](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0590000000-52b3a733f8b49582d3fb) |\n| [GC-MS Spectrum - GC-EI-TOF](https:\/\/go.drugbank.com\/spectra\/c_ms\/32278) | GC-MS | [splash10-0229-1900000000-d81c6f617bc486066136](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0229-1900000000-d81c6f617bc486066136) |\n| [Mass Spectrum (Electron Ionization)](https:\/\/go.drugbank.com\/spectra\/ei_ms\/505) | MS | [splash10-03k9-1900000000-45ee4fdc7acdb33dad3b](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-03k9-1900000000-45ee4fdc7acdb33dad3b) |\n| [MS\/MS Spectrum - Quattro\\_QQQ 10V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/1547) | LC-MS\/MS | [splash10-00di-0920000000-f90ec9b77e1a245e35a8](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0920000000-f90ec9b77e1a245e35a8) |\n| [MS\/MS Spectrum - Quattro\\_QQQ 25V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/1548) | LC-MS\/MS | [splash10-05fr-0900000000-49e4482c65e82ac64b66](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-05fr-0900000000-49e4482c65e82ac64b66) |\n| [MS\/MS Spectrum - Quattro\\_QQQ 40V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/1549) | LC-MS\/MS | [splash10-003r-0900000000-8a4ae0fd610cca992d74](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-003r-0900000000-8a4ae0fd610cca992d74) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5222) | LC-MS\/MS | [splash10-0159-0090000000-939a1caf5760c0ba189c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0159-0090000000-939a1caf5760c0ba189c) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5223) | LC-MS\/MS | [splash10-0006-0930000000-9e6fcea2c634ac9d85a0](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0930000000-9e6fcea2c634ac9d85a0) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5224) | LC-MS\/MS | [splash10-0006-0900000000-ddd29e731a7de56c1808](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-ddd29e731a7de56c1808) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5225) | LC-MS\/MS | [splash10-0006-0900000000-34b4fb52810a15ea5bd6](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-34b4fb52810a15ea5bd6) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5226) | LC-MS\/MS | [splash10-001i-0090000000-5ca2df63ec2baefdae8c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0090000000-5ca2df63ec2baefdae8c) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5227) | LC-MS\/MS | [splash10-001i-0190000000-5bae6e63e9b40e60e0a4](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0190000000-5bae6e63e9b40e60e0a4) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5228) | LC-MS\/MS | [splash10-00di-0900000000-529bf6d5c2091993f865](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-529bf6d5c2091993f865) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5229) | LC-MS\/MS | [splash10-00di-0900000000-158a60fe696120b23b41](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-158a60fe696120b23b41) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5230) | LC-MS\/MS | [splash10-0a5c-0900000000-5e86b2de659ce47762c0](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0a5c-0900000000-5e86b2de659ce47762c0) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5231) | LC-MS\/MS | [splash10-001i-0900000000-881c0d57239d56c46f2d](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0900000000-881c0d57239d56c46f2d) |\n| [LC-MS\/MS Spectrum - LC-ESI-IT (LC\/MSD Trap XCT, Agilent Technologies) , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5232) | LC-MS\/MS | [splash10-00di-0910000000-f256f78adbcbeb2464de](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0910000000-f256f78adbcbeb2464de) |\n| [LC-MS\/MS Spectrum - LC-ESI-IT (LC\/MSD Trap XCT, Agilent Technologies) , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5233) | LC-MS\/MS | [splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23) |\n| [MS\/MS Spectrum - DI-ESI-qTof , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/374102) | LC-MS\/MS | [splash10-05fr-0900000000-7acf9405f4beeb34566c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-05fr-0900000000-7acf9405f4beeb34566c) |\n| [MS\/MS Spectrum - DI-ESI-qTof , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/374103) | LC-MS\/MS | [splash10-00di-0900000000-13245183cd8c8cd511c3](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-13245183cd8c8cd511c3) |\n| [LC-MS\/MS Spectrum - LC-ESI-qTof , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/374702) | LC-MS\/MS | [splash10-05ai-2900000000-07b3d32f002dba733c10](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-05ai-2900000000-07b3d32f002dba733c10) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438131) | LC-MS\/MS | [splash10-0159-0090000000-939a1caf5760c0ba189c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0159-0090000000-939a1caf5760c0ba189c) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438132) | LC-MS\/MS | [splash10-0006-0930000000-9e6fcea2c634ac9d85a0](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0930000000-9e6fcea2c634ac9d85a0) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438133) | LC-MS\/MS | [splash10-0006-0900000000-ddd29e731a7de56c1808](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-ddd29e731a7de56c1808) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438134) | LC-MS\/MS | [splash10-0006-0900000000-34b4fb52810a15ea5bd6](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-34b4fb52810a15ea5bd6) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438135) | LC-MS\/MS | [splash10-001i-0090000000-5ca2df63ec2baefdae8c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0090000000-5ca2df63ec2baefdae8c) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/439444) | LC-MS\/MS | [splash10-00lr-0090000000-3c42f6997539afb44682](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00lr-0090000000-3c42f6997539afb44682) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/439448) | LC-MS\/MS | [splash10-014m-0960000000-7991e64dacb3c7f5cf32](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-014m-0960000000-7991e64dacb3c7f5cf32) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/439451) | LC-MS\/MS | [splash10-0006-0900000000-882be43bc196e928a3cf](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-882be43bc196e928a3cf) |\n| [MS\/MS Spectrum - , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/440134) | LC-MS\/MS | [splash10-014i-0190000000-ddda9232f0e8e1b402f7](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-014i-0190000000-ddda9232f0e8e1b402f7) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446535) | LC-MS\/MS | [splash10-001i-0190000000-5bae6e63e9b40e60e0a4](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0190000000-5bae6e63e9b40e60e0a4) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446536) | LC-MS\/MS | [splash10-00di-0900000000-529bf6d5c2091993f865](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-529bf6d5c2091993f865) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446537) | LC-MS\/MS | [splash10-00di-0900000000-158a60fe696120b23b41](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-158a60fe696120b23b41) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446538) | LC-MS\/MS | [splash10-0a5c-0900000000-5e86b2de659ce47762c0](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0a5c-0900000000-5e86b2de659ce47762c0) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446539) | LC-MS\/MS | [splash10-001i-0900000000-881c0d57239d56c46f2d](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0900000000-881c0d57239d56c46f2d) |\n| [LC-MS\/MS Spectrum - LC-ESI-IT , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/447247) | LC-MS\/MS | [splash10-00di-0910000000-d659c749adcab685e8bb](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0910000000-d659c749adcab685e8bb) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/449479) | LC-MS\/MS | [splash10-00di-0900000000-6817d8039761a9058337](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-6817d8039761a9058337) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/449485) | LC-MS\/MS | [splash10-00di-0900000000-349d5a97e2406d0db910](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-349d5a97e2406d0db910) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/449491) | LC-MS\/MS | [splash10-001i-0900000000-9e30dcf47c9eca14650e](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0900000000-9e30dcf47c9eca14650e) |\n| [MS\/MS Spectrum - , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/450591) | LC-MS\/MS | [splash10-00di-1900000000-73dc69b26b1fba60f253](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-1900000000-73dc69b26b1fba60f253) |\n| [MS\/MS Spectrum - , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/451347) | LC-MS\/MS | [splash10-05ai-2900000000-07b3d32f002dba733c10](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-05ai-2900000000-07b3d32f002dba733c10) |\n| [MS\/MS Spectrum - , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/451967) | LC-MS\/MS | [splash10-00di-0900000000-2e847095e37f4ffe7c8b](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-2e847095e37f4ffe7c8b) |\n| [Predicted MS\/MS Spectrum - 10V, Positive (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677259) | Predicted LC-MS\/MS | [splash10-0089-0960000000-9acd48062f28a100f9da](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0089-0960000000-9acd48062f28a100f9da) |\n| [Predicted MS\/MS Spectrum - 10V, Negative (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677289) | Predicted LC-MS\/MS | [splash10-03di-5790000000-571ee430d2b0391822e3](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-03di-5790000000-571ee430d2b0391822e3) |\n| [Predicted MS\/MS Spectrum - 20V, Positive (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677314) | Predicted LC-MS\/MS | [splash10-00di-0900000000-1a38178248f05cf91e65](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-1a38178248f05cf91e65) |\n| [Predicted MS\/MS Spectrum - 20V, Negative (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677334) | Predicted LC-MS\/MS | [splash10-052f-9000000000-9950a9dee5e36e935714](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-052f-9000000000-9950a9dee5e36e935714) |\n| [Predicted MS\/MS Spectrum - 40V, Positive (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677344) | Predicted LC-MS\/MS | [splash10-006x-0900000000-5d47768c1bb474f51f38](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-006x-0900000000-5d47768c1bb474f51f38) |\n| [Predicted MS\/MS Spectrum - 40V, Negative (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677384) | Predicted LC-MS\/MS | [splash10-0006-4900000000-9374ee5bf5eb87317f56](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-4900000000-9374ee5bf5eb87317f56) |\n| [1H NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/1693) | 1D NMR | Not Applicable |\n| [1H NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/2600) | 1D NMR | Not Applicable |\n| [13C NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/3303) | 1D NMR | Not Applicable |\n| [Predicted 1H NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/42674) | 1D NMR | Not Applicable |\n| [Predicted 13C NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/42679) | 1D NMR | Not Applicable |\n| [\\[1H,13C\\] 2D NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_two_d\/1634) | 2D NMR | Not Applicable |\n\nChromatographic Properties\n\n###### Collision Cross Sections (CCS)\n| Adduct | CCS Value (Å2) | Source type | Source |\n|---|---|---|---|\n| \\[M-H\\]- | 159\\.6858961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M-H\\]- | 152\\.8346632 | predicted | DarkChem Standard v0.1.0 |\n| \\[M-H\\]- | 152\\.9149983 | predicted | DarkChem Lite v0.1.0 |\n| \\[M-H\\]- | 165\\.2831961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M-H\\]- | 159\\.7026961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M-H\\]- | 150\\.02837 | predicted | DeepCCS 1.0 (2019) |\n| \\[M+H\\]+ | 159\\.1911961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+H\\]+ | 157\\.166152 | predicted | DarkChem Standard v0.1.0 |\n| \\[M+H\\]+ | 157\\.1763686 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+H\\]+ | 166\\.2821961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+H\\]+ | 159\\.7927961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+H\\]+ | 152\\.38637 | predicted | DeepCCS 1.0 (2019) |\n| \\[M+Na\\]+ | 158\\.6747961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 165\\.6858961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 167\\.0242025 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 165\\.6891961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 159\\.5635961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 158\\.4795 | predicted | DeepCCS 1.0 (2019) |\n\n### Targets\n[![](https:\/\/go.drugbank.com\/assets\/locked\/DrugTargets2-1d1d534575da54e734c316d80c9fb35f8210c070dca913c026f8e58660e3e71a.png) **Build, predict & validate machine-learning models** Use our structured and evidence-based datasets to **unlock newinsights and accelerate drug research.**Learn more](https:\/\/bit.ly\/3iYePSn)\n\n[Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.Learn more](https:\/\/bit.ly\/3zOIrse)\n\n##### Binding Properties\n×\n\n| Property | Measurement | pH | Temperature (°C) | References |\n|---|---|---|---|---|\n| EC 50 (nM) | 0\\.02 | N\/A | N\/A | Not Available |\n| IC 50 (nM) | 0\\.11 | N\/A | N\/A | Not Available |\n| Ki (nM) | 0\\.08 | N\/A | N\/A | Not Available |\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0000515)\n\nBinding Properties\n\n**1\\. [Melatonin receptor type 1A](https:\/\/go.drugbank.com\/bio_entities\/BE0000515)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nYes\n\nActions\n\nAgonist\n\nGeneral Function\n\nHigh affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity. Possibly involved in sleep induction, by melatonin activation of the potassium channel KCNMA1\/BK and the dissociation of G-beta and G-gamma subunits, thereby decreasing synaptic transmission (By similarity)\n\nSpecific Function\n\nG protein-coupled receptor activity\n\nGene Name\n\nMTNR1A\n\nUniprot ID\n\n[P48039](http:\/\/www.uniprot.org\/uniprot\/P48039)\n\nUniprot Name\n\nMelatonin receptor type 1A\n\nMolecular Weight\n\n39374\\.315 Da\n##### References\n1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15272)\\]\n2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. \\[[Article](https:\/\/go.drugbank.com\/articles\/A9)\\]\n3. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1674)\\]\n4. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15273)\\]\n5. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007\/s12325-010-0065-y. Epub 2010 Sep 6. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15274)\\]\n6. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016\/j.bmc.2010.06.100. Epub 2010 Jul 3. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15275)\\]\n7. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210\/en.2009-0710. Epub 2009 Dec 4. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15276)\\]\n8. Witt-Enderby PA, Chu GH, Gillen ML, Li PK: Development of a high-affinity ligand that binds irreversibly to Mel1b melatonin receptors. J Med Chem. 1997 Dec 19;40(26):4195-8. \\[[Article](https:\/\/go.drugbank.com\/articles\/A29415)\\]\n9. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n10. Hoashi Y, Takai T, Kosugi Y, Nakashima M, Nakayama M, Hirai K, Uchikawa O, Koike T: Discovery of a Potent and Orally Bioavailable Melatonin Receptor Agonist. J Med Chem. 2021 Mar 25;64(6):3059-3074. doi: 10.1021\/acs.jmedchem.0c01836. Epub 2021 Mar 7. \\[[Article](https:\/\/go.drugbank.com\/articles\/A268970)\\]\n11. Gunia-Krzyzak A, Zelaszczyk D, Rapacz A, Zeslawska E, Waszkielewicz AM, Panczyk K, Sloczynska K, Pekala E, Nitek W, Filipek B, Marona H: Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH(3) or 2-CH(3). Bioorg Med Chem. 2017 Jan 15;25(2):471-482. doi: 10.1016\/j.bmc.2016.11.014. Epub 2016 Nov 11. \\[[Article](https:\/\/go.drugbank.com\/articles\/A273460)\\]\n\n##### Binding Properties\n×\n\n| Property | Measurement | pH | Temperature (°C) | References |\n|---|---|---|---|---|\n| EC 50 (nM) | 0\\.07 | N\/A | N\/A | Not Available |\n| IC 50 (nM) | 0\\.3 | N\/A | N\/A | Not Available |\n| Ki (nM) | 0\\.12 | N\/A | N\/A | Not Available |\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0000327)\n\nBinding Properties\n\n**2\\. [Melatonin receptor type 1B](https:\/\/go.drugbank.com\/bio_entities\/BE0000327)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nYes\n\nActions\n\nAgonist\n\nGeneral Function\n\nHigh affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity\n\nSpecific Function\n\nG protein-coupled receptor activity\n\nGene Name\n\nMTNR1B\n\nUniprot ID\n\n[P49286](http:\/\/www.uniprot.org\/uniprot\/P49286)\n\nUniprot Name\n\nMelatonin receptor type 1B\n\nMolecular Weight\n\n40187\\.895 Da\n##### References\n1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15272)\\]\n2. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1674)\\]\n3. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15273)\\]\n4. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007\/s12325-010-0065-y. Epub 2010 Sep 6. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15274)\\]\n5. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016\/j.bmc.2010.06.100. Epub 2010 Jul 3. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15275)\\]\n6. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210\/en.2009-0710. Epub 2009 Dec 4. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15276)\\]\n7. Mattson RJ, Catt JD, Keavy D, Sloan CP, Epperson J, Gao Q, Hodges DB, Iben L, Mahle CD, Ryan E, Yocca FD: Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett. 2003 Mar 24;13(6):1199-202. \\[[Article](https:\/\/go.drugbank.com\/articles\/A29424)\\]\n8. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n9. Ferreira MA Jr, Azevedo H, Mascarello A, Segretti ND, Russo E, Russo V, Guimaraes CRW: Discovery of ACH-000143: A Novel Potent and Peripherally Preferred Melatonin Receptor Agonist that Reduces Liver Triglycerides and Steatosis in Diet-Induced Obese Rats. J Med Chem. 2021 Feb 25;64(4):1904-1929. doi: 10.1021\/acs.jmedchem.0c00627. Epub 2021 Feb 8. \\[[Article](https:\/\/go.drugbank.com\/articles\/A268965)\\]\n\n##### Binding Properties\n×\n\n| Property | Measurement | pH | Temperature (°C) | References |\n|---|---|---|---|---|\n| IC 50 (nM) | 65 | N\/A | N\/A | Not Available |\n| Ki (nM) | 28 | N\/A | N\/A | Not Available |\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0000220)\n\nBinding Properties\n\n**3\\. [Ribosyldihydronicotinamide dehydrogenase \\[quinone\\]](https:\/\/go.drugbank.com\/bio_entities\/BE0000220)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nYes\n\nActions\n\nInhibitor\n\nGeneral Function\n\nThe enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis\n\nSpecific Function\n\nchloride ion binding\n\nGene Name\n\nNQO2\n\nUniprot ID\n\n[P16083](http:\/\/www.uniprot.org\/uniprot\/P16083)\n\nUniprot Name\n\nRibosyldihydronicotinamide dehydrogenase \\[quinone\\]\n\nMolecular Weight\n\n25918\\.4 Da\n##### References\n1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15272)\\]\n2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093\/nar\/gkad751. \\[[Article](https:\/\/go.drugbank.com\/articles\/A264250)\\]\n3. Fukatsu K, Uchikawa O, Kawada M, Yamano T, Yamashita M, Kato K, Hirai K, Hinuma S, Miyamoto M, Ohkawa S: Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists. J Med Chem. 2002 Sep 12;45(19):4212-21. doi: 10.1021\/jm020114g. \\[[Article](https:\/\/go.drugbank.com\/articles\/A268565)\\]\n4. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n5. Du H, Wang J, Zhang X, Hu Z: A novel quantitative structure-activity relationship method to predict the affinities of MT3 melatonin binding site. Eur J Med Chem. 2008 Dec;43(12):2861-9. doi: 10.1016\/j.ejmech.2008.02.012. Epub 2008 Feb 29. \\[[Article](https:\/\/go.drugbank.com\/articles\/A29410)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0000123)\n\n**4\\. [Estrogen receptor](https:\/\/go.drugbank.com\/bio_entities\/BE0000123)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nAntagonist\n\nGeneral Function\n\nNuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1\/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA\/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA\/p65 and NFKB1\/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol\/E2) (By similarity)\n\nSpecific Function\n\n14-3-3 protein binding\n\nGene Name\n\nESR1\n\nUniprot ID\n\n[P03372](http:\/\/www.uniprot.org\/uniprot\/P03372)\n\nUniprot Name\n\nEstrogen receptor\n\nMolecular Weight\n\n66215\\.45 Da\n##### References\n1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15278)\\]\n2. Yoo YM, Jeung EB: Melatonin-induced estrogen receptor alpha-mediated calbindin-D9k expression plays a role in H2O2-mediated cell death in rat pituitary GH3 cells. J Pineal Res. 2009 Nov;47(4):301-7. doi: 10.1111\/j.1600-079X.2009.00714.x. Epub 2009 Oct 1. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15281)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0003554)\n\n**5\\. [Nuclear receptor ROR-beta](https:\/\/go.drugbank.com\/bio_entities\/BE0003554)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nAgonist\n\nGeneral Function\n\nNuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity)\n\nSpecific Function\n\nDNA-binding transcription activator activity, RNA polymerase II-specific\n\nGene Name\n\nRORB\n\nUniprot ID\n\n[Q92753](http:\/\/www.uniprot.org\/uniprot\/Q92753)\n\nUniprot Name\n\nNuclear receptor ROR-beta\n\nMolecular Weight\n\n53219\\.385 Da\n##### References\n1. Becker-Andre M, Wiesenberg I, Schaeren-Wiemers N, Andre E, Missbach M, Saurat JH, Carlberg C: Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily. J Biol Chem. 1994 Nov 18;269(46):28531-4. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15277)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0001075)\n\n**6\\. [Myeloperoxidase](https:\/\/go.drugbank.com\/bio_entities\/BE0001075)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nInhibitor\n\nGeneral Function\n\nPart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971)\n\nSpecific Function\n\nchromatin binding\n\nGene Name\n\nMPO\n\nUniprot ID\n\n[P05164](http:\/\/www.uniprot.org\/uniprot\/P05164)\n\nUniprot Name\n\nMyeloperoxidase\n\nMolecular Weight\n\n83867\\.71 Da\n##### References\n1. Galijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021\/bi702016q. Epub 2008 Feb 1. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15280)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0003555)\n\n**7\\. [Eosinophil peroxidase](https:\/\/go.drugbank.com\/bio_entities\/BE0003555)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nInhibitor\n\nGeneral Function\n\nMediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis\n\nSpecific Function\n\nheme binding\n\nGene Name\n\nEPX\n\nUniprot ID\n\n[P11678](http:\/\/www.uniprot.org\/uniprot\/P11678)\n\nUniprot Name\n\nEosinophil peroxidase\n\nMolecular Weight\n\n81039\\.5 Da\n##### References\n1. Lu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038\/bjp.2008.173. Epub 2008 Jun 2. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15282)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0002109)\n\n**8\\. [Calreticulin](https:\/\/go.drugbank.com\/bio_entities\/BE0002109)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nModulator\n\nGeneral Function\n\nCalcium-binding chaperone that promotes folding, oligomeric assembly and quality control in the endoplasmic reticulum (ER) via the calreticulin\/calnexin cycle. This lectin interacts transiently with almost all of the monoglucosylated glycoproteins that are synthesized in the ER (PubMed:7876246). Interacts with the DNA-binding domain of NR3C1 and mediates its nuclear export (PubMed:11149926). Involved in maternal gene expression regulation. May participate in oocyte maturation via the regulation of calcium homeostasis (By similarity). Present in the cortical granules of non-activated oocytes, is exocytosed during the cortical reaction in response to oocyte activation and might participate in the block to polyspermy (By similarity)\n\nSpecific Function\n\ncalcium ion binding\n\nGene Name\n\nCALR\n\nUniprot ID\n\n[P27797](http:\/\/www.uniprot.org\/uniprot\/P27797)\n\nUniprot Name\n\nCalreticulin\n\nMolecular Weight\n\n48141\\.2 Da\n##### References\n1. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15273)\\]\n2. Macias M, Escames G, Leon J, Coto A, Sbihi Y, Osuna A, Acuna-Castroviejo D: Calreticulin-melatonin. An unexpected relationship. Eur J Biochem. 2003 Mar;270(5):832-40. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15279)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0027477)\n\n**9\\. [Calmodulin (Protein Group)](https:\/\/go.drugbank.com\/bio_entities\/BE0027477)**\n\nKind\n\nProtein group\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nAntagonist\n\nGeneral Function\n\nCalmodulin acts as part of a calcium signal transduction pathway by mediating the control of a large number of enzymes, ion channels, aquaporins and other proteins through calcium-binding (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Calcium-binding is required for the activation of calmodulin (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Among the enzymes to be stimulated by the calmodulin-calcium complex are a number of protein kinases, such as myosin light-chain kinases and calmodulin-dependent protein kinase type II (CaMK2), and phosphatases (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis (PubMed:16760425). Is a regulator of voltage-dependent L-type calcium channels (PubMed:31454269). Mediates calcium-dependent inactivation of CACNA1C (PubMed:26969752). Positively regulates calcium-activated potassium channel activity of KCNN2 (PubMed:27165696). Forms a potassium channel complex with KCNQ1 and regulates electrophysiological activity of the channel via calcium-binding (PubMed:25441029). Acts as a sensor to modulate the endoplasmic reticulum contacts with other organelles mediated by VMP1:ATP2A2 (PubMed:28890335)\n\nSpecific Function\n\nadenylate cyclase activator activity\n***\n##### Components:\n| Name | UniProt ID |\n|---|---|\n| [Calmodulin-1](https:\/\/go.drugbank.com\/polypeptides\/P0DP23) | [P0DP23](http:\/\/www.uniprot.org\/uniprot\/P0DP23) |\n| [Calmodulin-2](https:\/\/go.drugbank.com\/polypeptides\/P0DP24) | [P0DP24](http:\/\/www.uniprot.org\/uniprot\/P0DP24) |\n| [Calmodulin-3](https:\/\/go.drugbank.com\/polypeptides\/P0DP25) | [P0DP25](http:\/\/www.uniprot.org\/uniprot\/P0DP25) |\n##### References\n1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15278)\\]\n2. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15272)\\]\n\n### Enzymes\n##### Binding Properties\n×\n\n| Property | Measurement | pH | Temperature (°C) | References |\n|---|---|---|---|---|\n| Ki (nM) | 59000 | N\/A | N\/A | Not Available |\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0003543)\n\nBinding Properties\n\n**1\\. [Cytochrome P450 1A1](https:\/\/go.drugbank.com\/bio_entities\/BE0003543)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nInhibitor\n\nGeneral Function\n\nA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195)\n\nSpecific Function\n\narachidonate monooxygenase activity\n\nGene Name\n\nCYP1A1\n\nUniprot ID\n\n[P04798](http:\/\/www.uniprot.org\/uniprot\/P04798)\n\nUniprot Name\n\nCytochrome P450 1A1\n\nMolecular Weight\n\n58164\\.815 Da\n##### References\n1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15283)\\]\n2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15284)\\]\n3. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. \\[[Article](https:\/\/go.drugbank.com\/articles\/A266010)\\]\n4. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n\n##### Binding Properties\n×\n\n| Property | Measurement | pH | Temperature (°C) | References |\n|---|---|---|---|---|\n| Ki (nM) | 12000 | N\/A | N\/A | Not Available |\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0002433)\n\nBinding Properties\n\n**2\\. [Cytochrome P450 1A2](https:\/\/go.drugbank.com\/bio_entities\/BE0002433)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral Function\n\nA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)\n\nSpecific Function\n\ncaffeine oxidase activity\n\nGene Name\n\nCYP1A2\n\nUniprot ID\n\n[P05177](http:\/\/www.uniprot.org\/uniprot\/P05177)\n\nUniprot Name\n\nCytochrome P450 1A2\n\nMolecular Weight\n\n58406\\.915 Da\n##### References\n1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15283)\\]\n2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15284)\\]\n3. Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15285)\\]\n4. Hartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. \\[[Article](https:\/\/go.drugbank.com\/articles\/A38895)\\]\n5. Hartter S, Wang X, Weigmann H, Friedberg T, Arand M, Oesch F, Hiemke C: Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin. J Clin Psychopharmacol. 2001 Apr;21(2):167-74. \\[[Article](https:\/\/go.drugbank.com\/articles\/A38975)\\]\n6. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. \\[[Article](https:\/\/go.drugbank.com\/articles\/A266010)\\]\n7. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n\n##### Binding Properties\n×\n\n| Property | Measurement | pH | Temperature (°C) | References |\n|---|---|---|---|---|\n| Ki (nM) | 14000 | N\/A | N\/A | Not Available |\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0001111)\n\nBinding Properties\n\n**3\\. [Cytochrome P450 1B1](https:\/\/go.drugbank.com\/bio_entities\/BE0001111)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nInhibitor\n\nGeneral Function\n\nA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity)\n\nSpecific Function\n\nestrogen 16-alpha-hydroxylase activity\n\nGene Name\n\nCYP1B1\n\nUniprot ID\n\n[Q16678](http:\/\/www.uniprot.org\/uniprot\/Q16678)\n\nUniprot Name\n\nCytochrome P450 1B1\n\nMolecular Weight\n\n60845\\.33 Da\n##### References\n1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15283)\\]\n2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15284)\\]\n3. Yu Z, Tian X, Peng Y, Sun Z, Wang C, Tang N, Li B, Jian Y, Wang W, Huo X, Ma X: Mitochondrial cytochrome P450 (CYP) 1B1 is responsible for melatonin-induced apoptosis in neural cancer cells. J Pineal Res. 2018 Aug;65(1):e12478. doi: 10.1111\/jpi.12478. Epub 2018 Mar 25. \\[[Article](https:\/\/go.drugbank.com\/articles\/A184151)\\]\n4. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. \\[[Article](https:\/\/go.drugbank.com\/articles\/A266010)\\]\n5. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0003536)\n\n**4\\. [Cytochrome P450 2C19](https:\/\/go.drugbank.com\/bio_entities\/BE0003536)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral Function\n\nA cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)\n\nSpecific Function\n\n(R)-limonene 6-monooxygenase activity\n\nGene Name\n\nCYP2C19\n\nUniprot ID\n\n[P33261](http:\/\/www.uniprot.org\/uniprot\/P33261)\n\nUniprot Name\n\nCytochrome P450 2C19\n\nMolecular Weight\n\n55944\\.565 Da\n##### References\n1. Huuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15286)\\]\n2. Facciola G, Hidestrand M, von Bahr C, Tybring G: Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes. Eur J Clin Pharmacol. 2001 Mar;56(12):881-8. doi: 10.1007\/s002280000245. \\[[Article](https:\/\/go.drugbank.com\/articles\/A184145)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0002793)\n\n**5\\. [Cytochrome P450 2C9](https:\/\/go.drugbank.com\/bio_entities\/BE0002793)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral Function\n\nA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)\n\nSpecific Function\n\n(R)-limonene 6-monooxygenase activity\n\nGene Name\n\nCYP2C9\n\nUniprot ID\n\n[P11712](http:\/\/www.uniprot.org\/uniprot\/P11712)\n\nUniprot Name\n\nCytochrome P450 2C9\n\nMolecular Weight\n\n55627\\.365 Da\n##### References\n1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. \\[[Article](https:\/\/go.drugbank.com\/articles\/A14815)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0003553)\n\n**6\\. [Acetylserotonin O-methyltransferase](https:\/\/go.drugbank.com\/bio_entities\/BE0003553)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral Function\n\nCatalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine)\n\nSpecific Function\n\nacetylserotonin O-methyltransferase activity\n\nGene Name\n\nASMT\n\nUniprot ID\n\n[P46597](http:\/\/www.uniprot.org\/uniprot\/P46597)\n\nUniprot Name\n\nAcetylserotonin O-methyltransferase\n\nMolecular Weight\n\n38452\\.51 Da\n##### References\n1. Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15271)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0000693)\n\n**7\\. [Indoleamine 2,3-dioxygenase 1](https:\/\/go.drugbank.com\/bio_entities\/BE0000693)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral Function\n\nCatalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, contributing to maintain homeostasis by preventing autoimmunity or immunopathology that would result from uncontrolled and overreacting immune responses (PubMed:25691885). Tryptophan shortage inhibits T lymphocytes division and accumulation of tryptophan catabolites induces T-cell apoptosis and differentiation of regulatory T-cells (PubMed:25691885). Acts as a suppressor of anti-tumor immunity (PubMed:14502282, PubMed:23103127, PubMed:25157255, PubMed:25691885). Limits the growth of intracellular pathogens by depriving tryptophan (PubMed:25691885). Protects the fetus from maternal immune rejection (PubMed:25691885)\n\nSpecific Function\n\nelectron transfer activity\n\nGene Name\n\nIDO1\n\nUniprot ID\n\n[P14902](http:\/\/www.uniprot.org\/uniprot\/P14902)\n\nUniprot Name\n\nIndoleamine 2,3-dioxygenase 1\n\nMolecular Weight\n\n45325\\.89 Da\n##### References\n1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15321)\\]\n\n##### Binding Properties\n×\n\n| Property | Measurement | pH | Temperature (°C) | References |\n|---|---|---|---|---|\n| IC 50 (nM) | 3000 | N\/A | N\/A | Not Available |\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0001075)\n\nBinding Properties\n\n**8\\. [Myeloperoxidase](https:\/\/go.drugbank.com\/bio_entities\/BE0001075)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nInhibitor\n\nGeneral Function\n\nPart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971)\n\nSpecific Function\n\nchromatin binding\n\nGene Name\n\nMPO\n\nUniprot ID\n\n[P05164](http:\/\/www.uniprot.org\/uniprot\/P05164)\n\nUniprot Name\n\nMyeloperoxidase\n\nMolecular Weight\n\n83867\\.71 Da\n##### References\n1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15321)\\]\n2. Galijasevic S: The development of myeloperoxidase inhibitors. Bioorg Med Chem Lett. 2019 Jan 1;29(1):1-7. doi: 10.1016\/j.bmcl.2018.11.031. Epub 2018 Nov 15. \\[[Article](https:\/\/go.drugbank.com\/articles\/A267170)\\]\n3. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0002090)\n\n**9\\. [Aromatase](https:\/\/go.drugbank.com\/bio_entities\/BE0002090)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nInhibitor\n\nGeneral Function\n\nA cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo\/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874)\n\nSpecific Function\n\naromatase activity\n\nGene Name\n\nCYP19A1\n\nUniprot ID\n\n[P11511](http:\/\/www.uniprot.org\/uniprot\/P11511)\n\nUniprot Name\n\nAromatase\n\nMolecular Weight\n\n57882\\.48 Da\n##### References\n1. Gonzalez A, Martinez-Campa C, Mediavilla MD, Alonso-Gonzalez C, Sanchez-Mateos S, Hill SM, Sanchez-Barcelo EJ, Cos S: Effects of MT1 melatonin receptor overexpression on the aromatase-suppressive effect of melatonin in MCF-7 human breast cancer cells. Oncol Rep. 2007 Apr;17(4):947-53. doi: 10.3892\/or.17.4.947. \\[[Article](https:\/\/go.drugbank.com\/articles\/A182687)\\]\n\n### Transporters\n[Details](https:\/\/go.drugbank.com\/bio_entities\/BE0003645)\n\n**1\\. [Organic anion transporter 3](https:\/\/go.drugbank.com\/bio_entities\/BE0003645)**\n\nKind\n\nProtein\n\nOrganism\n\nHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nInhibitor\n\nGeneral Function\n\nFunctions as an organic anion\/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S\/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification\/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate\/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)\n\nSpecific Function\n\norganic anion transmembrane transporter activity\n\nGene Name\n\nSLC22A8\n\nUniprot ID\n\n[Q8TCC7](http:\/\/www.uniprot.org\/uniprot\/Q8TCC7)\n\nUniprot Name\n\nOrganic anion transporter 3\n\nMolecular Weight\n\n59855\\.585 Da\n##### References\n1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. \\[[Article](https:\/\/go.drugbank.com\/articles\/A16319)\\]\n2. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. \\[[Article](https:\/\/go.drugbank.com\/articles\/A6152)\\]\n\n×\n\n![](https:\/\/go.drugbank.com\/assets\/locked\/Interactions-d8a042d89ef37357d141b7e23e305da46e3356a206fd25d371bb5a6069ab5df3.png)\n\nIdentify potential medication risks\n\nEasily compare up to 40 drugs with our drug interaction checker.\n\n**Get severity rating, description, and management advice.**\n\n[Learn more](https:\/\/bit.ly\/2TFmz2P)\n\nDrug created at June 13, 2005 13:24 \/ Updated at February 28, 2026 09:03\n\nThe contents of DrugBank are intended for educational and scientific research purposes only. DrugBank does not sell pharmaceuticals or chemicals, and it is not a substitute for professional medical advice, diagnosis or treatment. Be sure to contact a medical professional for any questions you may have.\n\n#### Product Image\n×\n\n![]()[Show full image](https:\/\/go.drugbank.com\/drugs\/DB01065)\n\n![](https:\/\/go.drugbank.com\/assets\/plus\/Article_Dark_Pink-17ef3dc892e28e001abbb0ae6bfc47fca8a64cd76af37ec2a80dbce89fe3bc72.png)\n\n## Stay up-to-date with the  **latest from DrugBank\\!**\n\n![](https:\/\/go.drugbank.com\/assets\/plus\/Article_Dark_Pink-17ef3dc892e28e001abbb0ae6bfc47fca8a64cd76af37ec2a80dbce89fe3bc72.png)\n\n## **Thank you**  for subscribing\\!\n\nDownloads\n\n- [Data Library](https:\/\/go.drugbank.com\/data_packages)\n- [Academic Downloads](https:\/\/go.drugbank.com\/releases\/latest)\n- [Contact Sales](https:\/\/go.drugbank.com\/contact\/sales)\n\nLearn More\n\n- [The New DrugBank](https:\/\/go.drugbank.com\/product_tour)\n- [Careers](https:\/\/drugbank.bamboohr.com\/careers)\n- [Blog](https:\/\/blog.drugbank.com\/)\n- [Clinical API](https:\/\/go.drugbank.com\/clinical)\n- [Contact Sales](https:\/\/go.drugbank.com\/contact\/sales)\n\nSupport\n\n- [Help Center](https:\/\/dev.drugbank.com\/guides\/index)\n- [DrugBank Online FAQs](https:\/\/dev.drugbank.com\/guides\/faqs)\n- [Contact Support](https:\/\/go.drugbank.com\/contact\/support)\n- [Citing DrugBank](https:\/\/dev.drugbank.com\/guides\/drugbank\/citing)\n- [Searching DrugBank](https:\/\/dev.drugbank.com\/guides\/drugbank\/searching)\n- [Other Databases](https:\/\/dev.drugbank.com\/guides\/drugbank\/other_databases)\n- [Data Sources](https:\/\/dev.drugbank.com\/guides\/fields\/drugs)\n\nAbout\n\n- [About DrugBank Online](https:\/\/go.drugbank.com\/about)\n- [Wishart Research Group](http:\/\/www.wishartlab.com\/)\n- [Statistics](https:\/\/go.drugbank.com\/stats)\n- [Terms of Use](https:\/\/trust.drugbank.com\/drugbank-trust-center\/drugbank-terms-of-service)\n- [Privacy Policy](https:\/\/trust.drugbank.com\/drugbank-trust-center\/drugbank-privacy-policy)\n\nUse or redistribution of any DrugBank content or data requires a license and proper citations. [Talk to sales](https:\/\/go.drugbank.com\/contact\/sales) for commercial licensing. [Apply](https:\/\/go.drugbank.com\/releases\/latest) for an academic license.","attrs_readable_markdown":"DescriptionA naturally occurring hormone that promotes sleep.\n\nDescriptionA naturally occurring hormone that promotes sleep.\n\nDrugBank IDDB01065\n\nModalitySmall Molecule\n\n[Clinical Trials](https:\/\/go.drugbank.com\/drugs\/DB01065#clinical-trials-header)\n\nPhase 0\n\n8\n\nPhase 1\n\n62\n\nPhase 2\n\n141\n\nPhase 3\n\n80\n\nPhase 4\n\n59\n\nSummary\n\n**Melatonin** is an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement.\n\nBrand Names\n\n*Circadin, Melatonin Neurim, Slenyto*\n\nGeneric NameMelatonin\n\nDrugBank Accession NumberDB01065\n\nBackground\n\nMelatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and lowering the body temperature. Melatonin is also implicated in the regulation of mood, learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders (ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.\n\nModalitySmall Molecule\n\nGroupsApproved, Investigational, Nutraceutical, Vet approved\n\nStructure\n\n[![](https:\/\/go.drugbank.com\/structures\/DB01065\/thumb.svg)](https:\/\/go.drugbank.com\/structures\/DB01065\/image.svg)\n\n![](https:\/\/go.drugbank.com\/structures\/DB01065\/image.svg)\n\nWeightAverage: 232.2783   \nMonoisotopic: 232.121177766\n\nChemical FormulaC13H16N2O2\n\nSynonyms\n\n- 5-methoxy-N-acetyl tryptamine\n- 5-methoxy-N-acetyltryptamine\n- Melatonin\n- Melatonina\n- Mélatonine\n- N-\\[2-(5-methoxyindol-3-yl)ethyl\\]acetamide\n- N-Acetyl-5-methoxytryptamine\n\nExternal IDs\n\n- BCI-049\n- J5.258B\n- NPC-15\n- NSC-113928\n- NSC-56423\n\nIndication\n\nUsed orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. Evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. It has received FDA orphan drug status as an oral medication for this use. A number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. It appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. It may also improve secondary insomnia associated with various sleep-wake cycle disturbances. Other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (DSPS), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with IL-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders.\n\n[![](https:\/\/go.drugbank.com\/assets\/locked\/Pharmacology-da701df37a1a51c9ee28326cbba45e6bdeef07bce6ddf5e2eb757439eea83e8e.png) **Reduce drug development failure rates** **Build, train, & validate machine-learning models**with evidence-based and structured datasets.See how](https:\/\/bit.ly\/3l5TIQu)\n\n[Build, train, & validate predictive machine-learning models with structured datasets.See how](https:\/\/bit.ly\/3yeDgkJ)\n\nAssociated Conditions\n\n| Indication Type | Indication | Combined Product Details | Approval Level | Age Group | Patient Characteristics | Dose Form |\n|---|---|---|---|---|---|---|\n| Management of | [Insomnia](https:\/\/go.drugbank.com\/conditions\/DBCOND0017531) |   | •••••••••••• |   |   |   |\n| Used in combination to manage | [Insomnia](https:\/\/go.drugbank.com\/conditions\/DBCOND0017531) | Combination Product in combination with: [Valerian (DB13196)](https:\/\/go.drugbank.com\/drugs\/DB13196), [gamma-Aminobutyric acid (DB02530)](https:\/\/go.drugbank.com\/drugs\/DB02530) | •••••••••••• |   |   |   |\n\nPharmacodynamics\n\nMelatonin is a hormone normally produced in the pineal gland and released into the blood. The essential amino acid L-tryptophan is a precursor in the synthesis of melatonin. It helps regulate sleep-wake cycles or the circadian rhythm. Production of melatonin is stimulated by darkness and inhibited by light. High levels of melatonin induce sleep and so consumption of the drug can be used to combat insomnia and jet lag. MT1 and MT2 receptors may be a target for the treatment of circadian and non circadian sleep disorders because of their differences in pharmacology and function within the SCN. SCN is responsible for maintaining the 24 hour cycle which regulates many different body functions ranging from sleep to immune functions\n\nMechanism of action\n\nMelatonin is a derivative of tryptophan. It binds to melatonin receptor type 1A, which then acts on adenylate cylcase and the inhibition of a cAMP signal transduction pathway. Melatonin not only inhibits adenylate cyclase, but it also activates phosphilpase C. This potentiates the release of arachidonate. By binding to melatonin receptors 1 and 2, the downstream signallling cascades have various effects in the body. The melatonin receptors are G protein-coupled receptors and are expressed in various tissues of the body. There are two subtypes of the receptor in humans, melatonin receptor 1 (MT1) and melatonin receptor 2 (MT2). Melatonin and melatonin receptor agonists, on market or in clinical trials, all bind to and activate both receptor types.The binding of the agonists to the receptors has been investigated for over two decades or since 1986. It is somewhat known, but still not fully understood. When melatonin receptor agonists bind to and activate their receptors it causes numerous physiological processes. MT1 receptors are expressed in many regions of the central nervous system (CNS): suprachiasmatic nucleus of the hypothalamus (SNC), hippocampus, substantia nigra, cerebellum, central dopaminergic pathways, ventral tegmental area and nucleus accumbens. MT1 is also expressed in the retina, ovary, testis, mammary gland, coronary circulation and aorta, gallbladder, liver, kidney, skin and the immune system. MT2 receptors are expressed mainly in the CNS, also in the lung, cardiac, coronary and aortic tissue, myometrium and granulosa cells, immune cells, duodenum and adipocytes. The binding of melatonin to melatonin receptors activates a few signaling pathways. MT1 receptor activation inhibits the adenylyl cyclase and its inhibition causes a rippling effect of non activation; starting with decreasing formation of cyclic adenosine monophosphate (cAMP), and then progressing to less protein kinase A (PKA) activity, which in turn hinders the phosphorilation of cAMP responsive element-binding protein (CREB binding protein) into P-CREB. MT1 receptors also activate phospholipase C (PLC), affect ion channels and regulate ion flux inside the cell. The binding of melatonin to MT2 receptors inhibits adenylyl cyclase which decreases the formation of cAMP.\\[4\\] As well it hinders guanylyl cyclase and therefore the forming of cyclic guanosine monophosphate (cGMP). Binding to MT2 receptors probably affects PLC which increases protein kinase C (PKC) activity. Activation of the receptor can lead to ion flux inside the cell.\n\n| Target | Actions | Organism |\n|---|---|---|\n| A[Melatonin receptor type 1A](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000515) | agonist | Humans |\n| A[Melatonin receptor type 1B](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000327) | agonist | Humans |\n| A[Ribosyldihydronicotinamide dehydrogenase \\[quinone\\]](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000220) | inhibitor | Humans |\n| U[Estrogen receptor](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0000123) | antagonist | Humans |\n| U[Nuclear receptor ROR-beta](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0003554) | agonist | Humans |\n| U[Myeloperoxidase](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0001075) | inhibitor | Humans |\n| U[Eosinophil peroxidase](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0003555) | inhibitor | Humans |\n| U[Calreticulin](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0002109) | modulator | Humans |\n| U[Calmodulin](https:\/\/go.drugbank.com\/drugs\/DB01065#BE0027477) | antagonist | Humans |\n\nAbsorption\n\nThe absorption and bioavailability of melatonin varies widely.\n\nVolume of distribution\n\nNot Available\n\nProtein binding\n\nn\/a\n\nMetabolism\n\nHepatically metabolized to at least 14 identified metabolites (identified in mouse urine): 6-hydroxymelatonin glucuronide, 6-hydroxymelatonin sulfate, N-acetylserotonin glucuronide, N-acetylserotonin sulfate, 6-hydroxymelatonin, 2-oxomelatonin, 3-hydroxymelatonin, melatonin glucuronide, cyclic melatonin, cyclic N-acetylserotonin glucuronide, cyclic 6-hydroxymelatonin, 5-hydroxyindole-3-acetaldehyde, di-hydroxymelatonin and its glucuronide conjugate. 6-Hydroxymelatonin glucuronide is the major metabolite found in mouse urine (65-88% of total melatonin metabolites in urine).\n\n**Hover over products below to view reaction partners**\n\nRoute of elimination\n\nNot Available\n\nHalf-life\n\n35 to 50 minutes\n\nClearance\n\nNot Available\n\nToxicity\n\nGenerally well-tolerated when taken orally. The most common side effects, day-time drowsiness, headache and dizziness, appear to occur at the same frequency as with placebo. Other reported side effects include transient depressive symptoms, mild tremor, mild anxiety, abdominal cramps, irritability, reduced alertness, confusion, nausea, vomiting, and hypotension. Safety in Adults: Evidence indicates that it is likely safe to use in oral and parenteral forms for up to two months when used appropriately. Some evidence indicates that it can be safely used orally for up to 9 months in some patients. It is also likely safe to use topically when used appropriately. Safety in Children: Melatonin appeared to be used safely in small numbers of children enrolled in short-term clinical trials. However, concerns regarding safety in children have arisen based on their developmental state. Compared to adults over 20 years of age, people under 20 produce high levels of melatonin. Melatonin levels are inversely related to gonadal development and it is thought that exogenous administration of melatonin may adversely affect gonadal development. Safety during Pregnancy: High doses of melatonin administered orally or parenterally may inhibit ovulation. Not advised for use in individuals who are pregnant or trying to become pregnant. Safety during Lactation: Not recommended as safety has not be established.\n\nOral, rat: LD50 ≥3200 mg\/kg\n\nPathways\n\n| Pathway | Category |\n|---|---|\n| [Tryptophan Metabolism](http:\/\/smpdb.ca\/view\/SMP0000063?highlight[compounds][]=DB01065&highlight[proteins][]=DB01065) | Metabolic |\n\nPharmacogenomic Effects\/ADRs\n\nNot Available\n\nDrug Interactions\n\nThis information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.\n\n- [Approved](https:\/\/go.drugbank.com\/drugs\/DB01065#show-approved)\n- [Vet approved](https:\/\/go.drugbank.com\/drugs\/DB01065#show-vet_approved)\n- [Nutraceutical](https:\/\/go.drugbank.com\/drugs\/DB01065#show-nutraceutical)\n- [Illicit](https:\/\/go.drugbank.com\/drugs\/DB01065#show-illicit)\n- [Withdrawn](https:\/\/go.drugbank.com\/drugs\/DB01065#show-withdrawn)\n- [Investigational](https:\/\/go.drugbank.com\/drugs\/DB01065#show-investigational)\n- [Experimental](https:\/\/go.drugbank.com\/drugs\/DB01065#show-experimental)\n- [All Drugs](https:\/\/go.drugbank.com\/drugs\/DB01065#show-all)\n\n| Drug | Interaction |\n|---|---|\n| Integrate drug-drug  interactions in your software |   |\n| [1,2-Benzodiazepine](https:\/\/go.drugbank.com\/drugs\/DB12537) | The risk or severity of CNS depression can be increased when Melatonin is combined with 1,2-Benzodiazepine. |\n| [Abametapir](https:\/\/go.drugbank.com\/drugs\/DB11932) | The serum concentration of Melatonin can be increased when it is combined with Abametapir. |\n| [Abatacept](https:\/\/go.drugbank.com\/drugs\/DB01281) | The metabolism of Melatonin can be increased when combined with Abatacept. |\n| [Abiraterone](https:\/\/go.drugbank.com\/drugs\/DB05812) | The serum concentration of Melatonin can be increased when it is combined with Abiraterone. |\n| [Acenocoumarol](https:\/\/go.drugbank.com\/drugs\/DB01418) | The metabolism of Acenocoumarol can be decreased when combined with Melatonin. |\n\nFood Interactions\n\n- Avoid alcohol. Ingesting alcohol may reduce the effects of melatonin.\n- Take after a meal. Administration of melatonin after eating slows the absorption and reduces the Cmax of melatonin.\n\nInternational\/Other BrandsMela-T (Alacer Corp. (Canada)) \/ Melatol (Elisium (Argentina)) \/ Melatonin (Biomed International Products Corp., Nutravite Pharmaceuticals (2008) Inc., Viva Pharmaceutical Inc., Kripps Pharmacy Ltd., SunOpta Inc.) \/ Nature'S Harmony (SunOpta Inc. (Canada)) \/ Revital Melatonin (Chin Tai Ginseng Co., Ltd (Canada)) \/ Rx Balance (SunOpta Inc. (Canada)) \/ Sleep Right (SunOpta Inc. (Canada)) \/ Vivitas (SunOpta Inc. (Canada))\n\nBrand Name Prescription Products\n\n| Name | Dosage | Strength | Route | Labeller | Marketing Start | Marketing End | Region | Image |\n|---|---|---|---|---|---|---|---|---|\n| Melatol | Liquid | 1 mg\/30mL | Oral | PureTek Corporation | 2024-10-17 | Not applicable | ![US flag](https:\/\/go.drugbank.com\/assets\/countries\/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) |   |\n| Circadin | Tablet, extended release | 2 mg | Oral | Rad Neurim Pharmaceuticals Eec Sarl | 2016-09-08 | Not applicable | ![EU flag](https:\/\/go.drugbank.com\/assets\/countries\/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) |   |\n| Circadin | Tablet, extended release | 2 mg | Oral | Rad Neurim Pharmaceuticals Eec Sarl | 2016-09-08 | Not applicable | ![EU flag](https:\/\/go.drugbank.com\/assets\/countries\/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) |   |\n| Circadin | Tablet, extended release | 2 mg | Oral | Rad Neurim Pharmaceuticals Eec Sarl | 2016-09-08 | Not applicable | ![EU flag](https:\/\/go.drugbank.com\/assets\/countries\/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) |   |\n| Circadin | Tablet, extended release | 2 mg | Oral | Rad Neurim Pharmaceuticals Eec Sarl | 2016-09-08 | Not applicable | ![EU flag](https:\/\/go.drugbank.com\/assets\/countries\/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) |   |\n\nOver the Counter Products\n\n| Name | Dosage | Strength | Route | Labeller | Marketing Start | Marketing End | Region | Image |\n|---|---|---|---|---|---|---|---|---|\n| Essential Oil | Oil | 2\\.5 mg\/10mL | Cutaneous | Shantou Youjia E-Commerce Co., Ltd. | 2024-02-01 | 2024-12-31 | ![US flag](https:\/\/go.drugbank.com\/assets\/countries\/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) |   |\n\nUnapproved\/Other Products\n\n| Name | Ingredients | Dosage | Route | Labeller | Marketing Start | Marketing End | Region | Image |\n|---|---|---|---|---|---|---|---|---|\n| Medi-doze Rx Sleep Aid | Melatonin (6 mg\/1) + [Valerian](https:\/\/go.drugbank.com\/drugs\/DB13196) (50 mg\/1) + [gamma-Aminobutyric acid](https:\/\/go.drugbank.com\/drugs\/DB02530) (30 mg\/1) | Tablet | Oral | Two Hip Consulting, Llc | 2013-02-20 | 2016-04-11 | ![US flag](https:\/\/go.drugbank.com\/assets\/countries\/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) |   |\n| Melatol | Melatonin (1 mg\/30mL) | Liquid | Oral | PureTek Corporation | 2024-10-17 | Not applicable | ![US flag](https:\/\/go.drugbank.com\/assets\/countries\/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) |   |\n\nDrug Categories\n\n- [Amines](https:\/\/go.drugbank.com\/categories\/DBCAT000266)\n- [Antioxidants](https:\/\/go.drugbank.com\/categories\/DBCAT000368)\n- [Biogenic Amines](https:\/\/go.drugbank.com\/categories\/DBCAT000285)\n- [Biogenic Monoamines](https:\/\/go.drugbank.com\/categories\/DBCAT000468)\n- [Biological Factors](https:\/\/go.drugbank.com\/categories\/DBCAT000036)\n- [Central Nervous System Agents](https:\/\/go.drugbank.com\/categories\/DBCAT000044)\n- [Central Nervous System Depressants](https:\/\/go.drugbank.com\/categories\/DBCAT000399)\n- [Compounds used in a research, industrial, or household setting](https:\/\/go.drugbank.com\/categories\/DBCAT000196)\n- [Cytochrome P-450 CYP1A1 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT006050)\n- [Cytochrome P-450 CYP1A2 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT002609)\n- [Cytochrome P-450 CYP2C19 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT002638)\n- [Cytochrome P-450 CYP2C9 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT002634)\n- [Cytochrome P-450 Substrates](https:\/\/go.drugbank.com\/categories\/DBCAT005101)\n- [Heterocyclic Compounds, Fused-Ring](https:\/\/go.drugbank.com\/categories\/DBCAT004973)\n- [Hormones](https:\/\/go.drugbank.com\/categories\/DBCAT000056)\n- [Hormones, Hormone Substitutes, and Hormone Antagonists](https:\/\/go.drugbank.com\/categories\/DBCAT000057)\n- [Hypnotics and Sedatives](https:\/\/go.drugbank.com\/categories\/DBCAT000452)\n- [Indoles](https:\/\/go.drugbank.com\/categories\/DBCAT000528)\n- [Melatonin Receptor Agonists](https:\/\/go.drugbank.com\/categories\/DBCAT002489)\n- [Melatonin, agonists](https:\/\/go.drugbank.com\/categories\/DBCAT001822)\n- [Nervous System](https:\/\/go.drugbank.com\/categories\/DBCAT002148)\n- [OAT3\/SLC22A8 Inhibitors](https:\/\/go.drugbank.com\/categories\/DBCAT003946)\n- [Protective Agents](https:\/\/go.drugbank.com\/categories\/DBCAT000367)\n- [Psycholeptics](https:\/\/go.drugbank.com\/categories\/DBCAT002185)\n- [Tryptamines](https:\/\/go.drugbank.com\/categories\/DBCAT001049)\n\nAffected organisms\n\n- Humans and other mammals\n\nUNII[JL5DK93RCL](https:\/\/drugs.ncats.io\/drug\/JL5DK93RCL)\n\nCAS number73-31-4\n\nInChI KeyDRLFMBDRBRZALE-UHFFFAOYSA-N\n\nInChI\n\nInChI=1S\/C13H16N2O2\/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13\/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)\n\nIUPAC Name\n\nN-\\[2-(5-methoxy-1H-indol-3-yl)ethyl\\]acetamide\n\nSMILES\n\nCOC1=CC2=C(NC=C2CCNC(C)=O)C=C1\n\nSynthesis Reference\n\nRobert A. S. Welch, Keith Betteridge, \"Method of stimulating cashmere growth on cashmere-producing goats using melatonin.\" U.S. Patent US4855313, issued August, 1986.\n\n[US4855313](https:\/\/www.google.com\/?tbm=pts#q=4855313&tbm=pts)\n\nGeneral References\n\n1. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1674)\\]\n2. Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1675)\\]\n3. Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1676)\\]\n4. Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1677)\\]\n5. Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210\/en.2007-1412. Epub 2008 Jan 10. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1678)\\]\n6. Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1679)\\]\n\nPDB Entries[2qwx](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=2qwx) \/ [2qx4](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=2qx4) \/ [2qx6](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=2qx6) \/ [4qog](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=4qog) \/ [4qoi](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=4qoi) \/ [5i8f](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=5i8f) \/ [5mxb](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=5mxb) \/ [5mxw](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=5mxw) \/ [6tr5](http:\/\/www.rcsb.org\/pdb\/explore.do?structureId=6tr5)\n\nClinical Trials\n\n###### Clinical Trial & Rare Diseases Add-on Data Package\nExplore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more.\n\n[Preview package](https:\/\/go.drugbank.com\/data_packages\/trial)\n\n| Phase | Status | Purpose | Conditions | Count | Start Date | Why Stopped | 100+ additional columns |\n|---|---|---|---|---|---|---|---|\n| Unlock 175K+ rows when you subscribe. [View sample data](https:\/\/go.drugbank.com\/data_packages\/trial\/data_modules\/clinical_trials) |   |   |   |   |   |   |   |\n| Not Available | Active Not Recruiting | Prevention | [Oral Lichen Planus](https:\/\/go.drugbank.com\/conditions\/DBCOND0030626) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0030626&phase=&purpose=prevention&status=active_not_recruiting) | somestatus | stop reason | just information to hide |\n| Not Available | Active Not Recruiting | Treatment | [Psychosis](https:\/\/go.drugbank.com\/conditions\/DBCOND0020753) \/ [Schizophrenia Disorders](https:\/\/go.drugbank.com\/conditions\/DBCOND0031361) \/ [Schizophrenias](https:\/\/go.drugbank.com\/conditions\/DBCOND0033618) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0020753%2CDBCOND0031361%2CDBCOND0033618&phase=&purpose=treatment&status=active_not_recruiting) | somestatus | stop reason | just information to hide |\n| Not Available | Completed | Not Available | [Insomnia](https:\/\/go.drugbank.com\/conditions\/DBCOND0017531) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0017531&phase=&status=completed) | somestatus | stop reason | just information to hide |\n| Not Available | Completed | Not Available | [Postoperative Delirium (POD)](https:\/\/go.drugbank.com\/conditions\/DBCOND0073043) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0073043&phase=&status=completed) | somestatus | stop reason | just information to hide |\n| Not Available | Completed | Not Available | [Postoperative pain](https:\/\/go.drugbank.com\/conditions\/DBCOND0022333) | [1](https:\/\/go.drugbank.com\/drugs\/DB01065\/clinical_trials?conditions=DBCOND0022333&phase=&status=completed) | somestatus | stop reason | just information to hide |\n\nManufacturers\n\nNot Available\n\nPackagers\n\n- Mason Distributors\n- Medisca Inc.\n- National Vitamin Company\n- Physiologics\n- Rugby Laboratories\n\nDosage Forms\n\n| Form | Route | Strength |\n|---|---|---|\n| Capsule | Not applicable | 10 mg\/1 |\n| Capsule | Oral | 5\\.00000 mg |\n| Capsule, coated | Oral | 3 mg |\n| Capsule, liquid filled | Oral | 3 mg |\n| Chewable gel | Oral | 2\\.5 mg\/1 |\n| Liquid | Oral | 1 mg\/4mL |\n| Liquid | Oral | 1 mg\/30mL |\n| Oil | Cutaneous | 2\\.5 mg\/10mL |\n| Solution | Oral | 1 mg\/ml |\n| Solution \/ drops | Oral | 1 mg\/1mL |\n| Tablet | Not applicable | 10 mg\/1 |\n| Tablet | Oral |   |\n| Tablet | Oral | 0\\.5 mg |\n| Tablet | Oral | 1 mg |\n| Tablet | Oral | 1\\.500 mg |\n| Tablet | Oral | 2 mg |\n| Tablet | Oral | 3 mg\/1 |\n| Tablet | Oral | 3 MG |\n| Tablet | Oral | 4 mg |\n| Tablet | Oral | 5 MG |\n| Tablet | Oral | 5 mg\/1 |\n| Tablet | Sublingual | 3\\.000 mg |\n| Tablet, chewable | Oral | 2\\.5 mg\/1 |\n| Tablet, extended release | Oral | 1 MG |\n| Tablet, extended release | Oral | 2 mg |\n| Tablet, extended release | Oral | 5 MG |\n| Tablet, film coated | Oral | 3 mg |\n| Tablet, film coated | Oral | 5 mg |\n\nPrices\n\n| Unit description | Cost | Unit |\n|---|---|---|\n| Melatonin powder | 45\\.6USD | g |\n| Melatonin 3 mg tablet | 0\\.22USD | tablet |\n| Melatonin 5 mg tablet | 0\\.12USD | tablet |\n| Melatonin 5 mg tablet sl | 0\\.1USD | tablet |\n| Melatonin sublingual tablet | 0\\.09USD | tablet |\n| Melatonin 1 mg tablet | 0\\.03USD | tablet |\n\nDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.\n\nPatentsNot Available\n\nStateSolid\n\nExperimental Properties\n\n| Property | Value | Source |\n|---|---|---|\n| melting point (°C) | 117 °C | PhysProp |\n| logP | 1\\.6 | Not Available |\n\nPredicted Properties\n\n| Property | Value | Source |\n|---|---|---|\n| Water Solubility | 0\\.143 mg\/mL | [ALOGPS](http:\/\/www.vcclab.org\/lab\/alogps\/) |\n| logP | 1\\.42 | [ALOGPS](http:\/\/www.vcclab.org\/lab\/alogps\/) |\n| logP | 1\\.15 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| logS | \\-3.2 | [ALOGPS](http:\/\/www.vcclab.org\/lab\/alogps\/) |\n| pKa (Strongest Acidic) | 15\\.8 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| pKa (Strongest Basic) | \\-1.6 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Physiological Charge | 0 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Hydrogen Acceptor Count | 2 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Hydrogen Donor Count | 2 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Polar Surface Area | 54\\.12 Å2 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Rotatable Bond Count | 4 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Refractivity | 66\\.28 m3·mol\\-1 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Polarizability | 25\\.65 Å3 | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| Number of Rings | 2 | [Chemaxon](https:\/\/chemaxon.com\/calculators-and-predictors) |\n| Bioavailability | 1 | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| Rule of Five | Yes | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| Ghose Filter | Yes | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| Veber's Rule | No | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n| MDDR-like Rule | No | [Chemaxon](https:\/\/docs.chemaxon.com\/display\/docs\/molecular-modeling-plugins.md) |\n\nPredicted ADMET Features\n\n| Property | Value | Probability |\n|---|---|---|\n| Human Intestinal Absorption | \\+ | 1\\.0 |\n| Blood Brain Barrier | \\+ | 0\\.9928 |\n| Caco-2 permeable | \\- | 0\\.5536 |\n| P-glycoprotein substrate | Substrate | 0\\.6188 |\n| P-glycoprotein inhibitor I | Non-inhibitor | 0\\.9569 |\n| P-glycoprotein inhibitor II | Non-inhibitor | 0\\.6838 |\n| Renal organic cation transporter | Non-inhibitor | 0\\.542 |\n| CYP450 2C9 substrate | Non-substrate | 0\\.8231 |\n| CYP450 2D6 substrate | Substrate | 0\\.5062 |\n| CYP450 3A4 substrate | Substrate | 0\\.6505 |\n| CYP450 1A2 substrate | Inhibitor | 0\\.9304 |\n| CYP450 2C9 inhibitor | Non-inhibitor | 0\\.9071 |\n| CYP450 2D6 inhibitor | Inhibitor | 0\\.8084 |\n| CYP450 2C19 inhibitor | Non-inhibitor | 0\\.9025 |\n| CYP450 3A4 inhibitor | Non-inhibitor | 0\\.7194 |\n| CYP450 inhibitory promiscuity | High CYP Inhibitory Promiscuity | 0\\.6803 |\n| Ames test | Non AMES toxic | 0\\.9132 |\n| Carcinogenicity | Non-carcinogens | 0\\.9498 |\n| Biodegradation | Not ready biodegradable | 0\\.8764 |\n| Rat acute toxicity | 1\\.8922 LD50, mol\/kg | Not applicable |\n| hERG inhibition (predictor I) | Weak inhibitor | 0\\.9631 |\n| hERG inhibition (predictor II) | Non-inhibitor | 0\\.5124 |\n\nADMET data is predicted using [admetSAR](http:\/\/lmmd.ecust.edu.cn:8000\/), a free tool for evaluating chemical ADMET properties. ([23092397](http:\/\/www.ncbi.nlm.nih.gov\/pubmed\/23092397))\n\nMass Spec (NIST)[Download](https:\/\/s3-us-west-2.amazonaws.com\/drugbank\/mass_specs\/DB01065.gif?1265922774) (8.2 KB)\n\nSpectra\n\n| Spectrum | Spectrum Type | [Splash Key](http:\/\/splash.fiehnlab.ucdavis.edu\/) |\n|---|---|---|\n| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https:\/\/go.drugbank.com\/spectra\/c_ms\/735) | GC-MS | [splash10-001i-0490000000-aa93967315af900a76ce](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0490000000-aa93967315af900a76ce) |\n| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https:\/\/go.drugbank.com\/spectra\/c_ms\/736) | GC-MS | [splash10-03k9-0900000000-a15ee6def3f8d75b1231](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-03k9-0900000000-a15ee6def3f8d75b1231) |\n| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https:\/\/go.drugbank.com\/spectra\/c_ms\/737) | GC-MS | [splash10-001j-0490000000-94ef1be9ab930060778a](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001j-0490000000-94ef1be9ab930060778a) |\n| [GC-MS Spectrum - GC-MS (2 TMS)](https:\/\/go.drugbank.com\/spectra\/c_ms\/1945) | GC-MS | [splash10-001i-1490000000-03e24298c7bd1ed4066a](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-1490000000-03e24298c7bd1ed4066a) |\n| [Predicted GC-MS Spectrum - GC-MS](https:\/\/go.drugbank.com\/spectra\/c_ms\/7100) | Predicted GC-MS | [splash10-0076-4920000000-a8d9d614e9f8769a1359](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0076-4920000000-a8d9d614e9f8769a1359) |\n| [GC-MS Spectrum - GC-MS](https:\/\/go.drugbank.com\/spectra\/c_ms\/31319) | GC-MS | [splash10-001i-1490000000-03e24298c7bd1ed4066a](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-1490000000-03e24298c7bd1ed4066a) |\n| [GC-MS Spectrum - GC-EI-TOF](https:\/\/go.drugbank.com\/spectra\/c_ms\/32276) | GC-MS | [splash10-001j-0590000000-63d5e32dd5f7877a4402](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001j-0590000000-63d5e32dd5f7877a4402) |\n| [GC-MS Spectrum - GC-EI-TOF](https:\/\/go.drugbank.com\/spectra\/c_ms\/32277) | GC-MS | [splash10-001i-0590000000-52b3a733f8b49582d3fb](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0590000000-52b3a733f8b49582d3fb) |\n| [GC-MS Spectrum - GC-EI-TOF](https:\/\/go.drugbank.com\/spectra\/c_ms\/32278) | GC-MS | [splash10-0229-1900000000-d81c6f617bc486066136](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0229-1900000000-d81c6f617bc486066136) |\n| [Mass Spectrum (Electron Ionization)](https:\/\/go.drugbank.com\/spectra\/ei_ms\/505) | MS | [splash10-03k9-1900000000-45ee4fdc7acdb33dad3b](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-03k9-1900000000-45ee4fdc7acdb33dad3b) |\n| [MS\/MS Spectrum - Quattro\\_QQQ 10V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/1547) | LC-MS\/MS | [splash10-00di-0920000000-f90ec9b77e1a245e35a8](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0920000000-f90ec9b77e1a245e35a8) |\n| [MS\/MS Spectrum - Quattro\\_QQQ 25V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/1548) | LC-MS\/MS | [splash10-05fr-0900000000-49e4482c65e82ac64b66](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-05fr-0900000000-49e4482c65e82ac64b66) |\n| [MS\/MS Spectrum - Quattro\\_QQQ 40V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/1549) | LC-MS\/MS | [splash10-003r-0900000000-8a4ae0fd610cca992d74](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-003r-0900000000-8a4ae0fd610cca992d74) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5222) | LC-MS\/MS | [splash10-0159-0090000000-939a1caf5760c0ba189c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0159-0090000000-939a1caf5760c0ba189c) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5223) | LC-MS\/MS | [splash10-0006-0930000000-9e6fcea2c634ac9d85a0](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0930000000-9e6fcea2c634ac9d85a0) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5224) | LC-MS\/MS | [splash10-0006-0900000000-ddd29e731a7de56c1808](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-ddd29e731a7de56c1808) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5225) | LC-MS\/MS | [splash10-0006-0900000000-34b4fb52810a15ea5bd6](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-34b4fb52810a15ea5bd6) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5226) | LC-MS\/MS | [splash10-001i-0090000000-5ca2df63ec2baefdae8c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0090000000-5ca2df63ec2baefdae8c) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5227) | LC-MS\/MS | [splash10-001i-0190000000-5bae6e63e9b40e60e0a4](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0190000000-5bae6e63e9b40e60e0a4) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5228) | LC-MS\/MS | [splash10-00di-0900000000-529bf6d5c2091993f865](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-529bf6d5c2091993f865) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5229) | LC-MS\/MS | [splash10-00di-0900000000-158a60fe696120b23b41](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-158a60fe696120b23b41) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5230) | LC-MS\/MS | [splash10-0a5c-0900000000-5e86b2de659ce47762c0](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0a5c-0900000000-5e86b2de659ce47762c0) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5231) | LC-MS\/MS | [splash10-001i-0900000000-881c0d57239d56c46f2d](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0900000000-881c0d57239d56c46f2d) |\n| [LC-MS\/MS Spectrum - LC-ESI-IT (LC\/MSD Trap XCT, Agilent Technologies) , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5232) | LC-MS\/MS | [splash10-00di-0910000000-f256f78adbcbeb2464de](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0910000000-f256f78adbcbeb2464de) |\n| [LC-MS\/MS Spectrum - LC-ESI-IT (LC\/MSD Trap XCT, Agilent Technologies) , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/5233) | LC-MS\/MS | [splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23) |\n| [MS\/MS Spectrum - DI-ESI-qTof , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/374102) | LC-MS\/MS | [splash10-05fr-0900000000-7acf9405f4beeb34566c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-05fr-0900000000-7acf9405f4beeb34566c) |\n| [MS\/MS Spectrum - DI-ESI-qTof , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/374103) | LC-MS\/MS | [splash10-00di-0900000000-13245183cd8c8cd511c3](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-13245183cd8c8cd511c3) |\n| [LC-MS\/MS Spectrum - LC-ESI-qTof , Positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/374702) | LC-MS\/MS | [splash10-05ai-2900000000-07b3d32f002dba733c10](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-05ai-2900000000-07b3d32f002dba733c10) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438131) | LC-MS\/MS | [splash10-0159-0090000000-939a1caf5760c0ba189c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0159-0090000000-939a1caf5760c0ba189c) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438132) | LC-MS\/MS | [splash10-0006-0930000000-9e6fcea2c634ac9d85a0](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0930000000-9e6fcea2c634ac9d85a0) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438133) | LC-MS\/MS | [splash10-0006-0900000000-ddd29e731a7de56c1808](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-ddd29e731a7de56c1808) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438134) | LC-MS\/MS | [splash10-0006-0900000000-34b4fb52810a15ea5bd6](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-34b4fb52810a15ea5bd6) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/438135) | LC-MS\/MS | [splash10-001i-0090000000-5ca2df63ec2baefdae8c](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0090000000-5ca2df63ec2baefdae8c) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/439444) | LC-MS\/MS | [splash10-00lr-0090000000-3c42f6997539afb44682](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00lr-0090000000-3c42f6997539afb44682) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/439448) | LC-MS\/MS | [splash10-014m-0960000000-7991e64dacb3c7f5cf32](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-014m-0960000000-7991e64dacb3c7f5cf32) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/439451) | LC-MS\/MS | [splash10-0006-0900000000-882be43bc196e928a3cf](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-0900000000-882be43bc196e928a3cf) |\n| [MS\/MS Spectrum - , negative](https:\/\/go.drugbank.com\/spectra\/ms_ms\/440134) | LC-MS\/MS | [splash10-014i-0190000000-ddda9232f0e8e1b402f7](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-014i-0190000000-ddda9232f0e8e1b402f7) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446535) | LC-MS\/MS | [splash10-001i-0190000000-5bae6e63e9b40e60e0a4](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0190000000-5bae6e63e9b40e60e0a4) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446536) | LC-MS\/MS | [splash10-00di-0900000000-529bf6d5c2091993f865](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-529bf6d5c2091993f865) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446537) | LC-MS\/MS | [splash10-00di-0900000000-158a60fe696120b23b41](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-158a60fe696120b23b41) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446538) | LC-MS\/MS | [splash10-0a5c-0900000000-5e86b2de659ce47762c0](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0a5c-0900000000-5e86b2de659ce47762c0) |\n| [LC-MS\/MS Spectrum - LC-ESI-QQ , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/446539) | LC-MS\/MS | [splash10-001i-0900000000-881c0d57239d56c46f2d](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0900000000-881c0d57239d56c46f2d) |\n| [LC-MS\/MS Spectrum - LC-ESI-IT , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/447247) | LC-MS\/MS | [splash10-00di-0910000000-d659c749adcab685e8bb](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0910000000-d659c749adcab685e8bb) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/449479) | LC-MS\/MS | [splash10-00di-0900000000-6817d8039761a9058337](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-6817d8039761a9058337) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/449485) | LC-MS\/MS | [splash10-00di-0900000000-349d5a97e2406d0db910](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-349d5a97e2406d0db910) |\n| [LC-MS\/MS Spectrum - LC-ESI-QTOF , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/449491) | LC-MS\/MS | [splash10-001i-0900000000-9e30dcf47c9eca14650e](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-001i-0900000000-9e30dcf47c9eca14650e) |\n| [MS\/MS Spectrum - , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/450591) | LC-MS\/MS | [splash10-00di-1900000000-73dc69b26b1fba60f253](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-1900000000-73dc69b26b1fba60f253) |\n| [MS\/MS Spectrum - , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/451347) | LC-MS\/MS | [splash10-05ai-2900000000-07b3d32f002dba733c10](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-05ai-2900000000-07b3d32f002dba733c10) |\n| [MS\/MS Spectrum - , positive](https:\/\/go.drugbank.com\/spectra\/ms_ms\/451967) | LC-MS\/MS | [splash10-00di-0900000000-2e847095e37f4ffe7c8b](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-2e847095e37f4ffe7c8b) |\n| [Predicted MS\/MS Spectrum - 10V, Positive (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677259) | Predicted LC-MS\/MS | [splash10-0089-0960000000-9acd48062f28a100f9da](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0089-0960000000-9acd48062f28a100f9da) |\n| [Predicted MS\/MS Spectrum - 10V, Negative (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677289) | Predicted LC-MS\/MS | [splash10-03di-5790000000-571ee430d2b0391822e3](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-03di-5790000000-571ee430d2b0391822e3) |\n| [Predicted MS\/MS Spectrum - 20V, Positive (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677314) | Predicted LC-MS\/MS | [splash10-00di-0900000000-1a38178248f05cf91e65](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-00di-0900000000-1a38178248f05cf91e65) |\n| [Predicted MS\/MS Spectrum - 20V, Negative (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677334) | Predicted LC-MS\/MS | [splash10-052f-9000000000-9950a9dee5e36e935714](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-052f-9000000000-9950a9dee5e36e935714) |\n| [Predicted MS\/MS Spectrum - 40V, Positive (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677344) | Predicted LC-MS\/MS | [splash10-006x-0900000000-5d47768c1bb474f51f38](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-006x-0900000000-5d47768c1bb474f51f38) |\n| [Predicted MS\/MS Spectrum - 40V, Negative (Annotated)](https:\/\/go.drugbank.com\/spectra\/ms_ms\/677384) | Predicted LC-MS\/MS | [splash10-0006-4900000000-9374ee5bf5eb87317f56](http:\/\/mona.fiehnlab.ucdavis.edu\/#\/spectra\/splash\/splash10-0006-4900000000-9374ee5bf5eb87317f56) |\n| [1H NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/1693) | 1D NMR | Not Applicable |\n| [1H NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/2600) | 1D NMR | Not Applicable |\n| [13C NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/3303) | 1D NMR | Not Applicable |\n| [Predicted 1H NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/42674) | 1D NMR | Not Applicable |\n| [Predicted 13C NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_one_d\/42679) | 1D NMR | Not Applicable |\n| [\\[1H,13C\\] 2D NMR Spectrum](https:\/\/go.drugbank.com\/spectra\/nmr_two_d\/1634) | 2D NMR | Not Applicable |\n\nChromatographic Properties\n\n###### Collision Cross Sections (CCS)\n| Adduct | CCS Value (Å2) | Source type | Source |\n|---|---|---|---|\n| \\[M-H\\]- | 159\\.6858961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M-H\\]- | 152\\.8346632 | predicted | DarkChem Standard v0.1.0 |\n| \\[M-H\\]- | 152\\.9149983 | predicted | DarkChem Lite v0.1.0 |\n| \\[M-H\\]- | 165\\.2831961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M-H\\]- | 159\\.7026961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M-H\\]- | 150\\.02837 | predicted | DeepCCS 1.0 (2019) |\n| \\[M+H\\]+ | 159\\.1911961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+H\\]+ | 157\\.166152 | predicted | DarkChem Standard v0.1.0 |\n| \\[M+H\\]+ | 157\\.1763686 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+H\\]+ | 166\\.2821961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+H\\]+ | 159\\.7927961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+H\\]+ | 152\\.38637 | predicted | DeepCCS 1.0 (2019) |\n| \\[M+Na\\]+ | 158\\.6747961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 165\\.6858961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 167\\.0242025 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 165\\.6891961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 159\\.5635961 | predicted | DarkChem Lite v0.1.0 |\n| \\[M+Na\\]+ | 158\\.4795 | predicted | DeepCCS 1.0 (2019) |\n\n### Targets\n[![](https:\/\/go.drugbank.com\/assets\/locked\/DrugTargets2-1d1d534575da54e734c316d80c9fb35f8210c070dca913c026f8e58660e3e71a.png) **Build, predict & validate machine-learning models** Use our structured and evidence-based datasets to **unlock newinsights and accelerate drug research.**Learn more](https:\/\/bit.ly\/3iYePSn)\n\n[Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.Learn more](https:\/\/bit.ly\/3zOIrse)\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nYes\n\nActions\n\nAgonist\n\nGeneral FunctionHigh affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity. Possibly involved in sleep induction, by melatonin activation of the potassium channel KCNMA1\/BK and the dissociation of G-beta and G-gamma subunits, thereby decreasing synaptic transmission (By similarity)\n\nSpecific FunctionG protein-coupled receptor activity\n\nGene NameMTNR1A\n\nUniprot ID[P48039](http:\/\/www.uniprot.org\/uniprot\/P48039)\n\nUniprot NameMelatonin receptor type 1A\n\nMolecular Weight39374\\.315 Da\n##### References\n1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15272)\\]\n2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. \\[[Article](https:\/\/go.drugbank.com\/articles\/A9)\\]\n3. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1674)\\]\n4. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15273)\\]\n5. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007\/s12325-010-0065-y. Epub 2010 Sep 6. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15274)\\]\n6. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016\/j.bmc.2010.06.100. Epub 2010 Jul 3. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15275)\\]\n7. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210\/en.2009-0710. Epub 2009 Dec 4. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15276)\\]\n8. Witt-Enderby PA, Chu GH, Gillen ML, Li PK: Development of a high-affinity ligand that binds irreversibly to Mel1b melatonin receptors. J Med Chem. 1997 Dec 19;40(26):4195-8. \\[[Article](https:\/\/go.drugbank.com\/articles\/A29415)\\]\n9. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n10. Hoashi Y, Takai T, Kosugi Y, Nakashima M, Nakayama M, Hirai K, Uchikawa O, Koike T: Discovery of a Potent and Orally Bioavailable Melatonin Receptor Agonist. J Med Chem. 2021 Mar 25;64(6):3059-3074. doi: 10.1021\/acs.jmedchem.0c01836. Epub 2021 Mar 7. \\[[Article](https:\/\/go.drugbank.com\/articles\/A268970)\\]\n11. Gunia-Krzyzak A, Zelaszczyk D, Rapacz A, Zeslawska E, Waszkielewicz AM, Panczyk K, Sloczynska K, Pekala E, Nitek W, Filipek B, Marona H: Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH(3) or 2-CH(3). Bioorg Med Chem. 2017 Jan 15;25(2):471-482. doi: 10.1016\/j.bmc.2016.11.014. Epub 2016 Nov 11. \\[[Article](https:\/\/go.drugbank.com\/articles\/A273460)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nYes\n\nActions\n\nAgonist\n\nGeneral FunctionHigh affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity\n\nSpecific FunctionG protein-coupled receptor activity\n\nGene NameMTNR1B\n\nUniprot ID[P49286](http:\/\/www.uniprot.org\/uniprot\/P49286)\n\nUniprot NameMelatonin receptor type 1B\n\nMolecular Weight40187\\.895 Da\n##### References\n1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15272)\\]\n2. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \\[[Article](https:\/\/go.drugbank.com\/articles\/A1674)\\]\n3. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15273)\\]\n4. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007\/s12325-010-0065-y. Epub 2010 Sep 6. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15274)\\]\n5. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016\/j.bmc.2010.06.100. Epub 2010 Jul 3. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15275)\\]\n6. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210\/en.2009-0710. Epub 2009 Dec 4. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15276)\\]\n7. Mattson RJ, Catt JD, Keavy D, Sloan CP, Epperson J, Gao Q, Hodges DB, Iben L, Mahle CD, Ryan E, Yocca FD: Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett. 2003 Mar 24;13(6):1199-202. \\[[Article](https:\/\/go.drugbank.com\/articles\/A29424)\\]\n8. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n9. Ferreira MA Jr, Azevedo H, Mascarello A, Segretti ND, Russo E, Russo V, Guimaraes CRW: Discovery of ACH-000143: A Novel Potent and Peripherally Preferred Melatonin Receptor Agonist that Reduces Liver Triglycerides and Steatosis in Diet-Induced Obese Rats. J Med Chem. 2021 Feb 25;64(4):1904-1929. doi: 10.1021\/acs.jmedchem.0c00627. Epub 2021 Feb 8. \\[[Article](https:\/\/go.drugbank.com\/articles\/A268965)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nYes\n\nActions\n\nInhibitor\n\nGeneral FunctionThe enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis\n\nSpecific Functionchloride ion binding\n\nGene NameNQO2\n\nUniprot ID[P16083](http:\/\/www.uniprot.org\/uniprot\/P16083)\n\nUniprot NameRibosyldihydronicotinamide dehydrogenase \\[quinone\\]\n\nMolecular Weight25918\\.4 Da\n##### References\n1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15272)\\]\n2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093\/nar\/gkad751. \\[[Article](https:\/\/go.drugbank.com\/articles\/A264250)\\]\n3. Fukatsu K, Uchikawa O, Kawada M, Yamano T, Yamashita M, Kato K, Hirai K, Hinuma S, Miyamoto M, Ohkawa S: Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists. J Med Chem. 2002 Sep 12;45(19):4212-21. doi: 10.1021\/jm020114g. \\[[Article](https:\/\/go.drugbank.com\/articles\/A268565)\\]\n4. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n5. Du H, Wang J, Zhang X, Hu Z: A novel quantitative structure-activity relationship method to predict the affinities of MT3 melatonin binding site. Eur J Med Chem. 2008 Dec;43(12):2861-9. doi: 10.1016\/j.ejmech.2008.02.012. Epub 2008 Feb 29. \\[[Article](https:\/\/go.drugbank.com\/articles\/A29410)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nAntagonist\n\nGeneral FunctionNuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1\/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA\/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA\/p65 and NFKB1\/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol\/E2) (By similarity)\n\nSpecific Function14-3-3 protein binding\n\nGene NameESR1\n\nUniprot ID[P03372](http:\/\/www.uniprot.org\/uniprot\/P03372)\n\nUniprot NameEstrogen receptor\n\nMolecular Weight66215\\.45 Da\n##### References\n1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15278)\\]\n2. Yoo YM, Jeung EB: Melatonin-induced estrogen receptor alpha-mediated calbindin-D9k expression plays a role in H2O2-mediated cell death in rat pituitary GH3 cells. J Pineal Res. 2009 Nov;47(4):301-7. doi: 10.1111\/j.1600-079X.2009.00714.x. Epub 2009 Oct 1. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15281)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nAgonist\n\nGeneral FunctionNuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity)\n\nSpecific FunctionDNA-binding transcription activator activity, RNA polymerase II-specific\n\nGene NameRORB\n\nUniprot ID[Q92753](http:\/\/www.uniprot.org\/uniprot\/Q92753)\n\nUniprot NameNuclear receptor ROR-beta\n\nMolecular Weight53219\\.385 Da\n##### References\n1. Becker-Andre M, Wiesenberg I, Schaeren-Wiemers N, Andre E, Missbach M, Saurat JH, Carlberg C: Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily. J Biol Chem. 1994 Nov 18;269(46):28531-4. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15277)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nInhibitor\n\nGeneral FunctionPart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971)\n\nSpecific Functionchromatin binding\n\nGene NameMPO\n\nUniprot ID[P05164](http:\/\/www.uniprot.org\/uniprot\/P05164)\n\nUniprot NameMyeloperoxidase\n\nMolecular Weight83867\\.71 Da\n##### References\n1. Galijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021\/bi702016q. Epub 2008 Feb 1. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15280)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nInhibitor\n\nGeneral FunctionMediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis\n\nSpecific Functionheme binding\n\nGene NameEPX\n\nUniprot ID[P11678](http:\/\/www.uniprot.org\/uniprot\/P11678)\n\nUniprot NameEosinophil peroxidase\n\nMolecular Weight81039\\.5 Da\n##### References\n1. Lu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038\/bjp.2008.173. Epub 2008 Jun 2. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15282)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nModulator\n\nGeneral FunctionCalcium-binding chaperone that promotes folding, oligomeric assembly and quality control in the endoplasmic reticulum (ER) via the calreticulin\/calnexin cycle. This lectin interacts transiently with almost all of the monoglucosylated glycoproteins that are synthesized in the ER (PubMed:7876246). Interacts with the DNA-binding domain of NR3C1 and mediates its nuclear export (PubMed:11149926). Involved in maternal gene expression regulation. May participate in oocyte maturation via the regulation of calcium homeostasis (By similarity). Present in the cortical granules of non-activated oocytes, is exocytosed during the cortical reaction in response to oocyte activation and might participate in the block to polyspermy (By similarity)\n\nSpecific Functioncalcium ion binding\n\nGene NameCALR\n\nUniprot ID[P27797](http:\/\/www.uniprot.org\/uniprot\/P27797)\n\nUniprot NameCalreticulin\n\nMolecular Weight48141\\.2 Da\n##### References\n1. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002\/biof.23. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15273)\\]\n2. Macias M, Escames G, Leon J, Coto A, Sbihi Y, Osuna A, Acuna-Castroviejo D: Calreticulin-melatonin. An unexpected relationship. Eur J Biochem. 2003 Mar;270(5):832-40. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15279)\\]\n\nKindProtein group\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nAntagonist\n\nGeneral FunctionCalmodulin acts as part of a calcium signal transduction pathway by mediating the control of a large number of enzymes, ion channels, aquaporins and other proteins through calcium-binding (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Calcium-binding is required for the activation of calmodulin (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Among the enzymes to be stimulated by the calmodulin-calcium complex are a number of protein kinases, such as myosin light-chain kinases and calmodulin-dependent protein kinase type II (CaMK2), and phosphatases (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis (PubMed:16760425). Is a regulator of voltage-dependent L-type calcium channels (PubMed:31454269). Mediates calcium-dependent inactivation of CACNA1C (PubMed:26969752). Positively regulates calcium-activated potassium channel activity of KCNN2 (PubMed:27165696). Forms a potassium channel complex with KCNQ1 and regulates electrophysiological activity of the channel via calcium-binding (PubMed:25441029). Acts as a sensor to modulate the endoplasmic reticulum contacts with other organelles mediated by VMP1:ATP2A2 (PubMed:28890335)\n\nSpecific Functionadenylate cyclase activator activity\n***\n##### Components:\n| Name | UniProt ID |\n|---|---|\n| [Calmodulin-1](https:\/\/go.drugbank.com\/polypeptides\/P0DP23) | [P0DP23](http:\/\/www.uniprot.org\/uniprot\/P0DP23) |\n| [Calmodulin-2](https:\/\/go.drugbank.com\/polypeptides\/P0DP24) | [P0DP24](http:\/\/www.uniprot.org\/uniprot\/P0DP24) |\n| [Calmodulin-3](https:\/\/go.drugbank.com\/polypeptides\/P0DP25) | [P0DP25](http:\/\/www.uniprot.org\/uniprot\/P0DP25) |\n##### References\n1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15278)\\]\n2. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016\/j.taap.2009.05.012. Epub 2009 May 19. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15272)\\]\n\n### Enzymes\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nInhibitor\n\nGeneral FunctionA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195)\n\nSpecific Functionarachidonate monooxygenase activity\n\nGene NameCYP1A1\n\nUniprot ID[P04798](http:\/\/www.uniprot.org\/uniprot\/P04798)\n\nUniprot NameCytochrome P450 1A1\n\nMolecular Weight58164\\.815 Da\n##### References\n1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15283)\\]\n2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15284)\\]\n3. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. \\[[Article](https:\/\/go.drugbank.com\/articles\/A266010)\\]\n4. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral FunctionA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)\n\nSpecific Functioncaffeine oxidase activity\n\nGene NameCYP1A2\n\nUniprot ID[P05177](http:\/\/www.uniprot.org\/uniprot\/P05177)\n\nUniprot NameCytochrome P450 1A2\n\nMolecular Weight58406\\.915 Da\n##### References\n1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15283)\\]\n2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15284)\\]\n3. Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15285)\\]\n4. Hartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. \\[[Article](https:\/\/go.drugbank.com\/articles\/A38895)\\]\n5. Hartter S, Wang X, Weigmann H, Friedberg T, Arand M, Oesch F, Hiemke C: Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin. J Clin Psychopharmacol. 2001 Apr;21(2):167-74. \\[[Article](https:\/\/go.drugbank.com\/articles\/A38975)\\]\n6. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. \\[[Article](https:\/\/go.drugbank.com\/articles\/A266010)\\]\n7. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nInhibitor\n\nGeneral FunctionA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity)\n\nSpecific Functionestrogen 16-alpha-hydroxylase activity\n\nGene NameCYP1B1\n\nUniprot ID[Q16678](http:\/\/www.uniprot.org\/uniprot\/Q16678)\n\nUniprot NameCytochrome P450 1B1\n\nMolecular Weight60845\\.33 Da\n##### References\n1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111\/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15283)\\]\n2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15284)\\]\n3. Yu Z, Tian X, Peng Y, Sun Z, Wang C, Tang N, Li B, Jian Y, Wang W, Huo X, Ma X: Mitochondrial cytochrome P450 (CYP) 1B1 is responsible for melatonin-induced apoptosis in neural cancer cells. J Pineal Res. 2018 Aug;65(1):e12478. doi: 10.1111\/jpi.12478. Epub 2018 Mar 25. \\[[Article](https:\/\/go.drugbank.com\/articles\/A184151)\\]\n4. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016\/j.ejmech.2017.04.042. Epub 2017 Apr 18. \\[[Article](https:\/\/go.drugbank.com\/articles\/A266010)\\]\n5. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral FunctionA cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)\n\nSpecific Function(R)-limonene 6-monooxygenase activity\n\nGene NameCYP2C19\n\nUniprot ID[P33261](http:\/\/www.uniprot.org\/uniprot\/P33261)\n\nUniprot NameCytochrome P450 2C19\n\nMolecular Weight55944\\.565 Da\n##### References\n1. Huuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15286)\\]\n2. Facciola G, Hidestrand M, von Bahr C, Tybring G: Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes. Eur J Clin Pharmacol. 2001 Mar;56(12):881-8. doi: 10.1007\/s002280000245. \\[[Article](https:\/\/go.drugbank.com\/articles\/A184145)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral FunctionA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)\n\nSpecific Function(R)-limonene 6-monooxygenase activity\n\nGene NameCYP2C9\n\nUniprot ID[P11712](http:\/\/www.uniprot.org\/uniprot\/P11712)\n\nUniprot NameCytochrome P450 2C9\n\nMolecular Weight55627\\.365 Da\n##### References\n1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. \\[[Article](https:\/\/go.drugbank.com\/articles\/A14815)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral FunctionCatalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine)\n\nSpecific Functionacetylserotonin O-methyltransferase activity\n\nGene NameASMT\n\nUniprot ID[P46597](http:\/\/www.uniprot.org\/uniprot\/P46597)\n\nUniprot NameAcetylserotonin O-methyltransferase\n\nMolecular Weight38452\\.51 Da\n##### References\n1. Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15271)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nGeneral FunctionCatalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, contributing to maintain homeostasis by preventing autoimmunity or immunopathology that would result from uncontrolled and overreacting immune responses (PubMed:25691885). Tryptophan shortage inhibits T lymphocytes division and accumulation of tryptophan catabolites induces T-cell apoptosis and differentiation of regulatory T-cells (PubMed:25691885). Acts as a suppressor of anti-tumor immunity (PubMed:14502282, PubMed:23103127, PubMed:25157255, PubMed:25691885). Limits the growth of intracellular pathogens by depriving tryptophan (PubMed:25691885). Protects the fetus from maternal immune rejection (PubMed:25691885)\n\nSpecific Functionelectron transfer activity\n\nGene NameIDO1\n\nUniprot ID[P14902](http:\/\/www.uniprot.org\/uniprot\/P14902)\n\nUniprot NameIndoleamine 2,3-dioxygenase 1\n\nMolecular Weight45325\\.89 Da\n##### References\n1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15321)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nSubstrate\n\nInhibitor\n\nGeneral FunctionPart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971)\n\nSpecific Functionchromatin binding\n\nGene NameMPO\n\nUniprot ID[P05164](http:\/\/www.uniprot.org\/uniprot\/P05164)\n\nUniprot NameMyeloperoxidase\n\nMolecular Weight83867\\.71 Da\n##### References\n1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. \\[[Article](https:\/\/go.drugbank.com\/articles\/A15321)\\]\n2. Galijasevic S: The development of myeloperoxidase inhibitors. Bioorg Med Chem Lett. 2019 Jan 1;29(1):1-7. doi: 10.1016\/j.bmcl.2018.11.031. Epub 2018 Nov 15. \\[[Article](https:\/\/go.drugbank.com\/articles\/A267170)\\]\n3. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093\/nar\/gkae1075. \\[[Article](https:\/\/go.drugbank.com\/articles\/A265110)\\]\n\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nInhibitor\n\nGeneral FunctionA cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo\/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874)\n\nSpecific Functionaromatase activity\n\nGene NameCYP19A1\n\nUniprot ID[P11511](http:\/\/www.uniprot.org\/uniprot\/P11511)\n\nUniprot NameAromatase\n\nMolecular Weight57882\\.48 Da\n##### References\n1. Gonzalez A, Martinez-Campa C, Mediavilla MD, Alonso-Gonzalez C, Sanchez-Mateos S, Hill SM, Sanchez-Barcelo EJ, Cos S: Effects of MT1 melatonin receptor overexpression on the aromatase-suppressive effect of melatonin in MCF-7 human breast cancer cells. Oncol Rep. 2007 Apr;17(4):947-53. doi: 10.3892\/or.17.4.947. \\[[Article](https:\/\/go.drugbank.com\/articles\/A182687)\\]\n\n### Transporters\nKindProtein\n\nOrganismHumans\n\nPharmacological action\n\nUnknown\n\nActions\n\nInhibitor\n\nGeneral FunctionFunctions as an organic anion\/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S\/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification\/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate\/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)\n\nSpecific Functionorganic anion transmembrane transporter activity\n\nGene NameSLC22A8\n\nUniprot ID[Q8TCC7](http:\/\/www.uniprot.org\/uniprot\/Q8TCC7)\n\nUniprot NameOrganic anion transporter 3\n\nMolecular Weight59855\\.585 Da\n##### References\n1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. \\[[Article](https:\/\/go.drugbank.com\/articles\/A16319)\\]\n2. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. \\[[Article](https:\/\/go.drugbank.com\/articles\/A6152)\\]","meta_canonical":null}

3. Robots.txt Check

Query:

Response:

4. Spam/Ban Check

Query:

Response:

5. Seen Status Check

ℹ️ Skipped - page is already crawled

📄

INDEXABLE

✅

CRAWLED

1 month ago

🤖

ROBOTS ALLOWED

Page Info Filters

Filter	Status	Condition	Details
HTTP status	PASS	`download_http_code = 200`	HTTP 200
Age cutoff	PASS	`download_stamp > now() - 6 MONTH`	1.1 months ago
History drop	PASS	`isNull(history_drop_reason)`	No drop reason
Spam/ban	PASS	`fh_dont_index != 1 AND ml_spam_score = 0`	ml_spam_score=0
Canonical	PASS	`meta_canonical IS NULL OR = '' OR = src_unparsed`	Not set

Page Details

Property	Value
URL	https://go.drugbank.com/drugs/DB01065
Last Crawled	2026-03-05 03:25:32 (1 month ago)
First Indexed	2020-09-18 02:47:43 (5 years ago)
HTTP Status Code	200
Meta Title	Melatonin: Uses, Interactions, Mechanism of Action \| DrugBank
Meta Description	Melatonin is an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement.
Meta Canonical	null
Boilerpipe Text	Description A naturally occurring hormone that promotes sleep. Description A naturally occurring hormone that promotes sleep. DrugBank ID DB01065 Modality Small Molecule Clinical Trials Phase 0 8 Phase 1 62 Phase 2 141 Phase 3 80 Phase 4 59 Summary Melatonin is an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement. Brand Names Circadin, Melatonin Neurim, Slenyto Generic Name Melatonin DrugBank Accession Number DB01065 Background Melatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and lowering the body temperature. Melatonin is also implicated in the regulation of mood, learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders (ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers. Modality Small Molecule Groups Approved, Investigational, Nutraceutical, Vet approved Structure Weight Average: 232.2783 Monoisotopic: 232.121177766 Chemical Formula C 13 H 16 N 2 O 2 Synonyms 5-methoxy-N-acetyl tryptamine 5-methoxy-N-acetyltryptamine Melatonin Melatonina Mélatonine N-[2-(5-methoxyindol-3-yl)ethyl]acetamide N-Acetyl-5-methoxytryptamine External IDs BCI-049 J5.258B NPC-15 NSC-113928 NSC-56423 Indication Used orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. Evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. It has received FDA orphan drug status as an oral medication for this use. A number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. It appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. It may also improve secondary insomnia associated with various sleep-wake cycle disturbances. Other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (DSPS), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with IL-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders. Reduce drug development failure rates Build, train, & validate machine-learning models with evidence-based and structured datasets. See how Build, train, & validate predictive machine-learning models with structured datasets. See how Associated Conditions Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Insomnia •••••••••••• Used in combination to manage Insomnia Combination Product in combination with: Valerian (DB13196) , gamma-Aminobutyric acid (DB02530) •••••••••••• Pharmacodynamics Melatonin is a hormone normally produced in the pineal gland and released into the blood. The essential amino acid L-tryptophan is a precursor in the synthesis of melatonin. It helps regulate sleep-wake cycles or the circadian rhythm. Production of melatonin is stimulated by darkness and inhibited by light. High levels of melatonin induce sleep and so consumption of the drug can be used to combat insomnia and jet lag. MT1 and MT2 receptors may be a target for the treatment of circadian and non circadian sleep disorders because of their differences in pharmacology and function within the SCN. SCN is responsible for maintaining the 24 hour cycle which regulates many different body functions ranging from sleep to immune functions Mechanism of action Melatonin is a derivative of tryptophan. It binds to melatonin receptor type 1A, which then acts on adenylate cylcase and the inhibition of a cAMP signal transduction pathway. Melatonin not only inhibits adenylate cyclase, but it also activates phosphilpase C. This potentiates the release of arachidonate. By binding to melatonin receptors 1 and 2, the downstream signallling cascades have various effects in the body. The melatonin receptors are G protein-coupled receptors and are expressed in various tissues of the body. There are two subtypes of the receptor in humans, melatonin receptor 1 (MT1) and melatonin receptor 2 (MT2). Melatonin and melatonin receptor agonists, on market or in clinical trials, all bind to and activate both receptor types.The binding of the agonists to the receptors has been investigated for over two decades or since 1986. It is somewhat known, but still not fully understood. When melatonin receptor agonists bind to and activate their receptors it causes numerous physiological processes. MT1 receptors are expressed in many regions of the central nervous system (CNS): suprachiasmatic nucleus of the hypothalamus (SNC), hippocampus, substantia nigra, cerebellum, central dopaminergic pathways, ventral tegmental area and nucleus accumbens. MT1 is also expressed in the retina, ovary, testis, mammary gland, coronary circulation and aorta, gallbladder, liver, kidney, skin and the immune system. MT2 receptors are expressed mainly in the CNS, also in the lung, cardiac, coronary and aortic tissue, myometrium and granulosa cells, immune cells, duodenum and adipocytes. The binding of melatonin to melatonin receptors activates a few signaling pathways. MT1 receptor activation inhibits the adenylyl cyclase and its inhibition causes a rippling effect of non activation; starting with decreasing formation of cyclic adenosine monophosphate (cAMP), and then progressing to less protein kinase A (PKA) activity, which in turn hinders the phosphorilation of cAMP responsive element-binding protein (CREB binding protein) into P-CREB. MT1 receptors also activate phospholipase C (PLC), affect ion channels and regulate ion flux inside the cell. The binding of melatonin to MT2 receptors inhibits adenylyl cyclase which decreases the formation of cAMP.[4] As well it hinders guanylyl cyclase and therefore the forming of cyclic guanosine monophosphate (cGMP). Binding to MT2 receptors probably affects PLC which increases protein kinase C (PKC) activity. Activation of the receptor can lead to ion flux inside the cell. Target Actions Organism A Melatonin receptor type 1A agonist Humans A Melatonin receptor type 1B agonist Humans A Ribosyldihydronicotinamide dehydrogenase [quinone] inhibitor Humans U Estrogen receptor antagonist Humans U Nuclear receptor ROR-beta agonist Humans U Myeloperoxidase inhibitor Humans U Eosinophil peroxidase inhibitor Humans U Calreticulin modulator Humans U Calmodulin antagonist Humans Absorption The absorption and bioavailability of melatonin varies widely. Volume of distribution Not Available Protein binding n/a Metabolism Hepatically metabolized to at least 14 identified metabolites (identified in mouse urine): 6-hydroxymelatonin glucuronide, 6-hydroxymelatonin sulfate, N-acetylserotonin glucuronide, N-acetylserotonin sulfate, 6-hydroxymelatonin, 2-oxomelatonin, 3-hydroxymelatonin, melatonin glucuronide, cyclic melatonin, cyclic N-acetylserotonin glucuronide, cyclic 6-hydroxymelatonin, 5-hydroxyindole-3-acetaldehyde, di-hydroxymelatonin and its glucuronide conjugate. 6-Hydroxymelatonin glucuronide is the major metabolite found in mouse urine (65-88% of total melatonin metabolites in urine). Hover over products below to view reaction partners Route of elimination Not Available Half-life 35 to 50 minutes Clearance Not Available Toxicity Generally well-tolerated when taken orally. The most common side effects, day-time drowsiness, headache and dizziness, appear to occur at the same frequency as with placebo. Other reported side effects include transient depressive symptoms, mild tremor, mild anxiety, abdominal cramps, irritability, reduced alertness, confusion, nausea, vomiting, and hypotension. Safety in Adults: Evidence indicates that it is likely safe to use in oral and parenteral forms for up to two months when used appropriately. Some evidence indicates that it can be safely used orally for up to 9 months in some patients. It is also likely safe to use topically when used appropriately. Safety in Children: Melatonin appeared to be used safely in small numbers of children enrolled in short-term clinical trials. However, concerns regarding safety in children have arisen based on their developmental state. Compared to adults over 20 years of age, people under 20 produce high levels of melatonin. Melatonin levels are inversely related to gonadal development and it is thought that exogenous administration of melatonin may adversely affect gonadal development. Safety during Pregnancy: High doses of melatonin administered orally or parenterally may inhibit ovulation. Not advised for use in individuals who are pregnant or trying to become pregnant. Safety during Lactation: Not recommended as safety has not be established. Oral, rat: LD 50 ≥3200 mg/kg Pathways Pathway Category Tryptophan Metabolism Metabolic Pharmacogenomic Effects/ADRs Not Available Drug Interactions This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist. Approved Vet approved Nutraceutical Illicit Withdrawn Investigational Experimental All Drugs Drug Interaction Integrate drug-drug interactions in your software 1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Melatonin is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Melatonin can be increased when it is combined with Abametapir. Abatacept The metabolism of Melatonin can be increased when combined with Abatacept. Abiraterone The serum concentration of Melatonin can be increased when it is combined with Abiraterone. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Melatonin. Food Interactions Avoid alcohol. Ingesting alcohol may reduce the effects of melatonin. Take after a meal. Administration of melatonin after eating slows the absorption and reduces the Cmax of melatonin. International/Other Brands Mela-T (Alacer Corp. (Canada)) / Melatol (Elisium (Argentina)) / Melatonin (Biomed International Products Corp., Nutravite Pharmaceuticals (2008) Inc., Viva Pharmaceutical Inc., Kripps Pharmacy Ltd., SunOpta Inc.) / Nature'S Harmony (SunOpta Inc. (Canada)) / Revital Melatonin (Chin Tai Ginseng Co., Ltd (Canada)) / Rx Balance (SunOpta Inc. (Canada)) / Sleep Right (SunOpta Inc. (Canada)) / Vivitas (SunOpta Inc. (Canada)) Brand Name Prescription Products Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Melatol Liquid 1 mg/30mL Oral PureTek Corporation 2024-10-17 Not applicable Circadin Tablet, extended release 2 mg Oral Rad Neurim Pharmaceuticals Eec Sarl 2016-09-08 Not applicable Circadin Tablet, extended release 2 mg Oral Rad Neurim Pharmaceuticals Eec Sarl 2016-09-08 Not applicable Circadin Tablet, extended release 2 mg Oral Rad Neurim Pharmaceuticals Eec Sarl 2016-09-08 Not applicable Circadin Tablet, extended release 2 mg Oral Rad Neurim Pharmaceuticals Eec Sarl 2016-09-08 Not applicable Over the Counter Products Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Essential Oil Oil 2.5 mg/10mL Cutaneous Shantou Youjia E-Commerce Co., Ltd. 2024-02-01 2024-12-31 Unapproved/Other Products Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Medi-doze Rx Sleep Aid Melatonin (6 mg/1) + Valerian (50 mg/1) + gamma-Aminobutyric acid (30 mg/1) Tablet Oral Two Hip Consulting, Llc 2013-02-20 2016-04-11 Melatol Melatonin (1 mg/30mL) Liquid Oral PureTek Corporation 2024-10-17 Not applicable Drug Categories Amines Antioxidants Biogenic Amines Biogenic Monoamines Biological Factors Central Nervous System Agents Central Nervous System Depressants Compounds used in a research, industrial, or household setting Cytochrome P-450 CYP1A1 Substrates Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 Substrates Heterocyclic Compounds, Fused-Ring Hormones Hormones, Hormone Substitutes, and Hormone Antagonists Hypnotics and Sedatives Indoles Melatonin Receptor Agonists Melatonin, agonists Nervous System OAT3/SLC22A8 Inhibitors Protective Agents Psycholeptics Tryptamines Affected organisms Humans and other mammals UNII JL5DK93RCL CAS number 73-31-4 InChI Key DRLFMBDRBRZALE-UHFFFAOYSA-N InChI InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16) IUPAC Name N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide SMILES COC1=CC2=C(NC=C2CCNC(C)=O)C=C1 Synthesis Reference Robert A. S. Welch, Keith Betteridge, "Method of stimulating cashmere growth on cashmere-producing goats using melatonin." U.S. Patent US4855313, issued August, 1986. US4855313 General References Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [ Article ] Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. [ Article ] Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. [ Article ] Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. [ Article ] Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210/en.2007-1412. Epub 2008 Jan 10. [ Article ] Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. [ Article ] PDB Entries 2qwx / 2qx4 / 2qx6 / 4qog / 4qoi / 5i8f / 5mxb / 5mxw / 6tr5 Clinical Trials Clinical Trial & Rare Diseases Add-on Data Package Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe. View sample data Not Available Active Not Recruiting Prevention Oral Lichen Planus 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Psychosis / Schizophrenia Disorders / Schizophrenias 1 somestatus stop reason just information to hide Not Available Completed Not Available Insomnia 1 somestatus stop reason just information to hide Not Available Completed Not Available Postoperative Delirium (POD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Postoperative pain 1 somestatus stop reason just information to hide Manufacturers Not Available Packagers Mason Distributors Medisca Inc. National Vitamin Company Physiologics Rugby Laboratories Dosage Forms Form Route Strength Capsule Not applicable 10 mg/1 Capsule Oral 5.00000 mg Capsule, coated Oral 3 mg Capsule, liquid filled Oral 3 mg Chewable gel Oral 2.5 mg/1 Liquid Oral 1 mg/4mL Liquid Oral 1 mg/30mL Oil Cutaneous 2.5 mg/10mL Solution Oral 1 mg/ml Solution / drops Oral 1 mg/1mL Tablet Not applicable 10 mg/1 Tablet Oral Tablet Oral 0.5 mg Tablet Oral 1 mg Tablet Oral 1.500 mg Tablet Oral 2 mg Tablet Oral 3 mg/1 Tablet Oral 3 MG Tablet Oral 4 mg Tablet Oral 5 MG Tablet Oral 5 mg/1 Tablet Sublingual 3.000 mg Tablet, chewable Oral 2.5 mg/1 Tablet, extended release Oral 1 MG Tablet, extended release Oral 2 mg Tablet, extended release Oral 5 MG Tablet, film coated Oral 3 mg Tablet, film coated Oral 5 mg Prices Unit description Cost Unit Melatonin powder 45.6USD g Melatonin 3 mg tablet 0.22USD tablet Melatonin 5 mg tablet 0.12USD tablet Melatonin 5 mg tablet sl 0.1USD tablet Melatonin sublingual tablet 0.09USD tablet Melatonin 1 mg tablet 0.03USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only. Patents Not Available State Solid Experimental Properties Property Value Source melting point (°C) 117 °C PhysProp logP 1.6 Not Available Predicted Properties Property Value Source Water Solubility 0.143 mg/mL ALOGPS logP 1.42 ALOGPS logP 1.15 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 15.8 Chemaxon pKa (Strongest Basic) -1.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 54.12 Å 2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 66.28 m 3 ·mol -1 Chemaxon Polarizability 25.65 Å 3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon Predicted ADMET Features Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9928 Caco-2 permeable - 0.5536 P-glycoprotein substrate Substrate 0.6188 P-glycoprotein inhibitor I Non-inhibitor 0.9569 P-glycoprotein inhibitor II Non-inhibitor 0.6838 Renal organic cation transporter Non-inhibitor 0.542 CYP450 2C9 substrate Non-substrate 0.8231 CYP450 2D6 substrate Substrate 0.5062 CYP450 3A4 substrate Substrate 0.6505 CYP450 1A2 substrate Inhibitor 0.9304 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8084 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.7194 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6803 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9498 Biodegradation Not ready biodegradable 0.8764 Rat acute toxicity 1.8922 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9631 hERG inhibition (predictor II) Non-inhibitor 0.5124 ADMET data is predicted using admetSAR , a free tool for evaluating chemical ADMET properties. ( 23092397 ) Mass Spec (NIST) Download (8.2 KB) Spectra Spectrum Spectrum Type Splash Key GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) GC-MS splash10-001i-0490000000-aa93967315af900a76ce GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) GC-MS splash10-03k9-0900000000-a15ee6def3f8d75b1231 GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) GC-MS splash10-001j-0490000000-94ef1be9ab930060778a GC-MS Spectrum - GC-MS (2 TMS) GC-MS splash10-001i-1490000000-03e24298c7bd1ed4066a Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0076-4920000000-a8d9d614e9f8769a1359 GC-MS Spectrum - GC-MS GC-MS splash10-001i-1490000000-03e24298c7bd1ed4066a GC-MS Spectrum - GC-EI-TOF GC-MS splash10-001j-0590000000-63d5e32dd5f7877a4402 GC-MS Spectrum - GC-EI-TOF GC-MS splash10-001i-0590000000-52b3a733f8b49582d3fb GC-MS Spectrum - GC-EI-TOF GC-MS splash10-0229-1900000000-d81c6f617bc486066136 Mass Spectrum (Electron Ionization) MS splash10-03k9-1900000000-45ee4fdc7acdb33dad3b MS/MS Spectrum - Quattro_QQQ 10V, Positive LC-MS/MS splash10-00di-0920000000-f90ec9b77e1a245e35a8 MS/MS Spectrum - Quattro_QQQ 25V, Positive LC-MS/MS splash10-05fr-0900000000-49e4482c65e82ac64b66 MS/MS Spectrum - Quattro_QQQ 40V, Positive LC-MS/MS splash10-003r-0900000000-8a4ae0fd610cca992d74 LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative LC-MS/MS splash10-0159-0090000000-939a1caf5760c0ba189c LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative LC-MS/MS splash10-0006-0930000000-9e6fcea2c634ac9d85a0 LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative LC-MS/MS splash10-0006-0900000000-ddd29e731a7de56c1808 LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative LC-MS/MS splash10-0006-0900000000-34b4fb52810a15ea5bd6 LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative LC-MS/MS splash10-001i-0090000000-5ca2df63ec2baefdae8c LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive LC-MS/MS splash10-001i-0190000000-5bae6e63e9b40e60e0a4 LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive LC-MS/MS splash10-00di-0900000000-529bf6d5c2091993f865 LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive LC-MS/MS splash10-00di-0900000000-158a60fe696120b23b41 LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive LC-MS/MS splash10-0a5c-0900000000-5e86b2de659ce47762c0 LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive LC-MS/MS splash10-001i-0900000000-881c0d57239d56c46f2d LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive LC-MS/MS splash10-00di-0910000000-f256f78adbcbeb2464de LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive LC-MS/MS splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23 MS/MS Spectrum - DI-ESI-qTof , Positive LC-MS/MS splash10-05fr-0900000000-7acf9405f4beeb34566c MS/MS Spectrum - DI-ESI-qTof , Positive LC-MS/MS splash10-00di-0900000000-13245183cd8c8cd511c3 LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS splash10-05ai-2900000000-07b3d32f002dba733c10 LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-0159-0090000000-939a1caf5760c0ba189c LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-0006-0930000000-9e6fcea2c634ac9d85a0 LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-0006-0900000000-ddd29e731a7de56c1808 LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-0006-0900000000-34b4fb52810a15ea5bd6 LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-001i-0090000000-5ca2df63ec2baefdae8c LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-00lr-0090000000-3c42f6997539afb44682 LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-014m-0960000000-7991e64dacb3c7f5cf32 LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-0006-0900000000-882be43bc196e928a3cf MS/MS Spectrum - , negative LC-MS/MS splash10-014i-0190000000-ddda9232f0e8e1b402f7 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-001i-0190000000-5bae6e63e9b40e60e0a4 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-00di-0900000000-529bf6d5c2091993f865 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-00di-0900000000-158a60fe696120b23b41 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-0a5c-0900000000-5e86b2de659ce47762c0 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-001i-0900000000-881c0d57239d56c46f2d LC-MS/MS Spectrum - LC-ESI-IT , positive LC-MS/MS splash10-00di-0910000000-d659c749adcab685e8bb LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-00di-0900000000-6817d8039761a9058337 LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-00di-0900000000-349d5a97e2406d0db910 LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-001i-0900000000-9e30dcf47c9eca14650e MS/MS Spectrum - , positive LC-MS/MS splash10-00di-1900000000-73dc69b26b1fba60f253 MS/MS Spectrum - , positive LC-MS/MS splash10-05ai-2900000000-07b3d32f002dba733c10 MS/MS Spectrum - , positive LC-MS/MS splash10-00di-0900000000-2e847095e37f4ffe7c8b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0089-0960000000-9acd48062f28a100f9da Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-5790000000-571ee430d2b0391822e3 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0900000000-1a38178248f05cf91e65 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-9000000000-9950a9dee5e36e935714 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-006x-0900000000-5d47768c1bb474f51f38 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-4900000000-9374ee5bf5eb87317f56 1H NMR Spectrum 1D NMR Not Applicable 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable [1H,13C] 2D NMR Spectrum 2D NMR Not Applicable Chromatographic Properties Collision Cross Sections (CCS) Adduct CCS Value (Å 2 ) Source type Source [M-H]- 159.6858961 predicted DarkChem Lite v0.1.0 [M-H]- 152.8346632 predicted DarkChem Standard v0.1.0 [M-H]- 152.9149983 predicted DarkChem Lite v0.1.0 [M-H]- 165.2831961 predicted DarkChem Lite v0.1.0 [M-H]- 159.7026961 predicted DarkChem Lite v0.1.0 [M-H]- 150.02837 predicted DeepCCS 1.0 (2019) [M+H]+ 159.1911961 predicted DarkChem Lite v0.1.0 [M+H]+ 157.166152 predicted DarkChem Standard v0.1.0 [M+H]+ 157.1763686 predicted DarkChem Lite v0.1.0 [M+H]+ 166.2821961 predicted DarkChem Lite v0.1.0 [M+H]+ 159.7927961 predicted DarkChem Lite v0.1.0 [M+H]+ 152.38637 predicted DeepCCS 1.0 (2019) [M+Na]+ 158.6747961 predicted DarkChem Lite v0.1.0 [M+Na]+ 165.6858961 predicted DarkChem Lite v0.1.0 [M+Na]+ 167.0242025 predicted DarkChem Lite v0.1.0 [M+Na]+ 165.6891961 predicted DarkChem Lite v0.1.0 [M+Na]+ 159.5635961 predicted DarkChem Lite v0.1.0 [M+Na]+ 158.4795 predicted DeepCCS 1.0 (2019) Targets Build, predict & validate machine-learning models Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research. Learn more Use our structured and evidence-based datasets to unlock new insights and accelerate drug research. Learn more Kind Protein Organism Humans Pharmacological action Yes Actions Agonist General Function High affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity. Possibly involved in sleep induction, by melatonin activation of the potassium channel KCNMA1/BK and the dissociation of G-beta and G-gamma subunits, thereby decreasing synaptic transmission (By similarity) Specific Function G protein-coupled receptor activity Gene Name MTNR1A Uniprot ID P48039 Uniprot Name Melatonin receptor type 1A Molecular Weight 39374.315 Da References Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [ Article ] Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [ Article ] Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [ Article ] Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. [ Article ] Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007/s12325-010-0065-y. Epub 2010 Sep 6. [ Article ] Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016/j.bmc.2010.06.100. Epub 2010 Jul 3. [ Article ] Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210/en.2009-0710. Epub 2009 Dec 4. [ Article ] Witt-Enderby PA, Chu GH, Gillen ML, Li PK: Development of a high-affinity ligand that binds irreversibly to Mel1b melatonin receptors. J Med Chem. 1997 Dec 19;40(26):4195-8. [ Article ] Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. [ Article ] Hoashi Y, Takai T, Kosugi Y, Nakashima M, Nakayama M, Hirai K, Uchikawa O, Koike T: Discovery of a Potent and Orally Bioavailable Melatonin Receptor Agonist. J Med Chem. 2021 Mar 25;64(6):3059-3074. doi: 10.1021/acs.jmedchem.0c01836. Epub 2021 Mar 7. [ Article ] Gunia-Krzyzak A, Zelaszczyk D, Rapacz A, Zeslawska E, Waszkielewicz AM, Panczyk K, Sloczynska K, Pekala E, Nitek W, Filipek B, Marona H: Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH(3) or 2-CH(3). Bioorg Med Chem. 2017 Jan 15;25(2):471-482. doi: 10.1016/j.bmc.2016.11.014. Epub 2016 Nov 11. [ Article ] Kind Protein Organism Humans Pharmacological action Yes Actions Agonist General Function High affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity Specific Function G protein-coupled receptor activity Gene Name MTNR1B Uniprot ID P49286 Uniprot Name Melatonin receptor type 1B Molecular Weight 40187.895 Da References Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [ Article ] Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [ Article ] Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. [ Article ] Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007/s12325-010-0065-y. Epub 2010 Sep 6. [ Article ] Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016/j.bmc.2010.06.100. Epub 2010 Jul 3. [ Article ] Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210/en.2009-0710. Epub 2009 Dec 4. [ Article ] Mattson RJ, Catt JD, Keavy D, Sloan CP, Epperson J, Gao Q, Hodges DB, Iben L, Mahle CD, Ryan E, Yocca FD: Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett. 2003 Mar 24;13(6):1199-202. [ Article ] Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. [ Article ] Ferreira MA Jr, Azevedo H, Mascarello A, Segretti ND, Russo E, Russo V, Guimaraes CRW: Discovery of ACH-000143: A Novel Potent and Peripherally Preferred Melatonin Receptor Agonist that Reduces Liver Triglycerides and Steatosis in Diet-Induced Obese Rats. J Med Chem. 2021 Feb 25;64(4):1904-1929. doi: 10.1021/acs.jmedchem.0c00627. Epub 2021 Feb 8. [ Article ] Kind Protein Organism Humans Pharmacological action Yes Actions Inhibitor General Function The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis Specific Function chloride ion binding Gene Name NQO2 Uniprot ID P16083 Uniprot Name Ribosyldihydronicotinamide dehydrogenase [quinone] Molecular Weight 25918.4 Da References Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [ Article ] Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [ Article ] Fukatsu K, Uchikawa O, Kawada M, Yamano T, Yamashita M, Kato K, Hirai K, Hinuma S, Miyamoto M, Ohkawa S: Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists. J Med Chem. 2002 Sep 12;45(19):4212-21. doi: 10.1021/jm020114g. [ Article ] Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. [ Article ] Du H, Wang J, Zhang X, Hu Z: A novel quantitative structure-activity relationship method to predict the affinities of MT3 melatonin binding site. Eur J Med Chem. 2008 Dec;43(12):2861-9. doi: 10.1016/j.ejmech.2008.02.012. Epub 2008 Feb 29. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Antagonist General Function Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity) Specific Function 14-3-3 protein binding Gene Name ESR1 Uniprot ID P03372 Uniprot Name Estrogen receptor Molecular Weight 66215.45 Da References del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. [ Article ] Yoo YM, Jeung EB: Melatonin-induced estrogen receptor alpha-mediated calbindin-D9k expression plays a role in H2O2-mediated cell death in rat pituitary GH3 cells. J Pineal Res. 2009 Nov;47(4):301-7. doi: 10.1111/j.1600-079X.2009.00714.x. Epub 2009 Oct 1. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Agonist General Function Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity) Specific Function DNA-binding transcription activator activity, RNA polymerase II-specific Gene Name RORB Uniprot ID Q92753 Uniprot Name Nuclear receptor ROR-beta Molecular Weight 53219.385 Da References Becker-Andre M, Wiesenberg I, Schaeren-Wiemers N, Andre E, Missbach M, Saurat JH, Carlberg C: Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily. J Biol Chem. 1994 Nov 18;269(46):28531-4. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971) Specific Function chromatin binding Gene Name MPO Uniprot ID P05164 Uniprot Name Myeloperoxidase Molecular Weight 83867.71 Da References Galijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021/bi702016q. Epub 2008 Feb 1. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis Specific Function heme binding Gene Name EPX Uniprot ID P11678 Uniprot Name Eosinophil peroxidase Molecular Weight 81039.5 Da References Lu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038/bjp.2008.173. Epub 2008 Jun 2. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Modulator General Function Calcium-binding chaperone that promotes folding, oligomeric assembly and quality control in the endoplasmic reticulum (ER) via the calreticulin/calnexin cycle. This lectin interacts transiently with almost all of the monoglucosylated glycoproteins that are synthesized in the ER (PubMed:7876246). Interacts with the DNA-binding domain of NR3C1 and mediates its nuclear export (PubMed:11149926). Involved in maternal gene expression regulation. May participate in oocyte maturation via the regulation of calcium homeostasis (By similarity). Present in the cortical granules of non-activated oocytes, is exocytosed during the cortical reaction in response to oocyte activation and might participate in the block to polyspermy (By similarity) Specific Function calcium ion binding Gene Name CALR Uniprot ID P27797 Uniprot Name Calreticulin Molecular Weight 48141.2 Da References Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. [ Article ] Macias M, Escames G, Leon J, Coto A, Sbihi Y, Osuna A, Acuna-Castroviejo D: Calreticulin-melatonin. An unexpected relationship. Eur J Biochem. 2003 Mar;270(5):832-40. [ Article ] Kind Protein group Organism Humans Pharmacological action Unknown Actions Antagonist General Function Calmodulin acts as part of a calcium signal transduction pathway by mediating the control of a large number of enzymes, ion channels, aquaporins and other proteins through calcium-binding (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Calcium-binding is required for the activation of calmodulin (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Among the enzymes to be stimulated by the calmodulin-calcium complex are a number of protein kinases, such as myosin light-chain kinases and calmodulin-dependent protein kinase type II (CaMK2), and phosphatases (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis (PubMed:16760425). Is a regulator of voltage-dependent L-type calcium channels (PubMed:31454269). Mediates calcium-dependent inactivation of CACNA1C (PubMed:26969752). Positively regulates calcium-activated potassium channel activity of KCNN2 (PubMed:27165696). Forms a potassium channel complex with KCNQ1 and regulates electrophysiological activity of the channel via calcium-binding (PubMed:25441029). Acts as a sensor to modulate the endoplasmic reticulum contacts with other organelles mediated by VMP1:ATP2A2 (PubMed:28890335) Specific Function adenylate cyclase activator activity Components: Name UniProt ID Calmodulin-1 P0DP23 Calmodulin-2 P0DP24 Calmodulin-3 P0DP25 References del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. [ Article ] Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [ Article ] Enzymes Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate Inhibitor General Function A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195) Specific Function arachidonate monooxygenase activity Gene Name CYP1A1 Uniprot ID P04798 Uniprot Name Cytochrome P450 1A1 Molecular Weight 58164.815 Da References Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [ Article ] Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [ Article ] Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. [ Article ] Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable) Specific Function caffeine oxidase activity Gene Name CYP1A2 Uniprot ID P05177 Uniprot Name Cytochrome P450 1A2 Molecular Weight 58406.915 Da References Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [ Article ] Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [ Article ] Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. [ Article ] Hartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. [ Article ] Hartter S, Wang X, Weigmann H, Friedberg T, Arand M, Oesch F, Hiemke C: Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin. J Clin Psychopharmacol. 2001 Apr;21(2):167-74. [ Article ] Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. [ Article ] Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate Inhibitor General Function A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity) Specific Function estrogen 16-alpha-hydroxylase activity Gene Name CYP1B1 Uniprot ID Q16678 Uniprot Name Cytochrome P450 1B1 Molecular Weight 60845.33 Da References Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [ Article ] Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [ Article ] Yu Z, Tian X, Peng Y, Sun Z, Wang C, Tang N, Li B, Jian Y, Wang W, Huo X, Ma X: Mitochondrial cytochrome P450 (CYP) 1B1 is responsible for melatonin-induced apoptosis in neural cancer cells. J Pineal Res. 2018 Aug;65(1):e12478. doi: 10.1111/jpi.12478. Epub 2018 Mar 25. [ Article ] Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. [ Article ] Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307) Specific Function (R)-limonene 6-monooxygenase activity Gene Name CYP2C19 Uniprot ID P33261 Uniprot Name Cytochrome P450 2C19 Molecular Weight 55944.565 Da References Huuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. [ Article ] Facciola G, Hidestrand M, von Bahr C, Tybring G: Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes. Eur J Clin Pharmacol. 2001 Mar;56(12):881-8. doi: 10.1007/s002280000245. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031) Specific Function (R)-limonene 6-monooxygenase activity Gene Name CYP2C9 Uniprot ID P11712 Uniprot Name Cytochrome P450 2C9 Molecular Weight 55627.365 Da References Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function Catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine) Specific Function acetylserotonin O-methyltransferase activity Gene Name ASMT Uniprot ID P46597 Uniprot Name Acetylserotonin O-methyltransferase Molecular Weight 38452.51 Da References Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function Catalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, contributing to maintain homeostasis by preventing autoimmunity or immunopathology that would result from uncontrolled and overreacting immune responses (PubMed:25691885). Tryptophan shortage inhibits T lymphocytes division and accumulation of tryptophan catabolites induces T-cell apoptosis and differentiation of regulatory T-cells (PubMed:25691885). Acts as a suppressor of anti-tumor immunity (PubMed:14502282, PubMed:23103127, PubMed:25157255, PubMed:25691885). Limits the growth of intracellular pathogens by depriving tryptophan (PubMed:25691885). Protects the fetus from maternal immune rejection (PubMed:25691885) Specific Function electron transfer activity Gene Name IDO1 Uniprot ID P14902 Uniprot Name Indoleamine 2,3-dioxygenase 1 Molecular Weight 45325.89 Da References Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate Inhibitor General Function Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971) Specific Function chromatin binding Gene Name MPO Uniprot ID P05164 Uniprot Name Myeloperoxidase Molecular Weight 83867.71 Da References Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [ Article ] Galijasevic S: The development of myeloperoxidase inhibitors. Bioorg Med Chem Lett. 2019 Jan 1;29(1):1-7. doi: 10.1016/j.bmcl.2018.11.031. Epub 2018 Nov 15. [ Article ] Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. [ Article ] Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874) Specific Function aromatase activity Gene Name CYP19A1 Uniprot ID P11511 Uniprot Name Aromatase Molecular Weight 57882.48 Da References Gonzalez A, Martinez-Campa C, Mediavilla MD, Alonso-Gonzalez C, Sanchez-Mateos S, Hill SM, Sanchez-Barcelo EJ, Cos S: Effects of MT1 melatonin receptor overexpression on the aromatase-suppressive effect of melatonin in MCF-7 human breast cancer cells. Oncol Rep. 2007 Apr;17(4):947-53. doi: 10.3892/or.17.4.947. [ Article ] Transporters Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity) Specific Function organic anion transmembrane transporter activity Gene Name SLC22A8 Uniprot ID Q8TCC7 Uniprot Name Organic anion transporter 3 Molecular Weight 59855.585 Da References Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [ Article ] Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [ Article ]
Markdown	[Accelerate decision confidence with proactive biopharma intelligence Discover How](https://go.drugbank.com/product_tour) [Log in](https://go.drugbank.com/public_users/log_in) - [Explore](https://go.drugbank.com/drugs/DB01065) [Drug Knowledgebase Start here! Dig into essential drug information](https://go.drugbank.com/drugs) [Interaction Checker Check interactions in up to 5 drugs at a time](https://go.drugbank.com/drug-interaction-checker) Advanced Exploration - [Categories & ATC Classifications](https://go.drugbank.com/categories) - [Pathways](https://go.drugbank.com/pathways) - [Drug Reactions](https://go.drugbank.com/reactions) - [Drug Classification](https://go.drugbank.com/classyfication) - [Drug Targets](https://go.drugbank.com/targets) - [Advanced Search](https://go.drugbank.com/unearth/advanced/drugs) - [Target Sequence](https://go.drugbank.com/structures/search/bonds/sequence) - [Spectra Search](https://go.drugbank.com/spectra/ms/search) - [Pharmaco-omics](https://go.drugbank.com/pharmaco/search) - [Chemical Structure](https://go.drugbank.com/structures/search/small_molecule_drugs/structure) - [For Drug Discovery](https://go.drugbank.com/drugs/DB01065) [Products Biopharma Intelligence Operating System Enable critical research decisions using AI‑powered intelligence.](https://go.drugbank.com/product_tour) [Use Case Drug Discovery & Repurposing Access detailed drug and target data for your pharmaceutical research.](https://go.drugbank.com/use_cases/ml_drug_discovery_repurposing) [Products Data Library Explore detailed drug information packages to support your research & drug discovery.](https://go.drugbank.com/data_packages) [![Snowflake](https://go.drugbank.com/assets/snowflake-64d406433cc6454a57e1fbb945b310dbe7ed1bc795123729e029c38b072854ed.svg)Products Data access in Snowflake Increase scalability & security by streamlining data sharing & analysis in the cloud.](https://app.snowflake.com/marketplace/providers/GZTYZJ6Q7UU/DrugBank) - [For Clinical Software](https://go.drugbank.com/drugs/DB01065) [Products Clinical Intelligence API Learn about our seamless integration into healthcare software.](https://go.drugbank.com/clinical) [Use Case Telehealth Power your remote care software.](https://go.drugbank.com/use_cases/telehealth) [Use Case Electronic Medical Records Empower providers with reliable drug information.](https://go.drugbank.com/use_cases/electronic_medical_records) Learn more about API Features - [Drug Search](https://go.drugbank.com/clinical/drug_search) - [Drug-Drug Interaction Checker](https://go.drugbank.com/clinical/drug_drug_interaction_checker) - [Drug Allergy](https://go.drugbank.com/clinical/drug_allergy) - [US Drug Labels](https://go.drugbank.com/clinical/us_drug_labels) - [For Academic Research](https://go.drugbank.com/releases/latest) - [Resources](https://go.drugbank.com/drugs/DB01065) Company - [About Us](https://go.drugbank.com/about) - [Newsroom](https://go.drugbank.com/press) - [Careers](https://drugbank.bamboohr.com/careers) Learn More - [Help Center](https://dev.drugbank.com/guides/index) - [Blog](https://blog.drugbank.com/) - [E-Books & Webinars](https://go.drugbank.com/resources) - [Customer Stories](https://go.drugbank.com/customers) - [Book a Demo](https://go.drugbank.com/contact/sales) - [Log in](https://go.drugbank.com/public_users/log_in) [Ask AI](https://go.drugbank.com/product_tour) Log in or create an account for full access to this data. [Create Account](https://go.drugbank.com/public_users/sign_up) [Log in](https://go.drugbank.com/public_users/log_in) [NAV](https://go.drugbank.com/drugs/DB01065) [Identification](https://go.drugbank.com/drugs/DB01065#identification-header) [Summary](https://go.drugbank.com/drugs/DB01065#summary)[Brand Names](https://go.drugbank.com/drugs/DB01065#brand-names)[Name](https://go.drugbank.com/drugs/DB01065#name)[Accession Number](https://go.drugbank.com/drugs/DB01065#accession-number)[Background](https://go.drugbank.com/drugs/DB01065#background)[Modality](https://go.drugbank.com/drugs/DB01065#modality)[Groups](https://go.drugbank.com/drugs/DB01065#groups)[Structure](https://go.drugbank.com/drugs/DB01065#structure)[Weight](https://go.drugbank.com/drugs/DB01065#weight)[Chemical Formula](https://go.drugbank.com/drugs/DB01065#chemical-formula)[Synonyms](https://go.drugbank.com/drugs/DB01065#synonyms)[External IDs](https://go.drugbank.com/drugs/DB01065#external-ids) [Pharmacology](https://go.drugbank.com/drugs/DB01065#pharmacology-header) [Indication](https://go.drugbank.com/drugs/DB01065#indication)[Associated Conditions](https://go.drugbank.com/drugs/DB01065#associated-conditions)[Contraindications & Blackbox Warnings](https://go.drugbank.com/drugs/DB01065#contraindications-blackbox-warnings)[Pharmacodynamics](https://go.drugbank.com/drugs/DB01065#pharmacodynamics)[Mechanism of action](https://go.drugbank.com/drugs/DB01065#mechanism-of-action)[Absorption](https://go.drugbank.com/drugs/DB01065#absorption)[Volume of distribution](https://go.drugbank.com/drugs/DB01065#volume-of-distribution)[Protein binding](https://go.drugbank.com/drugs/DB01065#protein-binding)[Metabolism](https://go.drugbank.com/drugs/DB01065#metabolism)[Route of elimination](https://go.drugbank.com/drugs/DB01065#route-of-elimination)[Half-life](https://go.drugbank.com/drugs/DB01065#half-life)[Clearance](https://go.drugbank.com/drugs/DB01065#clearance)[Adverse Effects](https://go.drugbank.com/drugs/DB01065#adverse-effects)[Toxicity](https://go.drugbank.com/drugs/DB01065#toxicity)[Pathways](https://go.drugbank.com/drugs/DB01065#pathways)[Pharmacogenomic Effects/ADRs](https://go.drugbank.com/drugs/DB01065#pharmacogenomic-effects-adrs) [Interactions](https://go.drugbank.com/drugs/DB01065#interactions-header) [Drug Interactions](https://go.drugbank.com/drugs/DB01065#drug-interactions)[Food Interactions](https://go.drugbank.com/drugs/DB01065#food-interactions) [Products](https://go.drugbank.com/drugs/DB01065#products-header) [International/Other Brands](https://go.drugbank.com/drugs/DB01065#international-other-brands)[Brand Name Prescription Products](https://go.drugbank.com/drugs/DB01065#brand-name-prescription-products)[Over the Counter Products](https://go.drugbank.com/drugs/DB01065#over-the-counter-products)[Unapproved/Other Products](https://go.drugbank.com/drugs/DB01065#unapproved-other-products) [Categories](https://go.drugbank.com/drugs/DB01065#categories-header) [ATC Codes](https://go.drugbank.com/drugs/DB01065#atc-codes)[Drug Categories](https://go.drugbank.com/drugs/DB01065#drug-categories)[Chemical Taxonomy](https://go.drugbank.com/drugs/DB01065#chemical-taxonomy)[Affected organisms](https://go.drugbank.com/drugs/DB01065#affected-organisms) [Chemical Identifiers](https://go.drugbank.com/drugs/DB01065#chemical-identifiers-header) [UNII](https://go.drugbank.com/drugs/DB01065#unii)[CAS number](https://go.drugbank.com/drugs/DB01065#cas-number)[InChI Key](https://go.drugbank.com/drugs/DB01065#inchi-key)[InChI](https://go.drugbank.com/drugs/DB01065#inchi)[IUPAC Name](https://go.drugbank.com/drugs/DB01065#iupac-name)[SMILES](https://go.drugbank.com/drugs/DB01065#smiles) [References](https://go.drugbank.com/drugs/DB01065#references-header) [Synthesis Reference](https://go.drugbank.com/drugs/DB01065#synthesis-reference)[General References](https://go.drugbank.com/drugs/DB01065#general-references)[External Links](https://go.drugbank.com/drugs/DB01065#external-links)[PDB Entries](https://go.drugbank.com/drugs/DB01065#pdb-entries)[MSDS](https://go.drugbank.com/drugs/DB01065#msds) [Clinical Trials](https://go.drugbank.com/drugs/DB01065#clinical-trials-header) [Pharmacoeconomics](https://go.drugbank.com/drugs/DB01065#pharmacoeconomics-header) [Manufacturers](https://go.drugbank.com/drugs/DB01065#manufacturers)[Packagers](https://go.drugbank.com/drugs/DB01065#packagers)[Dosage Forms](https://go.drugbank.com/drugs/DB01065#dosage-forms)[Prices](https://go.drugbank.com/drugs/DB01065#prices)[Patents](https://go.drugbank.com/drugs/DB01065#patents) [Properties](https://go.drugbank.com/drugs/DB01065#properties-header) [State](https://go.drugbank.com/drugs/DB01065#state)[Experimental Properties](https://go.drugbank.com/drugs/DB01065#experimental-properties)[Predicted Properties](https://go.drugbank.com/drugs/DB01065#predicted-properties)[Predicted ADMET Features](https://go.drugbank.com/drugs/DB01065#predicted-admet-features) [Spectra](https://go.drugbank.com/drugs/DB01065#spectra-header) [Mass Spec](https://go.drugbank.com/drugs/DB01065#mass-spec)[Spectra](https://go.drugbank.com/drugs/DB01065#spectra) [Targets (9)](https://go.drugbank.com/drugs/DB01065#targets) [Enzymes (9)](https://go.drugbank.com/drugs/DB01065#enzymes) [Transporters (1)](https://go.drugbank.com/drugs/DB01065#transporters) # Melatonin [Star](https://go.drugbank.com/public_users/log_in?record_star_accession=DB01065 "You must be signed in to star an entry") [31](https://go.drugbank.com/drugs/DB01065) [![](https://go.drugbank.com/assets/locked/AI-Chat-a64a3de153fd7ca4457e73bcec8b2358868da6c4dda160f9b4693e2d85af5a37.png) The AI Assistant built for biopharma intelligence. Access detailed, actionable insights to your most complex research questions. Leverage validated reasoning and citable data to power your critical research decisions.Learn More](https://go.drugbank.com/product_tour) [The AI Assistant built for biopharma intelligence.Learn More](https://go.drugbank.com/product_tour) ## Overview Description A naturally occurring hormone that promotes sleep. [Structure](https://go.drugbank.com/drugs/DB01065#structure) ![](https://go.drugbank.com/structures/DB01065/thumb.svg) Description A naturally occurring hormone that promotes sleep. DrugBank ID DB01065 Modality Small Molecule [Patents](https://go.drugbank.com/drugs/DB01065#patents) 0 [Indicated Conditions](https://go.drugbank.com/drugs/DB01065#indication) 1 [Clinical Trials](https://go.drugbank.com/drugs/DB01065#clinical-trials-header) Phase 0 8 Phase 1 62 Phase 2 141 Phase 3 80 Phase 4 59 Mechanism of Action - [Melatonin receptor type 1A](https://go.drugbank.com/drugs/DB01065#BE0000515) Agonist - [Melatonin receptor type 1B](https://go.drugbank.com/drugs/DB01065#BE0000327) Agonist - [Ribosyldihydronicotinamide dehydrogenase \[quinone\]](https://go.drugbank.com/drugs/DB01065#BE0000220) Inhibitor ## Identification Summary Melatonin is an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement. Brand Names Circadin, Melatonin Neurim, Slenyto Generic Name Melatonin DrugBank Accession Number DB01065 Background Melatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and lowering the body temperature. Melatonin is also implicated in the regulation of mood, learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders (ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers. Modality Small Molecule Groups Approved, Investigational, Nutraceutical, Vet approved Structure [![](https://go.drugbank.com/structures/DB01065/thumb.svg)](https://go.drugbank.com/structures/DB01065/image.svg) [3D](https://go.drugbank.com/structures/small_molecule_drugs/DB01065) Download [MOL](https://go.drugbank.com/structures/small_molecule_drugs/DB01065.mol)[SDF](https://go.drugbank.com/structures/small_molecule_drugs/DB01065.sdf)[3D-SDF](https://go.drugbank.com/structures/small_molecule_drugs/DB01065.sdf?type=3d)[PDB](https://go.drugbank.com/structures/small_molecule_drugs/DB01065.pdb)[SMILES](https://go.drugbank.com/structures/small_molecule_drugs/DB01065.smiles)[InChI](https://go.drugbank.com/structures/small_molecule_drugs/DB01065.inchi) [Similar Structures](https://go.drugbank.com/structures/search/small_molecule_drugs/structure?database_id=DB01065&search_type=similarity#results) #### Structure for Melatonin (DB01065) × ![](https://go.drugbank.com/structures/DB01065/image.svg) Close Weight Average: 232.2783 Monoisotopic: 232.121177766 Chemical Formula C13H16N2O2 Synonyms - 5-methoxy-N-acetyl tryptamine - 5-methoxy-N-acetyltryptamine - Melatonin - Melatonina - Mélatonine - N-\[2-(5-methoxyindol-3-yl)ethyl\]acetamide - N-Acetyl-5-methoxytryptamine External IDs - BCI-049 - J5.258B - NPC-15 - NSC-113928 - NSC-56423 ## Pharmacology [![](https://go.drugbank.com/assets/locked/AI-Chat-a64a3de153fd7ca4457e73bcec8b2358868da6c4dda160f9b4693e2d85af5a37.png) The AI Assistant built for biopharma intelligence. Access detailed, actionable insights to your most complex research questions. Leverage validated reasoning and citable data to power your critical research decisions.Learn More](https://go.drugbank.com/product_tour) [The AI Assistant built for biopharma intelligence.Learn More](https://go.drugbank.com/product_tour) Indication Used orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. Evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. It has received FDA orphan drug status as an oral medication for this use. A number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. It appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. It may also improve secondary insomnia associated with various sleep-wake cycle disturbances. Other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (DSPS), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with IL-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders. [![](https://go.drugbank.com/assets/locked/Pharmacology-da701df37a1a51c9ee28326cbba45e6bdeef07bce6ddf5e2eb757439eea83e8e.png) Reduce drug development failure rates Build, train, & validate machine-learning modelswith evidence-based and structured datasets.See how](https://bit.ly/3l5TIQu) [Build, train, & validate predictive machine-learning models with structured datasets.See how](https://bit.ly/3yeDgkJ) Associated Conditions \| Indication Type \| Indication \| Combined Product Details \| Approval Level \| Age Group \| Patient Characteristics \| Dose Form \| \|---\|---\|---\|---\|---\|---\|---\| \| Management of \| [Insomnia](https://go.drugbank.com/conditions/DBCOND0017531) \| \| •••••••••••• \| \| \| \| \| Used in combination to manage \| [Insomnia](https://go.drugbank.com/conditions/DBCOND0017531) \| Combination Product in combination with: [Valerian (DB13196)](https://go.drugbank.com/drugs/DB13196), [gamma-Aminobutyric acid (DB02530)](https://go.drugbank.com/drugs/DB02530) \| •••••••••••• \| \| \| \| [Create Account](https://go.drugbank.com/public_users/sign_up) Contraindications & Blackbox Warnings [![](https://go.drugbank.com/assets/locked/Contraindications-32d728a7df37129e96c82b2461211bfec263a710b0cf8adcd77a85600db2d24b.png) Prevent Adverse Drug Events Today Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Learn more](https://www.drugbank.com/clinical#add-on-modules) [Avoid life-threatening adverse drug events with our Clinical APILearn more](https://www.drugbank.com/clinical#add-on-modules) Pharmacodynamics Melatonin is a hormone normally produced in the pineal gland and released into the blood. The essential amino acid L-tryptophan is a precursor in the synthesis of melatonin. It helps regulate sleep-wake cycles or the circadian rhythm. Production of melatonin is stimulated by darkness and inhibited by light. High levels of melatonin induce sleep and so consumption of the drug can be used to combat insomnia and jet lag. MT1 and MT2 receptors may be a target for the treatment of circadian and non circadian sleep disorders because of their differences in pharmacology and function within the SCN. SCN is responsible for maintaining the 24 hour cycle which regulates many different body functions ranging from sleep to immune functions Mechanism of action Melatonin is a derivative of tryptophan. It binds to melatonin receptor type 1A, which then acts on adenylate cylcase and the inhibition of a cAMP signal transduction pathway. Melatonin not only inhibits adenylate cyclase, but it also activates phosphilpase C. This potentiates the release of arachidonate. By binding to melatonin receptors 1 and 2, the downstream signallling cascades have various effects in the body. The melatonin receptors are G protein-coupled receptors and are expressed in various tissues of the body. There are two subtypes of the receptor in humans, melatonin receptor 1 (MT1) and melatonin receptor 2 (MT2). Melatonin and melatonin receptor agonists, on market or in clinical trials, all bind to and activate both receptor types.The binding of the agonists to the receptors has been investigated for over two decades or since 1986. It is somewhat known, but still not fully understood. When melatonin receptor agonists bind to and activate their receptors it causes numerous physiological processes. MT1 receptors are expressed in many regions of the central nervous system (CNS): suprachiasmatic nucleus of the hypothalamus (SNC), hippocampus, substantia nigra, cerebellum, central dopaminergic pathways, ventral tegmental area and nucleus accumbens. MT1 is also expressed in the retina, ovary, testis, mammary gland, coronary circulation and aorta, gallbladder, liver, kidney, skin and the immune system. MT2 receptors are expressed mainly in the CNS, also in the lung, cardiac, coronary and aortic tissue, myometrium and granulosa cells, immune cells, duodenum and adipocytes. The binding of melatonin to melatonin receptors activates a few signaling pathways. MT1 receptor activation inhibits the adenylyl cyclase and its inhibition causes a rippling effect of non activation; starting with decreasing formation of cyclic adenosine monophosphate (cAMP), and then progressing to less protein kinase A (PKA) activity, which in turn hinders the phosphorilation of cAMP responsive element-binding protein (CREB binding protein) into P-CREB. MT1 receptors also activate phospholipase C (PLC), affect ion channels and regulate ion flux inside the cell. The binding of melatonin to MT2 receptors inhibits adenylyl cyclase which decreases the formation of cAMP.\[4\] As well it hinders guanylyl cyclase and therefore the forming of cyclic guanosine monophosphate (cGMP). Binding to MT2 receptors probably affects PLC which increases protein kinase C (PKC) activity. Activation of the receptor can lead to ion flux inside the cell. \| Target \| Actions \| Organism \| \|---\|---\|---\| \| A[Melatonin receptor type 1A](https://go.drugbank.com/drugs/DB01065#BE0000515) \| agonist \| Humans \| \| A[Melatonin receptor type 1B](https://go.drugbank.com/drugs/DB01065#BE0000327) \| agonist \| Humans \| \| A[Ribosyldihydronicotinamide dehydrogenase \[quinone\]](https://go.drugbank.com/drugs/DB01065#BE0000220) \| inhibitor \| Humans \| \| U[Estrogen receptor](https://go.drugbank.com/drugs/DB01065#BE0000123) \| antagonist \| Humans \| \| U[Nuclear receptor ROR-beta](https://go.drugbank.com/drugs/DB01065#BE0003554) \| agonist \| Humans \| \| U[Myeloperoxidase](https://go.drugbank.com/drugs/DB01065#BE0001075) \| inhibitor \| Humans \| \| U[Eosinophil peroxidase](https://go.drugbank.com/drugs/DB01065#BE0003555) \| inhibitor \| Humans \| \| U[Calreticulin](https://go.drugbank.com/drugs/DB01065#BE0002109) \| modulator \| Humans \| \| U[Calmodulin](https://go.drugbank.com/drugs/DB01065#BE0027477) \| antagonist \| Humans \| Absorption The absorption and bioavailability of melatonin varies widely. Volume of distribution Not Available Protein binding n/a Metabolism Hepatically metabolized to at least 14 identified metabolites (identified in mouse urine): 6-hydroxymelatonin glucuronide, 6-hydroxymelatonin sulfate, N-acetylserotonin glucuronide, N-acetylserotonin sulfate, 6-hydroxymelatonin, 2-oxomelatonin, 3-hydroxymelatonin, melatonin glucuronide, cyclic melatonin, cyclic N-acetylserotonin glucuronide, cyclic 6-hydroxymelatonin, 5-hydroxyindole-3-acetaldehyde, di-hydroxymelatonin and its glucuronide conjugate. 6-Hydroxymelatonin glucuronide is the major metabolite found in mouse urine (65-88% of total melatonin metabolites in urine). Hover over products below to view reaction partners - Melatonin - [6-Hydroxymelatonin](https://go.drugbank.com/reactions/259) - [6-Hydroxymelatonin glucuronide](https://go.drugbank.com/reactions/1547) - [6-Hydroxymelatonin sulfate](https://go.drugbank.com/reactions/1544) - [N-Acetyl-5-hydroxytryptamine](https://go.drugbank.com/reactions/414) - [N-Acetyl-5-hydroxytryptamine glucuronide](https://go.drugbank.com/reactions/1546) - [N-Acetyl-5-hydroxytryptamine sulfate](https://go.drugbank.com/reactions/1545) - [5-Methoxytryptamine](https://go.drugbank.com/reactions/1548) - [Bufotenine](https://go.drugbank.com/reactions/1551) - [N,N-Dimethyltryptamine](https://go.drugbank.com/reactions/1552) - [Pinoline](https://go.drugbank.com/reactions/1550) Route of elimination Not Available Half-life 35 to 50 minutes Clearance Not Available Adverse Effects [![](https://go.drugbank.com/assets/locked/AdverseEffects-5c75088f6dd600a6c494e9851006309fd1e423f24e4beba13dd0171d4f511993.png) Improve decision support & research outcomes With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library\!See the data](https://go.drugbank.com/data_packages/target/data_modules/structured_adverse_effects#adverse_effect_incidences) [Improve decision support & research outcomes with our structured adverse effects data.See a data sample](https://go.drugbank.com/data_packages/target/data_modules/structured_adverse_effects#adverse_effect_incidences) Toxicity Generally well-tolerated when taken orally. The most common side effects, day-time drowsiness, headache and dizziness, appear to occur at the same frequency as with placebo. Other reported side effects include transient depressive symptoms, mild tremor, mild anxiety, abdominal cramps, irritability, reduced alertness, confusion, nausea, vomiting, and hypotension. Safety in Adults: Evidence indicates that it is likely safe to use in oral and parenteral forms for up to two months when used appropriately. Some evidence indicates that it can be safely used orally for up to 9 months in some patients. It is also likely safe to use topically when used appropriately. Safety in Children: Melatonin appeared to be used safely in small numbers of children enrolled in short-term clinical trials. However, concerns regarding safety in children have arisen based on their developmental state. Compared to adults over 20 years of age, people under 20 produce high levels of melatonin. Melatonin levels are inversely related to gonadal development and it is thought that exogenous administration of melatonin may adversely affect gonadal development. Safety during Pregnancy: High doses of melatonin administered orally or parenterally may inhibit ovulation. Not advised for use in individuals who are pregnant or trying to become pregnant. Safety during Lactation: Not recommended as safety has not be established. Oral, rat: LD50 ≥3200 mg/kg Pathways \| Pathway \| Category \| \|---\|---\| \| [Tryptophan Metabolism](http://smpdb.ca/view/SMP0000063?highlight[compounds][]=DB01065&highlight[proteins][]=DB01065) \| Metabolic \| Pharmacogenomic Effects/ADRs Not Available ## Interactions [![](https://go.drugbank.com/assets/locked/AI-Chat-a64a3de153fd7ca4457e73bcec8b2358868da6c4dda160f9b4693e2d85af5a37.png) The AI Assistant built for biopharma intelligence. Access detailed, actionable insights to your most complex research questions. Leverage validated reasoning and citable data to power your critical research decisions.Learn More](https://go.drugbank.com/product_tour) [The AI Assistant built for biopharma intelligence.Learn More](https://go.drugbank.com/product_tour) Drug Interactions This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist. - [Approved](https://go.drugbank.com/drugs/DB01065#show-approved) - [Vet approved](https://go.drugbank.com/drugs/DB01065#show-vet_approved) - [Nutraceutical](https://go.drugbank.com/drugs/DB01065#show-nutraceutical) - [Illicit](https://go.drugbank.com/drugs/DB01065#show-illicit) - [Withdrawn](https://go.drugbank.com/drugs/DB01065#show-withdrawn) - [Investigational](https://go.drugbank.com/drugs/DB01065#show-investigational) - [Experimental](https://go.drugbank.com/drugs/DB01065#show-experimental) - [All Drugs](https://go.drugbank.com/drugs/DB01065#show-all) \| Drug \| Interaction \| \|---\|---\| \| Integrate drug-drug interactions in your software \| \| \| [1,2-Benzodiazepine](https://go.drugbank.com/drugs/DB12537) \| The risk or severity of CNS depression can be increased when Melatonin is combined with 1,2-Benzodiazepine. \| \| [Abametapir](https://go.drugbank.com/drugs/DB11932) \| The serum concentration of Melatonin can be increased when it is combined with Abametapir. \| \| [Abatacept](https://go.drugbank.com/drugs/DB01281) \| The metabolism of Melatonin can be increased when combined with Abatacept. \| \| [Abiraterone](https://go.drugbank.com/drugs/DB05812) \| The serum concentration of Melatonin can be increased when it is combined with Abiraterone. \| \| [Acenocoumarol](https://go.drugbank.com/drugs/DB01418) \| The metabolism of Acenocoumarol can be decreased when combined with Melatonin. \| Food Interactions - Avoid alcohol. Ingesting alcohol may reduce the effects of melatonin. - Take after a meal. Administration of melatonin after eating slows the absorption and reduces the Cmax of melatonin. ## Products International/Other Brands Mela-T (Alacer Corp. (Canada)) / Melatol (Elisium (Argentina)) / Melatonin (Biomed International Products Corp., Nutravite Pharmaceuticals (2008) Inc., Viva Pharmaceutical Inc., Kripps Pharmacy Ltd., SunOpta Inc.) / Nature'S Harmony (SunOpta Inc. (Canada)) / Revital Melatonin (Chin Tai Ginseng Co., Ltd (Canada)) / Rx Balance (SunOpta Inc. (Canada)) / Sleep Right (SunOpta Inc. (Canada)) / Vivitas (SunOpta Inc. (Canada)) Brand Name Prescription Products \| Name \| Dosage \| Strength \| Route \| Labeller \| Marketing Start \| Marketing End \| Region \| Image \| \|---\|---\|---\|---\|---\|---\|---\|---\|---\| \| Melatol \| Liquid \| 1 mg/30mL \| Oral \| PureTek Corporation \| 2024-10-17 \| Not applicable \| US![US flag](https://go.drugbank.com/assets/countries/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) \| \| \| Circadin \| Tablet, extended release \| 2 mg \| Oral \| Rad Neurim Pharmaceuticals Eec Sarl \| 2016-09-08 \| Not applicable \| EU![EU flag](https://go.drugbank.com/assets/countries/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) \| \| \| Circadin \| Tablet, extended release \| 2 mg \| Oral \| Rad Neurim Pharmaceuticals Eec Sarl \| 2016-09-08 \| Not applicable \| EU![EU flag](https://go.drugbank.com/assets/countries/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) \| \| \| Circadin \| Tablet, extended release \| 2 mg \| Oral \| Rad Neurim Pharmaceuticals Eec Sarl \| 2016-09-08 \| Not applicable \| EU![EU flag](https://go.drugbank.com/assets/countries/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) \| \| \| Circadin \| Tablet, extended release \| 2 mg \| Oral \| Rad Neurim Pharmaceuticals Eec Sarl \| 2016-09-08 \| Not applicable \| EU![EU flag](https://go.drugbank.com/assets/countries/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) \| \| Over the Counter Products \| Name \| Dosage \| Strength \| Route \| Labeller \| Marketing Start \| Marketing End \| Region \| Image \| \|---\|---\|---\|---\|---\|---\|---\|---\|---\| \| Essential Oil \| Oil \| 2\.5 mg/10mL \| Cutaneous \| Shantou Youjia E-Commerce Co., Ltd. \| 2024-02-01 \| 2024-12-31 \| US![US flag](https://go.drugbank.com/assets/countries/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) \| \| Unapproved/Other Products \| Name \| Ingredients \| Dosage \| Route \| Labeller \| Marketing Start \| Marketing End \| Region \| Image \| \|---\|---\|---\|---\|---\|---\|---\|---\|---\| \| Medi-doze Rx Sleep Aid \| Melatonin (6 mg/1) + [Valerian](https://go.drugbank.com/drugs/DB13196) (50 mg/1) + [gamma-Aminobutyric acid](https://go.drugbank.com/drugs/DB02530) (30 mg/1) \| Tablet \| Oral \| Two Hip Consulting, Llc \| 2013-02-20 \| 2016-04-11 \| US![US flag](https://go.drugbank.com/assets/countries/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) \| \| \| Melatol \| Melatonin (1 mg/30mL) \| Liquid \| Oral \| PureTek Corporation \| 2024-10-17 \| Not applicable \| US![US flag](https://go.drugbank.com/assets/countries/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) \| \| ## Categories ATC Codes [N05CH01 — Melatonin](https://go.drugbank.com/atc/N05CH01) - [N05CH — Melatonin receptor agonists](https://go.drugbank.com/atc/N05CH) - [N05C — HYPNOTICS AND SEDATIVES](https://go.drugbank.com/atc/N05C) - [N05 — PSYCHOLEPTICS](https://go.drugbank.com/atc/N05) - [N — NERVOUS SYSTEM](https://go.drugbank.com/atc/N) Drug Categories - [Amines](https://go.drugbank.com/categories/DBCAT000266) - [Antioxidants](https://go.drugbank.com/categories/DBCAT000368) - [Biogenic Amines](https://go.drugbank.com/categories/DBCAT000285) - [Biogenic Monoamines](https://go.drugbank.com/categories/DBCAT000468) - [Biological Factors](https://go.drugbank.com/categories/DBCAT000036) - [Central Nervous System Agents](https://go.drugbank.com/categories/DBCAT000044) - [Central Nervous System Depressants](https://go.drugbank.com/categories/DBCAT000399) - [Compounds used in a research, industrial, or household setting](https://go.drugbank.com/categories/DBCAT000196) - [Cytochrome P-450 CYP1A1 Substrates](https://go.drugbank.com/categories/DBCAT006050) - [Cytochrome P-450 CYP1A2 Substrates](https://go.drugbank.com/categories/DBCAT002609) - [Cytochrome P-450 CYP2C19 Substrates](https://go.drugbank.com/categories/DBCAT002638) - [Cytochrome P-450 CYP2C9 Substrates](https://go.drugbank.com/categories/DBCAT002634) - [Cytochrome P-450 Substrates](https://go.drugbank.com/categories/DBCAT005101) - [Heterocyclic Compounds, Fused-Ring](https://go.drugbank.com/categories/DBCAT004973) - [Hormones](https://go.drugbank.com/categories/DBCAT000056) - [Hormones, Hormone Substitutes, and Hormone Antagonists](https://go.drugbank.com/categories/DBCAT000057) - [Hypnotics and Sedatives](https://go.drugbank.com/categories/DBCAT000452) - [Indoles](https://go.drugbank.com/categories/DBCAT000528) - [Melatonin Receptor Agonists](https://go.drugbank.com/categories/DBCAT002489) - [Melatonin, agonists](https://go.drugbank.com/categories/DBCAT001822) - [Nervous System](https://go.drugbank.com/categories/DBCAT002148) - [OAT3/SLC22A8 Inhibitors](https://go.drugbank.com/categories/DBCAT003946) - [Protective Agents](https://go.drugbank.com/categories/DBCAT000367) - [Psycholeptics](https://go.drugbank.com/categories/DBCAT002185) - [Tryptamines](https://go.drugbank.com/categories/DBCAT001049) Chemical TaxonomyProvided by [Classyfire](http://classyfire.wishartlab.com/) Description This compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Kingdom [Organic compounds](http://classyfire.wishartlab.com/tax_nodes/C0000000) Super Class [Organoheterocyclic compounds](http://classyfire.wishartlab.com/tax_nodes/C0000002) Class [Indoles and derivatives](http://classyfire.wishartlab.com/tax_nodes/C0000211) Sub Class [Indoles](http://classyfire.wishartlab.com/tax_nodes/C0002497) Direct Parent [3-alkylindoles](http://classyfire.wishartlab.com/tax_nodes/C0004196) Alternative Parents [Anisoles](http://classyfire.wishartlab.com/tax_nodes/C0000138) / [Alkyl aryl ethers](http://classyfire.wishartlab.com/tax_nodes/C0000128) / [Substituted pyrroles](http://classyfire.wishartlab.com/tax_nodes/C0002257) / [Heteroaromatic compounds](http://classyfire.wishartlab.com/tax_nodes/C0004144) / [Propargyl-type 1,3-dipolar organic compounds](http://classyfire.wishartlab.com/tax_nodes/C0003633) / [Carboximidic acids](http://classyfire.wishartlab.com/tax_nodes/C0002484) / [Azacyclic compounds](http://classyfire.wishartlab.com/tax_nodes/C0004139) / [Organopnictogen compounds](http://classyfire.wishartlab.com/tax_nodes/C0004557) / [Organonitrogen compounds](http://classyfire.wishartlab.com/tax_nodes/C0000278) / [Hydrocarbon derivatives](http://classyfire.wishartlab.com/tax_nodes/C0004150) Substituents 3-alkylindole / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboximidic acid / Carboximidic acid derivative / Ether / Heteroaromatic compound Molecular Framework Aromatic heteropolycyclic compounds External Descriptors acetamides, tryptamines ([CHEBI:16796](http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16796)) / Indole alkaloids, Melatonin ([C01598](http://www.genome.jp/dbget-bin/www_bget?cpd:C01598)) / a small molecule ([N-ACETYL-5-METHOXY-TRYPTAMINE](http://metacyc.org/META/new-image?type=COMPOUND&object=N-ACETYL-5-METHOXY-TRYPTAMINE)) Affected organisms - Humans and other mammals ## Chemical Identifiers UNII [JL5DK93RCL](https://drugs.ncats.io/drug/JL5DK93RCL) CAS number 73-31-4 InChI Key DRLFMBDRBRZALE-UHFFFAOYSA-N InChI InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16) IUPAC Name N-\[2-(5-methoxy-1H-indol-3-yl)ethyl\]acetamide SMILES COC1=CC2=C(NC=C2CCNC(C)=O)C=C1 ## References Synthesis Reference Robert A. S. Welch, Keith Betteridge, "Method of stimulating cashmere growth on cashmere-producing goats using melatonin." U.S. Patent US4855313, issued August, 1986. [US4855313](https://www.google.com/?tbm=pts#q=4855313&tbm=pts) General References 1. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \[[Article](https://go.drugbank.com/articles/A1674)\] 2. Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. \[[Article](https://go.drugbank.com/articles/A1675)\] 3. Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. \[[Article](https://go.drugbank.com/articles/A1676)\] 4. Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. \[[Article](https://go.drugbank.com/articles/A1677)\] 5. Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210/en.2007-1412. Epub 2008 Jan 10. \[[Article](https://go.drugbank.com/articles/A1678)\] 6. Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. \[[Article](https://go.drugbank.com/articles/A1679)\] External Links Human Metabolome Database [HMDB0001389](http://www.hmdb.ca/metabolites/HMDB0001389) KEGG Drug [D08170](http://www.genome.jp/dbget-bin/www_bget?drug:D08170) KEGG Compound [C01598](http://www.genome.jp/dbget-bin/www_bget?cpd:C01598) PubChem Compound [896](http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=896) PubChem Substance [46509101](http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46509101) ChemSpider [872](http://www.chemspider.com/Chemical-Structure.872.html) BindingDB [53978](http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=53978) RxNav [6711](https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&searchTerm=6711) ChEBI [16796](http://www.ebi.ac.uk/chebi/searchId.do?chebiId=16796) ChEMBL [CHEMBL45](http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL45) ZINC [ZINC000000057060](https://zinc.docking.org/substances/ZINC000000057060) Therapeutic Targets Database [DAP000429](http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000429) PharmGKB [PA164752558](http://www.pharmgkb.org/drug/PA164752558) Guide to Pharmacology [GtP Drug Page](http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=1357) PDBe Ligand [ML1](http://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/ML1) Drugs.com [Drugs.com Drug Page](https://www.drugs.com/melatonin.html) PDRhealth [PDRhealth Drug Page](http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/mel_0286.shtml) Wikipedia [Melatonin](https://en.wikipedia.org/wiki/Melatonin) PDB Entries [2qwx](http://www.rcsb.org/pdb/explore.do?structureId=2qwx) / [2qx4](http://www.rcsb.org/pdb/explore.do?structureId=2qx4) / [2qx6](http://www.rcsb.org/pdb/explore.do?structureId=2qx6) / [4qog](http://www.rcsb.org/pdb/explore.do?structureId=4qog) / [4qoi](http://www.rcsb.org/pdb/explore.do?structureId=4qoi) / [5i8f](http://www.rcsb.org/pdb/explore.do?structureId=5i8f) / [5mxb](http://www.rcsb.org/pdb/explore.do?structureId=5mxb) / [5mxw](http://www.rcsb.org/pdb/explore.do?structureId=5mxw) / [6tr5](http://www.rcsb.org/pdb/explore.do?structureId=6tr5) MSDS [Download](https://s3-us-west-2.amazonaws.com/drugbank/msds/DB01065.pdf?1265922741) (72 KB) ## Clinical Trials Clinical Trials ###### Clinical Trial & Rare Diseases Add-on Data Package Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. [Preview package](https://go.drugbank.com/data_packages/trial) \| Phase \| Status \| Purpose \| Conditions \| Count \| Start Date \| Why Stopped \| 100+ additional columns \| \|---\|---\|---\|---\|---\|---\|---\|---\| \| Unlock 175K+ rows when you subscribe. [View sample data](https://go.drugbank.com/data_packages/trial/data_modules/clinical_trials) \| \| \| \| \| \| \| \| \| Not Available \| Active Not Recruiting \| Prevention \| [Oral Lichen Planus](https://go.drugbank.com/conditions/DBCOND0030626) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0030626&phase=&purpose=prevention&status=active_not_recruiting) \| somestatus \| stop reason \| just information to hide \| \| Not Available \| Active Not Recruiting \| Treatment \| [Psychosis](https://go.drugbank.com/conditions/DBCOND0020753) / [Schizophrenia Disorders](https://go.drugbank.com/conditions/DBCOND0031361) / [Schizophrenias](https://go.drugbank.com/conditions/DBCOND0033618) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0020753%2CDBCOND0031361%2CDBCOND0033618&phase=&purpose=treatment&status=active_not_recruiting) \| somestatus \| stop reason \| just information to hide \| \| Not Available \| Completed \| Not Available \| [Insomnia](https://go.drugbank.com/conditions/DBCOND0017531) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0017531&phase=&status=completed) \| somestatus \| stop reason \| just information to hide \| \| Not Available \| Completed \| Not Available \| [Postoperative Delirium (POD)](https://go.drugbank.com/conditions/DBCOND0073043) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0073043&phase=&status=completed) \| somestatus \| stop reason \| just information to hide \| \| Not Available \| Completed \| Not Available \| [Postoperative pain](https://go.drugbank.com/conditions/DBCOND0022333) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0022333&phase=&status=completed) \| somestatus \| stop reason \| just information to hide \| Unlock 75,000+ rows when you subscribe Explore data packages curated & structured to speed up your pharmaceutical research [View Sample Data](https://go.drugbank.com/data_packages/trial/data_modules/clinical_trials) ## Pharmacoeconomics Manufacturers Not Available Packagers - Mason Distributors - Medisca Inc. - National Vitamin Company - Physiologics - Rugby Laboratories Dosage Forms \| Form \| Route \| Strength \| \|---\|---\|---\| \| Capsule \| Not applicable \| 10 mg/1 \| \| Capsule \| Oral \| 5\.00000 mg \| \| Capsule, coated \| Oral \| 3 mg \| \| Capsule, liquid filled \| Oral \| 3 mg \| \| Chewable gel \| Oral \| 2\.5 mg/1 \| \| Liquid \| Oral \| 1 mg/4mL \| \| Liquid \| Oral \| 1 mg/30mL \| \| Oil \| Cutaneous \| 2\.5 mg/10mL \| \| Solution \| Oral \| 1 mg/ml \| \| Solution / drops \| Oral \| 1 mg/1mL \| \| Tablet \| Not applicable \| 10 mg/1 \| \| Tablet \| Oral \| \| \| Tablet \| Oral \| 0\.5 mg \| \| Tablet \| Oral \| 1 mg \| \| Tablet \| Oral \| 1\.500 mg \| \| Tablet \| Oral \| 2 mg \| \| Tablet \| Oral \| 3 mg/1 \| \| Tablet \| Oral \| 3 MG \| \| Tablet \| Oral \| 4 mg \| \| Tablet \| Oral \| 5 MG \| \| Tablet \| Oral \| 5 mg/1 \| \| Tablet \| Sublingual \| 3\.000 mg \| \| Tablet, chewable \| Oral \| 2\.5 mg/1 \| \| Tablet, extended release \| Oral \| 1 MG \| \| Tablet, extended release \| Oral \| 2 mg \| \| Tablet, extended release \| Oral \| 5 MG \| \| Tablet, film coated \| Oral \| 3 mg \| \| Tablet, film coated \| Oral \| 5 mg \| Prices \| Unit description \| Cost \| Unit \| \|---\|---\|---\| \| Melatonin powder \| 45\.6USD \| g \| \| Melatonin 3 mg tablet \| 0\.22USD \| tablet \| \| Melatonin 5 mg tablet \| 0\.12USD \| tablet \| \| Melatonin 5 mg tablet sl \| 0\.1USD \| tablet \| \| Melatonin sublingual tablet \| 0\.09USD \| tablet \| \| Melatonin 1 mg tablet \| 0\.03USD \| tablet \| DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only. Patents Not Available ## Properties State Solid Experimental Properties \| Property \| Value \| Source \| \|---\|---\|---\| \| melting point (°C) \| 117 °C \| PhysProp \| \| logP \| 1\.6 \| Not Available \| Predicted Properties \| Property \| Value \| Source \| \|---\|---\|---\| \| Water Solubility \| 0\.143 mg/mL \| [ALOGPS](http://www.vcclab.org/lab/alogps/) \| \| logP \| 1\.42 \| [ALOGPS](http://www.vcclab.org/lab/alogps/) \| \| logP \| 1\.15 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| logS \| \-3.2 \| [ALOGPS](http://www.vcclab.org/lab/alogps/) \| \| pKa (Strongest Acidic) \| 15\.8 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| pKa (Strongest Basic) \| \-1.6 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Physiological Charge \| 0 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Hydrogen Acceptor Count \| 2 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Hydrogen Donor Count \| 2 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Polar Surface Area \| 54\.12 Å2 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Rotatable Bond Count \| 4 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Refractivity \| 66\.28 m3·mol\-1 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Polarizability \| 25\.65 Å3 \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| Number of Rings \| 2 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Bioavailability \| 1 \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| Rule of Five \| Yes \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| Ghose Filter \| Yes \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| Veber's Rule \| No \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| MDDR-like Rule \| No \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| Predicted ADMET Features \| Property \| Value \| Probability \| \|---\|---\|---\| \| Human Intestinal Absorption \| \+ \| 1\.0 \| \| Blood Brain Barrier \| \+ \| 0\.9928 \| \| Caco-2 permeable \| \- \| 0\.5536 \| \| P-glycoprotein substrate \| Substrate \| 0\.6188 \| \| P-glycoprotein inhibitor I \| Non-inhibitor \| 0\.9569 \| \| P-glycoprotein inhibitor II \| Non-inhibitor \| 0\.6838 \| \| Renal organic cation transporter \| Non-inhibitor \| 0\.542 \| \| CYP450 2C9 substrate \| Non-substrate \| 0\.8231 \| \| CYP450 2D6 substrate \| Substrate \| 0\.5062 \| \| CYP450 3A4 substrate \| Substrate \| 0\.6505 \| \| CYP450 1A2 substrate \| Inhibitor \| 0\.9304 \| \| CYP450 2C9 inhibitor \| Non-inhibitor \| 0\.9071 \| \| CYP450 2D6 inhibitor \| Inhibitor \| 0\.8084 \| \| CYP450 2C19 inhibitor \| Non-inhibitor \| 0\.9025 \| \| CYP450 3A4 inhibitor \| Non-inhibitor \| 0\.7194 \| \| CYP450 inhibitory promiscuity \| High CYP Inhibitory Promiscuity \| 0\.6803 \| \| Ames test \| Non AMES toxic \| 0\.9132 \| \| Carcinogenicity \| Non-carcinogens \| 0\.9498 \| \| Biodegradation \| Not ready biodegradable \| 0\.8764 \| \| Rat acute toxicity \| 1\.8922 LD50, mol/kg \| Not applicable \| \| hERG inhibition (predictor I) \| Weak inhibitor \| 0\.9631 \| \| hERG inhibition (predictor II) \| Non-inhibitor \| 0\.5124 \| ADMET data is predicted using [admetSAR](http://lmmd.ecust.edu.cn:8000/), a free tool for evaluating chemical ADMET properties. ([23092397](http://www.ncbi.nlm.nih.gov/pubmed/23092397)) ## Spectra Mass Spec (NIST) [Download](https://s3-us-west-2.amazonaws.com/drugbank/mass_specs/DB01065.gif?1265922774) (8.2 KB) Spectra \| Spectrum \| Spectrum Type \| [Splash Key](http://splash.fiehnlab.ucdavis.edu/) \| \|---\|---\|---\| \| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https://go.drugbank.com/spectra/c_ms/735) \| GC-MS \| [splash10-001i-0490000000-aa93967315af900a76ce](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0490000000-aa93967315af900a76ce) \| \| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https://go.drugbank.com/spectra/c_ms/736) \| GC-MS \| [splash10-03k9-0900000000-a15ee6def3f8d75b1231](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-03k9-0900000000-a15ee6def3f8d75b1231) \| \| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https://go.drugbank.com/spectra/c_ms/737) \| GC-MS \| [splash10-001j-0490000000-94ef1be9ab930060778a](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001j-0490000000-94ef1be9ab930060778a) \| \| [GC-MS Spectrum - GC-MS (2 TMS)](https://go.drugbank.com/spectra/c_ms/1945) \| GC-MS \| [splash10-001i-1490000000-03e24298c7bd1ed4066a](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-1490000000-03e24298c7bd1ed4066a) \| \| [Predicted GC-MS Spectrum - GC-MS](https://go.drugbank.com/spectra/c_ms/7100) \| Predicted GC-MS \| [splash10-0076-4920000000-a8d9d614e9f8769a1359](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0076-4920000000-a8d9d614e9f8769a1359) \| \| [GC-MS Spectrum - GC-MS](https://go.drugbank.com/spectra/c_ms/31319) \| GC-MS \| [splash10-001i-1490000000-03e24298c7bd1ed4066a](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-1490000000-03e24298c7bd1ed4066a) \| \| [GC-MS Spectrum - GC-EI-TOF](https://go.drugbank.com/spectra/c_ms/32276) \| GC-MS \| [splash10-001j-0590000000-63d5e32dd5f7877a4402](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001j-0590000000-63d5e32dd5f7877a4402) \| \| [GC-MS Spectrum - GC-EI-TOF](https://go.drugbank.com/spectra/c_ms/32277) \| GC-MS \| [splash10-001i-0590000000-52b3a733f8b49582d3fb](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0590000000-52b3a733f8b49582d3fb) \| \| [GC-MS Spectrum - GC-EI-TOF](https://go.drugbank.com/spectra/c_ms/32278) \| GC-MS \| [splash10-0229-1900000000-d81c6f617bc486066136](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0229-1900000000-d81c6f617bc486066136) \| \| [Mass Spectrum (Electron Ionization)](https://go.drugbank.com/spectra/ei_ms/505) \| MS \| [splash10-03k9-1900000000-45ee4fdc7acdb33dad3b](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-03k9-1900000000-45ee4fdc7acdb33dad3b) \| \| [MS/MS Spectrum - Quattro\_QQQ 10V, Positive](https://go.drugbank.com/spectra/ms_ms/1547) \| LC-MS/MS \| [splash10-00di-0920000000-f90ec9b77e1a245e35a8](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0920000000-f90ec9b77e1a245e35a8) \| \| [MS/MS Spectrum - Quattro\_QQQ 25V, Positive](https://go.drugbank.com/spectra/ms_ms/1548) \| LC-MS/MS \| [splash10-05fr-0900000000-49e4482c65e82ac64b66](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-05fr-0900000000-49e4482c65e82ac64b66) \| \| [MS/MS Spectrum - Quattro\_QQQ 40V, Positive](https://go.drugbank.com/spectra/ms_ms/1549) \| LC-MS/MS \| [splash10-003r-0900000000-8a4ae0fd610cca992d74](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-003r-0900000000-8a4ae0fd610cca992d74) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative](https://go.drugbank.com/spectra/ms_ms/5222) \| LC-MS/MS \| [splash10-0159-0090000000-939a1caf5760c0ba189c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0159-0090000000-939a1caf5760c0ba189c) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative](https://go.drugbank.com/spectra/ms_ms/5223) \| LC-MS/MS \| [splash10-0006-0930000000-9e6fcea2c634ac9d85a0](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0930000000-9e6fcea2c634ac9d85a0) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative](https://go.drugbank.com/spectra/ms_ms/5224) \| LC-MS/MS \| [splash10-0006-0900000000-ddd29e731a7de56c1808](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-ddd29e731a7de56c1808) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative](https://go.drugbank.com/spectra/ms_ms/5225) \| LC-MS/MS \| [splash10-0006-0900000000-34b4fb52810a15ea5bd6](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-34b4fb52810a15ea5bd6) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative](https://go.drugbank.com/spectra/ms_ms/5226) \| LC-MS/MS \| [splash10-001i-0090000000-5ca2df63ec2baefdae8c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0090000000-5ca2df63ec2baefdae8c) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive](https://go.drugbank.com/spectra/ms_ms/5227) \| LC-MS/MS \| [splash10-001i-0190000000-5bae6e63e9b40e60e0a4](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0190000000-5bae6e63e9b40e60e0a4) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive](https://go.drugbank.com/spectra/ms_ms/5228) \| LC-MS/MS \| [splash10-00di-0900000000-529bf6d5c2091993f865](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-529bf6d5c2091993f865) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive](https://go.drugbank.com/spectra/ms_ms/5229) \| LC-MS/MS \| [splash10-00di-0900000000-158a60fe696120b23b41](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-158a60fe696120b23b41) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive](https://go.drugbank.com/spectra/ms_ms/5230) \| LC-MS/MS \| [splash10-0a5c-0900000000-5e86b2de659ce47762c0](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0a5c-0900000000-5e86b2de659ce47762c0) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive](https://go.drugbank.com/spectra/ms_ms/5231) \| LC-MS/MS \| [splash10-001i-0900000000-881c0d57239d56c46f2d](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0900000000-881c0d57239d56c46f2d) \| \| [LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive](https://go.drugbank.com/spectra/ms_ms/5232) \| LC-MS/MS \| [splash10-00di-0910000000-f256f78adbcbeb2464de](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0910000000-f256f78adbcbeb2464de) \| \| [LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive](https://go.drugbank.com/spectra/ms_ms/5233) \| LC-MS/MS \| [splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23) \| \| [MS/MS Spectrum - DI-ESI-qTof , Positive](https://go.drugbank.com/spectra/ms_ms/374102) \| LC-MS/MS \| [splash10-05fr-0900000000-7acf9405f4beeb34566c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-05fr-0900000000-7acf9405f4beeb34566c) \| \| [MS/MS Spectrum - DI-ESI-qTof , Positive](https://go.drugbank.com/spectra/ms_ms/374103) \| LC-MS/MS \| [splash10-00di-0900000000-13245183cd8c8cd511c3](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-13245183cd8c8cd511c3) \| \| [LC-MS/MS Spectrum - LC-ESI-qTof , Positive](https://go.drugbank.com/spectra/ms_ms/374702) \| LC-MS/MS \| [splash10-05ai-2900000000-07b3d32f002dba733c10](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-05ai-2900000000-07b3d32f002dba733c10) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438131) \| LC-MS/MS \| [splash10-0159-0090000000-939a1caf5760c0ba189c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0159-0090000000-939a1caf5760c0ba189c) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438132) \| LC-MS/MS \| [splash10-0006-0930000000-9e6fcea2c634ac9d85a0](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0930000000-9e6fcea2c634ac9d85a0) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438133) \| LC-MS/MS \| [splash10-0006-0900000000-ddd29e731a7de56c1808](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-ddd29e731a7de56c1808) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438134) \| LC-MS/MS \| [splash10-0006-0900000000-34b4fb52810a15ea5bd6](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-34b4fb52810a15ea5bd6) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438135) \| LC-MS/MS \| [splash10-001i-0090000000-5ca2df63ec2baefdae8c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0090000000-5ca2df63ec2baefdae8c) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , negative](https://go.drugbank.com/spectra/ms_ms/439444) \| LC-MS/MS \| [splash10-00lr-0090000000-3c42f6997539afb44682](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00lr-0090000000-3c42f6997539afb44682) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , negative](https://go.drugbank.com/spectra/ms_ms/439448) \| LC-MS/MS \| [splash10-014m-0960000000-7991e64dacb3c7f5cf32](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-014m-0960000000-7991e64dacb3c7f5cf32) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , negative](https://go.drugbank.com/spectra/ms_ms/439451) \| LC-MS/MS \| [splash10-0006-0900000000-882be43bc196e928a3cf](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-882be43bc196e928a3cf) \| \| [MS/MS Spectrum - , negative](https://go.drugbank.com/spectra/ms_ms/440134) \| LC-MS/MS \| [splash10-014i-0190000000-ddda9232f0e8e1b402f7](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-014i-0190000000-ddda9232f0e8e1b402f7) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446535) \| LC-MS/MS \| [splash10-001i-0190000000-5bae6e63e9b40e60e0a4](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0190000000-5bae6e63e9b40e60e0a4) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446536) \| LC-MS/MS \| [splash10-00di-0900000000-529bf6d5c2091993f865](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-529bf6d5c2091993f865) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446537) \| LC-MS/MS \| [splash10-00di-0900000000-158a60fe696120b23b41](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-158a60fe696120b23b41) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446538) \| LC-MS/MS \| [splash10-0a5c-0900000000-5e86b2de659ce47762c0](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0a5c-0900000000-5e86b2de659ce47762c0) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446539) \| LC-MS/MS \| [splash10-001i-0900000000-881c0d57239d56c46f2d](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0900000000-881c0d57239d56c46f2d) \| \| [LC-MS/MS Spectrum - LC-ESI-IT , positive](https://go.drugbank.com/spectra/ms_ms/447247) \| LC-MS/MS \| [splash10-00di-0910000000-d659c749adcab685e8bb](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0910000000-d659c749adcab685e8bb) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , positive](https://go.drugbank.com/spectra/ms_ms/449479) \| LC-MS/MS \| [splash10-00di-0900000000-6817d8039761a9058337](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-6817d8039761a9058337) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , positive](https://go.drugbank.com/spectra/ms_ms/449485) \| LC-MS/MS \| [splash10-00di-0900000000-349d5a97e2406d0db910](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-349d5a97e2406d0db910) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , positive](https://go.drugbank.com/spectra/ms_ms/449491) \| LC-MS/MS \| [splash10-001i-0900000000-9e30dcf47c9eca14650e](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0900000000-9e30dcf47c9eca14650e) \| \| [MS/MS Spectrum - , positive](https://go.drugbank.com/spectra/ms_ms/450591) \| LC-MS/MS \| [splash10-00di-1900000000-73dc69b26b1fba60f253](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-1900000000-73dc69b26b1fba60f253) \| \| [MS/MS Spectrum - , positive](https://go.drugbank.com/spectra/ms_ms/451347) \| LC-MS/MS \| [splash10-05ai-2900000000-07b3d32f002dba733c10](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-05ai-2900000000-07b3d32f002dba733c10) \| \| [MS/MS Spectrum - , positive](https://go.drugbank.com/spectra/ms_ms/451967) \| LC-MS/MS \| [splash10-00di-0900000000-2e847095e37f4ffe7c8b](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-2e847095e37f4ffe7c8b) \| \| [Predicted MS/MS Spectrum - 10V, Positive (Annotated)](https://go.drugbank.com/spectra/ms_ms/677259) \| Predicted LC-MS/MS \| [splash10-0089-0960000000-9acd48062f28a100f9da](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0089-0960000000-9acd48062f28a100f9da) \| \| [Predicted MS/MS Spectrum - 10V, Negative (Annotated)](https://go.drugbank.com/spectra/ms_ms/677289) \| Predicted LC-MS/MS \| [splash10-03di-5790000000-571ee430d2b0391822e3](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-03di-5790000000-571ee430d2b0391822e3) \| \| [Predicted MS/MS Spectrum - 20V, Positive (Annotated)](https://go.drugbank.com/spectra/ms_ms/677314) \| Predicted LC-MS/MS \| [splash10-00di-0900000000-1a38178248f05cf91e65](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-1a38178248f05cf91e65) \| \| [Predicted MS/MS Spectrum - 20V, Negative (Annotated)](https://go.drugbank.com/spectra/ms_ms/677334) \| Predicted LC-MS/MS \| [splash10-052f-9000000000-9950a9dee5e36e935714](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-052f-9000000000-9950a9dee5e36e935714) \| \| [Predicted MS/MS Spectrum - 40V, Positive (Annotated)](https://go.drugbank.com/spectra/ms_ms/677344) \| Predicted LC-MS/MS \| [splash10-006x-0900000000-5d47768c1bb474f51f38](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-006x-0900000000-5d47768c1bb474f51f38) \| \| [Predicted MS/MS Spectrum - 40V, Negative (Annotated)](https://go.drugbank.com/spectra/ms_ms/677384) \| Predicted LC-MS/MS \| [splash10-0006-4900000000-9374ee5bf5eb87317f56](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-4900000000-9374ee5bf5eb87317f56) \| \| [1H NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/1693) \| 1D NMR \| Not Applicable \| \| [1H NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/2600) \| 1D NMR \| Not Applicable \| \| [13C NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/3303) \| 1D NMR \| Not Applicable \| \| [Predicted 1H NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/42674) \| 1D NMR \| Not Applicable \| \| [Predicted 13C NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/42679) \| 1D NMR \| Not Applicable \| \| [\[1H,13C\] 2D NMR Spectrum](https://go.drugbank.com/spectra/nmr_two_d/1634) \| 2D NMR \| Not Applicable \| Chromatographic Properties ###### Collision Cross Sections (CCS) \| Adduct \| CCS Value (Å2) \| Source type \| Source \| \|---\|---\|---\|---\| \| \[M-H\]- \| 159\.6858961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M-H\]- \| 152\.8346632 \| predicted \| DarkChem Standard v0.1.0 \| \| \[M-H\]- \| 152\.9149983 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M-H\]- \| 165\.2831961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M-H\]- \| 159\.7026961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M-H\]- \| 150\.02837 \| predicted \| DeepCCS 1.0 (2019) \| \| \[M+H\]+ \| 159\.1911961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+H\]+ \| 157\.166152 \| predicted \| DarkChem Standard v0.1.0 \| \| \[M+H\]+ \| 157\.1763686 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+H\]+ \| 166\.2821961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+H\]+ \| 159\.7927961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+H\]+ \| 152\.38637 \| predicted \| DeepCCS 1.0 (2019) \| \| \[M+Na\]+ \| 158\.6747961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 165\.6858961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 167\.0242025 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 165\.6891961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 159\.5635961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 158\.4795 \| predicted \| DeepCCS 1.0 (2019) \| ### Targets [![](https://go.drugbank.com/assets/locked/DrugTargets2-1d1d534575da54e734c316d80c9fb35f8210c070dca913c026f8e58660e3e71a.png) Build, predict & validate machine-learning models Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.Learn more](https://bit.ly/3iYePSn) [Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.Learn more](https://bit.ly/3zOIrse) ##### Binding Properties × \| Property \| Measurement \| pH \| Temperature (°C) \| References \| \|---\|---\|---\|---\|---\| \| EC 50 (nM) \| 0\.02 \| N/A \| N/A \| Not Available \| \| IC 50 (nM) \| 0\.11 \| N/A \| N/A \| Not Available \| \| Ki (nM) \| 0\.08 \| N/A \| N/A \| Not Available \| [Details](https://go.drugbank.com/bio_entities/BE0000515) Binding Properties 1\. [Melatonin receptor type 1A](https://go.drugbank.com/bio_entities/BE0000515) Kind Protein Organism Humans Pharmacological action Yes Actions Agonist General Function High affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity. Possibly involved in sleep induction, by melatonin activation of the potassium channel KCNMA1/BK and the dissociation of G-beta and G-gamma subunits, thereby decreasing synaptic transmission (By similarity) Specific Function G protein-coupled receptor activity Gene Name MTNR1A Uniprot ID [P48039](http://www.uniprot.org/uniprot/P48039) Uniprot Name Melatonin receptor type 1A Molecular Weight 39374\.315 Da ##### References 1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. \[[Article](https://go.drugbank.com/articles/A15272)\] 2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. \[[Article](https://go.drugbank.com/articles/A9)\] 3. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \[[Article](https://go.drugbank.com/articles/A1674)\] 4. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. \[[Article](https://go.drugbank.com/articles/A15273)\] 5. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007/s12325-010-0065-y. Epub 2010 Sep 6. \[[Article](https://go.drugbank.com/articles/A15274)\] 6. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016/j.bmc.2010.06.100. Epub 2010 Jul 3. \[[Article](https://go.drugbank.com/articles/A15275)\] 7. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210/en.2009-0710. Epub 2009 Dec 4. \[[Article](https://go.drugbank.com/articles/A15276)\] 8. Witt-Enderby PA, Chu GH, Gillen ML, Li PK: Development of a high-affinity ligand that binds irreversibly to Mel1b melatonin receptors. J Med Chem. 1997 Dec 19;40(26):4195-8. \[[Article](https://go.drugbank.com/articles/A29415)\] 9. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] 10. Hoashi Y, Takai T, Kosugi Y, Nakashima M, Nakayama M, Hirai K, Uchikawa O, Koike T: Discovery of a Potent and Orally Bioavailable Melatonin Receptor Agonist. J Med Chem. 2021 Mar 25;64(6):3059-3074. doi: 10.1021/acs.jmedchem.0c01836. Epub 2021 Mar 7. \[[Article](https://go.drugbank.com/articles/A268970)\] 11. Gunia-Krzyzak A, Zelaszczyk D, Rapacz A, Zeslawska E, Waszkielewicz AM, Panczyk K, Sloczynska K, Pekala E, Nitek W, Filipek B, Marona H: Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH(3) or 2-CH(3). Bioorg Med Chem. 2017 Jan 15;25(2):471-482. doi: 10.1016/j.bmc.2016.11.014. Epub 2016 Nov 11. \[[Article](https://go.drugbank.com/articles/A273460)\] ##### Binding Properties × \| Property \| Measurement \| pH \| Temperature (°C) \| References \| \|---\|---\|---\|---\|---\| \| EC 50 (nM) \| 0\.07 \| N/A \| N/A \| Not Available \| \| IC 50 (nM) \| 0\.3 \| N/A \| N/A \| Not Available \| \| Ki (nM) \| 0\.12 \| N/A \| N/A \| Not Available \| [Details](https://go.drugbank.com/bio_entities/BE0000327) Binding Properties 2\. [Melatonin receptor type 1B](https://go.drugbank.com/bio_entities/BE0000327) Kind Protein Organism Humans Pharmacological action Yes Actions Agonist General Function High affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity Specific Function G protein-coupled receptor activity Gene Name MTNR1B Uniprot ID [P49286](http://www.uniprot.org/uniprot/P49286) Uniprot Name Melatonin receptor type 1B Molecular Weight 40187\.895 Da ##### References 1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. \[[Article](https://go.drugbank.com/articles/A15272)\] 2. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \[[Article](https://go.drugbank.com/articles/A1674)\] 3. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. \[[Article](https://go.drugbank.com/articles/A15273)\] 4. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007/s12325-010-0065-y. Epub 2010 Sep 6. \[[Article](https://go.drugbank.com/articles/A15274)\] 5. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016/j.bmc.2010.06.100. Epub 2010 Jul 3. \[[Article](https://go.drugbank.com/articles/A15275)\] 6. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210/en.2009-0710. Epub 2009 Dec 4. \[[Article](https://go.drugbank.com/articles/A15276)\] 7. Mattson RJ, Catt JD, Keavy D, Sloan CP, Epperson J, Gao Q, Hodges DB, Iben L, Mahle CD, Ryan E, Yocca FD: Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett. 2003 Mar 24;13(6):1199-202. \[[Article](https://go.drugbank.com/articles/A29424)\] 8. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] 9. Ferreira MA Jr, Azevedo H, Mascarello A, Segretti ND, Russo E, Russo V, Guimaraes CRW: Discovery of ACH-000143: A Novel Potent and Peripherally Preferred Melatonin Receptor Agonist that Reduces Liver Triglycerides and Steatosis in Diet-Induced Obese Rats. J Med Chem. 2021 Feb 25;64(4):1904-1929. doi: 10.1021/acs.jmedchem.0c00627. Epub 2021 Feb 8. \[[Article](https://go.drugbank.com/articles/A268965)\] ##### Binding Properties × \| Property \| Measurement \| pH \| Temperature (°C) \| References \| \|---\|---\|---\|---\|---\| \| IC 50 (nM) \| 65 \| N/A \| N/A \| Not Available \| \| Ki (nM) \| 28 \| N/A \| N/A \| Not Available \| [Details](https://go.drugbank.com/bio_entities/BE0000220) Binding Properties 3\. [Ribosyldihydronicotinamide dehydrogenase \[quinone\]](https://go.drugbank.com/bio_entities/BE0000220) Kind Protein Organism Humans Pharmacological action Yes Actions Inhibitor General Function The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis Specific Function chloride ion binding Gene Name NQO2 Uniprot ID [P16083](http://www.uniprot.org/uniprot/P16083) Uniprot Name Ribosyldihydronicotinamide dehydrogenase \[quinone\] Molecular Weight 25918\.4 Da ##### References 1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. \[[Article](https://go.drugbank.com/articles/A15272)\] 2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. \[[Article](https://go.drugbank.com/articles/A264250)\] 3. Fukatsu K, Uchikawa O, Kawada M, Yamano T, Yamashita M, Kato K, Hirai K, Hinuma S, Miyamoto M, Ohkawa S: Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists. J Med Chem. 2002 Sep 12;45(19):4212-21. doi: 10.1021/jm020114g. \[[Article](https://go.drugbank.com/articles/A268565)\] 4. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] 5. Du H, Wang J, Zhang X, Hu Z: A novel quantitative structure-activity relationship method to predict the affinities of MT3 melatonin binding site. Eur J Med Chem. 2008 Dec;43(12):2861-9. doi: 10.1016/j.ejmech.2008.02.012. Epub 2008 Feb 29. \[[Article](https://go.drugbank.com/articles/A29410)\] [Details](https://go.drugbank.com/bio_entities/BE0000123) 4\. [Estrogen receptor](https://go.drugbank.com/bio_entities/BE0000123) Kind Protein Organism Humans Pharmacological action Unknown Actions Antagonist General Function Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity) Specific Function 14-3-3 protein binding Gene Name ESR1 Uniprot ID [P03372](http://www.uniprot.org/uniprot/P03372) Uniprot Name Estrogen receptor Molecular Weight 66215\.45 Da ##### References 1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. \[[Article](https://go.drugbank.com/articles/A15278)\] 2. Yoo YM, Jeung EB: Melatonin-induced estrogen receptor alpha-mediated calbindin-D9k expression plays a role in H2O2-mediated cell death in rat pituitary GH3 cells. J Pineal Res. 2009 Nov;47(4):301-7. doi: 10.1111/j.1600-079X.2009.00714.x. Epub 2009 Oct 1. \[[Article](https://go.drugbank.com/articles/A15281)\] [Details](https://go.drugbank.com/bio_entities/BE0003554) 5\. [Nuclear receptor ROR-beta](https://go.drugbank.com/bio_entities/BE0003554) Kind Protein Organism Humans Pharmacological action Unknown Actions Agonist General Function Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity) Specific Function DNA-binding transcription activator activity, RNA polymerase II-specific Gene Name RORB Uniprot ID [Q92753](http://www.uniprot.org/uniprot/Q92753) Uniprot Name Nuclear receptor ROR-beta Molecular Weight 53219\.385 Da ##### References 1. Becker-Andre M, Wiesenberg I, Schaeren-Wiemers N, Andre E, Missbach M, Saurat JH, Carlberg C: Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily. J Biol Chem. 1994 Nov 18;269(46):28531-4. \[[Article](https://go.drugbank.com/articles/A15277)\] [Details](https://go.drugbank.com/bio_entities/BE0001075) 6\. [Myeloperoxidase](https://go.drugbank.com/bio_entities/BE0001075) Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971) Specific Function chromatin binding Gene Name MPO Uniprot ID [P05164](http://www.uniprot.org/uniprot/P05164) Uniprot Name Myeloperoxidase Molecular Weight 83867\.71 Da ##### References 1. Galijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021/bi702016q. Epub 2008 Feb 1. \[[Article](https://go.drugbank.com/articles/A15280)\] [Details](https://go.drugbank.com/bio_entities/BE0003555) 7\. [Eosinophil peroxidase](https://go.drugbank.com/bio_entities/BE0003555) Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis Specific Function heme binding Gene Name EPX Uniprot ID [P11678](http://www.uniprot.org/uniprot/P11678) Uniprot Name Eosinophil peroxidase Molecular Weight 81039\.5 Da ##### References 1. Lu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038/bjp.2008.173. Epub 2008 Jun 2. \[[Article](https://go.drugbank.com/articles/A15282)\] [Details](https://go.drugbank.com/bio_entities/BE0002109) 8\. [Calreticulin](https://go.drugbank.com/bio_entities/BE0002109) Kind Protein Organism Humans Pharmacological action Unknown Actions Modulator General Function Calcium-binding chaperone that promotes folding, oligomeric assembly and quality control in the endoplasmic reticulum (ER) via the calreticulin/calnexin cycle. This lectin interacts transiently with almost all of the monoglucosylated glycoproteins that are synthesized in the ER (PubMed:7876246). Interacts with the DNA-binding domain of NR3C1 and mediates its nuclear export (PubMed:11149926). Involved in maternal gene expression regulation. May participate in oocyte maturation via the regulation of calcium homeostasis (By similarity). Present in the cortical granules of non-activated oocytes, is exocytosed during the cortical reaction in response to oocyte activation and might participate in the block to polyspermy (By similarity) Specific Function calcium ion binding Gene Name CALR Uniprot ID [P27797](http://www.uniprot.org/uniprot/P27797) Uniprot Name Calreticulin Molecular Weight 48141\.2 Da ##### References 1. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. \[[Article](https://go.drugbank.com/articles/A15273)\] 2. Macias M, Escames G, Leon J, Coto A, Sbihi Y, Osuna A, Acuna-Castroviejo D: Calreticulin-melatonin. An unexpected relationship. Eur J Biochem. 2003 Mar;270(5):832-40. \[[Article](https://go.drugbank.com/articles/A15279)\] [Details](https://go.drugbank.com/bio_entities/BE0027477) 9\. [Calmodulin (Protein Group)](https://go.drugbank.com/bio_entities/BE0027477) Kind Protein group Organism Humans Pharmacological action Unknown Actions Antagonist General Function Calmodulin acts as part of a calcium signal transduction pathway by mediating the control of a large number of enzymes, ion channels, aquaporins and other proteins through calcium-binding (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Calcium-binding is required for the activation of calmodulin (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Among the enzymes to be stimulated by the calmodulin-calcium complex are a number of protein kinases, such as myosin light-chain kinases and calmodulin-dependent protein kinase type II (CaMK2), and phosphatases (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis (PubMed:16760425). Is a regulator of voltage-dependent L-type calcium channels (PubMed:31454269). Mediates calcium-dependent inactivation of CACNA1C (PubMed:26969752). Positively regulates calcium-activated potassium channel activity of KCNN2 (PubMed:27165696). Forms a potassium channel complex with KCNQ1 and regulates electrophysiological activity of the channel via calcium-binding (PubMed:25441029). Acts as a sensor to modulate the endoplasmic reticulum contacts with other organelles mediated by VMP1:ATP2A2 (PubMed:28890335) Specific Function adenylate cyclase activator activity * ##### Components: \| Name \| UniProt ID \| \|---\|---\| \| [Calmodulin-1](https://go.drugbank.com/polypeptides/P0DP23) \| [P0DP23](http://www.uniprot.org/uniprot/P0DP23) \| \| [Calmodulin-2](https://go.drugbank.com/polypeptides/P0DP24) \| [P0DP24](http://www.uniprot.org/uniprot/P0DP24) \| \| [Calmodulin-3](https://go.drugbank.com/polypeptides/P0DP25) \| [P0DP25](http://www.uniprot.org/uniprot/P0DP25) \| ##### References 1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. \[[Article](https://go.drugbank.com/articles/A15278)\] 2. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. \[[Article](https://go.drugbank.com/articles/A15272)\] ### Enzymes ##### Binding Properties × \| Property \| Measurement \| pH \| Temperature (°C) \| References \| \|---\|---\|---\|---\|---\| \| Ki (nM) \| 59000 \| N/A \| N/A \| Not Available \| [Details](https://go.drugbank.com/bio_entities/BE0003543) Binding Properties 1\. [Cytochrome P450 1A1](https://go.drugbank.com/bio_entities/BE0003543) Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate Inhibitor General Function A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195) Specific Function arachidonate monooxygenase activity Gene Name CYP1A1 Uniprot ID [P04798](http://www.uniprot.org/uniprot/P04798) Uniprot Name Cytochrome P450 1A1 Molecular Weight 58164\.815 Da ##### References 1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \[[Article](https://go.drugbank.com/articles/A15283)\] 2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \[[Article](https://go.drugbank.com/articles/A15284)\] 3. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. \[[Article](https://go.drugbank.com/articles/A266010)\] 4. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] ##### Binding Properties × \| Property \| Measurement \| pH \| Temperature (°C) \| References \| \|---\|---\|---\|---\|---\| \| Ki (nM) \| 12000 \| N/A \| N/A \| Not Available \| [Details](https://go.drugbank.com/bio_entities/BE0002433) Binding Properties 2\. [Cytochrome P450 1A2](https://go.drugbank.com/bio_entities/BE0002433) Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable) Specific Function caffeine oxidase activity Gene Name CYP1A2 Uniprot ID [P05177](http://www.uniprot.org/uniprot/P05177) Uniprot Name Cytochrome P450 1A2 Molecular Weight 58406\.915 Da ##### References 1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \[[Article](https://go.drugbank.com/articles/A15283)\] 2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \[[Article](https://go.drugbank.com/articles/A15284)\] 3. Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. \[[Article](https://go.drugbank.com/articles/A15285)\] 4. Hartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. \[[Article](https://go.drugbank.com/articles/A38895)\] 5. Hartter S, Wang X, Weigmann H, Friedberg T, Arand M, Oesch F, Hiemke C: Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin. J Clin Psychopharmacol. 2001 Apr;21(2):167-74. \[[Article](https://go.drugbank.com/articles/A38975)\] 6. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. \[[Article](https://go.drugbank.com/articles/A266010)\] 7. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] ##### Binding Properties × \| Property \| Measurement \| pH \| Temperature (°C) \| References \| \|---\|---\|---\|---\|---\| \| Ki (nM) \| 14000 \| N/A \| N/A \| Not Available \| [Details](https://go.drugbank.com/bio_entities/BE0001111) Binding Properties 3\. [Cytochrome P450 1B1](https://go.drugbank.com/bio_entities/BE0001111) Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate Inhibitor General Function A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity) Specific Function estrogen 16-alpha-hydroxylase activity Gene Name CYP1B1 Uniprot ID [Q16678](http://www.uniprot.org/uniprot/Q16678) Uniprot Name Cytochrome P450 1B1 Molecular Weight 60845\.33 Da ##### References 1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \[[Article](https://go.drugbank.com/articles/A15283)\] 2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \[[Article](https://go.drugbank.com/articles/A15284)\] 3. Yu Z, Tian X, Peng Y, Sun Z, Wang C, Tang N, Li B, Jian Y, Wang W, Huo X, Ma X: Mitochondrial cytochrome P450 (CYP) 1B1 is responsible for melatonin-induced apoptosis in neural cancer cells. J Pineal Res. 2018 Aug;65(1):e12478. doi: 10.1111/jpi.12478. Epub 2018 Mar 25. \[[Article](https://go.drugbank.com/articles/A184151)\] 4. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. \[[Article](https://go.drugbank.com/articles/A266010)\] 5. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] [Details](https://go.drugbank.com/bio_entities/BE0003536) 4\. [Cytochrome P450 2C19](https://go.drugbank.com/bio_entities/BE0003536) Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307) Specific Function (R)-limonene 6-monooxygenase activity Gene Name CYP2C19 Uniprot ID [P33261](http://www.uniprot.org/uniprot/P33261) Uniprot Name Cytochrome P450 2C19 Molecular Weight 55944\.565 Da ##### References 1. Huuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. \[[Article](https://go.drugbank.com/articles/A15286)\] 2. Facciola G, Hidestrand M, von Bahr C, Tybring G: Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes. Eur J Clin Pharmacol. 2001 Mar;56(12):881-8. doi: 10.1007/s002280000245. \[[Article](https://go.drugbank.com/articles/A184145)\] [Details](https://go.drugbank.com/bio_entities/BE0002793) 5\. [Cytochrome P450 2C9](https://go.drugbank.com/bio_entities/BE0002793) Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031) Specific Function (R)-limonene 6-monooxygenase activity Gene Name CYP2C9 Uniprot ID [P11712](http://www.uniprot.org/uniprot/P11712) Uniprot Name Cytochrome P450 2C9 Molecular Weight 55627\.365 Da ##### References 1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. \[[Article](https://go.drugbank.com/articles/A14815)\] [Details](https://go.drugbank.com/bio_entities/BE0003553) 6\. [Acetylserotonin O-methyltransferase](https://go.drugbank.com/bio_entities/BE0003553) Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function Catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine) Specific Function acetylserotonin O-methyltransferase activity Gene Name ASMT Uniprot ID [P46597](http://www.uniprot.org/uniprot/P46597) Uniprot Name Acetylserotonin O-methyltransferase Molecular Weight 38452\.51 Da ##### References 1. Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. \[[Article](https://go.drugbank.com/articles/A15271)\] [Details](https://go.drugbank.com/bio_entities/BE0000693) 7\. [Indoleamine 2,3-dioxygenase 1](https://go.drugbank.com/bio_entities/BE0000693) Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate General Function Catalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, contributing to maintain homeostasis by preventing autoimmunity or immunopathology that would result from uncontrolled and overreacting immune responses (PubMed:25691885). Tryptophan shortage inhibits T lymphocytes division and accumulation of tryptophan catabolites induces T-cell apoptosis and differentiation of regulatory T-cells (PubMed:25691885). Acts as a suppressor of anti-tumor immunity (PubMed:14502282, PubMed:23103127, PubMed:25157255, PubMed:25691885). Limits the growth of intracellular pathogens by depriving tryptophan (PubMed:25691885). Protects the fetus from maternal immune rejection (PubMed:25691885) Specific Function electron transfer activity Gene Name IDO1 Uniprot ID [P14902](http://www.uniprot.org/uniprot/P14902) Uniprot Name Indoleamine 2,3-dioxygenase 1 Molecular Weight 45325\.89 Da ##### References 1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. \[[Article](https://go.drugbank.com/articles/A15321)\] ##### Binding Properties × \| Property \| Measurement \| pH \| Temperature (°C) \| References \| \|---\|---\|---\|---\|---\| \| IC 50 (nM) \| 3000 \| N/A \| N/A \| Not Available \| [Details](https://go.drugbank.com/bio_entities/BE0001075) Binding Properties 8\. [Myeloperoxidase](https://go.drugbank.com/bio_entities/BE0001075) Kind Protein Organism Humans Pharmacological action Unknown Actions Substrate Inhibitor General Function Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971) Specific Function chromatin binding Gene Name MPO Uniprot ID [P05164](http://www.uniprot.org/uniprot/P05164) Uniprot Name Myeloperoxidase Molecular Weight 83867\.71 Da ##### References 1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. \[[Article](https://go.drugbank.com/articles/A15321)\] 2. Galijasevic S: The development of myeloperoxidase inhibitors. Bioorg Med Chem Lett. 2019 Jan 1;29(1):1-7. doi: 10.1016/j.bmcl.2018.11.031. Epub 2018 Nov 15. \[[Article](https://go.drugbank.com/articles/A267170)\] 3. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] [Details](https://go.drugbank.com/bio_entities/BE0002090) 9\. [Aromatase](https://go.drugbank.com/bio_entities/BE0002090) Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874) Specific Function aromatase activity Gene Name CYP19A1 Uniprot ID [P11511](http://www.uniprot.org/uniprot/P11511) Uniprot Name Aromatase Molecular Weight 57882\.48 Da ##### References 1. Gonzalez A, Martinez-Campa C, Mediavilla MD, Alonso-Gonzalez C, Sanchez-Mateos S, Hill SM, Sanchez-Barcelo EJ, Cos S: Effects of MT1 melatonin receptor overexpression on the aromatase-suppressive effect of melatonin in MCF-7 human breast cancer cells. Oncol Rep. 2007 Apr;17(4):947-53. doi: 10.3892/or.17.4.947. \[[Article](https://go.drugbank.com/articles/A182687)\] ### Transporters [Details](https://go.drugbank.com/bio_entities/BE0003645) 1\. [Organic anion transporter 3](https://go.drugbank.com/bio_entities/BE0003645) Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity) Specific Function organic anion transmembrane transporter activity Gene Name SLC22A8 Uniprot ID [Q8TCC7](http://www.uniprot.org/uniprot/Q8TCC7) Uniprot Name Organic anion transporter 3 Molecular Weight 59855\.585 Da ##### References 1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. \[[Article](https://go.drugbank.com/articles/A16319)\] 2. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. \[[Article](https://go.drugbank.com/articles/A6152)\] × ![](https://go.drugbank.com/assets/locked/Interactions-d8a042d89ef37357d141b7e23e305da46e3356a206fd25d371bb5a6069ab5df3.png) Identify potential medication risks Easily compare up to 40 drugs with our drug interaction checker. Get severity rating, description, and management advice. [Learn more](https://bit.ly/2TFmz2P) Drug created at June 13, 2005 13:24 / Updated at February 28, 2026 09:03 The contents of DrugBank are intended for educational and scientific research purposes only. DrugBank does not sell pharmaceuticals or chemicals, and it is not a substitute for professional medical advice, diagnosis or treatment. Be sure to contact a medical professional for any questions you may have. #### Product Image × ![]()[Show full image](https://go.drugbank.com/drugs/DB01065) ![](https://go.drugbank.com/assets/plus/Article_Dark_Pink-17ef3dc892e28e001abbb0ae6bfc47fca8a64cd76af37ec2a80dbce89fe3bc72.png) ## Stay up-to-date with the latest from DrugBank\! ![](https://go.drugbank.com/assets/plus/Article_Dark_Pink-17ef3dc892e28e001abbb0ae6bfc47fca8a64cd76af37ec2a80dbce89fe3bc72.png) ## Thank you** for subscribing\! Downloads - [Data Library](https://go.drugbank.com/data_packages) - [Academic Downloads](https://go.drugbank.com/releases/latest) - [Contact Sales](https://go.drugbank.com/contact/sales) Learn More - [The New DrugBank](https://go.drugbank.com/product_tour) - [Careers](https://drugbank.bamboohr.com/careers) - [Blog](https://blog.drugbank.com/) - [Clinical API](https://go.drugbank.com/clinical) - [Contact Sales](https://go.drugbank.com/contact/sales) Support - [Help Center](https://dev.drugbank.com/guides/index) - [DrugBank Online FAQs](https://dev.drugbank.com/guides/faqs) - [Contact Support](https://go.drugbank.com/contact/support) - [Citing DrugBank](https://dev.drugbank.com/guides/drugbank/citing) - [Searching DrugBank](https://dev.drugbank.com/guides/drugbank/searching) - [Other Databases](https://dev.drugbank.com/guides/drugbank/other_databases) - [Data Sources](https://dev.drugbank.com/guides/fields/drugs) About - [About DrugBank Online](https://go.drugbank.com/about) - [Wishart Research Group](http://www.wishartlab.com/) - [Statistics](https://go.drugbank.com/stats) - [Terms of Use](https://trust.drugbank.com/drugbank-trust-center/drugbank-terms-of-service) - [Privacy Policy](https://trust.drugbank.com/drugbank-trust-center/drugbank-privacy-policy) Use or redistribution of any DrugBank content or data requires a license and proper citations. [Talk to sales](https://go.drugbank.com/contact/sales) for commercial licensing. [Apply](https://go.drugbank.com/releases/latest) for an academic license.
Readable Markdown	DescriptionA naturally occurring hormone that promotes sleep. DescriptionA naturally occurring hormone that promotes sleep. DrugBank IDDB01065 ModalitySmall Molecule [Clinical Trials](https://go.drugbank.com/drugs/DB01065#clinical-trials-header) Phase 0 8 Phase 1 62 Phase 2 141 Phase 3 80 Phase 4 59 Summary Melatonin is an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement. Brand Names Circadin, Melatonin Neurim, Slenyto Generic NameMelatonin DrugBank Accession NumberDB01065 Background Melatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and lowering the body temperature. Melatonin is also implicated in the regulation of mood, learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders (ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers. ModalitySmall Molecule GroupsApproved, Investigational, Nutraceutical, Vet approved Structure [![](https://go.drugbank.com/structures/DB01065/thumb.svg)](https://go.drugbank.com/structures/DB01065/image.svg) ![](https://go.drugbank.com/structures/DB01065/image.svg) WeightAverage: 232.2783 Monoisotopic: 232.121177766 Chemical FormulaC13H16N2O2 Synonyms - 5-methoxy-N-acetyl tryptamine - 5-methoxy-N-acetyltryptamine - Melatonin - Melatonina - Mélatonine - N-\[2-(5-methoxyindol-3-yl)ethyl\]acetamide - N-Acetyl-5-methoxytryptamine External IDs - BCI-049 - J5.258B - NPC-15 - NSC-113928 - NSC-56423 Indication Used orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. Evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. It has received FDA orphan drug status as an oral medication for this use. A number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. It appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. It may also improve secondary insomnia associated with various sleep-wake cycle disturbances. Other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (DSPS), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with IL-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders. [![](https://go.drugbank.com/assets/locked/Pharmacology-da701df37a1a51c9ee28326cbba45e6bdeef07bce6ddf5e2eb757439eea83e8e.png) Reduce drug development failure rates Build, train, & validate machine-learning modelswith evidence-based and structured datasets.See how](https://bit.ly/3l5TIQu) [Build, train, & validate predictive machine-learning models with structured datasets.See how](https://bit.ly/3yeDgkJ) Associated Conditions \| Indication Type \| Indication \| Combined Product Details \| Approval Level \| Age Group \| Patient Characteristics \| Dose Form \| \|---\|---\|---\|---\|---\|---\|---\| \| Management of \| [Insomnia](https://go.drugbank.com/conditions/DBCOND0017531) \| \| •••••••••••• \| \| \| \| \| Used in combination to manage \| [Insomnia](https://go.drugbank.com/conditions/DBCOND0017531) \| Combination Product in combination with: [Valerian (DB13196)](https://go.drugbank.com/drugs/DB13196), [gamma-Aminobutyric acid (DB02530)](https://go.drugbank.com/drugs/DB02530) \| •••••••••••• \| \| \| \| Pharmacodynamics Melatonin is a hormone normally produced in the pineal gland and released into the blood. The essential amino acid L-tryptophan is a precursor in the synthesis of melatonin. It helps regulate sleep-wake cycles or the circadian rhythm. Production of melatonin is stimulated by darkness and inhibited by light. High levels of melatonin induce sleep and so consumption of the drug can be used to combat insomnia and jet lag. MT1 and MT2 receptors may be a target for the treatment of circadian and non circadian sleep disorders because of their differences in pharmacology and function within the SCN. SCN is responsible for maintaining the 24 hour cycle which regulates many different body functions ranging from sleep to immune functions Mechanism of action Melatonin is a derivative of tryptophan. It binds to melatonin receptor type 1A, which then acts on adenylate cylcase and the inhibition of a cAMP signal transduction pathway. Melatonin not only inhibits adenylate cyclase, but it also activates phosphilpase C. This potentiates the release of arachidonate. By binding to melatonin receptors 1 and 2, the downstream signallling cascades have various effects in the body. The melatonin receptors are G protein-coupled receptors and are expressed in various tissues of the body. There are two subtypes of the receptor in humans, melatonin receptor 1 (MT1) and melatonin receptor 2 (MT2). Melatonin and melatonin receptor agonists, on market or in clinical trials, all bind to and activate both receptor types.The binding of the agonists to the receptors has been investigated for over two decades or since 1986. It is somewhat known, but still not fully understood. When melatonin receptor agonists bind to and activate their receptors it causes numerous physiological processes. MT1 receptors are expressed in many regions of the central nervous system (CNS): suprachiasmatic nucleus of the hypothalamus (SNC), hippocampus, substantia nigra, cerebellum, central dopaminergic pathways, ventral tegmental area and nucleus accumbens. MT1 is also expressed in the retina, ovary, testis, mammary gland, coronary circulation and aorta, gallbladder, liver, kidney, skin and the immune system. MT2 receptors are expressed mainly in the CNS, also in the lung, cardiac, coronary and aortic tissue, myometrium and granulosa cells, immune cells, duodenum and adipocytes. The binding of melatonin to melatonin receptors activates a few signaling pathways. MT1 receptor activation inhibits the adenylyl cyclase and its inhibition causes a rippling effect of non activation; starting with decreasing formation of cyclic adenosine monophosphate (cAMP), and then progressing to less protein kinase A (PKA) activity, which in turn hinders the phosphorilation of cAMP responsive element-binding protein (CREB binding protein) into P-CREB. MT1 receptors also activate phospholipase C (PLC), affect ion channels and regulate ion flux inside the cell. The binding of melatonin to MT2 receptors inhibits adenylyl cyclase which decreases the formation of cAMP.\[4\] As well it hinders guanylyl cyclase and therefore the forming of cyclic guanosine monophosphate (cGMP). Binding to MT2 receptors probably affects PLC which increases protein kinase C (PKC) activity. Activation of the receptor can lead to ion flux inside the cell. \| Target \| Actions \| Organism \| \|---\|---\|---\| \| A[Melatonin receptor type 1A](https://go.drugbank.com/drugs/DB01065#BE0000515) \| agonist \| Humans \| \| A[Melatonin receptor type 1B](https://go.drugbank.com/drugs/DB01065#BE0000327) \| agonist \| Humans \| \| A[Ribosyldihydronicotinamide dehydrogenase \[quinone\]](https://go.drugbank.com/drugs/DB01065#BE0000220) \| inhibitor \| Humans \| \| U[Estrogen receptor](https://go.drugbank.com/drugs/DB01065#BE0000123) \| antagonist \| Humans \| \| U[Nuclear receptor ROR-beta](https://go.drugbank.com/drugs/DB01065#BE0003554) \| agonist \| Humans \| \| U[Myeloperoxidase](https://go.drugbank.com/drugs/DB01065#BE0001075) \| inhibitor \| Humans \| \| U[Eosinophil peroxidase](https://go.drugbank.com/drugs/DB01065#BE0003555) \| inhibitor \| Humans \| \| U[Calreticulin](https://go.drugbank.com/drugs/DB01065#BE0002109) \| modulator \| Humans \| \| U[Calmodulin](https://go.drugbank.com/drugs/DB01065#BE0027477) \| antagonist \| Humans \| Absorption The absorption and bioavailability of melatonin varies widely. Volume of distribution Not Available Protein binding n/a Metabolism Hepatically metabolized to at least 14 identified metabolites (identified in mouse urine): 6-hydroxymelatonin glucuronide, 6-hydroxymelatonin sulfate, N-acetylserotonin glucuronide, N-acetylserotonin sulfate, 6-hydroxymelatonin, 2-oxomelatonin, 3-hydroxymelatonin, melatonin glucuronide, cyclic melatonin, cyclic N-acetylserotonin glucuronide, cyclic 6-hydroxymelatonin, 5-hydroxyindole-3-acetaldehyde, di-hydroxymelatonin and its glucuronide conjugate. 6-Hydroxymelatonin glucuronide is the major metabolite found in mouse urine (65-88% of total melatonin metabolites in urine). Hover over products below to view reaction partners Route of elimination Not Available Half-life 35 to 50 minutes Clearance Not Available Toxicity Generally well-tolerated when taken orally. The most common side effects, day-time drowsiness, headache and dizziness, appear to occur at the same frequency as with placebo. Other reported side effects include transient depressive symptoms, mild tremor, mild anxiety, abdominal cramps, irritability, reduced alertness, confusion, nausea, vomiting, and hypotension. Safety in Adults: Evidence indicates that it is likely safe to use in oral and parenteral forms for up to two months when used appropriately. Some evidence indicates that it can be safely used orally for up to 9 months in some patients. It is also likely safe to use topically when used appropriately. Safety in Children: Melatonin appeared to be used safely in small numbers of children enrolled in short-term clinical trials. However, concerns regarding safety in children have arisen based on their developmental state. Compared to adults over 20 years of age, people under 20 produce high levels of melatonin. Melatonin levels are inversely related to gonadal development and it is thought that exogenous administration of melatonin may adversely affect gonadal development. Safety during Pregnancy: High doses of melatonin administered orally or parenterally may inhibit ovulation. Not advised for use in individuals who are pregnant or trying to become pregnant. Safety during Lactation: Not recommended as safety has not be established. Oral, rat: LD50 ≥3200 mg/kg Pathways \| Pathway \| Category \| \|---\|---\| \| [Tryptophan Metabolism](http://smpdb.ca/view/SMP0000063?highlight[compounds][]=DB01065&highlight[proteins][]=DB01065) \| Metabolic \| Pharmacogenomic Effects/ADRs Not Available Drug Interactions This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist. - [Approved](https://go.drugbank.com/drugs/DB01065#show-approved) - [Vet approved](https://go.drugbank.com/drugs/DB01065#show-vet_approved) - [Nutraceutical](https://go.drugbank.com/drugs/DB01065#show-nutraceutical) - [Illicit](https://go.drugbank.com/drugs/DB01065#show-illicit) - [Withdrawn](https://go.drugbank.com/drugs/DB01065#show-withdrawn) - [Investigational](https://go.drugbank.com/drugs/DB01065#show-investigational) - [Experimental](https://go.drugbank.com/drugs/DB01065#show-experimental) - [All Drugs](https://go.drugbank.com/drugs/DB01065#show-all) \| Drug \| Interaction \| \|---\|---\| \| Integrate drug-drug interactions in your software \| \| \| [1,2-Benzodiazepine](https://go.drugbank.com/drugs/DB12537) \| The risk or severity of CNS depression can be increased when Melatonin is combined with 1,2-Benzodiazepine. \| \| [Abametapir](https://go.drugbank.com/drugs/DB11932) \| The serum concentration of Melatonin can be increased when it is combined with Abametapir. \| \| [Abatacept](https://go.drugbank.com/drugs/DB01281) \| The metabolism of Melatonin can be increased when combined with Abatacept. \| \| [Abiraterone](https://go.drugbank.com/drugs/DB05812) \| The serum concentration of Melatonin can be increased when it is combined with Abiraterone. \| \| [Acenocoumarol](https://go.drugbank.com/drugs/DB01418) \| The metabolism of Acenocoumarol can be decreased when combined with Melatonin. \| Food Interactions - Avoid alcohol. Ingesting alcohol may reduce the effects of melatonin. - Take after a meal. Administration of melatonin after eating slows the absorption and reduces the Cmax of melatonin. International/Other BrandsMela-T (Alacer Corp. (Canada)) / Melatol (Elisium (Argentina)) / Melatonin (Biomed International Products Corp., Nutravite Pharmaceuticals (2008) Inc., Viva Pharmaceutical Inc., Kripps Pharmacy Ltd., SunOpta Inc.) / Nature'S Harmony (SunOpta Inc. (Canada)) / Revital Melatonin (Chin Tai Ginseng Co., Ltd (Canada)) / Rx Balance (SunOpta Inc. (Canada)) / Sleep Right (SunOpta Inc. (Canada)) / Vivitas (SunOpta Inc. (Canada)) Brand Name Prescription Products \| Name \| Dosage \| Strength \| Route \| Labeller \| Marketing Start \| Marketing End \| Region \| Image \| \|---\|---\|---\|---\|---\|---\|---\|---\|---\| \| Melatol \| Liquid \| 1 mg/30mL \| Oral \| PureTek Corporation \| 2024-10-17 \| Not applicable \| ![US flag](https://go.drugbank.com/assets/countries/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) \| \| \| Circadin \| Tablet, extended release \| 2 mg \| Oral \| Rad Neurim Pharmaceuticals Eec Sarl \| 2016-09-08 \| Not applicable \| ![EU flag](https://go.drugbank.com/assets/countries/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) \| \| \| Circadin \| Tablet, extended release \| 2 mg \| Oral \| Rad Neurim Pharmaceuticals Eec Sarl \| 2016-09-08 \| Not applicable \| ![EU flag](https://go.drugbank.com/assets/countries/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) \| \| \| Circadin \| Tablet, extended release \| 2 mg \| Oral \| Rad Neurim Pharmaceuticals Eec Sarl \| 2016-09-08 \| Not applicable \| ![EU flag](https://go.drugbank.com/assets/countries/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) \| \| \| Circadin \| Tablet, extended release \| 2 mg \| Oral \| Rad Neurim Pharmaceuticals Eec Sarl \| 2016-09-08 \| Not applicable \| ![EU flag](https://go.drugbank.com/assets/countries/eu-dda0a77d72bbe9085912a87221977afb68d43d8dbf280688345b7a73f2498514.svg) \| \| Over the Counter Products \| Name \| Dosage \| Strength \| Route \| Labeller \| Marketing Start \| Marketing End \| Region \| Image \| \|---\|---\|---\|---\|---\|---\|---\|---\|---\| \| Essential Oil \| Oil \| 2\.5 mg/10mL \| Cutaneous \| Shantou Youjia E-Commerce Co., Ltd. \| 2024-02-01 \| 2024-12-31 \| ![US flag](https://go.drugbank.com/assets/countries/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) \| \| Unapproved/Other Products \| Name \| Ingredients \| Dosage \| Route \| Labeller \| Marketing Start \| Marketing End \| Region \| Image \| \|---\|---\|---\|---\|---\|---\|---\|---\|---\| \| Medi-doze Rx Sleep Aid \| Melatonin (6 mg/1) + [Valerian](https://go.drugbank.com/drugs/DB13196) (50 mg/1) + [gamma-Aminobutyric acid](https://go.drugbank.com/drugs/DB02530) (30 mg/1) \| Tablet \| Oral \| Two Hip Consulting, Llc \| 2013-02-20 \| 2016-04-11 \| ![US flag](https://go.drugbank.com/assets/countries/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) \| \| \| Melatol \| Melatonin (1 mg/30mL) \| Liquid \| Oral \| PureTek Corporation \| 2024-10-17 \| Not applicable \| ![US flag](https://go.drugbank.com/assets/countries/us-827348b033d3b349931e036455f341029a75d10b2533057ebfbfdb0ca0e45c47.svg) \| \| Drug Categories - [Amines](https://go.drugbank.com/categories/DBCAT000266) - [Antioxidants](https://go.drugbank.com/categories/DBCAT000368) - [Biogenic Amines](https://go.drugbank.com/categories/DBCAT000285) - [Biogenic Monoamines](https://go.drugbank.com/categories/DBCAT000468) - [Biological Factors](https://go.drugbank.com/categories/DBCAT000036) - [Central Nervous System Agents](https://go.drugbank.com/categories/DBCAT000044) - [Central Nervous System Depressants](https://go.drugbank.com/categories/DBCAT000399) - [Compounds used in a research, industrial, or household setting](https://go.drugbank.com/categories/DBCAT000196) - [Cytochrome P-450 CYP1A1 Substrates](https://go.drugbank.com/categories/DBCAT006050) - [Cytochrome P-450 CYP1A2 Substrates](https://go.drugbank.com/categories/DBCAT002609) - [Cytochrome P-450 CYP2C19 Substrates](https://go.drugbank.com/categories/DBCAT002638) - [Cytochrome P-450 CYP2C9 Substrates](https://go.drugbank.com/categories/DBCAT002634) - [Cytochrome P-450 Substrates](https://go.drugbank.com/categories/DBCAT005101) - [Heterocyclic Compounds, Fused-Ring](https://go.drugbank.com/categories/DBCAT004973) - [Hormones](https://go.drugbank.com/categories/DBCAT000056) - [Hormones, Hormone Substitutes, and Hormone Antagonists](https://go.drugbank.com/categories/DBCAT000057) - [Hypnotics and Sedatives](https://go.drugbank.com/categories/DBCAT000452) - [Indoles](https://go.drugbank.com/categories/DBCAT000528) - [Melatonin Receptor Agonists](https://go.drugbank.com/categories/DBCAT002489) - [Melatonin, agonists](https://go.drugbank.com/categories/DBCAT001822) - [Nervous System](https://go.drugbank.com/categories/DBCAT002148) - [OAT3/SLC22A8 Inhibitors](https://go.drugbank.com/categories/DBCAT003946) - [Protective Agents](https://go.drugbank.com/categories/DBCAT000367) - [Psycholeptics](https://go.drugbank.com/categories/DBCAT002185) - [Tryptamines](https://go.drugbank.com/categories/DBCAT001049) Affected organisms - Humans and other mammals UNII[JL5DK93RCL](https://drugs.ncats.io/drug/JL5DK93RCL) CAS number73-31-4 InChI KeyDRLFMBDRBRZALE-UHFFFAOYSA-N InChI InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16) IUPAC Name N-\[2-(5-methoxy-1H-indol-3-yl)ethyl\]acetamide SMILES COC1=CC2=C(NC=C2CCNC(C)=O)C=C1 Synthesis Reference Robert A. S. Welch, Keith Betteridge, "Method of stimulating cashmere growth on cashmere-producing goats using melatonin." U.S. Patent US4855313, issued August, 1986. [US4855313](https://www.google.com/?tbm=pts#q=4855313&tbm=pts) General References 1. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \[[Article](https://go.drugbank.com/articles/A1674)\] 2. Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. \[[Article](https://go.drugbank.com/articles/A1675)\] 3. Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. \[[Article](https://go.drugbank.com/articles/A1676)\] 4. Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. \[[Article](https://go.drugbank.com/articles/A1677)\] 5. Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210/en.2007-1412. Epub 2008 Jan 10. \[[Article](https://go.drugbank.com/articles/A1678)\] 6. Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. \[[Article](https://go.drugbank.com/articles/A1679)\] PDB Entries[2qwx](http://www.rcsb.org/pdb/explore.do?structureId=2qwx) / [2qx4](http://www.rcsb.org/pdb/explore.do?structureId=2qx4) / [2qx6](http://www.rcsb.org/pdb/explore.do?structureId=2qx6) / [4qog](http://www.rcsb.org/pdb/explore.do?structureId=4qog) / [4qoi](http://www.rcsb.org/pdb/explore.do?structureId=4qoi) / [5i8f](http://www.rcsb.org/pdb/explore.do?structureId=5i8f) / [5mxb](http://www.rcsb.org/pdb/explore.do?structureId=5mxb) / [5mxw](http://www.rcsb.org/pdb/explore.do?structureId=5mxw) / [6tr5](http://www.rcsb.org/pdb/explore.do?structureId=6tr5) Clinical Trials ###### Clinical Trial & Rare Diseases Add-on Data Package Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. [Preview package](https://go.drugbank.com/data_packages/trial) \| Phase \| Status \| Purpose \| Conditions \| Count \| Start Date \| Why Stopped \| 100+ additional columns \| \|---\|---\|---\|---\|---\|---\|---\|---\| \| Unlock 175K+ rows when you subscribe. [View sample data](https://go.drugbank.com/data_packages/trial/data_modules/clinical_trials) \| \| \| \| \| \| \| \| \| Not Available \| Active Not Recruiting \| Prevention \| [Oral Lichen Planus](https://go.drugbank.com/conditions/DBCOND0030626) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0030626&phase=&purpose=prevention&status=active_not_recruiting) \| somestatus \| stop reason \| just information to hide \| \| Not Available \| Active Not Recruiting \| Treatment \| [Psychosis](https://go.drugbank.com/conditions/DBCOND0020753) / [Schizophrenia Disorders](https://go.drugbank.com/conditions/DBCOND0031361) / [Schizophrenias](https://go.drugbank.com/conditions/DBCOND0033618) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0020753%2CDBCOND0031361%2CDBCOND0033618&phase=&purpose=treatment&status=active_not_recruiting) \| somestatus \| stop reason \| just information to hide \| \| Not Available \| Completed \| Not Available \| [Insomnia](https://go.drugbank.com/conditions/DBCOND0017531) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0017531&phase=&status=completed) \| somestatus \| stop reason \| just information to hide \| \| Not Available \| Completed \| Not Available \| [Postoperative Delirium (POD)](https://go.drugbank.com/conditions/DBCOND0073043) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0073043&phase=&status=completed) \| somestatus \| stop reason \| just information to hide \| \| Not Available \| Completed \| Not Available \| [Postoperative pain](https://go.drugbank.com/conditions/DBCOND0022333) \| [1](https://go.drugbank.com/drugs/DB01065/clinical_trials?conditions=DBCOND0022333&phase=&status=completed) \| somestatus \| stop reason \| just information to hide \| Manufacturers Not Available Packagers - Mason Distributors - Medisca Inc. - National Vitamin Company - Physiologics - Rugby Laboratories Dosage Forms \| Form \| Route \| Strength \| \|---\|---\|---\| \| Capsule \| Not applicable \| 10 mg/1 \| \| Capsule \| Oral \| 5\.00000 mg \| \| Capsule, coated \| Oral \| 3 mg \| \| Capsule, liquid filled \| Oral \| 3 mg \| \| Chewable gel \| Oral \| 2\.5 mg/1 \| \| Liquid \| Oral \| 1 mg/4mL \| \| Liquid \| Oral \| 1 mg/30mL \| \| Oil \| Cutaneous \| 2\.5 mg/10mL \| \| Solution \| Oral \| 1 mg/ml \| \| Solution / drops \| Oral \| 1 mg/1mL \| \| Tablet \| Not applicable \| 10 mg/1 \| \| Tablet \| Oral \| \| \| Tablet \| Oral \| 0\.5 mg \| \| Tablet \| Oral \| 1 mg \| \| Tablet \| Oral \| 1\.500 mg \| \| Tablet \| Oral \| 2 mg \| \| Tablet \| Oral \| 3 mg/1 \| \| Tablet \| Oral \| 3 MG \| \| Tablet \| Oral \| 4 mg \| \| Tablet \| Oral \| 5 MG \| \| Tablet \| Oral \| 5 mg/1 \| \| Tablet \| Sublingual \| 3\.000 mg \| \| Tablet, chewable \| Oral \| 2\.5 mg/1 \| \| Tablet, extended release \| Oral \| 1 MG \| \| Tablet, extended release \| Oral \| 2 mg \| \| Tablet, extended release \| Oral \| 5 MG \| \| Tablet, film coated \| Oral \| 3 mg \| \| Tablet, film coated \| Oral \| 5 mg \| Prices \| Unit description \| Cost \| Unit \| \|---\|---\|---\| \| Melatonin powder \| 45\.6USD \| g \| \| Melatonin 3 mg tablet \| 0\.22USD \| tablet \| \| Melatonin 5 mg tablet \| 0\.12USD \| tablet \| \| Melatonin 5 mg tablet sl \| 0\.1USD \| tablet \| \| Melatonin sublingual tablet \| 0\.09USD \| tablet \| \| Melatonin 1 mg tablet \| 0\.03USD \| tablet \| DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only. PatentsNot Available StateSolid Experimental Properties \| Property \| Value \| Source \| \|---\|---\|---\| \| melting point (°C) \| 117 °C \| PhysProp \| \| logP \| 1\.6 \| Not Available \| Predicted Properties \| Property \| Value \| Source \| \|---\|---\|---\| \| Water Solubility \| 0\.143 mg/mL \| [ALOGPS](http://www.vcclab.org/lab/alogps/) \| \| logP \| 1\.42 \| [ALOGPS](http://www.vcclab.org/lab/alogps/) \| \| logP \| 1\.15 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| logS \| \-3.2 \| [ALOGPS](http://www.vcclab.org/lab/alogps/) \| \| pKa (Strongest Acidic) \| 15\.8 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| pKa (Strongest Basic) \| \-1.6 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Physiological Charge \| 0 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Hydrogen Acceptor Count \| 2 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Hydrogen Donor Count \| 2 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Polar Surface Area \| 54\.12 Å2 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Rotatable Bond Count \| 4 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Refractivity \| 66\.28 m3·mol\-1 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Polarizability \| 25\.65 Å3 \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| Number of Rings \| 2 \| [Chemaxon](https://chemaxon.com/calculators-and-predictors) \| \| Bioavailability \| 1 \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| Rule of Five \| Yes \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| Ghose Filter \| Yes \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| Veber's Rule \| No \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| \| MDDR-like Rule \| No \| [Chemaxon](https://docs.chemaxon.com/display/docs/molecular-modeling-plugins.md) \| Predicted ADMET Features \| Property \| Value \| Probability \| \|---\|---\|---\| \| Human Intestinal Absorption \| \+ \| 1\.0 \| \| Blood Brain Barrier \| \+ \| 0\.9928 \| \| Caco-2 permeable \| \- \| 0\.5536 \| \| P-glycoprotein substrate \| Substrate \| 0\.6188 \| \| P-glycoprotein inhibitor I \| Non-inhibitor \| 0\.9569 \| \| P-glycoprotein inhibitor II \| Non-inhibitor \| 0\.6838 \| \| Renal organic cation transporter \| Non-inhibitor \| 0\.542 \| \| CYP450 2C9 substrate \| Non-substrate \| 0\.8231 \| \| CYP450 2D6 substrate \| Substrate \| 0\.5062 \| \| CYP450 3A4 substrate \| Substrate \| 0\.6505 \| \| CYP450 1A2 substrate \| Inhibitor \| 0\.9304 \| \| CYP450 2C9 inhibitor \| Non-inhibitor \| 0\.9071 \| \| CYP450 2D6 inhibitor \| Inhibitor \| 0\.8084 \| \| CYP450 2C19 inhibitor \| Non-inhibitor \| 0\.9025 \| \| CYP450 3A4 inhibitor \| Non-inhibitor \| 0\.7194 \| \| CYP450 inhibitory promiscuity \| High CYP Inhibitory Promiscuity \| 0\.6803 \| \| Ames test \| Non AMES toxic \| 0\.9132 \| \| Carcinogenicity \| Non-carcinogens \| 0\.9498 \| \| Biodegradation \| Not ready biodegradable \| 0\.8764 \| \| Rat acute toxicity \| 1\.8922 LD50, mol/kg \| Not applicable \| \| hERG inhibition (predictor I) \| Weak inhibitor \| 0\.9631 \| \| hERG inhibition (predictor II) \| Non-inhibitor \| 0\.5124 \| ADMET data is predicted using [admetSAR](http://lmmd.ecust.edu.cn:8000/), a free tool for evaluating chemical ADMET properties. ([23092397](http://www.ncbi.nlm.nih.gov/pubmed/23092397)) Mass Spec (NIST)[Download](https://s3-us-west-2.amazonaws.com/drugbank/mass_specs/DB01065.gif?1265922774) (8.2 KB) Spectra \| Spectrum \| Spectrum Type \| [Splash Key](http://splash.fiehnlab.ucdavis.edu/) \| \|---\|---\|---\| \| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https://go.drugbank.com/spectra/c_ms/735) \| GC-MS \| [splash10-001i-0490000000-aa93967315af900a76ce](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0490000000-aa93967315af900a76ce) \| \| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https://go.drugbank.com/spectra/c_ms/736) \| GC-MS \| [splash10-03k9-0900000000-a15ee6def3f8d75b1231](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-03k9-0900000000-a15ee6def3f8d75b1231) \| \| [GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)](https://go.drugbank.com/spectra/c_ms/737) \| GC-MS \| [splash10-001j-0490000000-94ef1be9ab930060778a](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001j-0490000000-94ef1be9ab930060778a) \| \| [GC-MS Spectrum - GC-MS (2 TMS)](https://go.drugbank.com/spectra/c_ms/1945) \| GC-MS \| [splash10-001i-1490000000-03e24298c7bd1ed4066a](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-1490000000-03e24298c7bd1ed4066a) \| \| [Predicted GC-MS Spectrum - GC-MS](https://go.drugbank.com/spectra/c_ms/7100) \| Predicted GC-MS \| [splash10-0076-4920000000-a8d9d614e9f8769a1359](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0076-4920000000-a8d9d614e9f8769a1359) \| \| [GC-MS Spectrum - GC-MS](https://go.drugbank.com/spectra/c_ms/31319) \| GC-MS \| [splash10-001i-1490000000-03e24298c7bd1ed4066a](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-1490000000-03e24298c7bd1ed4066a) \| \| [GC-MS Spectrum - GC-EI-TOF](https://go.drugbank.com/spectra/c_ms/32276) \| GC-MS \| [splash10-001j-0590000000-63d5e32dd5f7877a4402](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001j-0590000000-63d5e32dd5f7877a4402) \| \| [GC-MS Spectrum - GC-EI-TOF](https://go.drugbank.com/spectra/c_ms/32277) \| GC-MS \| [splash10-001i-0590000000-52b3a733f8b49582d3fb](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0590000000-52b3a733f8b49582d3fb) \| \| [GC-MS Spectrum - GC-EI-TOF](https://go.drugbank.com/spectra/c_ms/32278) \| GC-MS \| [splash10-0229-1900000000-d81c6f617bc486066136](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0229-1900000000-d81c6f617bc486066136) \| \| [Mass Spectrum (Electron Ionization)](https://go.drugbank.com/spectra/ei_ms/505) \| MS \| [splash10-03k9-1900000000-45ee4fdc7acdb33dad3b](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-03k9-1900000000-45ee4fdc7acdb33dad3b) \| \| [MS/MS Spectrum - Quattro\_QQQ 10V, Positive](https://go.drugbank.com/spectra/ms_ms/1547) \| LC-MS/MS \| [splash10-00di-0920000000-f90ec9b77e1a245e35a8](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0920000000-f90ec9b77e1a245e35a8) \| \| [MS/MS Spectrum - Quattro\_QQQ 25V, Positive](https://go.drugbank.com/spectra/ms_ms/1548) \| LC-MS/MS \| [splash10-05fr-0900000000-49e4482c65e82ac64b66](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-05fr-0900000000-49e4482c65e82ac64b66) \| \| [MS/MS Spectrum - Quattro\_QQQ 40V, Positive](https://go.drugbank.com/spectra/ms_ms/1549) \| LC-MS/MS \| [splash10-003r-0900000000-8a4ae0fd610cca992d74](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-003r-0900000000-8a4ae0fd610cca992d74) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative](https://go.drugbank.com/spectra/ms_ms/5222) \| LC-MS/MS \| [splash10-0159-0090000000-939a1caf5760c0ba189c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0159-0090000000-939a1caf5760c0ba189c) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative](https://go.drugbank.com/spectra/ms_ms/5223) \| LC-MS/MS \| [splash10-0006-0930000000-9e6fcea2c634ac9d85a0](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0930000000-9e6fcea2c634ac9d85a0) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative](https://go.drugbank.com/spectra/ms_ms/5224) \| LC-MS/MS \| [splash10-0006-0900000000-ddd29e731a7de56c1808](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-ddd29e731a7de56c1808) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative](https://go.drugbank.com/spectra/ms_ms/5225) \| LC-MS/MS \| [splash10-0006-0900000000-34b4fb52810a15ea5bd6](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-34b4fb52810a15ea5bd6) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative](https://go.drugbank.com/spectra/ms_ms/5226) \| LC-MS/MS \| [splash10-001i-0090000000-5ca2df63ec2baefdae8c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0090000000-5ca2df63ec2baefdae8c) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive](https://go.drugbank.com/spectra/ms_ms/5227) \| LC-MS/MS \| [splash10-001i-0190000000-5bae6e63e9b40e60e0a4](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0190000000-5bae6e63e9b40e60e0a4) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive](https://go.drugbank.com/spectra/ms_ms/5228) \| LC-MS/MS \| [splash10-00di-0900000000-529bf6d5c2091993f865](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-529bf6d5c2091993f865) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive](https://go.drugbank.com/spectra/ms_ms/5229) \| LC-MS/MS \| [splash10-00di-0900000000-158a60fe696120b23b41](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-158a60fe696120b23b41) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive](https://go.drugbank.com/spectra/ms_ms/5230) \| LC-MS/MS \| [splash10-0a5c-0900000000-5e86b2de659ce47762c0](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0a5c-0900000000-5e86b2de659ce47762c0) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive](https://go.drugbank.com/spectra/ms_ms/5231) \| LC-MS/MS \| [splash10-001i-0900000000-881c0d57239d56c46f2d](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0900000000-881c0d57239d56c46f2d) \| \| [LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive](https://go.drugbank.com/spectra/ms_ms/5232) \| LC-MS/MS \| [splash10-00di-0910000000-f256f78adbcbeb2464de](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0910000000-f256f78adbcbeb2464de) \| \| [LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive](https://go.drugbank.com/spectra/ms_ms/5233) \| LC-MS/MS \| [splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23) \| \| [MS/MS Spectrum - DI-ESI-qTof , Positive](https://go.drugbank.com/spectra/ms_ms/374102) \| LC-MS/MS \| [splash10-05fr-0900000000-7acf9405f4beeb34566c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-05fr-0900000000-7acf9405f4beeb34566c) \| \| [MS/MS Spectrum - DI-ESI-qTof , Positive](https://go.drugbank.com/spectra/ms_ms/374103) \| LC-MS/MS \| [splash10-00di-0900000000-13245183cd8c8cd511c3](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-13245183cd8c8cd511c3) \| \| [LC-MS/MS Spectrum - LC-ESI-qTof , Positive](https://go.drugbank.com/spectra/ms_ms/374702) \| LC-MS/MS \| [splash10-05ai-2900000000-07b3d32f002dba733c10](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-05ai-2900000000-07b3d32f002dba733c10) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438131) \| LC-MS/MS \| [splash10-0159-0090000000-939a1caf5760c0ba189c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0159-0090000000-939a1caf5760c0ba189c) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438132) \| LC-MS/MS \| [splash10-0006-0930000000-9e6fcea2c634ac9d85a0](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0930000000-9e6fcea2c634ac9d85a0) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438133) \| LC-MS/MS \| [splash10-0006-0900000000-ddd29e731a7de56c1808](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-ddd29e731a7de56c1808) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438134) \| LC-MS/MS \| [splash10-0006-0900000000-34b4fb52810a15ea5bd6](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-34b4fb52810a15ea5bd6) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , negative](https://go.drugbank.com/spectra/ms_ms/438135) \| LC-MS/MS \| [splash10-001i-0090000000-5ca2df63ec2baefdae8c](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0090000000-5ca2df63ec2baefdae8c) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , negative](https://go.drugbank.com/spectra/ms_ms/439444) \| LC-MS/MS \| [splash10-00lr-0090000000-3c42f6997539afb44682](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00lr-0090000000-3c42f6997539afb44682) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , negative](https://go.drugbank.com/spectra/ms_ms/439448) \| LC-MS/MS \| [splash10-014m-0960000000-7991e64dacb3c7f5cf32](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-014m-0960000000-7991e64dacb3c7f5cf32) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , negative](https://go.drugbank.com/spectra/ms_ms/439451) \| LC-MS/MS \| [splash10-0006-0900000000-882be43bc196e928a3cf](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-0900000000-882be43bc196e928a3cf) \| \| [MS/MS Spectrum - , negative](https://go.drugbank.com/spectra/ms_ms/440134) \| LC-MS/MS \| [splash10-014i-0190000000-ddda9232f0e8e1b402f7](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-014i-0190000000-ddda9232f0e8e1b402f7) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446535) \| LC-MS/MS \| [splash10-001i-0190000000-5bae6e63e9b40e60e0a4](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0190000000-5bae6e63e9b40e60e0a4) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446536) \| LC-MS/MS \| [splash10-00di-0900000000-529bf6d5c2091993f865](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-529bf6d5c2091993f865) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446537) \| LC-MS/MS \| [splash10-00di-0900000000-158a60fe696120b23b41](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-158a60fe696120b23b41) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446538) \| LC-MS/MS \| [splash10-0a5c-0900000000-5e86b2de659ce47762c0](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0a5c-0900000000-5e86b2de659ce47762c0) \| \| [LC-MS/MS Spectrum - LC-ESI-QQ , positive](https://go.drugbank.com/spectra/ms_ms/446539) \| LC-MS/MS \| [splash10-001i-0900000000-881c0d57239d56c46f2d](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0900000000-881c0d57239d56c46f2d) \| \| [LC-MS/MS Spectrum - LC-ESI-IT , positive](https://go.drugbank.com/spectra/ms_ms/447247) \| LC-MS/MS \| [splash10-00di-0910000000-d659c749adcab685e8bb](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0910000000-d659c749adcab685e8bb) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , positive](https://go.drugbank.com/spectra/ms_ms/449479) \| LC-MS/MS \| [splash10-00di-0900000000-6817d8039761a9058337](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-6817d8039761a9058337) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , positive](https://go.drugbank.com/spectra/ms_ms/449485) \| LC-MS/MS \| [splash10-00di-0900000000-349d5a97e2406d0db910](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-349d5a97e2406d0db910) \| \| [LC-MS/MS Spectrum - LC-ESI-QTOF , positive](https://go.drugbank.com/spectra/ms_ms/449491) \| LC-MS/MS \| [splash10-001i-0900000000-9e30dcf47c9eca14650e](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-001i-0900000000-9e30dcf47c9eca14650e) \| \| [MS/MS Spectrum - , positive](https://go.drugbank.com/spectra/ms_ms/450591) \| LC-MS/MS \| [splash10-00di-1900000000-73dc69b26b1fba60f253](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-1900000000-73dc69b26b1fba60f253) \| \| [MS/MS Spectrum - , positive](https://go.drugbank.com/spectra/ms_ms/451347) \| LC-MS/MS \| [splash10-05ai-2900000000-07b3d32f002dba733c10](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-05ai-2900000000-07b3d32f002dba733c10) \| \| [MS/MS Spectrum - , positive](https://go.drugbank.com/spectra/ms_ms/451967) \| LC-MS/MS \| [splash10-00di-0900000000-2e847095e37f4ffe7c8b](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-2e847095e37f4ffe7c8b) \| \| [Predicted MS/MS Spectrum - 10V, Positive (Annotated)](https://go.drugbank.com/spectra/ms_ms/677259) \| Predicted LC-MS/MS \| [splash10-0089-0960000000-9acd48062f28a100f9da](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0089-0960000000-9acd48062f28a100f9da) \| \| [Predicted MS/MS Spectrum - 10V, Negative (Annotated)](https://go.drugbank.com/spectra/ms_ms/677289) \| Predicted LC-MS/MS \| [splash10-03di-5790000000-571ee430d2b0391822e3](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-03di-5790000000-571ee430d2b0391822e3) \| \| [Predicted MS/MS Spectrum - 20V, Positive (Annotated)](https://go.drugbank.com/spectra/ms_ms/677314) \| Predicted LC-MS/MS \| [splash10-00di-0900000000-1a38178248f05cf91e65](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-00di-0900000000-1a38178248f05cf91e65) \| \| [Predicted MS/MS Spectrum - 20V, Negative (Annotated)](https://go.drugbank.com/spectra/ms_ms/677334) \| Predicted LC-MS/MS \| [splash10-052f-9000000000-9950a9dee5e36e935714](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-052f-9000000000-9950a9dee5e36e935714) \| \| [Predicted MS/MS Spectrum - 40V, Positive (Annotated)](https://go.drugbank.com/spectra/ms_ms/677344) \| Predicted LC-MS/MS \| [splash10-006x-0900000000-5d47768c1bb474f51f38](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-006x-0900000000-5d47768c1bb474f51f38) \| \| [Predicted MS/MS Spectrum - 40V, Negative (Annotated)](https://go.drugbank.com/spectra/ms_ms/677384) \| Predicted LC-MS/MS \| [splash10-0006-4900000000-9374ee5bf5eb87317f56](http://mona.fiehnlab.ucdavis.edu/#/spectra/splash/splash10-0006-4900000000-9374ee5bf5eb87317f56) \| \| [1H NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/1693) \| 1D NMR \| Not Applicable \| \| [1H NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/2600) \| 1D NMR \| Not Applicable \| \| [13C NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/3303) \| 1D NMR \| Not Applicable \| \| [Predicted 1H NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/42674) \| 1D NMR \| Not Applicable \| \| [Predicted 13C NMR Spectrum](https://go.drugbank.com/spectra/nmr_one_d/42679) \| 1D NMR \| Not Applicable \| \| [\[1H,13C\] 2D NMR Spectrum](https://go.drugbank.com/spectra/nmr_two_d/1634) \| 2D NMR \| Not Applicable \| Chromatographic Properties ###### Collision Cross Sections (CCS) \| Adduct \| CCS Value (Å2) \| Source type \| Source \| \|---\|---\|---\|---\| \| \[M-H\]- \| 159\.6858961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M-H\]- \| 152\.8346632 \| predicted \| DarkChem Standard v0.1.0 \| \| \[M-H\]- \| 152\.9149983 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M-H\]- \| 165\.2831961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M-H\]- \| 159\.7026961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M-H\]- \| 150\.02837 \| predicted \| DeepCCS 1.0 (2019) \| \| \[M+H\]+ \| 159\.1911961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+H\]+ \| 157\.166152 \| predicted \| DarkChem Standard v0.1.0 \| \| \[M+H\]+ \| 157\.1763686 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+H\]+ \| 166\.2821961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+H\]+ \| 159\.7927961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+H\]+ \| 152\.38637 \| predicted \| DeepCCS 1.0 (2019) \| \| \[M+Na\]+ \| 158\.6747961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 165\.6858961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 167\.0242025 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 165\.6891961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 159\.5635961 \| predicted \| DarkChem Lite v0.1.0 \| \| \[M+Na\]+ \| 158\.4795 \| predicted \| DeepCCS 1.0 (2019) \| ### Targets [![](https://go.drugbank.com/assets/locked/DrugTargets2-1d1d534575da54e734c316d80c9fb35f8210c070dca913c026f8e58660e3e71a.png) Build, predict & validate machine-learning models Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.Learn more](https://bit.ly/3iYePSn) [Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.Learn more](https://bit.ly/3zOIrse) KindProtein OrganismHumans Pharmacological action Yes Actions Agonist General FunctionHigh affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity. Possibly involved in sleep induction, by melatonin activation of the potassium channel KCNMA1/BK and the dissociation of G-beta and G-gamma subunits, thereby decreasing synaptic transmission (By similarity) Specific FunctionG protein-coupled receptor activity Gene NameMTNR1A Uniprot ID[P48039](http://www.uniprot.org/uniprot/P48039) Uniprot NameMelatonin receptor type 1A Molecular Weight39374\.315 Da ##### References 1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. \[[Article](https://go.drugbank.com/articles/A15272)\] 2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. \[[Article](https://go.drugbank.com/articles/A9)\] 3. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \[[Article](https://go.drugbank.com/articles/A1674)\] 4. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. \[[Article](https://go.drugbank.com/articles/A15273)\] 5. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007/s12325-010-0065-y. Epub 2010 Sep 6. \[[Article](https://go.drugbank.com/articles/A15274)\] 6. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016/j.bmc.2010.06.100. Epub 2010 Jul 3. \[[Article](https://go.drugbank.com/articles/A15275)\] 7. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210/en.2009-0710. Epub 2009 Dec 4. \[[Article](https://go.drugbank.com/articles/A15276)\] 8. Witt-Enderby PA, Chu GH, Gillen ML, Li PK: Development of a high-affinity ligand that binds irreversibly to Mel1b melatonin receptors. J Med Chem. 1997 Dec 19;40(26):4195-8. \[[Article](https://go.drugbank.com/articles/A29415)\] 9. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] 10. Hoashi Y, Takai T, Kosugi Y, Nakashima M, Nakayama M, Hirai K, Uchikawa O, Koike T: Discovery of a Potent and Orally Bioavailable Melatonin Receptor Agonist. J Med Chem. 2021 Mar 25;64(6):3059-3074. doi: 10.1021/acs.jmedchem.0c01836. Epub 2021 Mar 7. \[[Article](https://go.drugbank.com/articles/A268970)\] 11. Gunia-Krzyzak A, Zelaszczyk D, Rapacz A, Zeslawska E, Waszkielewicz AM, Panczyk K, Sloczynska K, Pekala E, Nitek W, Filipek B, Marona H: Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH(3) or 2-CH(3). Bioorg Med Chem. 2017 Jan 15;25(2):471-482. doi: 10.1016/j.bmc.2016.11.014. Epub 2016 Nov 11. \[[Article](https://go.drugbank.com/articles/A273460)\] KindProtein OrganismHumans Pharmacological action Yes Actions Agonist General FunctionHigh affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity Specific FunctionG protein-coupled receptor activity Gene NameMTNR1B Uniprot ID[P49286](http://www.uniprot.org/uniprot/P49286) Uniprot NameMelatonin receptor type 1B Molecular Weight40187\.895 Da ##### References 1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. \[[Article](https://go.drugbank.com/articles/A15272)\] 2. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. \[[Article](https://go.drugbank.com/articles/A1674)\] 3. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. \[[Article](https://go.drugbank.com/articles/A15273)\] 4. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007/s12325-010-0065-y. Epub 2010 Sep 6. \[[Article](https://go.drugbank.com/articles/A15274)\] 5. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016/j.bmc.2010.06.100. Epub 2010 Jul 3. \[[Article](https://go.drugbank.com/articles/A15275)\] 6. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210/en.2009-0710. Epub 2009 Dec 4. \[[Article](https://go.drugbank.com/articles/A15276)\] 7. Mattson RJ, Catt JD, Keavy D, Sloan CP, Epperson J, Gao Q, Hodges DB, Iben L, Mahle CD, Ryan E, Yocca FD: Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett. 2003 Mar 24;13(6):1199-202. \[[Article](https://go.drugbank.com/articles/A29424)\] 8. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] 9. Ferreira MA Jr, Azevedo H, Mascarello A, Segretti ND, Russo E, Russo V, Guimaraes CRW: Discovery of ACH-000143: A Novel Potent and Peripherally Preferred Melatonin Receptor Agonist that Reduces Liver Triglycerides and Steatosis in Diet-Induced Obese Rats. J Med Chem. 2021 Feb 25;64(4):1904-1929. doi: 10.1021/acs.jmedchem.0c00627. Epub 2021 Feb 8. \[[Article](https://go.drugbank.com/articles/A268965)\] KindProtein OrganismHumans Pharmacological action Yes Actions Inhibitor General FunctionThe enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis Specific Functionchloride ion binding Gene NameNQO2 Uniprot ID[P16083](http://www.uniprot.org/uniprot/P16083) Uniprot NameRibosyldihydronicotinamide dehydrogenase \[quinone\] Molecular Weight25918\.4 Da ##### References 1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. \[[Article](https://go.drugbank.com/articles/A15272)\] 2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. \[[Article](https://go.drugbank.com/articles/A264250)\] 3. Fukatsu K, Uchikawa O, Kawada M, Yamano T, Yamashita M, Kato K, Hirai K, Hinuma S, Miyamoto M, Ohkawa S: Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists. J Med Chem. 2002 Sep 12;45(19):4212-21. doi: 10.1021/jm020114g. \[[Article](https://go.drugbank.com/articles/A268565)\] 4. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] 5. Du H, Wang J, Zhang X, Hu Z: A novel quantitative structure-activity relationship method to predict the affinities of MT3 melatonin binding site. Eur J Med Chem. 2008 Dec;43(12):2861-9. doi: 10.1016/j.ejmech.2008.02.012. Epub 2008 Feb 29. \[[Article](https://go.drugbank.com/articles/A29410)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Antagonist General FunctionNuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity) Specific Function14-3-3 protein binding Gene NameESR1 Uniprot ID[P03372](http://www.uniprot.org/uniprot/P03372) Uniprot NameEstrogen receptor Molecular Weight66215\.45 Da ##### References 1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. \[[Article](https://go.drugbank.com/articles/A15278)\] 2. Yoo YM, Jeung EB: Melatonin-induced estrogen receptor alpha-mediated calbindin-D9k expression plays a role in H2O2-mediated cell death in rat pituitary GH3 cells. J Pineal Res. 2009 Nov;47(4):301-7. doi: 10.1111/j.1600-079X.2009.00714.x. Epub 2009 Oct 1. \[[Article](https://go.drugbank.com/articles/A15281)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Agonist General FunctionNuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity) Specific FunctionDNA-binding transcription activator activity, RNA polymerase II-specific Gene NameRORB Uniprot ID[Q92753](http://www.uniprot.org/uniprot/Q92753) Uniprot NameNuclear receptor ROR-beta Molecular Weight53219\.385 Da ##### References 1. Becker-Andre M, Wiesenberg I, Schaeren-Wiemers N, Andre E, Missbach M, Saurat JH, Carlberg C: Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily. J Biol Chem. 1994 Nov 18;269(46):28531-4. \[[Article](https://go.drugbank.com/articles/A15277)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Inhibitor General FunctionPart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971) Specific Functionchromatin binding Gene NameMPO Uniprot ID[P05164](http://www.uniprot.org/uniprot/P05164) Uniprot NameMyeloperoxidase Molecular Weight83867\.71 Da ##### References 1. Galijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021/bi702016q. Epub 2008 Feb 1. \[[Article](https://go.drugbank.com/articles/A15280)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Inhibitor General FunctionMediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis Specific Functionheme binding Gene NameEPX Uniprot ID[P11678](http://www.uniprot.org/uniprot/P11678) Uniprot NameEosinophil peroxidase Molecular Weight81039\.5 Da ##### References 1. Lu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038/bjp.2008.173. Epub 2008 Jun 2. \[[Article](https://go.drugbank.com/articles/A15282)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Modulator General FunctionCalcium-binding chaperone that promotes folding, oligomeric assembly and quality control in the endoplasmic reticulum (ER) via the calreticulin/calnexin cycle. This lectin interacts transiently with almost all of the monoglucosylated glycoproteins that are synthesized in the ER (PubMed:7876246). Interacts with the DNA-binding domain of NR3C1 and mediates its nuclear export (PubMed:11149926). Involved in maternal gene expression regulation. May participate in oocyte maturation via the regulation of calcium homeostasis (By similarity). Present in the cortical granules of non-activated oocytes, is exocytosed during the cortical reaction in response to oocyte activation and might participate in the block to polyspermy (By similarity) Specific Functioncalcium ion binding Gene NameCALR Uniprot ID[P27797](http://www.uniprot.org/uniprot/P27797) Uniprot NameCalreticulin Molecular Weight48141\.2 Da ##### References 1. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. \[[Article](https://go.drugbank.com/articles/A15273)\] 2. Macias M, Escames G, Leon J, Coto A, Sbihi Y, Osuna A, Acuna-Castroviejo D: Calreticulin-melatonin. An unexpected relationship. Eur J Biochem. 2003 Mar;270(5):832-40. \[[Article](https://go.drugbank.com/articles/A15279)\] KindProtein group OrganismHumans Pharmacological action Unknown Actions Antagonist General FunctionCalmodulin acts as part of a calcium signal transduction pathway by mediating the control of a large number of enzymes, ion channels, aquaporins and other proteins through calcium-binding (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Calcium-binding is required for the activation of calmodulin (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Among the enzymes to be stimulated by the calmodulin-calcium complex are a number of protein kinases, such as myosin light-chain kinases and calmodulin-dependent protein kinase type II (CaMK2), and phosphatases (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis (PubMed:16760425). Is a regulator of voltage-dependent L-type calcium channels (PubMed:31454269). Mediates calcium-dependent inactivation of CACNA1C (PubMed:26969752). Positively regulates calcium-activated potassium channel activity of KCNN2 (PubMed:27165696). Forms a potassium channel complex with KCNQ1 and regulates electrophysiological activity of the channel via calcium-binding (PubMed:25441029). Acts as a sensor to modulate the endoplasmic reticulum contacts with other organelles mediated by VMP1:ATP2A2 (PubMed:28890335) Specific Functionadenylate cyclase activator activity *** ##### Components: \| Name \| UniProt ID \| \|---\|---\| \| [Calmodulin-1](https://go.drugbank.com/polypeptides/P0DP23) \| [P0DP23](http://www.uniprot.org/uniprot/P0DP23) \| \| [Calmodulin-2](https://go.drugbank.com/polypeptides/P0DP24) \| [P0DP24](http://www.uniprot.org/uniprot/P0DP24) \| \| [Calmodulin-3](https://go.drugbank.com/polypeptides/P0DP25) \| [P0DP25](http://www.uniprot.org/uniprot/P0DP25) \| ##### References 1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. \[[Article](https://go.drugbank.com/articles/A15278)\] 2. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. \[[Article](https://go.drugbank.com/articles/A15272)\] ### Enzymes KindProtein OrganismHumans Pharmacological action Unknown Actions Substrate Inhibitor General FunctionA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195) Specific Functionarachidonate monooxygenase activity Gene NameCYP1A1 Uniprot ID[P04798](http://www.uniprot.org/uniprot/P04798) Uniprot NameCytochrome P450 1A1 Molecular Weight58164\.815 Da ##### References 1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \[[Article](https://go.drugbank.com/articles/A15283)\] 2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \[[Article](https://go.drugbank.com/articles/A15284)\] 3. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. \[[Article](https://go.drugbank.com/articles/A266010)\] 4. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Substrate General FunctionA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable) Specific Functioncaffeine oxidase activity Gene NameCYP1A2 Uniprot ID[P05177](http://www.uniprot.org/uniprot/P05177) Uniprot NameCytochrome P450 1A2 Molecular Weight58406\.915 Da ##### References 1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \[[Article](https://go.drugbank.com/articles/A15283)\] 2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \[[Article](https://go.drugbank.com/articles/A15284)\] 3. Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. \[[Article](https://go.drugbank.com/articles/A15285)\] 4. Hartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. \[[Article](https://go.drugbank.com/articles/A38895)\] 5. Hartter S, Wang X, Weigmann H, Friedberg T, Arand M, Oesch F, Hiemke C: Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin. J Clin Psychopharmacol. 2001 Apr;21(2):167-74. \[[Article](https://go.drugbank.com/articles/A38975)\] 6. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. \[[Article](https://go.drugbank.com/articles/A266010)\] 7. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Substrate Inhibitor General FunctionA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity) Specific Functionestrogen 16-alpha-hydroxylase activity Gene NameCYP1B1 Uniprot ID[Q16678](http://www.uniprot.org/uniprot/Q16678) Uniprot NameCytochrome P450 1B1 Molecular Weight60845\.33 Da ##### References 1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. \[[Article](https://go.drugbank.com/articles/A15283)\] 2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. \[[Article](https://go.drugbank.com/articles/A15284)\] 3. Yu Z, Tian X, Peng Y, Sun Z, Wang C, Tang N, Li B, Jian Y, Wang W, Huo X, Ma X: Mitochondrial cytochrome P450 (CYP) 1B1 is responsible for melatonin-induced apoptosis in neural cancer cells. J Pineal Res. 2018 Aug;65(1):e12478. doi: 10.1111/jpi.12478. Epub 2018 Mar 25. \[[Article](https://go.drugbank.com/articles/A184151)\] 4. Dutour R, Poirier D: Inhibitors of cytochrome P450 (CYP) 1B1. Eur J Med Chem. 2017 Jul 28;135:296-306. doi: 10.1016/j.ejmech.2017.04.042. Epub 2017 Apr 18. \[[Article](https://go.drugbank.com/articles/A266010)\] 5. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Substrate General FunctionA cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307) Specific Function(R)-limonene 6-monooxygenase activity Gene NameCYP2C19 Uniprot ID[P33261](http://www.uniprot.org/uniprot/P33261) Uniprot NameCytochrome P450 2C19 Molecular Weight55944\.565 Da ##### References 1. Huuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. \[[Article](https://go.drugbank.com/articles/A15286)\] 2. Facciola G, Hidestrand M, von Bahr C, Tybring G: Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes. Eur J Clin Pharmacol. 2001 Mar;56(12):881-8. doi: 10.1007/s002280000245. \[[Article](https://go.drugbank.com/articles/A184145)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Substrate General FunctionA cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031) Specific Function(R)-limonene 6-monooxygenase activity Gene NameCYP2C9 Uniprot ID[P11712](http://www.uniprot.org/uniprot/P11712) Uniprot NameCytochrome P450 2C9 Molecular Weight55627\.365 Da ##### References 1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. \[[Article](https://go.drugbank.com/articles/A14815)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Substrate General FunctionCatalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine) Specific Functionacetylserotonin O-methyltransferase activity Gene NameASMT Uniprot ID[P46597](http://www.uniprot.org/uniprot/P46597) Uniprot NameAcetylserotonin O-methyltransferase Molecular Weight38452\.51 Da ##### References 1. Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. \[[Article](https://go.drugbank.com/articles/A15271)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Substrate General FunctionCatalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, contributing to maintain homeostasis by preventing autoimmunity or immunopathology that would result from uncontrolled and overreacting immune responses (PubMed:25691885). Tryptophan shortage inhibits T lymphocytes division and accumulation of tryptophan catabolites induces T-cell apoptosis and differentiation of regulatory T-cells (PubMed:25691885). Acts as a suppressor of anti-tumor immunity (PubMed:14502282, PubMed:23103127, PubMed:25157255, PubMed:25691885). Limits the growth of intracellular pathogens by depriving tryptophan (PubMed:25691885). Protects the fetus from maternal immune rejection (PubMed:25691885) Specific Functionelectron transfer activity Gene NameIDO1 Uniprot ID[P14902](http://www.uniprot.org/uniprot/P14902) Uniprot NameIndoleamine 2,3-dioxygenase 1 Molecular Weight45325\.89 Da ##### References 1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. \[[Article](https://go.drugbank.com/articles/A15321)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Substrate Inhibitor General FunctionPart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity (PubMed:9922160). Mediates the proteolytic cleavage of alpha-1-microglobulin to form t-alpha-1-microglobulin, which potently inhibits oxidation of low-density lipoprotein particles and limits vascular damage (PubMed:25698971) Specific Functionchromatin binding Gene NameMPO Uniprot ID[P05164](http://www.uniprot.org/uniprot/P05164) Uniprot NameMyeloperoxidase Molecular Weight83867\.71 Da ##### References 1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. \[[Article](https://go.drugbank.com/articles/A15321)\] 2. Galijasevic S: The development of myeloperoxidase inhibitors. Bioorg Med Chem Lett. 2019 Jan 1;29(1):1-7. doi: 10.1016/j.bmcl.2018.11.031. Epub 2018 Nov 15. \[[Article](https://go.drugbank.com/articles/A267170)\] 3. Liu T, Hwang L, Burley SK, Nitsche CI, Southan C, Walters WP, Gilson MK: BindingDB in 2024: a FAIR knowledgebase of protein-small molecule binding data. Nucleic Acids Res. 2025 Jan 6;53(D1):D1633-D1644. doi: 10.1093/nar/gkae1075. \[[Article](https://go.drugbank.com/articles/A265110)\] KindProtein OrganismHumans Pharmacological action Unknown Actions Inhibitor General FunctionA cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874) Specific Functionaromatase activity Gene NameCYP19A1 Uniprot ID[P11511](http://www.uniprot.org/uniprot/P11511) Uniprot NameAromatase Molecular Weight57882\.48 Da ##### References 1. Gonzalez A, Martinez-Campa C, Mediavilla MD, Alonso-Gonzalez C, Sanchez-Mateos S, Hill SM, Sanchez-Barcelo EJ, Cos S: Effects of MT1 melatonin receptor overexpression on the aromatase-suppressive effect of melatonin in MCF-7 human breast cancer cells. Oncol Rep. 2007 Apr;17(4):947-53. doi: 10.3892/or.17.4.947. \[[Article](https://go.drugbank.com/articles/A182687)\] ### Transporters KindProtein OrganismHumans Pharmacological action Unknown Actions Inhibitor General FunctionFunctions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity) Specific Functionorganic anion transmembrane transporter activity Gene NameSLC22A8 Uniprot ID[Q8TCC7](http://www.uniprot.org/uniprot/Q8TCC7) Uniprot NameOrganic anion transporter 3 Molecular Weight59855\.585 Da ##### References 1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. \[[Article](https://go.drugbank.com/articles/A16319)\] 2. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. \[[Article](https://go.drugbank.com/articles/A6152)\]
Shard	93 (laksa)
Root Hash	15397128513976815493
Unparsed URL	com,drugbank!go,/drugs/DB01065 s443