{"ATC Code":["N02CC01","N - Nervous system","N02 - Analgesics","N02C - Antimigraine preparations","N02CC - Selective serotonin (5ht1) agonists","N02CC01 - Sumatriptan","QN - Nervous system","QN02 - Analgesics","QN02C - Antimigraine preparations","QN02CC - Selective serotonin (5ht1) agonists","QN02CC01 - Sumatriptan","N02CC01"],"Absorption, Distribution and Excretion":"A 6mg subcutaneous injection of sumatriptan reaches a Cmax of 69.5ng/mL (95% CI  of 62.8-76.9ng/mL) with a Tmax of 0.17h (95% CI  of 0.08-0.33h), an AUC of 9.0h\\*ng/mL (95% CI of 7.5-10.9h\\*ng/mL), and a bioavailability of 100%.  A 25mg oral dose of sumatriptan reaches a Cmax of 16.5ng/mL (95% CI  of 13.5-20.1ng/mL) with a Tmax of 1.50h (95% CI  of 0.50-2.00h), an AUC of 8.7h\\*ng/mL (95% CI of 6.1-12.5h\\*ng/mL), and a bioavailability of 14.3% (95% CI of 11.4-17.9%).  A 20mg intranasal dose of sumatriptan reaches a Cmax of 12.9ng/mL (95% CI  of 10.5-15.9ng/mL) with a Tmax of 1.50h (95% CI  of 0.25-3.00h), an AUC of 7.4h\\*ng/mL (95% CI of 5.0-10.8h\\*ng/mL), and a bioavailability of 15.8% (95% CI of 12.6-19.8%).  A 25mg rectal dose of sumatriptan reaches a Cmax of 22.9ng/mL (95% CI  of 18.4-28.6ng/mL) with a Tmax of 1.00h (95% CI  of 0.75-3.00h), an AUC of 14.6h\\*ng/mL (95% CI of 11.3-18.8h\\*ng/mL), and a bioavailability of 19.2% (95% CI of 15.3-24.1%).","Adverse Effects":"The safety of treating more than 4 headaches in a month with sumatriptan has not been investigated yet. Notably, adverse reactions to sumatriptan are influenced by the dosage and can be dose-dependent. Individuals experiencing nausea and vomiting can opt for subcutaneous injection instead of the oral form of sumatriptan. However, it is noteworthy that subcutaneous administration of the drug is associated with a higher occurrence of adverse events.","Aliases":["Sumatriptan","Imitrex","Sumatran","Sumax","Imigran","Sumatriptanum","3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide","1-(3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide","1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide","Imigran Recovery","1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide","TOSYMRA","DFN-11","3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide","Dtxsid4023628","N02CC01","1H-Indole-5-methanesulfonamide, 3-[2-(dimethylamino)ethyl]-N-methyl-","3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide","Dfn-11","Dtxcid303628","Chebi:10650","(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide","1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide","1H-Indole-5-methanesulfonamide, 3-(2-(dimethylamino)ethyl)-N-methyl-","3-(2-(Dimethylamino)ethyl)-N-methylindole-5-methanesulfonamide","Imigran Radis","(3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide","{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide","1-(3-(2-dimethylaminoethyl)-1H-indol-5-yl)-N-methyl-methanesulfonamide","1-(3-(2-dimethylaminoethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide","GR43175","Succinate, Sumatriptan","600-462-9","GR 43175","CHEMBL128","Mfcd00866222","Ncgc00095838-01","GR-43175","GR 43175X","Smr000596517","Cas-103628-46-2","Brn 6930870","Unii-8r78f6l9vo","AVP825","HSDB 7742","AVP 825","AVP-825","Tosymra","Sumatriptan Impurity 16","GTPL54","Schembl1482","BSPBio_002304","Mls001195659","Mls001304742","Bidd:gt0248","Spectrum1505372","orb1704027","Schembl29450235","Sumatriptan - Bio-X trade mark","HY-B0121B","HMS2231B21","HMS3369A05","Albb-038603","MSK11291","Tox21_111528","Bdbm50005835","EBC-26501","STL451003","1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methyl-methanesulfonamide","Akos015894924","Tox21_111528_1","CCG-230331","DB00669","Ncgc00095838-02","Ncgc00095838-03","Ncgc00095838-04","BS164424","FD146133","SY398829","Sbi-0206837.p001","CS-0009565","NS00009397","C07319","C90357","D00451","En300-123008","T23405","Ab00698285-12","Ab00698285-13","Ab00698285_14","Ab00698285_15","F600616","L000584","Brd-k50938287-001-01-7","Brd-k50938287-001-09-0","Brd-k50938287-036-12-0","Brd-k50938287-036-13-8","3-[2-(Dimethylamino)ethyl]-N-methy-1H-indole-5-methanesulfonamide","3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulphonamide","(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide #","1-[3-[2-(Dimethylamino)ethyl]-5-indolyl]-N-methylmethanesulfonamide","3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole -5-methanesulphonamide"],"Biological Half-Life":"Subcutaneous sumatriptan has a half life of 1.9h (95% CI  of 1.7-2.0h). Oral sumatriptan has a half life of 1.7h (95% CI  of 1.4-1.9h). Rectal sumatriptan has a half life of 1.8h (95% CI  of 1.6-2.2h). Intranasal sumatriptan has a half life of 1.8h (95% CI  of 1.7-2.0h).","CAS":"103628-46-2","ChemicalClasses":["tryptamine"],"Chirality":"achiral","DBI-IGS":["Sumatriptan"],"Dosing Info":[],"Drug Classes":["Breast Feeding","Lactation","Milk, Human","Serotonin Receptor Agonists","Serotonin 5-HT1 Receptor Agonists","Triptans","Vasoconstrictor Agents"],"Drug Indication":"A combination sumatriptan and [naproxen] tablet is indicated for the treatment of migraines with or without auras in patients 12 years of age and older. Sumatriptan nasal powder, nasal spray, subcutaneous injection, and tablets are indicated to treat migraines with or without auras in adults. One of the subcutaneous formulations of sumatriptan is also indicated to treat cluster headaches in adults, while the other subcutaneous formulation is not.","Drug Warnings":"Most adverse effects associated with sumatriptan are well defined, transient, and mild to moderate in intensity, although serious cardiac events (coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia, ventricular fibrillation) have been reported rarely in patients receiving the drug subcutaneously or orally. Adverse effects associated with the drug usually occur within 1 hour after subcutaneous or oral administration of sumatriptan and generally resolve within 10-30 minutes (subcutaneous) or 1 hour (oral). The incidence of adverse effects associated with sumatriptan generally remains unchanged or decreases with repeated use of the drug. However, the incidence of adverse effects appears to increase with higher than recommended doses of the drug. In addition, the overall incidence of adverse effects among patients receiving sumatriptan injection for the treatment of cluster headache is lower than that in patients being treated with the drug for migraine.","EliminationHalfLife":"2.5 hours","Erowid Experience Reports":[{"Author":"LadyLovelyLocks","Id":84042,"Title":"I'm a Giant Bruise"},{"Author":"well wisher","Id":32614,"Title":"Fire in the Brain"},{"Author":"Migraine Moll","Id":112344,"Title":"Post Dosage Malaise"},{"Author":"ClusterFluck","Id":117260,"Title":"Not a Good Time"},{"Author":"Luciferi","Id":63110,"Title":"A Horrible Choice for Recreational Use..."}],"Esters":[],"European Community (EC) Number":"600-462-9","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"String":"8R78F6L9VO"}]}},{"Name":"Active Moiety","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"String":"SUMATRIPTAN"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5202","Length":9,"Start":29,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Mechanisms of Action [MoA] - Serotonin 1b Receptor Agonists"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"String":"Mechanisms of Action [MoA] - Serotonin 1d Receptor Agonists"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5202","Length":9,"Start":40,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Established Pharmacologic Class [EPC] - Serotonin-1b and Serotonin-1d Receptor Agonist"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5358","Length":11,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Sumatriptan"},{"Extra":"CID-5202","Length":9,"Start":17,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"},{"Extra":"CID-5358","Length":11,"Start":92,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/sumatriptan"},{"Extra":"CID-5202","Length":9,"Start":112,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Sumatriptan is a Serotonin-1b and Serotonin-1d Receptor Agonist. The mechanism of action of sumatriptan is as a Serotonin 1b Receptor Agonist, and Serotonin 1d Receptor Agonist."}]}},{"Name":"Non-Proprietary Name","ReferenceNumber":46,"Value":{"StringWithMarkup":[{"String":"SUMATRIPTAN"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":46,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5202","Length":9,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"},{"Extra":"CID-5202","Length":9,"Start":38,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Serotonin 1b Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1d Receptor Agonists [MoA]"}]}}],"Formating":[],"HMDB ID":"HMDB0005037","HeavyAtomCount":20,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Serotonin Receptor Agonists; Serotonin 5-HT1 Receptor Agonists; Triptans; Vasoconstrictor Agents","IUPACName":"1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide","Impurities":"[3-[2-(dimethylamino)ethyl]]-2-[[3-[2-(dimethylamino)ethanyl]]-1H-indol-5-yl]]-N-methylmethane-sulphonamide","InChI":"InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3","InChIKey":"KQKPFRSPSRPDEB-UHFFFAOYSA-N","Interactions":"Alcohol consumed 30 minutes prior to sumatriptan ingestion had no effect on the pharmacokinetics of sumatriptan.","KEGG Entries":[{"Id":"D00451","Interactions":[],"Synonyms":["Sumatriptan","Imigran","Imitrex"]},{"Id":"D00676","Interactions":[],"Synonyms":["Sumatriptan succinate","Alsuma","Imitrex","Sumave dosepro","Zecutity"]},{"Id":"D00451","Interactions":[],"Synonyms":["Sumatriptan","Imigran","Imitrex"]},{"Id":"D00676","Interactions":[],"Synonyms":["Sumatriptan succinate","Alsuma","Imitrex","Sumave dosepro","Zecutity"]},{"Id":"D00451","Interactions":[],"Synonyms":["Sumatriptan","Imigran","Imitrex"]},{"Id":"D00676","Interactions":[],"Synonyms":["Sumatriptan succinate","Alsuma","Imitrex","Sumave dosepro","Zecutity"]},{"Id":"D00451","Interactions":[],"Synonyms":["Sumatriptan","Imigran","Imitrex"]}],"MeSH Headers":[{"Id":"M0027392","Link":"https://id.nlm.nih.gov/mesh/M0027392.html","Name":"Sumatriptan","Ref":79},{"Id":"M0027394","Link":"https://id.nlm.nih.gov/mesh/M0027394.html","Name":"Imigran","Ref":81},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":82},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":109},{"Id":"M0022551","Link":"https://id.nlm.nih.gov/mesh/M0022551.html","Name":"Vasoconstrictor Agents","Ref":110},{"Id":"M0026368","Link":"https://id.nlm.nih.gov/mesh/M0026368.html","Name":"Serotonin 5-HT1 Receptor Agonists","Ref":111}],"MeSH Pharmacological Classification":[{"Id":"M0022551","Link":"https://id.nlm.nih.gov/mesh/M0022551.html","Name":"Vasoconstrictor Agent","Ref":110},{"Id":"M0026368","Link":"https://id.nlm.nih.gov/mesh/M0026368.html","Name":"Serotonin 5-HT1 Receptor Agonist","Ref":111}],"Mechanism of Action":"Sumatriptan is an agonist of 5-HT\u003csub\u003e1B\u003c/sub\u003e and 5-HT\u003csub\u003e1D\u003c/sub\u003e. This agonism leads to constriction of cranial blood vessels and inhibits the release of pro-inflammatory neuropeptides. Sumatriptan decreases carotid arterial blood flow, but increases blood flow velocity in the internal carotid artery and middle cerebral artery.[A179734 Agonism of the 5-HT\u003csub\u003e1B\u003c/sub\u003e and 5-HT\u003csub\u003e1D\u003c/sub\u003e receptors also inhibits sensory neurons, preventing the release of vasoactive peptides.[A179734 Sumatriptan does not cross the blood brain barrier.","Melting Point":"169-170","Metabolism/Metabolites":"Sumatriptan is predominantly metabolized by monoamine oxidase A. The main metabolites are the inactive indole acetic acid and indole acetic acid glucuronide.","MolecularFormula":"C\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS","MolecularWeight":"295.40 g/mol","Pharmacodynamics":"Sumatriptan constricts cranial blood vessels and prevents the release of vasoactive peptides. The dose of sumatriptan varies widely by route of administration and in most cases, no more than 2 doses should be given daily. Medication overuse headaches may occur in patients who use sumatriptan frequently.","Physical Description":"Solid","PubChemId":5358,"Record Description":["LiverTox|CNS|Migraine|5HT-1 receptor agonist"],"Records":{"UNII":{"Impurities":["gr-112504","didesmethyl sumatriptan","monodesmethyl sumatriptan","(3-(2-(dimethylamino)ethyl)-2-((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)-1h-indol-5-yl)-n-methylmethanesulfonamide","n-nitroso-desmethyl-sumatriptan"]}},"RefChem":"56076","RefCount":6,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Sumatriptan","Name":"Sumatriptan","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q416978","Name":"Sumatriptan","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00669","Name":"Sumatriptan","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5358","Name":"Sumatriptan","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=103628-46-2","Name":"Sumatriptan","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0005037","Name":"Sumatriptan","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07319","Name":"Sumatriptan","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/8R78F6L9VO","Name":"Sumatriptan","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID4023628","Name":"Sumatriptan","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 5358, Sumatriptan. Accessed May 4, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/5358\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/5358\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Sumatriptan. UNII: 8R78F6L9VO. Global Substance Registration System. Accessed May 4, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/8R78F6L9VO\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/8R78F6L9VO\u003c/a\u003e","Imitrex- sumatriptan injection. February 8, 2023. Accessed May 4, 2026. \u003ca href=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fee7d073-0b99-48f2-7985-0d8cf970894b\u003ehttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fee7d073-0b99-48f2-7985-0d8cf970894b\u003c/a\u003e","Imitrex- sumatriptan spray. March 22, 2024. Accessed May 4, 2026. \u003ca href=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc11b09d-e6cc-4cf8-1495-5ac64d5aae5f\u003ehttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc11b09d-e6cc-4cf8-1495-5ac64d5aae5f\u003c/a\u003e","Imitrex- sumatriptan tablet, film coated. February 21, 2024. Accessed May 4, 2026. \u003ca href=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=584abe73-8290-4484-ff8e-5890831c095e\u003ehttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=584abe73-8290-4484-ff8e-5890831c095e\u003c/a\u003e"],"SMILES":"CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C","SaltData":[{"AcidCount":1,"Amine":"Sumatriptan","AmineCount":1,"Formula":"C(CC(=O)O)C(=O)O","Name":"succinate","RName":"succinate","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 215.904 81.513\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h216v82H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m.975.975 11.596 2.467M17.11 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stroke=\"#c6c62c\" d=\"m19.392 14.957-1.141-3.514M23.487 19.258l6.004 1.277\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m55.178 74.843-2.771-4.767M55.178 74.843l-2.771-4.767M60.616 77.801l5.78-1.225M60.616 77.801l5.78-1.225M110.207 54.476l-5.027 2.894M116.514 54.485l5.018 2.906M113.366 48.81l.007-5.695\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Therapeutic Uses":"Serotonin Agonists; Vasoconstrictor Agents","Title":"Sumatriptan","UNII":"8R78F6L9VO","Wikidata":"Q416978","Wikipedia":"Sumatriptan","XLogP":0.9}