Editing Sumatriptan (section)

{{Short description|Medication used for migraines & cluster headaches}}
{{Use American English|date=February 2018}}
{{Use dmy dates|date=October 2022}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 477173943
| IUPAC_name = 1-[3-(2-Dimethylaminoethyl)-1''H''-indol-5-yl]-''N''-methyl-methanesulfonamide
| image = Sumatriptan.svg
| alt = 
| image2 = Sumatriptan 3D ball-and-stick.png
| alt2 = Sumatriptan molecule

<!-- Clinical data -->| tradename = Imitrex, Imigran, others
| Drugs.com = {{drugs.com|monograph|sumatriptan}}
| DailyMedID = Sumatriptan
| routes_of_administration = [[By mouth]], [[subcutaneous injection|subcutaneous]], [[intranasal]], [[transdermal]]
| ATC_prefix = N02
| ATC_suffix = CC01

<!-- Legal status -->| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment = 
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment = 
| legal_CA = Rx-only
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = POM
| legal_UK_comment = /&nbsp;P
| legal_US = Rx-only
| legal_US_comment = 
| legal_EU = 
| legal_EU_comment = 
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = Rx-only

<!-- Pharmacokinetic data -->| bioavailability = 15% ([[oral administration|oral]]); 96% ([[subcutaneous injection|subcutaneous]])
| protein_bound = 14–21%
| metabolism = [[Monoamine oxidase]] (MAO)
| elimination_half-life = 2.5 hours
| excretion = 60% [[urine]]; 40% [[feces]]

<!-- Identifiers -->| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 103628-46-2
| PubChem = 5358
| IUPHAR_ligand = 54
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00669
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5165
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8R78F6L9VO
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00451
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 10650
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 128

<!-- Chemical data -->| C = 14
| H = 21
| N = 3
| O = 2
| S = 1
| smiles = O=S(=O)(NC)Cc1cc2c(cc1)[nH]cc2CCN(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KQKPFRSPSRPDEB-UHFFFAOYSA-N
}}
<!-- Definition and medical uses -->

'''Sumatriptan''', sold under the brand name '''Imitrex''' among others, is a [[medication]] used to treat [[migraine headaches]] and [[cluster headaches]].<ref name=BNF76>{{cite book|title=British National Formulary: BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=474|edition=76}}</ref> It is taken [[Oral administration|orally]], [[Nasal administration|intranasally]], or by [[Subcutaneous injection|subcutaneous]] [[Injection under the skin|injection]].<ref name="AHFS2019">{{cite web |title=Sumatriptan Monograph for Professionals |url=https://www.drugs.com/monograph/sumatriptan.html |access-date=3 March 2019 |website=Drugs.com |publisher=American Society of Health-System Pharmacists}}</ref> Therapeutic effects generally occur within three hours.<ref name=AHFS2019/>

<!-- Side effects and mechanisms -->
Its primary effect as a serotonin [[5-HT1B|5-HT<sub>1B</sub>]]/[[5-HT1D receptor|5-HT<sub>1D</sub>]] receptor agonist<ref>{{cite journal | vauthors = Syed YY | title = Sumatriptan/Naproxen Sodium: A Review in Migraine | journal = Drugs | volume = 76 | issue = 1 | pages = 111–121 | date = January 2016 | pmid = 26628293 | doi = 10.1007/s40265-015-0521-8 | s2cid = 25060147 }}</ref> can create common side effects such as [[chest pressure]], fatigue, vomiting, [[tingling]], and [[vertigo]]. Serious side effects may include [[serotonin syndrome]], [[heart attack]], [[stroke]], and [[seizure]]s. With excessive use, [[medication overuse headache]]s may occur.<ref name=AHFS2019/> It is unclear if use during [[pregnancy]] or [[breastfeeding]] is safe.<ref name=Preg2019>{{cite web |title=Sumatriptan Use During Pregnancy |url=https://www.drugs.com/pregnancy/sumatriptan.html |website=Drugs.com |access-date=3 March 2019 }}</ref> The mechanism of action is not entirely clear. It is in the [[triptan]] class of medications.<ref name=AHFS2019/>

<!-- Society and culture -->
Sumatriptan was patented in 1982 and approved for medical use in 1991.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=531 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA531 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> It is available as a [[generic medication]].<ref name=BNF76/> In 2022, it was the 95th most commonly prescribed medication in the United States, with more than 6{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Sumatriptan Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Sumatriptan | access-date = 30 August 2024 }}</ref> It is also available as the combination product [[sumatriptan/naproxen]].