Sumatriptan

Sumatriptan
Clinical data
Trade names	Imitrex, Imigran, others
AHFS/Drugs.com	Monograph
License data	US DailyMed: Sumatriptan;
Routes of; administration	oral, subcutaneous injection, nasal spray, transdermal electrophoresis
ATC code	N02CC01 (WHO) ;
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only) / P; US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	15% (oral) / 96% (by subcutaneous injection)
Protein binding	14–21%
Metabolism	Monoamine oxidase (MAO)
Elimination half-life	2.5 hours
Excretion	60% urine; 40% feces
Identifiers
	IUPAC name 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide;
CAS Number	103628-46-2 ;
PubChem CID	5358;
IUPHAR/BPS	54;
DrugBank	DB00669 ;
ChemSpider	5165 ;
UNII	8R78F6L9VO;
KEGG	D00451 ;
ChEBI	CHEBI:10650 ;
ChEMBL	ChEMBL128 ;
CompTox Dashboard (EPA)	DTXSID4023628 ;
ECHA InfoCard	100.130.518
Chemical and physical data
Formula	C14H21N3O2S
Molar mass	295.40 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(NC)Cc1cc2c(cc1)[nH]cc2CCN(C)C;
	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 ; Key:KQKPFRSPSRPDEB-UHFFFAOYSA-N ;
	(verify)

Sumatriptan, sold under the brand name Imitrex among others, is a medication used to treat migraine headaches and cluster headaches.^[1] It is taken orally, intranasally, or by subcutaneous injection.^[2] Therapeutic effects generally occur within three hours.^[2]

Its primary effect as a serotonin 5-HT1B/5-HT1D receptor agonist^[3] can create common side effects such as chest pressure, fatigue, vomiting, tingling, and vertigo.^[2] Serious side effects may include serotonin syndrome, heart attacks, strokes, and seizures.^[2] With excessive use, medication overuse headaches may occur.^[2] It is unclear if use during pregnancy or breastfeeding is safe.^[4] The mechanism of action is not entirely clear.^[2] It is in the triptan class of medications.^[2]

Sumatriptan was patented in 1982 and approved for medical use in 1991.^[5] It is on the World Health Organization's List of Essential Medicines.^[6] It is available as a generic medication.^[1] In 2021, it was the 109th most commonly prescribed medication in the United States, with more than 5 million prescriptions.^[7]^[8] It is also available as the combination product sumatriptan/naproxen.

^ ^a ^b British National Formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 474. ISBN 9780857113382.
^ ^a ^b ^c ^d ^e ^f ^g "Sumatriptan Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
^ Syed YY (January 2016). "Sumatriptan/Naproxen Sodium: A Review in Migraine". Drugs. 76 (1): 111–121. doi:10.1007/s40265-015-0521-8. PMID 26628293. S2CID 25060147.
^ "Sumatriptan Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Sumatriptan - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.