Sumatriptan

Sumatriptan
Clinical data
Trade names	Imitrex, Imigran, others
AHFS/Drugs.com	Monograph
License data	US DailyMed: Sumatriptan;
Routes of; administration	By mouth, subcutaneous, intranasal, transdermal
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% (subcutaneous)
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. It is taken orally, intranasally, or by subcutaneous injection. Therapeutic effects generally occur within three hours.

Its primary effect as a serotonin 5-HT_1B/5-HT_1D receptor agonist 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 seizures. With excessive use, medication overuse headaches may occur. It is unclear if use during pregnancy or breastfeeding is safe. The mechanism of action is not entirely clear. It is in the triptan class of medications.

Sumatriptan was patented in 1982 and approved for medical use in 1991. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2022, it was the 95th most commonly prescribed medication in the United States, with more than 6 million prescriptions. It is also available as the combination product sumatriptan/naproxen.