Sumatriptan

Sumatriptan

Clinical data
Trade names	Imitrex, Imigran,Treximet
AHFS/Drugs.com	Monograph
License data	US FDA: Sumatriptan
Pregnancy category	C
Routes of administration	tablet, subcutaneous injection, nasal spray, transdermal electrophoresis
ATC code	N02CC01 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	15% (oral)/ 96% (s.c)
Protein binding	14–21%
Metabolism	MAO
Biological 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 Y
PubChem (CID)	5358
IUPHAR/BPS	54
DrugBank	DB00669 Y
ChemSpider	5165 Y
UNII	8R78F6L9VO Y
KEGG	D00451 Y
ChEBI	CHEBI:10650 Y
ChEMBL	CHEMBL128 Y
ECHA InfoCard	100.130.518
Chemical and physical data
Formula	C14H21N3O2S
Molar mass	295.402 g/mol
3D model (Jmol)	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 Y Key:KQKPFRSPSRPDEB-UHFFFAOYSA-N Y

Sumatriptan is a medication used for the treatment of migraine and cluster headaches.

It is a synthetic drug belonging to the triptan class. Structurally, it is an analog of the naturally occurring neuro-active alkaloids dimethyltryptamine (DMT), bufotenine, and 5-methoxy-dimethyltryptamine, with an N-methyl sulfonamidomethyl- group at position C-5 on the indole ring.

Sumatriptan is produced and marketed by various drug manufacturers with many different trade names such as Imitrex, Imigran, Sumatran, Sumatriptanum, and Sumax, also as Treximet as a combination product with naproxen.

Sumatriptan is effective for ending or relieving the intensity of migraine and cluster headaches. It is most effective taken early after the start of the pain. Injected sumatriptan is more effective than other formulations.

Large doses of sumatriptan can cause sulfhemoglobinemia, a rare condition in which the blood changes from red to greenish-black, due to the integration of sulfur into the hemoglobin molecule. If sumatriptan is discontinued, the condition reverses within a few weeks.

Serious cardiac events, including some that have been fatal, have occurred following the use of sumatriptan injection or tablets. Events reported have included coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia, and ventricular fibrillation (V-Fib).