Sumatriptan

Sumatriptan
Sumatriptan molecule
Clinical data
Trade namesImitrex, Imigran, others
AHFS/Drugs.comMonograph
License data
Routes of
administration		oral, subcutaneous injection, nasal spray, transdermal electrophoresis
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability15% (oral) / 96% (by subcutaneous injection)
Protein binding14–21%
MetabolismMonoamine oxidase (MAO)
Elimination half-life2.5 hours
Excretion60% urine; 40% feces
Identifiers
  • 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.130.518 Edit this at Wikidata
Chemical and physical data
FormulaC14H21N3O2S
Molar mass295.40 g·mol−1
3D model (JSmol)
  • O=S(=O)(NC)Cc1cc2c(cc1)[nH]cc2CCN(C)C
  • 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 checkY
  • Key:KQKPFRSPSRPDEB-UHFFFAOYSA-N checkY
  (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. Serious side effects may include serotonin syndrome, heart attacks, strokes, and seizures. 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. 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 2022, it was the 95th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[7][8] It is also available as the combination product sumatriptan/naproxen.

  1. ^ a b British National Formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 474. ISBN 9780857113382.
  2. ^ a b c d "Sumatriptan Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  3. ^ 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.
  4. ^ "Sumatriptan Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495.
  6. ^ 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.
  7. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  8. ^ "Sumatriptan Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.