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Sumatriptan information


Sumatriptan
Sumatriptan molecule
Clinical data
Trade namesImitrex, Imigran, others
AHFS/Drugs.comMonograph
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
Bioavailability15% (oral) / 96% (by subcutaneous injection)
Protein binding14–21%
MetabolismMonoamine oxidase (MAO)
Elimination half-life2.5 hours
Excretion60% urine; 40% feces
Identifiers
IUPAC name
  • 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide
CAS Number
  • 103628-46-2 checkY
PubChem CID
  • 5358
IUPHAR/BPS
  • 54
DrugBank
  • DB00669 checkY
ChemSpider
  • 5165 checkY
UNII
  • 8R78F6L9VO
KEGG
  • D00451 checkY
ChEBI
  • CHEBI:10650 checkY
ChEMBL
  • ChEMBL128 checkY
CompTox Dashboard (EPA)
  • DTXSID4023628 Edit this at Wikidata
ECHA InfoCard100.130.518 Edit this at Wikidata
Chemical and physical data
FormulaC14H21N3O2S
Molar mass295.40 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 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.[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.

  1. ^ a b British National Formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 474. ISBN 9780857113382.
  2. ^ a b c d e f g "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 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  8. ^ "Sumatriptan - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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ATC code N02

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MDMA

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Metergoline

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of sumatriptan and metergoline at the human 5-HT1D beta receptor: further evidence for a role of the 5-HT1D receptor in the action of sumatriptan". European...

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