Structure via PubChem · Public domain (PubChem)
Sumatriptan
Sign in to saveAlso known as GR-43175C, Imigran®, 3-(2-(dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide, 3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide, (3-[2-(dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide, 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide, Sumatran, Sumax
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. Sumatriptan is a serotonin (5-HT1B/1D) receptor agonist (triptan).
In the Vinony graph
Vinony's link graph records 1,662 inbound references to Sumatriptan, and connects out to N-methylserotonin, tryptamines and migraine.
It sits within the topics 5-HT1B agonists, 5-HT1D agonists and 5-HT1F agonists.
Vinony links it to 29 Wikipedia language editions.
Chemical data
- Formula
- C14H21N3O2S
- Molecular weight
- 295.4 g/mol
- IUPAC name
- 1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide
- SMILES
- CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C
- InChIKey
- KQKPFRSPSRPDEB-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 73.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1992
- Admin. routes
- oral, parenteral, topical
- Indications
- obesity, migraine disorder, migraine with aura, migraine without aura
via ChEMBL · EBI
Research
3,493 papers- Sumatriptan as a First-Line Treatment for Headache in the Pediatric Emergency Department.Pediatric neurology · 2023
- Comparison between the efficacy of ginger and sumatriptan in the ablative treatment of the common migraine.Phytotherapy research : PTR · 2014
- Sumatriptan clinical pharmacokinetics.Clinical pharmacokinetics · 1994
- Sumatriptan/Naproxen Sodium: A Review in Migraine.Drugs · 2016
- Metabolism of sumatriptan revisited.Pharmacology research & perspectives · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 295.135448
- Has use
- medication
Show 8 more facts
- Commons category
- Sumatriptan
- chemical formula
- C₁₄H₂₁N₃O₂S
- significant drug interaction
- (−)-selegiline
- defined daily dose
- 25
- canonical SMILES
- CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C
- World Health Organisation international non-proprietary name
- sumatriptan
- medical condition treated
- giant cell arteritis
- stylized name
- SUMAtriptan
Sources (7)
via Wikidata · CC0