sumatriptan

Also 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).

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 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

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

Mass: 295.135448

Show 6 more facts

Commons category: Sumatriptan
chemical formula: C₁₄H₂₁N₃O₂S
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
stylized name: SUMAtriptan

Sources (7)

via Wikidata · CC0

~14 min read

Article

20 sections

Contents

Medical uses
Contraindications
Adverse effects
Overdose
Interactions
Pharmacology
Mechanism of action
Pharmacokinetics
Absorption
Distribution
Metabolism
Elimination
Chemistry
History
Society and culture
Legal status
Generics
Controversy
References
External links

The drug acts as a serotonin 5-HT1B, 5-HT1D, and 5-HT1F receptor agonist and its common side effects include 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.