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).
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
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
~14 min read
Encyclopedic overview
20 sectionsContents
- 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
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).
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.
Excerpted from Wikipedia’s “sumatriptan” article, available under the CC BY-SA 4.0 licence.