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Sumatriptan

Catalog No. DB00669 Name DrugBank
CAS Number 103628-46-2 Website http://www.ualberta.ca/
M. F. C14H21N3O2S Telephone (780) 492-3111
M. W. 295.40044 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 551

SYNONYMS

IUPAC name
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
IUPAC Traditional name
sumatriptan
Brand Name
Imitrex
Sumatran
Imigran
Sumax
Imitrex Oral
Synonyms
Sumatriptan Succinate
Sumatriptanum [INN-Latin]
NP101
sumatriptan
triptan

DATABASE IDS

CAS Number 103628-46-2
PubChem CID 5358
PubChem SID 46506520

PROPERTIES

Hydrophobicity(logP) 0.8
Solubility 21.4 mg/ml

DETAILS

Description (English)
Item Information
Drug Groups approved; investigational
Description A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraine disorders. A transdermal patch version of sumatriptan is currently in phase I trials in the U.S. under the code name NP101 (NuPathe).
Indication For the treatment of migraine attacks with or without aura.
Pharmacology Sumatriptan, an antimigraine drug, is a selective agonist of vascular serotonin ((5-hydroxytryptamine; 5-HT) type 1-like receptors, likely the 5-HT1D and 5-HT1B subtypes. It has no significant affinity (as measured using standard radioligand binding assays) or pharmacological activity at 5-HT2, 5-HT3 receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic; dopamine1; dopamine2; muscarinic; or benzodiazepine receptors.
Toxicity Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. In vitro studies with human microsomes suggest that sumatriptan is metabolized by monoamine oxidase (MAO), predominantly the A isoenzyme.
Absorption Approximately 15%
Half Life 2.5 hours
Protein Binding 14%-21%
Elimination Only 3% of the dose is excreted in the urine as unchanged sumatriptan; 42% of the dose is excreted as the major metabolite, the indole acetic acid analogue of sumatriptan.
Distribution * 2.7 L/kg [subcutaneous dosing]
Clearance * 1200 mL/min [Following a 6-mg SC injection]
References
Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. Epub 2008 Aug 23. [Pubmed]
External Links
Wikipedia
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REFERENCES

  • Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. Epub 2008 Aug 23. Pubmed