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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
• RxList
• Drugs.com

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