sumatriptan   Click here for help

GtoPdb Ligand ID: 54

Synonyms: GR-43175C | Imigran® | Tosymra® (nasal spray)
Approved drug
sumatriptan is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Sumatriptan is a selective serotonin 5-HT1B/ID receptor agonist.
Marketed formulations contain sumatriptan succinate (PubChem CID 59772).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 73.58
Molecular weight 295.14
XLogP 0.88
No. Lipinski's rules broken 0
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Canonical SMILES CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
Isomeric SMILES CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
InChI InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
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Summary of Clinical Use Click here for help
Used in the treatment of acute migraine attacks. Oral, injectable (Zembrace SymTouch®, a pre-filled single-dose, disposable autoinjector) and inhalation (Onzetra Xsail®, sumatriptan powder delivered using the novel XsailTM breath powered delivery device) formulations of sumatriptan succinate are available.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Agonist of 5-HT1B and 5-HT1D receptors. Following binding of sumatripan to these receptors, adenylate cyclase activity is inhibited, increasing intracellular calcium resulting in vasoconstriction and inhibition of sensory nocieptive nerve firing and vasoactive peptide release.
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