naratriptan   Click here for help

GtoPdb Ligand ID: 45

Synonyms: Amerge® | GR-85548A
Approved drug
naratriptan is an approved drug (FDA (1998))
Compound class: Synthetic organic
Comment: Marketed formulations may contain naratriptan hydrochloride (PubChem CID 60875).
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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 5
Topological polar surface area 73.58
Molecular weight 335.17
XLogP 1.61
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNS(=O)(=O)CCc1ccc2c(c1)c(c[nH]2)C1CCN(CC1)C
Isomeric SMILES CNS(=O)(=O)CCc1ccc2c(c1)c(c[nH]2)C1CCN(CC1)C
InChI InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3
InChI Key AMKVXSZCKVJAGH-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of migraine.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Agonism of presynaptic 5-HT1D receptors by naratriptan inhibits both dural vasodilation and inflammation. Agonism of 5-HT1B and 5-HT1D receptors in the brainstem leads to inhibition of trigeminal nuclei cell excitability while vascular 5-HT1B receptor agonism leads to vasoconstriction or meningeal, dural cerebraland pial vessels. The combination of these three properties of naratriptan are belived to account for its effect as an anti-migraine drug.
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