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).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: naratriptan

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
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.
External links Click here for help