capsaicin   Click here for help

GtoPdb Ligand ID: 2486

Synonyms: Qutenza®
Approved drug PDB Ligand
capsaicin is an approved drug (EMA & FDA (2009))
Comment: Although capsaicin was approved by the US FDA in 2009, this compound was previously marketed so was not subject to a New Drug Application.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 58.56
Molecular weight 305.2
XLogP 4.32
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(CNC(=O)CCCCC=CC(C)C)ccc1O
Isomeric SMILES COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
InChI InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChI Key YKPUWZUDDOIDPM-SOFGYWHQSA-N
No information available.
Summary of Clinical Use Click here for help
Topically applied capsaicin is used to relieve muscle and joint pain and neuralgia. With regular use it causes a reduction in the pain messenger substance P.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Capsaicin selectively binds to the TRPV1 channel that resides on the membranes of pain and heat-sensing neurons and causes these channels to open at a temperature below normal channel operation. This gives rise ot the sensation of heat. Prolonged activation of these neurons by capsaicin depletes presynaptic substance P and the neuons become unable to signal pain for an extended period of time.