Structure via PubChem · Public domain (PubChem)
capsazepine
Sign in to saveAlso known as ST50826300, N-(2-[4-chlorophenyl]ethyl)-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide, N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbothioamide, 2-[2-(4-chlorophenyl)ethylamino-thiocarbonyl]-7,8-dihydroxy-2,3,4,5-tetrahydro-1H-2-benzazepine, N-[2-(4-chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide, capsazepin
Capsazepine is a synthetic antagonist of capsaicin. It is used as a biochemical tool in the study of TRPV ion channels.
In the Vinony graph
Vinony's link graph records 209 inbound references to capsazepine, and connects out to chili pepper, molarity and antagonist.
It is catalogued under topics including 4-Chlorophenyl compounds, Benzazepines and Capsaicinoids.
Vinony links it to 6 Wikipedia language editions.
Chemical data
- Formula
- C19H21ClN2O2S
- Molecular weight
- 376.9 g/mol
- IUPAC name
- N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2-benzazepine-2-carbothioamide
- SMILES
- C1CC2=CC(=C(C=C2CN(C1)C(=S)NCCC3=CC=C(C=C3)Cl)O)O
- InChIKey
- DRCMAZOSEIMCHM-UHFFFAOYSA-N
- XLogP
- 3.9
- Polar surface area
- 87.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 376.101
Show 4 more facts
- chemical formula
- C₁₉H₂₁ClN₂O₂S
- canonical SMILES
- C1CC2=CC(=C(C=C2CN(C1)C(=S)NCCC3=CC=C(C=C3)Cl)O)O
- physically interacts with
- Transient receptor potential cation channel subfamily V member 1
- Commons category
- Capsazepine
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Pharmacology
- Development
- Use in biotechnology
- See also
- References
Capsazepine is a synthetic antagonist of capsaicin. It is used as a biochemical tool in the study of TRPV ion channels.
==Pharmacology== Capsazepine blocks the painful sensation of heat caused by capsaicin (the active ingredient of chilli pepper) which activates the TRPV1 ion channel. Capsazepine is therefore considered to be a TRPV1 antagonist. The TRPV1 channel functions as a pain and temperature sensor in mammalians. Capsazepine blocks the activation of TRPV1 channels by other chemicals, but not by other painful stimuli such as heat. Depending on the pharmacological assay, the IC50 is in the nanomolar to low micromolar range. In addition to its effects on TRPV1 channels, it was also shown to activate the noxious chemical sensor TRPA1 channel, inhibit the cold activated TRPM8 channel, voltage-activated calcium channels and nicotinic acetylcholine receptors. It mainly serves as a tool to study the TRPV1 ion channel.
Excerpted from Wikipedia’s “capsazepine” article, available under the CC BY-SA 4.0 licence.