C191
Capsazepine
≥98% (HPLC), solid, TRPV1 antagonist
Synonym(s):
N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide
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About This Item
Empirical Formula (Hill Notation):
C19H21ClN2O2S
CAS Number:
Molecular Weight:
376.90
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Capsazepine, ≥98% (HPLC), solid
Quality Level
assay
≥98% (HPLC)
form
solid
color
off-white
solubility
DMSO: >10 mg/mL, clear
storage temp.
2-8°C
SMILES string
Oc1cc2CCCN(Cc2cc1O)C(=S)NCCc3ccc(Cl)cc3
InChI
1S/C19H21ClN2O2S/c20-16-5-3-13(4-6-16)7-8-21-19(25)22-9-1-2-14-10-17(23)18(24)11-15(14)12-22/h3-6,10-11,23-24H,1-2,7-9,12H2,(H,21,25)
InChI key
DRCMAZOSEIMCHM-UHFFFAOYSA-N
Gene Information
human ... TRPV1(7442), TRPV4(59341)
rat ... Trpv1(83810)
Application
Capsazepine has been used as a transient receptor potential vanilloid-1 (TRPV1) antagonist:
- to study its effect on capsaicin induced extracellular signal-regulated kinase (ERK) phosphorylation
- to study the role of TRPV1 in central terminals on nociception in rats
- for functional characterization of the TRPV1 in bull spermatozoa
Biochem/physiol Actions
Capsazepine is a synthetic analog of capsaicin and a transient receptor potential vanilloid-1 (TRPV1) antagonist. It exhibits anti-proliferative and anti-cancer effects in various cancer types including oral squamous cell carcinoma, non-small cell lung cancer (NSCLC), breast cancer, and prostate cancer cell lines (HSC-3, H460, MDA-231, and PC-3 respectively). Capsazepine recovers impaired lung mechanics during endotoxemia and it may be a potential therapeutic target for acute lung injury (ALI).
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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S Bevan et al.
British journal of pharmacology, 107(2), 544-552 (1992-10-01)
1. Capsazepine is a synthetic analogue of the sensory neurone excitotoxin, capsaicin. The present study shows the capsazepine acts as a competitive antagonist of capsaicin. 2. Capsazepine (10 microM) reversibly reduced or abolished the current response to capsaicin (500 nM)
Ablation and regeneration of peripheral and central TRPV1 expressing nerve terminals and the consequence of nociception
Yu SQ and Premkumar LS
Open Medicine : A Peer-Reviewed, Independent, Open-Access Journal, 8(1) (2015)
Jorge De La Chapa et al.
Bioorganic & medicinal chemistry, 27(1), 208-215 (2018-12-12)
We previously demonstrated that capsazepine (CPZ), a synthetic transient receptor potential Vanilloid subtype 1 (TRPV1) antagonist, has significant anti-cancer effects in vivo. The purpose of this study was to develop more potent analogs based upon CPZ pharmacophore and structure-activity relationships
Global Trade Item Number
| SKU | GTIN |
|---|---|
| C191-25MG | 04061833468883 |
| C191-5MG | 04061835370177 |