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C191

Sigma-Aldrich

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:
138977-28-3
Molecular Weight:
376.90
MDL number:
MFCD00153778
UNSPSC Code:
12352200
PubChem Substance ID:
24277967
NACRES:
NA.77

Product Name

Capsazepine, ≥98% (HPLC), solid

Quality Level

100

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)

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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).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000069287
0000044339
0000065459
0000065458
0000023505

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Alyssa M Myers et al.
British journal of pharmacology, 176(10), 1552-1567 (2018-01-18)
It has been suggested that the non-euphorogenic phytocannabinoid cannabidiol (CBD) can ameliorate adverse effects of Δ9 -tetrahydrocannabinol (THC). We determined whether CBD ameliorates cognitive deficits and withdrawal signs induced by cannabinoid CB1 /CB2 receptor agonists or produces these pharmacological effects
Hugo Balleza-Tapia et al.
eLife, 7 (2018-11-13)
Amyloid-β peptide (Aβ) forms plaques in Alzheimer's disease (AD) and is responsible for early cognitive deficits in AD patients. Advancing cognitive decline is accompanied by progressive impairment of cognition-relevant EEG patterns such as gamma oscillations. The endocannabinoid anandamide, a TrpV1-receptor
Tatsuo Iwashita et al.
Neuroscience research, 77(1-2), 110-119 (2013-08-22)
Extracellular signal-regulated kinase (ERK) is known to be phosphorylated after exposure to noxious stimuli. In this study, we investigated the response in the dura mater to nociceptive stimulation, which is thought to be responsible for the pathogenesis of headaches, including
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
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)
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