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MilliporeSigma

C191

Sigma-Aldrich

Capsazepine

≥98% (HPLC), solid, TRPV1 antagonist

Sinónimos:

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

Fórmula empírica (notación de Hill):
C19H21ClN2O2S
Número de CAS:
Peso molecular:
376.90
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Nombre del producto

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

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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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
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
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)
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)
Matusica Dusan et al.
Molecular pain, 16, 1744806920970368-1744806920970368 (2020-12-15)
The embryonic rat dorsal root ganglion (DRG) neuron-derived 50B11 cell line is a promising sensory neuron model expressing markers characteristic of NGF and GDNF-dependent C-fibre nociceptors. Whether these cells have the capacity to develop into distinct nociceptive subtypes based on

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