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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Mustafa Nazıroğlu et al.
PloS one, 12(6), e0179950-e0179950 (2017-06-24)
There is convincing epidemiological and experimental evidence that capsaicin, a potent natural transient receptor potential cation channel vanilloid member 1 (TRPV1) agonist, has anticancer activity. However, capsaicin cannot be given systemically in large doses, because of its induction of acute
Giulia Donvito et al.
The Journal of pharmacology and experimental therapeutics, 359(2), 310-318 (2016-10-21)
Chemotherapy-induced peripheral neuropathy (CIPN) represents a serious complication associated with antineoplastic drugs. Although there are no medications available that effectively prevent CIPN, many classes of drugs have been used to treat this condition, including anticonvulsants, serotonin and noradrenaline reuptake inhibitors
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