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C191

Sigma-Aldrich

Capsazepine

≥98% (HPLC), solid, TRPV1 antagonist

Synonyme(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

Formule empirique (notation de Hill):
C19H21ClN2O2S
Numéro CAS:
138977-28-3
Poids moléculaire :
376.90
Numéro MDL:
MFCD00153778
Code UNSPSC :
12352200
ID de substance PubChem :
24277967
Nomenclature NACRES :
NA.77

product name

Capsazepine, ≥98% (HPLC), solid

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

solid

Couleur

off-white

Solubilité

DMSO: >10 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

DRCMAZOSEIMCHM-UHFFFAOYSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Sigma-Aldrich

211275

Capsaicin

Capsaicin natural

Sigma-Aldrich

360376

Capsaicin

RN-1734 ≥98% (HPLC)

Sigma-Aldrich

R0658

RN-1734

Ruthenium Red Technical grade

Sigma-Aldrich

R2751

Ruthenium Red

Capsaicin analytical standard

Supelco

12084

Capsaicin

GW6471 ≥98% (HPLC)

Sigma-Aldrich

G5045

GW6471

6′-Iodoresiniferatoxin amorphous semi-solid

Sigma-Aldrich

I7033

6′-Iodoresiniferatoxin

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
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
Layla D M Cabral et al.
Basic & clinical pharmacology & toxicology, 119(5), 421-427 (2016-04-20)
Acute lung injury (ALI) caused by systemic inflammatory response remains a leading cause of morbidity and mortality in critically ill patients. Management of patients with sepsis is largely limited to supportive therapies, reflecting an incomplete understanding of the underlying pathophysiology.
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