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C191

Sigma-Aldrich

Capsazepine

≥98% (HPLC), solid, TRPV1 antagonist

Sinonimo/i:

N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide

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CHF 178.00
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CHF 689.00

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5 MG
CHF 178.00
25 MG
CHF 689.00

About This Item

Formula empirica (notazione di Hill):
C19H21ClN2O2S
Numero CAS:
138977-28-3
Peso molecolare:
376.90
Numero MDL:
MFCD00153778
Codice UNSPSC:
12352200
ID PubChem:
24277967
NACRES:
NA.77

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Nome del prodotto

Capsazepine, ≥98% (HPLC), solid

Livello qualitativo

100

Saggio

≥98% (HPLC)

Stato

solid

Colore

off-white

Solubilità

DMSO: >10 mg/mL, clear

Temperatura di conservazione

2-8°C

Stringa SMILE

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)
DRCMAZOSEIMCHM-UHFFFAOYSA-N

Informazioni sul gene

human ... TRPV1(7442) , TRPV4(59341)
rat ... Trpv1(83810)

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Applicazioni

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[1]
  • to study the role of TRPV1 in central terminals on nociception in rats[2]
  • for functional characterization of the TRPV1 in bull spermatozoa[3]

Azioni biochim/fisiol

Capsazepine is a synthetic analog of capsaicin and a transient receptor potential vanilloid-1 (TRPV1) antagonist.[1] 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).[4] Capsazepine recovers impaired lung mechanics during endotoxemia and it may be a potential therapeutic target for acute lung injury (ALI).[5]

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
039K46156V
039K46155
039K46154
039K46153
039K46152

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Capsaicin An active constituent of cayenne pepper with excitatory and desensitizing effects on a subset of primary afferent sensory neurons.

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

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)
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
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
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