C191

Capsazepine

Name: Capsazepine
Brand: SIGMA

≥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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Fórmula empírica (notación de Hill):

C₁₉H₂₁ClN₂O₂S

Número CAS:

138977-28-3

Peso molecular:

376.90

UNSPSC Code:

12352200

PubChem Substance ID:

24277967

NACRES:

NA.77

MDL number:

MFCD00153778

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Nombre del producto

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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Categorías relacionadas

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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1 of 4

Este artículo	211280	Z0127	S2694
Sigma-Aldrich C191 Capsazepine	Sigma-Aldrich 211280 Capsazepine	Sigma-Aldrich Z0127 Zatebradine hydrochloride	Sigma-Aldrich S2694 SB-408124
form solid	form solid	form powder	form solid
assay ≥98% (HPLC)	assay ≥97% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 10-30°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: >10 mg/mL, clear	solubility DMSO: soluble, methanol: soluble	solubility H₂O: >10 mg/mL	solubility DMSO: >10 mg/mL
color off-white	color off-white	color white	color off-white

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

Biochem/physiol Actions

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).[3] Capsazepine recovers impaired lung mechanics during endotoxemia and it may be a potential therapeutic target for acute lung injury (ALI).[4]

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number

0000388599

0000276793

0000069287

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Synthesis and SAR of novel capsazepine analogs with significant anti-cancer effects in multiple cancer types.

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

Capsazepine: a competitive antagonist of the sensory neurone excitant capsaicin.

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)

Activation of extracellular signal-regulated kinase in the trigeminal ganglion following both treatment of the dura mater with capsaicin and cortical spreading depression.

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

The Transient Receptor Potential Vanilloid 1 Antagonist Capsazepine Improves the Impaired Lung Mechanics during Endotoxemia.

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.

Single and combined effects of plant-derived and synthetic cannabinoids on cognition and cannabinoid-associated withdrawal signs in mice.

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

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Número de artículo de comercio global

SKU	GTIN
C191-25MG	04061833468883
C191-5MG	04061835370177

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