C191

Capsazepine

Name: Capsazepine
Brand: SIGMA
Price: 312 CAD

≥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

UNSPSC Code:

12352200

PubChem Substance ID:

24277967

NACRES:

NA.77

MDL number:

MFCD00153778

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

Key Documents

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Product Name

Capsazepine, ≥98% (HPLC), solid

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

assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: >10 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Gene Information

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

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Show Differences

1 of 4

This Item	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[2]
for functional characterization of the TRPV1 in bull spermatozoa[3]

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).[4] Capsazepine recovers impaired lung mechanics during endotoxemia and it may be a potential therapeutic target for acute lung injury (ALI).[5]

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number

0000388599

0000276793

0000069287

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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)

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

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

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)

TrpV1 receptor activation rescues neuronal function and network gamma oscillations from Aβ-induced impairment in mouse hippocampus in vitro.

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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Capsazepine