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C191

Capsazepine

Name: Capsazepine
Brand: SIGMA

≥98% (HPLC), solid

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₁₉H₂₁ClN₂O₂S

CAS Number:

138977-28-3

Molecular Weight:

376.90

MDL number:

MFCD00153778

PubChem Substance ID:

24277967

NACRES:

NA.77

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

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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

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

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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