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CAPSAZEPINE

Product Name
CAPSAZEPINE
CAS No.
138977-28-3
Chemical Name
CAPSAZEPINE
Synonyms
Capsazepin;CAPSAZEPINE;capasazepine;Capsazepine,98%;CAPSAZEPINE SYNTHETIC ANALOG OF C;8-dihydroxy-2H-2-benzazepine-2-carbothioamide;7;8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE;N-(4-Chlorophenethyl)-7,8-dihydroxy-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide;2-[[2-(4-Chlorophenyl)ethylamino]thiocarbonyl]-2,3,4,5-tetrahydro-1H-2-benzazepine-7,8-diol;N-[2-(CHLOROPHENYL)ETHYL]-1,3,4,5-TETRAHYDRO-7,8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE
CBNumber
CB0144302
Molecular Formula
C19H21ClN2O2S
Formula Weight
376.9
MOL File
138977-28-3.mol
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CAPSAZEPINE Property

Melting point:
155-157°C
Boiling point:
581.1±60.0 °C(Predicted)
Density 
1.350±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
methanol: soluble
pka
9.73±0.20(Predicted)
form 
solid
color 
off-white
InChIKey
DRCMAZOSEIMCHM-UHFFFAOYSA-N
CAS DataBase Reference
138977-28-3(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
22-24/25-36-26
RIDADR 
2811
WGK Germany 
3
HazardClass 
6.1(a)
PackingGroup 
II
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C191
Product name
Capsazepine
Purity
≥98% (HPLC), solid
Packaging
5mg
Price
$240
Updated
2024/03/01
Sigma-Aldrich
Product number
C191
Product name
Capsazepine
Purity
≥98% (HPLC), solid
Packaging
25mg
Price
$844
Updated
2024/03/01
Alfa Aesar
Product number
J63055
Product name
Capsazepine, 99+%
Packaging
10mg
Price
$321
Updated
2024/03/01
Alfa Aesar
Product number
J63055
Product name
Capsazepine, 99+%
Packaging
50mg
Price
$1347.65
Updated
2024/03/01
Cayman Chemical
Product number
10007518
Product name
Capsazepine
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
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CAPSAZEPINE Chemical Properties,Usage,Production

Description

Transient receptor potential vanilloid type 1 (TRPV1) is a member of the transient receptor potential (TRP) family that is activated or sensitized by a variety of endogenous stimuli as a result of tissue injury and inflammation. TRPV1 is upregulated during inflammation and plays a role in the perception of pain. Capsazepine is a competitive antagonist of transient receptor potential vanilloid type 1 (TRPV1) which blocks the capsaicin-induced uptake of Ca2+ in neonatal rat dorsal root ganglia with an IC50 of 0.42 μM and Chinese hamster ovary cells with an IC50 of 17 nM. It does not block acid- or heat-induced activation of TRPV1 and may block receptors other than TRPV1.

Chemical Properties

Light Yellow Solid

Uses

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

Uses

A selective vanilloid receptor antagonist (Ki=3.2uM

Uses

Capsazepine is shown to inhibit the development of mechanical hyperalgesia induced by intraplanar capsaicin injection. Capsazepine is described to block Resiniferatoxin (sc-24015)- and Capsaicin-induced contractions of guinea pig treacheal smooth muscle. Studies investigating the function of the VR1 (TRPV1 receptor) have employed Capsazepine as a tool for perturbing systemic neuronal response to Capsaicin.

Definition

ChEBI: A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of caps icin, it was the first reported capsaicin receptor antagonist.

Hazard

A poison.

Biological Activity

Selective vanilloid receptor antagonist (K i = 3.2 μ M). Inhibits carrageenan inflammation-induced hyperalgesic responses in the rat. Also activates amiloride-sensitive epithelial Na + channel ENaC δ . Also available as part of the Vanilloid TRPV1 Receptor Tocriset™ .

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

Room temperature

References

1. c. s. walpole, s. bevan, g. bovermann, j. j. boelsterli, r. breckenridge, j. w. davies, g. a. hughes, i. james, l. oberer, j. winter and et al., j med chem 1994, 37, 1942-1954. 2. r. j. docherty, j. c. yeats and a. s. piper, br j pharmacol 1997, 121, 1461-1467. 3. h. j. behrendt, t. germann, c. gillen, h. hatt and r. jostock, br j pharmacol 2004, 141, 737-745. 4. l. liu and s. a. simon, neurosci lett 1997, 228, 29-32. 5. b. sung, s. prasad, j. ravindran, v. r. yadav and b. b. aggarwal, free radic biol med 2012, 53, 1977-1987.

CAPSAZEPINE Preparation Products And Raw materials

Raw materials

Preparation Products

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CAPSAZEPINE Suppliers

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View Lastest Price from CAPSAZEPINE manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
CAPSAZEPINE 138977-28-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-10

138977-28-3, CAPSAZEPINERelated Search:

1-BENZYL-3-PHENETHYL-2-THIOUREA 2,3,4,5-Tetrahydro-1H-2-benzazepine Hydrochloride 2,3,4,5-TETRAHYDRO-1H-BENZO[C]AZEPIN-8-OL CAPSAZEPINE 1-(3-PHENYLPROPYL)-2-THIOUREA N,N'-DI-N-PROPYLTHIOUREA 2-PHENYLETHYLTHIOUREA

  • CAPSAZEPINE
  • N-[2-(CHLOROPHENYL)ETHYL]-1,3,4,5-TETRAHYDRO-7,8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE
  • N-[2-(4-CHLOROPHENYL)ETHYL]-1,3,4,5-TETRAHYDRO-7,8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE
  • CAPSAZEPINE SYNTHETIC ANALOG OF C
  • 2-[[2-(4-Chlorophenyl)ethylamino]thiocarbonyl]-2,3,4,5-tetrahydro-1H-2-benzazepine-7,8-diol
  • Capsazepine,98%
  • 7;8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE
  • 8-dihydroxy-2H-2-benzazepine-2-carbothioamide
  • capasazepine
  • 2H-2-Benzazepine-2-carbothioamide, N-[2-(4-chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-
  • Capsazepin
  • N-(4-Chlorophenethyl)-7,8-dihydroxy-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide
  • 138977-28-3
  • 38977-28-3
  • C19H21ClN2O2S
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Vanilloid/TRPV channel
  • Ion Channels
  • Amines
  • Aromatics