CAPSAZEPINE
CAPSAZEPINE Basic information
- Product Name:
- CAPSAZEPINE
- Synonyms:
-
- 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
- CAS:
- 138977-28-3
- MF:
- C19H21ClN2O2S
- MW:
- 376.9
- Product Categories:
-
- Inhibitors
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Vanilloid/TRPV channel
- Ion Channels
- Amines
- Aromatics
- Mol File:
- 138977-28-3.mol
CAPSAZEPINE Chemical Properties
- 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)
Safety Information
- 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
MSDS
- Language:English Provider:SigmaAldrich
CAPSAZEPINE Usage And Synthesis
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-
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.
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