| Identification | More | [Name]
CAPSAZEPINE | [CAS]
138977-28-3 | [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
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
N-[2-(4-CHLOROPHENYL)ETHYL]-1,3,4,5-TETRAHYDRO-7,8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE
2H-2-Benzazepine-2-carbothioamide, N-[2-(4-chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy- | [Molecular Formula]
C19H21ClN2O2S | [MDL Number]
MFCD00153778 | [Molecular Weight]
376.9 | [MOL File]
138977-28-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Solid | [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
| [form ]
solid
| [pka]
9.73±0.20(Predicted) | [color ]
off-white
| [Usage]
A selective vanilloid receptor antagonist (Ki=3.2uM | [InChI]
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) | [InChIKey]
DRCMAZOSEIMCHM-UHFFFAOYSA-N | [SMILES]
N1(C(NCCC2=CC=C(Cl)C=C2)=S)CC2=CC(O)=C(O)C=C2CCC1 | [CAS DataBase Reference]
138977-28-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard statements ]
H402 | [Precautionary statements ]
P273-P501 | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
2811 | [WGK Germany ]
3
| [HazardClass ]
6.1(a) | [PackingGroup ]
II |
| Hazard Information | Back Directory | [Hazard]
A poison. | [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.1,2 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.1,3 It does not block acid- or heat-induced activation of TRPV1 and may block receptors other than TRPV1.4,5 | [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. | [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]
Store at -20°C | [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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