138977-28-3 Usage
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
Different sources of media describe the Uses of 138977-28-3 differently. You can refer to the following data:
1. 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 ratsfor functional characterization of the TRPV1 in bull spermatozoa
2. A selective vanilloid receptor antagonist (Ki=3.2uM
3. 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).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 138977-28-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,8,9,7 and 7 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 138977-28:
(8*1)+(7*3)+(6*8)+(5*9)+(4*7)+(3*7)+(2*2)+(1*8)=183
183 % 10 = 3
So 138977-28-3 is a valid CAS Registry Number.
InChI:InChI=1/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)
138977-28-3Relevant articles and documents
The Discovery of Capsazepine, the First Competitive Antagonist of the Sensory Neuron Excitants Capsaicin and Resiniferatoxin
Walpole, Christopher S. J.,Bevan, Stuart,Bovermann, Guenter,Boelsterli, Johann J.,Breckenridge, Robin,et al.
, p. 1942 - 1954 (1994)
Capsaicin and resiniferatoxin are natural products which act specifically on a subset of primary afferent sensory neurons to open a novel cation-selective ion channel in the plasma membrane.These sensory neurons are involved in nociception, and so, these
Bronchorelaxing compounds
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Page/Page column 16, (2010/02/13)
A compound of the general formula (I) including its pharmaceutically acceptable acid addition salts wherein A is CHR9, wherein R9 is H, C1-C6 alkyl; n is 1-3; B is CHR10, wherein R10 is H, C1-C6 alkyl; m is 1 or 2; D is O or S or optionally NR16, wherein R16 is H, C1-C6 alkyl or C2-C6 acyl; E is CR11R12 or NR13, wherein R11 and R12 are, independent of each other, H or C1-C6 alkyl, R13 is H or C1-C6 alkyl; F is C1-C18 alkyl which may be mono- or di-unsaturated and/or substituted, is useful in treating and preventing pulmonary disease characterized by bronchoconstriction. Also disclosed are pharmaceutical compositions comprising the compound and methods for their manufacture.
