138977-28-3 Usage
Description
CAPSAZEPINE is a synthetic analogue of capsaicin, belonging to the benzazepine class. It is a competitive antagonist of the transient receptor potential vanilloid type 1 (TRPV1), which is a member of the transient receptor potential (TRP) family. TRPV1 is activated or sensitized by various endogenous stimuli due to tissue injury and inflammation, playing a role in pain perception. CAPSAZEPINE blocks the capsaicin-induced uptake of Ca2+ in neonatal rat dorsal root ganglia and Chinese hamster ovary cells. It is a light yellow solid and does not block acidor heat-induced activation of TRPV1.
Uses
Used in Pharmaceutical Research:
CAPSAZEPINE is used as a transient receptor potential vanilloid-1 (TRPV1) antagonist for studying its effect on capsaicin-induced extracellular signal-regulated kinase (ERK) phosphorylation. It is also used to study the role of TRPV1 in central terminals on nociception in rats and for the functional characterization of TRPV1 in bull spermatozoa.
Used in Pain Management Research:
CAPSAZEPINE is used as a selective vanilloid receptor antagonist (Ki=3.2uM) to inhibit the development of mechanical hyperalgesia induced by intraplanar capsaicin injection. It is also used to block Resiniferatoxin (sc-24015)and Capsaicin-induced contractions of guinea pig tracheal smooth muscle.
Used in Neurophysiology Research:
Studies investigating the function of the VR1 (TRPV1 receptor) have employed CAPSAZEPINE as a tool for perturbing systemic neuronal response to Capsaicin.
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.