CapsazepineAn antagonist of TRPV1 and activator of ENaC

Capsazepine (CAS 138977-28-3)

Capsazepine | CAS 138977-28-3 is rated 5.0 out of 5 by 1.
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Synonym: N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide
Application: An antagonist of TRPV1 and activator of ENaC
CAS Number: 138977-28-3
Purity: ≥97%
Molecular Weight: 376.90
Molecular Formula: C19H21ClN2O2S
* Refer to Certificate of Analysis for lot specific data (including water content).
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Capsazepine is a competitive antagonist of the VR1 (TRPV1, also transient receptor potential vanilloid type 1), antagonizing the effects produced by Capsaicin at this receptor (sc-3577). The VR1 (TRPV1 receptor) is a non-selective ligand-gated cation channel that responds to noxious heat, protons, and Capsaicin, producing nociception signals. Capsazepine also activates ENaCδ (amiloride-sensitive epithelial Na+ channel). 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.


References

1. Urban, L. and Dray, A. 1991. Neurosci. Lett. 134: 9-11. PMID: 1726117
2. Bevan, S., et al. 1992. Br. J. Pharmacol. 107: 544-552. PMID: 1422598
3. Maggi, C.A., et al. 1993. Br. J. Pharmacol. 108: 801-805. PMID: 7682139
4. Walpole, C.S., et al. 1994. J. Med. Chem. 37: 1942-1954. PMID: 8027976
5. Ellis, J.L. and Undem, B.J. 1994. J. Pharmacol. Exp. Ther. 268: 85-89. PMID: 8301598
6. Liu, L. and Simon, S.A. 1997. Neurosci. Lett. 228: 29-32. PMID: 9197280
7. Walker, K.M., et al. 2003. J. Pharmacol. Exp. Ther. 304: 56-62. PMID: 12490575
8. Valenzano, K.J. and Sun, Q. 2004. Curr. Med. Chem. 11: 3185-3202. PMID: 15579007

Physical State :
Solid
Solubility :
Soluble in methanol, DMF (~20 mg/ml), a 1:1 solution of DMSO:PBS(pH7.2) (~0.45 mg/ml), water (0.45 mg/ml) at 25° C, ethanol (25 mg/ml), and DMSO (25 mg/ml).
Storage :
Store at -20° C
Melting Point :
159-161° C
Boiling Point :
~581.1° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.67 (Predicted)
IC50 :
Vanilloid receptor: IC50 = 3 nM (human); Vanilloid receptor: IC50 = 4 nM (Rattus norvegicus); Transient receptor potential cation channel subfamily V member 2: IC50 = 590 nM (Rattus norvegicus); Rattus norvegicus: IC50 = 420 nM; Rattus norvegicus: EC5050 = >100 µM; Transient receptor potential cation channel subfamily V member 4: EC5050 = >100 µM (Rattus norvegicus); TRPV1: IC50 = 0.42 µM (neonatal rat dorsal root ganglia); TRPV1: IC50 = 17 nM ( Chinese hamster ovary cells)
Ki Data :
vanilloid receptor: Ki= 3.2 µM; Vanilloid receptor: Ki= 0.12 µM (human); Vanilloid receptor: Ki= 0.52 µM (Rattus norvegicus)
pK Values :
pKa: 9.73 (Predicted), pKb: 1.06 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
2733484
MDL Number :
MFCD00153778
SMILES :
C1CC2=CC(=C(C=C2CN(C1)C(=S)NCCC3=CC=C(C=C3)Cl)O)O

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Capsazepine  Product Citations

See how others have used Capsazepine. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 25307418  Venier, NA. et al. 2015. Prostate. 75: 113-25.

PMID: # 26099309  Özdemir, ÜS. et al. 2015. Mol. Neurobiol.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Many articles reported Capsazepine as a specific Many articles reported Capsazepine as a specific antagonist of TRPV1. -SCBT Publication Review
Date published: 2015-02-19
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