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VCHSR

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
VCHSR
Identifiers
  • 5-(4-chlorophenyl)- 3-[(E)-2-cyclohexylethenyl]-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole
CAS Number
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC24H23Cl3N2
Molar mass445.81 g·mol−1
3D model (JSmol)
  • C4CCCCC4C=Cc(c(C)c1-c(cc3)ccc3Cl)nn1-c2ccc(Cl)cc2Cl
  • InChI=1S/C24H23Cl3N2/c1-16-22(13-7-17-5-3-2-4-6-17)28-29(23-14-12-20(26)15-21(23)27)24(16)18-8-10-19(25)11-9-18/h7-15,17H,2-6H2,1H3/b13-7+
  • Key:UMOLSRBHNLXWGD-NTUHNPAUSA-N
  (verify)

VCHSR is a drug used in scientific research which acts as a selectiveantagonist of thecannabinoid receptorCB1. It is derived from the widely used CB1 antagonistrimonabant, and has similar potency and selectivity for the CB1 receptor, but has been modified to remove thehydrogen bonding capability in the C-3 substituent region, which removes theinverse agonist effect that rimonabant produces at high doses, so that VCHSR instead acts as aneutral antagonist, blocking the receptor but producing no physiological effect of its own.[1][2]

References

[edit]
  1. ^Hurst DP, Lynch DL, Barnett-Norris J, Hyatt SM, Seltzman HH, Zhong M, et al. (December 2002). "N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A) interaction with LYS 3.28(192) is crucial for its inverse agonism at the cannabinoid CB1 receptor".Molecular Pharmacology.62 (6):1274–87.doi:10.1124/mol.62.6.1274.PMID 12435794.
  2. ^Hurst D, Umejiego U, Lynch D, Seltzman H, Hyatt S, Roche M, et al. (October 2006). "Biarylpyrazole inverse agonists at the cannabinoid CB1 receptor: importance of the C-3 carboxamide oxygen/lysine3.28(192) interaction".Journal of Medicinal Chemistry.49 (20):5969–87.doi:10.1021/jm060446b.PMID 17004712.
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