VCHSR

VCHSR
	File:VCHSR.png
Identifiers
	IUPAC name 5-(4- chlorophenyl)-3-[(E)-2-cyclohexylethenyl]-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C24H23Cl3N2
Molar mass	445.811
3D model (JSmol)	Interactive image;
	SMILES C4CCCCC4C=Cc(c(C)c1-c(cc3)ccc3Cl)nn1-c2ccc(Cl)cc2Cl;

VCHSR is a drug used in scientific research which acts as a selective antagonist of the cannabinoid receptor CB₁. It is derived from the widely used CB₁ antagonist rimonabant, and has similar potency and selectivity for the CB₁ receptor, but has been modified to remove the hydrogen bonding capability in the C3 substituent region, which removes the inverse agonist effect that rimonabant produces at high doses, so that VCHSR instead acts as a neutral antagonist, blocking the receptor but producing no physiological effect of its own.^[1]^[2]

References

↑ Hurst DP, Lynch DL, Barnett-Norris J, Hyatt SM, Seltzman HH, Zhong M, Song Z-H, Nie J, Lewis D, Reggio PH (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. 2002 Dec;62(6):1274-87. PMID 12435794
↑ Hurst D, Umejiego U, Lynch D, Seltzman H, Hyatt S, Roche M, McAllister S, Fleischer D, Kapur A, Abood M, Shi S, Jones J, Lewis D, Reggio P. Biarylpyrazole inverse agonists at the cannabinoid CB1 receptor: importance of the C-3 carboxamide oxygen/lysine3.28(192) interaction. Journal of Medicinal Chemistry. 2006 Oct 5;49(20):5969-87. PMID 17004712

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Template:WikiDoc Sources

[1] Hurst DP, Lynch DL, Barnett-Norris J, Hyatt SM, Seltzman HH, Zhong M, Song Z-H, Nie J, Lewis D, Reggio PH (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. 2002 Dec;62(6):1274-87. PMID 12435794

[2] Hurst D, Umejiego U, Lynch D, Seltzman H, Hyatt S, Roche M, McAllister S, Fleischer D, Kapur A, Abood M, Shi S, Jones J, Lewis D, Reggio P. Biarylpyrazole inverse agonists at the cannabinoid CB1 receptor: importance of the C-3 carboxamide oxygen/lysine3.28(192) interaction. Journal of Medicinal Chemistry. 2006 Oct 5;49(20):5969-87. PMID 17004712

[1]

[2]

Identifiers
File:VCHSR.png
IUPAC name 5-(4- chlorophenyl)-3-[(E)-2-cyclohexylethenyl]-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₄H₂₃Cl₃N₂
Molar mass	445.811
3D model (JSmol)	Interactive image
SMILES C4CCCCC4C=Cc(c(C)c1-c(cc3)ccc3Cl)nn1-c2ccc(Cl)cc2Cl

VCHSR

References

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