Content deleted Content added
Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox va |
auto mw |
||
| (10 intermediate revisions by 9 users not shown) | |||
| Line 1: | Line 1: | ||
{{Short description|Chemical compound}} |
|||
{{Drugbox |
{{Drugbox |
||
| ⚫ | |||
| Watchedfields = changed |
|||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
<!--Clinical data--> |
<!--Clinical data--> |
||
| Line 25: | Line 25: | ||
<!--Identifiers--> |
<!--Identifiers--> |
||
| CAS_number_Ref = {{cascite|correct|??}} |
|||
| CAS_number = |
| CAS_number = |
||
| ATC_prefix = |
| ATC_prefix = |
||
| Line 31: | Line 32: | ||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
||
| DrugBank = |
| DrugBank = |
||
| ChemSpiderID = 21378331 |
|||
<!--Chemical data--> |
<!--Chemical data--> |
||
| chemical_formula = |
| chemical_formula = |
||
| C=24 | H=23 | Cl=3 | N=2 |
| C=24 | H=23 | Cl=3 | N=2 |
||
| molecular_weight = 445.811 |
|||
| smiles = C4CCCCC4C=Cc(c(C)c1-c(cc3)ccc3Cl)nn1-c2ccc(Cl)cc2Cl |
| smiles = C4CCCCC4C=Cc(c(C)c1-c(cc3)ccc3Cl)nn1-c2ccc(Cl)cc2Cl |
||
| StdInChI = 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+ |
|||
| StdInChIKey = UMOLSRBHNLXWGD-NTUHNPAUSA-N |
|||
}} |
}} |
||
'''VCHSR''' is a drug used in scientific research which acts as a selective [[Antagonist (pharmacology)|antagonist]] of the [[cannabinoid receptor]] [[cannabinoid receptor 1|CB<sub>1</sub>]]. It is derived from the widely used CB<sub>1</sub> antagonist [[rimonabant]], and has similar potency and selectivity for the CB<sub>1</sub> receptor, but has been modified to remove the [[hydrogen bonding]] capability in the C-3 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.<ref>{{cite journal | |
'''VCHSR''' is a drug used in scientific research which acts as a selective [[Antagonist (pharmacology)|antagonist]] of the [[cannabinoid receptor]] [[cannabinoid receptor 1|CB<sub>1</sub>]]. It is derived from the widely used CB<sub>1</sub> antagonist [[rimonabant]], and has similar potency and selectivity for the CB<sub>1</sub> receptor, but has been modified to remove the [[hydrogen bonding]] capability in the C-3 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.<ref>{{cite journal | vauthors = Hurst DP, Lynch DL, Barnett-Norris J, Hyatt SM, Seltzman HH, Zhong M, Song ZH, Nie J, Lewis D, Reggio PH | display-authors = 6 | title = 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 | journal = Molecular Pharmacology | volume = 62 | issue = 6 | pages = 1274–87 | date = December 2002 | pmid = 12435794 | doi = 10.1124/mol.62.6.1274 }}</ref><ref>{{cite journal | vauthors = 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 | display-authors = 6 | title = Biarylpyrazole inverse agonists at the cannabinoid CB1 receptor: importance of the C-3 carboxamide oxygen/lysine3.28(192) interaction | journal = Journal of Medicinal Chemistry | volume = 49 | issue = 20 | pages = 5969–87 | date = October 2006 | pmid = 17004712 | doi = 10.1021/jm060446b }}</ref> |
||
==References== |
== References == |
||
{{Reflist}} |
{{Reflist}} |
||
| Line 49: | Line 52: | ||
[[Category:CB1 receptor antagonists]] |
[[Category:CB1 receptor antagonists]] |
||
[[Category:Pyrazoles]] |
[[Category:Pyrazoles]] |
||
[[Category: |
[[Category:Chloroarenes]] |
||
{{cannabinoid-stub}} |
{{cannabinoid-stub}} |
||
Latest revision as of 09:42, 23 March 2024
 | |
| Identifiers | |
|---|---|
| |
| ChemSpider | |
| Chemical and physical data | |
| Formula | C24H23Cl3N2 |
| Molar mass | 445.81 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
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 C-3 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[edit]
- ^ 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.
- ^ 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.