Content deleted Content added
Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
Updating {{chembox}} (changes to verified fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|errors... |
||
| Line 1: | Line 1: | ||
{{chembox |
{{chembox |
||
| Verifiedfields = changed |
|||
| verifiedrevid = |
| verifiedrevid = 477866431 |
||
|ImageFile=URB 602.svg |
|ImageFile=URB 602.svg |
||
|ImageSize=200px |
|ImageSize=200px |
||
| Line 7: | Line 8: | ||
|Section1= {{Chembox Identifiers |
|Section1= {{Chembox Identifiers |
||
| CASNo=565460-15-3 |
| CASNo=565460-15-3 |
||
| CASNo_Ref = {{cascite| |
| CASNo_Ref = {{cascite|changed|??}} |
||
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|||
| |
| ChEMBL = 77767 |
||
| PubChem = 10979337 |
| PubChem = 10979337 |
||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
||
Revision as of 11:30, 20 February 2012
| |
| Names | |
|---|---|
| IUPAC name
Cyclohexyl [1,1'-biphenyl]-3-ylcarbamate
| |
| Other names
[1,1'-Biphenyl]-3-yl-carbamic acid, cyclohexyl ester
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C19H21NO2 | |
| Molar mass | 295.382 g·mol−1 |
| Appearance | Crystalline solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
URB602 ([1,1'-biphenyl]-3-yl-carbamic acid, cyclohexyl ester) is a compound that has been found to inhibit hydrolysis of monoacyl glycerol compounds, such as 2-arachidonoylglycerol (2-AG) and 2-oleoylglycerol (2-OG). It was first described in 2003.[1] A study performed in 2005 found that the compound had specificity for metabolizing 2-AG over anandamide (another cannabinoid ligand) in rat brain presumably by inhibiting the enzyme monoacylglycerol lipase (MAGL), which is the primary metabolic enzyme of 2-AG.[2] However, subsequent studies have shown that URB602 lacks specificity for MAGL inhibition in vitro.[3]
References
- ^ Tarzia, G; Duranti, A; Tontini, A; Piersanti, G; Mor, M; Rivara, S; Plazzi, PV; Park, C; Kathuria, S (2003). "Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors". Journal of medicinal chemistry. 46 (12): 2352–60. doi:10.1021/jm021119g. PMID 12773040.
- ^ Hohmann, Andrea G.; Suplita, Richard L.; Bolton, Nathan M.; Neely, Mark H.; Fegley, Darren; Mangieri, Regina; Krey, Jocelyn F.; Michael Walker, J.; Holmes, Philip V. (2005). "An endocannabinoid mechanism for stress-induced analgesia". Nature. 435 (7045): 1108–12. Bibcode:2005Natur.435.1108H. doi:10.1038/nature03658. PMID 15973410.
- ^ Vandevoorde, S; Jonsson, K-O; Labar, G; Persson, E; Lambert, D M; Fowler, C J (2007). "Lack of selectivity of URB602 for 2-oleoylglycerol compared to anandamide hydrolysisin vitro". British Journal of Pharmacology. 150 (2): 186–91. doi:10.1038/sj.bjp.0706971. PMC 2042901. PMID 17143303.