URB597

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URB597
URB597.svg
Names
IUPAC name
[3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate
Identifiers
546141-08-6 N
ChEMBL ChEMBL184238 YesY
ChemSpider 1156960 YesY
Jmol-3D images Image
MeSH URB597
PubChem 1383884
Properties
C20H22N2O3
Molar mass 338.4 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

URB597 is a relatively selective inhibitor of the enzyme fatty acid amide hydrolase (FAAH).[1][2] FAAH is the primary degradatory enzyme for the endocannabinoid anandamide and, as such, inhibition of FAAH leads to an accumulation of anandamide in the CNS and periphery where it activates cannabinoid receptors. In pre-clinical laboratory tests researchers found URB597 increased the production of endocannabinoids resulting in measurable antidepressant and analgesic effects.[3]

URB597 is also known as KDS-4103. KDS-4103 is being developed by Kadmus Pharmaceuticals, Inc. for clinical trials in humans. Kadmus claims, on their website (linked below) that this class of compounds may have antidepressant, anti-anxiety, and pain-killing effects.

See also[edit]

References[edit]

  1. ^ Mor, Marco; Rivara, S; Lodola, A; Plazzi, PV; Tarzia, G; Duranti, A; Tontini, A; Piersanti, G; Kathuria, S; Piomelli, Daniele (2004). "Cyclohexylcarbamic acid 3'- or 4'-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies". J Med Chem. 47 (21): 4998–5008. doi:10.1021/jm031140x. PMID 15456244. 
  2. ^ Alexander, JP; Cravatt, BF (2005). "Mechanism of Carbamate Inactivation of FAAH: Implications for the Design of Covalent Inhibitors and In Vivo Functional Probes for Enzymes". Chem Biol. 12 (11): 1179–87. doi:10.1016/j.chembiol.2005.08.011. PMC 1994809. PMID 16298297. 
  3. ^ Russo, R; Loverme, J; La Rana, G; Compton, TR; Parrott, J; Duranti, A; Tontini, A; Mor, M; Tarzia, G; Calignano, A.; Piomelli, D. (2007). "The fatty-acid amide hydrolase inhibitor URB597 (cyclohexyl carbamic acid 3'-carbamoyl-biphenyl-3-yl ester) reduces neuropathic pain after oral administration in mice". J Pharmacol Exp Ther. 322 (1): 236–42. doi:10.1124/jpet.107.119941. PMID 17412883. 

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