URB597

From Wikipedia, the free encyclopedia
  (Redirected from URB-597)
Jump to: navigation, search
URB597
URB597.svg
Names
IUPAC name
[3-(3-Carbamoylphenyl)phenyl] N-cyclohexylcarbamate
Identifiers
546141-08-6 N
ChEMBL ChEMBL184238 YesY
ChemSpider 1156960 YesY
4339
Jmol 3D model Interactive image
MeSH URB597
PubChem 1383884
Properties
C20H22N2O3
Molar mass 338.41 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

URB597 (KDS-4103) 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. URB597 has been found to elevate anandamide levels and have activity against neuropathic pain in a mouse model.[3]

URB597 was at one point being developed by Kadmus Pharmaceuticals, Inc. for clinical trials in humans.[4]

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 1994809free to read. 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. 
  4. ^ Kadmus Pharmaceuticals official website Archived December 19, 2005, at the Wayback Machine.

External links[edit]