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URB597
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URB597

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URB597
URB597.svg
Names
Preferred IUPAC name
3′-Carbamoyl[1,1′-biphenyl]-3-yl cyclohexylcarbamate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.164.994
MeSH URB597
PubChem CID
UNII
  • InChI=1S/C20H22N2O3/c21-19(23)16-8-4-6-14(12-16)15-7-5-11-18(13-15)25-20(24)22-17-9-2-1-3-10-17/h4-8,11-13,17H,1-3,9-10H2,(H2,21,23)(H,22,24) checkY
    Key: ROFVXGGUISEHAM-UHFFFAOYSA-N checkY
  • InChI=1/C20H22N2O3/c21-19(23)16-8-4-6-14(12-16)15-7-5-11-18(13-15)25-20(24)22-17-9-2-1-3-10-17/h4-8,11-13,17H,1-3,9-10H2,(H2,21,23)(H,22,24)
    Key: ROFVXGGUISEHAM-UHFFFAOYAO
  • O=C(NC1CCCCC1)OC2=CC=CC(C3=CC=CC(C(N)=O)=C3)=C2
Properties
C20H22N2O3
Molar mass 338.407 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 checkY☒N ?)

URB597 (KDS-4103) is a relatively selective and irreversible inhibitor of the enzyme fatty acid amide hydrolase (FAAH). 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.

Preclinical studies have shown FAAH inhibitors to increase BDNF levels in the hippocampus and prefrontal cortex, highlighting their potential in addiction treatment as "enviromimetics". Indeed, Chauvet et al. found that chronic URB597 administration in rats "significantly reduces cocaine-seeking behaviour and cue- and stress-induced relapse".

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

See also

External links


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