EX-597

EX-597 (former developmental code names URB-597, KDS-4103, and ORG-231295) is a fatty acid amide hydrolase inhibitor (FAAH inhibitor)^[1] which is under development for the treatment of social anxiety disorder (or social phobia) and post-traumatic stress disorder (PTSD).^[2]

EX-597

Clinical data
Other names	URB597; URB-597; KDS-4103; ORG-231295
Identifiers
IUPAC name [3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate
CAS Number	546141-08-6 Y
PubChem CID	1383884
IUPHAR/BPS	4339
ChemSpider	1156960 Y
UNII	PX47LB88FO
ChEBI	CHEBI:188061
ChEMBL	ChEMBL184238 Y
CompTox Dashboard (EPA)	DTXSID70203046
ECHA InfoCard	100.164.994
Chemical and physical data
Formula	C20H22N2O3
Molar mass	338.407 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CCC(CC1)NC(=O)OC2=CC=CC(=C2)C3=CC(=CC=C3)C(=O)N
InChI 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) Y Key:ROFVXGGUISEHAM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

It is a relatively selective and irreversible inhibitor of the enzyme fatty acid amide hydrolase (FAAH).^[3][4] 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. EX-597 has been found to elevate anandamide levels and have activity against neuropathic pain in a mouse model.^[5]

Preclinical studies have shown FAAH inhibitors to increase brain-derived neurotrophic factor (BDNF) levels in the hippocampus and prefrontal cortex,^[6] highlighting their potential in addiction treatment as "enviromimetics".^[7] Indeed, Chauvet et al. found that chronic EX-597 administration in rats "significantly reduces cocaine-seeking behaviour and cue- and stress-induced relapse".^[8]

EX-597 was at one point being developed by Kadmus Pharmaceuticals, Inc. for clinical trials in humans.^[9]

See also

• 4-Nonylphenylboronic acid
• LY-2183240
• PF-04457845