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EX-597

Chemical compound

Field	Value
verifiedrevid	470619330
Verifiedfields	changed
Watchedfields	changed
image	URB597.svg
image_class	skin-invert-image
CAS_number_Ref
CAS_number	546141-08-6
PubChem	1383884
IUPHAR_ligand	4339
ChemSpiderID_Ref
ChemSpiderID	1156960
UNII_Ref
UNII	PX47LB88FO
ChEBI	188061
ChEMBL_Ref
ChEMBL	184238
synonyms	URB597; URB-597; KDS-4103; ORG-231295
IUPAC_name	[3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate
C	20	H=22	N=2	O=3
SMILES	C1CCC(CC1)NC(=O)OC2=CC=CC(=C2)C3=CC(=CC=C3)C(=O)N
StdInChI_Ref
StdInChI	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)
StdInChIKey_Ref
StdInChIKey	ROFVXGGUISEHAM-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

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

It 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. EX-597 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 brain-derived neurotrophic factor (BDNF) levels in the hippocampus and prefrontal cortex, highlighting their potential in addiction treatment as "enviromimetics". Indeed, Chauvet et al. found that chronic EX-597 administration in rats "significantly reduces cocaine-seeking behaviour and cue- and stress-induced relapse".

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

References

(28 November 2023). "EX 597". Springer Nature Switzerland AG.
(October 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". Journal of Medicinal Chemistry.
(November 2005). "Mechanism of carbamate inactivation of FAAH: implications for the design of covalent inhibitors and in vivo functional probes for enzymes". Chemistry & Biology.
(July 2007). "The fatty acid amide hydrolase inhibitor URB597 (cyclohexylcarbamic acid 3'-carbamoylbiphenyl-3-yl ester) reduces neuropathic pain after oral administration in mice". The Journal of Pharmacology and Experimental Therapeutics.
(March 2016). "The fatty acid amide hydrolase inhibitor URB597 modulates serotonin-dependent emotional behaviour, and serotonin1A and serotonin2A/C activity in the hippocampus". European Neuropsychopharmacology.
(February 2021). "Environmental enrichment-inspired pharmacological tools for the treatment of addiction". Current Opinion in Pharmacology.
(December 2014). "Chronic stimulation of the tone of endogenous anandamide reduces cue- and stress-induced relapse in rats". The International Journal of Neuropsychopharmacology.
"Kadmus Pharmaceuticals".

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benzamides biphenyls carbamates cyclohexyl-compounds endocannabinoid-reuptake-inhibitors experimental-antidepressants experimental-anxiolytics fatty-acid-amide-hydrolase-inhibitors phenol-esters

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