URB597

URB597
Names
	IUPAC name [3-(3-Carbamoylphenyl)phenyl] N-cyclohexylcarbamate
Identifiers
CAS Number	546141-08-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL184238 ;
ChemSpider	1156960 ;
ECHA InfoCard	100.164.994
IUPHAR/BPS	4339;
MeSH	URB597
PubChem CID	1383884;
UNII	PX47LB88FO ;
CompTox Dashboard (EPA)	DTXSID70203046 ;
	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) Key: ROFVXGGUISEHAM-UHFFFAOYSA-N ; 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;
	SMILES O=C(NC1CCCCC1)OC2=CC=CC(C3=CC=CC(C(N)=O)=C3)=C2;
Properties
Chemical formula	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).

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]

References

^ 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" (PDF). J Med Chem. 47 (21): 4998–5008. doi:10.1021/jm031140x. PMID 15456244.
^ 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.
^ 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" (PDF). J Pharmacol Exp Ther. 322 (1): 236–42. doi:10.1124/jpet.107.119941. PMID 17412883. S2CID 40603248.
^ Kadmus Pharmaceuticals official website Archived December 19, 2005, at the Wayback Machine

External links

Modulation of anxiety through blockade of anandamide hydrolysis in Nature

[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" (PDF). 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" (PDF). J Pharmacol Exp Ther. 322 (1): 236–42. doi:10.1124/jpet.107.119941. PMID 17412883. S2CID 40603248.

[4] Kadmus Pharmaceuticals official website Archived December 19, 2005, at the Wayback Machine

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Names

IUPAC name [3-(3-Carbamoylphenyl)phenyl] N-cyclohexylcarbamate
Identifiers
CAS Number	546141-08-6
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL184238
ChemSpider	1156960
ECHA InfoCard	100.164.994
IUPHAR/BPS	4339
MeSH	URB597
PubChem CID	1383884
UNII	PX47LB88FO
CompTox Dashboard (EPA)	DTXSID70203046
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) Key: ROFVXGGUISEHAM-UHFFFAOYSA-N 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
SMILES O=C(NC1CCCCC1)OC2=CC=CC(C3=CC=CC(C(N)=O)=C3)=C2
Properties
Chemical formula	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).

URB597

See also

References

External links