URB597

Names

[ Name ]:
URB597

[Synonym ]:
cyclohexyl carbamic acid 3'-carbamoylbiphenyl-3-yl ester
URB597
3'-Carbamoyl-3-biphenylyl cyclohexylcarbamate
Carbamic acid, N-cyclohexyl-, 3'-(aminocarbonyl)[1,1'-biphenyl]-3-yl ester
3'-Carbamoylbiphenyl-3-yl cyclohexylcarbamate
Cyclohexyl-carbamic acid 3'-carbamoyl-biphenyl-3-yl ester
[3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate
3'-(aminocarbonyl)-1,1'-biphenyl-3-yl cyclohexylcarbamate
URB-597

Biological Activity

[Description]:

URB597 is a potent, orally bioavailable FAAH inhibitor with IC50 of 4.6 nM, with no activity on other cannabinoid-related targets.IC50 value: 4.6 nM [1]Target: FAAH in vitro: URB597 binds in the hydrophobic pocket and catalytic core of FAAH that connects the active site residues to the membrane surface of FAAH [1]. URB597 reduces the expression of the LPS-induced enzymes cyclo-oxygenase 2 (COX-2) and inducible nitric oxide synthase (iNOS; NOS2) in primary rat microglial cell, with a concomitant reduction in the release of the inflammatory mediators prostaglandin E2 (PGE2) and (NO) nitric oxide [2]. in vivo: URB597 inhibits [3H]anandamide hydrolysis in rat brain membranes with a parallel increase in brain anandamide, OEA, and PEA content by inhibition of FAAH. URB597 enhances the hypothermia effect induced by ethanolamide by inhibiting FAAH [3]. When delivered intraperitonealy (0.3 mg/kg) URB597 reduces allodynia and hyperalgesia through cannabinoid CB1 and CB2 receptor-mediated analgesia in rats with inflammatory pain [4].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> FAAH

Signaling Pathways >> Neuronal Signaling >> FAAH

Signaling Pathways >> Autophagy >> Mitophagy

Research Areas >> Neurological Disease

[References]

[1]. Mor M, et al. 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, 2004, 47(21), 4998-5008.

[2]. Tham CS, et al. Inhibition of microglial fatty acid amide hydrolase modulates LPS stimulated release of inflammatory mediators. FEBS Lett, 2007, 581(16), 2899-2904.

[3]. Fegley D, et al. Characterization of the fatty acid amide hydrolase inhibitor cyclohexyl carbamic acid 3'-carbamoyl-biphenyl-3-yl ester (URB597): effects on anandamide and oleoylethanolamide deactivation. J Pharmacol Exp Ther. 2005 Apr;313(1):352-8.

[4]. Jayamanne A, et al. Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models. Br J Pharmacol, 2006, 147(3), 281-288.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
533.2±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₂₂N₂O₃

[ Molecular Weight ]:
338.400

[ Flash Point ]:
276.3±30.1 °C

[ Exact Mass ]:
338.163055

[ PSA ]:
81.42000

[ LogP ]:
3.51

[ Appearance of Characters ]:
powder | white

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.618

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: ~14 mg/mL, soluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H319-H410

[ Precautionary Statements ]:
P273-P305 + P351 + P338-P501

[ Personal Protective Equipment ]:
Eyeshields;Gloves

[ Hazard Codes ]:
N

[ Risk Phrases ]:
50/53

[ Safety Phrases ]:
22-24/25-60-61

[ RIDADR ]:
UN 3077 9/PG 3

[ WGK Germany ]:
3

[ HS Code ]:
2924299090

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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