CAS 546141-08-6|URB597

Introduction：Basic information about CAS 546141-08-6|URB597, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. URB597 BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Customs
6. Articles39
7. Synonyms

Common Name	URB597
CAS Number	546141-08-6	Molecular Weight	338.400
Density	1.2±0.1 g/cm3	Boiling Point	533.2±50.0 °C at 760 mmHg
Molecular Formula	C₂₀H₂₂N₂O₃	Melting Point	/
MSDS	ChineseUSA	Flash Point	276.3±30.1 °C
Symbol	GHS07, GHS09	Signal Word	Warning

Names

Name	3'-Carbamoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbamate
Synonym	More Synonyms

URB597 BiologicalActivity

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 >>AutophagySignaling Pathways >>Metabolic Enzyme/Protease >>FAAHSignaling Pathways >>Neuronal Signaling >>FAAHSignaling Pathways >>Autophagy >>MitophagyResearch 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.

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 >>AutophagySignaling Pathways >>Metabolic Enzyme/Protease >>FAAHSignaling Pathways >>Neuronal Signaling >>FAAHSignaling Pathways >>Autophagy >>MitophagyResearch 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.

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
InChIKey	ROFVXGGUISEHAM-UHFFFAOYSA-N
SMILES	NC(=O)c1cccc(-c2cccc(OC(=O)NC3CCCCC3)c2)c1
Storage condition	2-8°C
Water Solubility	DMSO: ~14 mg/mL, soluble

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%

Articles39

Activation of PPAR gamma receptors reduces levodopa-induced dyskinesias in 6-OHDA-lesioned rats.

Neurobiol. Dis. 74 , 295-304, (2015)

Long-term administration of l-3,4-dihydroxyphenylalanine (levodopa), the mainstay treatment for Parkinson's disease (PD), is accompanied by fluctuations in its duration of action and motor complicatio...

Endocannabinoids regulate the activity of astrocytic hemichannels and the microglial response against an injury: In vivo studies.

Neurobiol. Dis. 79 , 41-50, (2015)

Anandamide (AEA) is an endocannabinoid (EC) that modulates multiple functions in the CNS and that is released in areas of injury, exerting putative neuroprotective actions. In the present study, we ha...

Correlating FAAH and anandamide cellular uptake inhibition using N-alkylcarbamate inhibitors: from ultrapotent to hyperpotent.

Biochem. Pharmacol. 92(4) , 669-89, (2014)

Besides the suggested role of a putative endocannabinoid membrane transporter mediating the cellular uptake of the endocannabinoid anandamide (AEA), this process is intrinsically coupled to AEA degrad...

Synonyms

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

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