CAS Number546141-08-6
Synonymscyclohexyl 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
Molecular FormulaC20H22N2O3
Molecular Weight338.400
Purity96+%
Density1.2±0.1 g/cm3
Boiling Point533.2±50.0 °C at 760 mmHg
Appearancepowder | white
EINECS0
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 546141-08-6 |
| Catalog No. | 2A-1166335 |
| Chinese Name | URB-597 |
| 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 |
| Molecular Formula | C20H22N2O3 |
| Molecular Weight | 338.400 |
| Purity | 96+ |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 533.2±50.0 °C at 760 mmHg |
| Appearance | powder | white |
| Water Solubility | DMSO: ~14 mg/mL, soluble |
| Storage Condition | 2-8°C |
| Application | URB597 is an orally biocompatible FAAH inhibitor with an IC50 of 4.6 nM and is inactive against other cannabinoid-related targets. |
| EINECS | 0 |
| HTC | 2924299090 |
| UN(IATA) | 0 |
| PubChem ID | 4117632 |
| SMILES | NC(=O)c1cccc(-c2cccc(OC(=O)NC3CCCCC3)c2)c1 |
| 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) |
| InChI Key | ROFVXGGUISEHAM-UHFFFAOYSA-N |
| MSDS | msds/166335_2_546141_08_6.pdf |
| Bioactivity | 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. 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 |
| Use of | Properties Articles39 Name 3'-Carbamoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbamate Synonym More Synonyms URB597 Biological Activity 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 [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 Molecular Formula C20H22N2O3 Exact Mass 338.163055 PSA 81.42000 Appearance of Characters powder | white Index of Refraction 1.618 InChIKey ROFVXGGUISEHAM-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 30.0% |
| Transport Info | Product name: 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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