3-(3-carbamoylphenyl)phenyl N-cyclohexylcarbamate

• ChemBase编号: 69295
• 分子式: C20H22N2O3
• 平均质量: 338.40028
• 单一同位素质量: 338.16304257
• SMILES: C(=O)(NC1CCCCC1)Oc1cc(ccc1)c1cc(ccc1)C(=O)N
• Canonical SMILES: O=C(Oc1cccc(c1)c1cccc(c1)C(=O)N)NC1CCCCC1
• 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)
• InChIKey: ROFVXGGUISEHAM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-(3-carbamoylphenyl)phenyl N-cyclohexylcarbamate
• IUPAC传统名: 3-(3-carbamoylphenyl)phenyl N-cyclohexylcarbamate
• 别名: Cyclohexylcarbamic acid 3′-carbamoyl-biphenyl-3-yl ester; URB597; KDS-4103; URB597; 3'-Carbamoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbamate

登记号

• CAS号: 546141-08-6
• MDL号: MFCD05863934
• PubChem SID: 162035022
• PubChem CID: 1383884
• CHEMBL: 184238
• Chemspider ID: 1156960
• 医学主题词(MeSH): URB597
• 维基百科标题: URB597

理论计算性质

• Acid pKa: 14.306808
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 3.767773
• LogD (pH = 7.4): 3.7677734
• Log P: 3.7677736
• 摩尔折射率: 95.9926 cm^3
• 极化性: 38.14706 Å^3
• 极化表面积: 81.42 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble ~14 mg/mL
• 外观: white powder

安全信息

• 保存条件: -20°C
• 保存注意事项: IRRITANT
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N)
• 联合国危险货物编号: 3077
• 德国WGK号: 3
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 50/53
• 安全公开号: 22-24/25-60-61
• TSCA收录: false
• GHS危险品标识: GHS07; GHS09
• GHS警示词: Warning
• GHS危险声明: H319-H410
• GHS警示性声明: P273-P305 + P351 + P338-P501
• 个人保护装置: Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• 保存温度: 2-8°C

药理学性质

• 作用靶点: fatty acid amide hydrolase (FAAH)

产品相关信息

• 纯度: ≥98% (HPLC); 95+%; 97%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C20H22N2O3

详细说明

Selleck Chemicals - S2631

Research Area

• Description: Cancer

Biological Activity

• Description: URB597 (KDS-4103) is a potent FAAH inhibitor with IC50 of 4.6 nM.
• Targets:

  FAAH

• IC50:

  4.6 nM ^[1]

• 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 inhibits FAAH activity in human liver microsomes with IC50 of 3 nM. ^[2] URB597 reduces the expression of the LPS-induced enzymes cyclo-oxygenase 2 (COX2) 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. ^[3] URB597 evokes Ca₂₊ entry in HEK293-F Cells transiently expressing human or rat TRPA1 gene. URB597 also activates Ca₂₊ entry in rat DRG neurons natively expressed TRPA1 channels. ^[4]
• 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. ^[5] 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. ^[6] URB597 reduces the reduction in body weight gain and sucrose intake induced by the chronic mild stress in rats through inhibition of brain FAAH activity. ^[7] URB597 could reverse most depressive-like symptoms induced by adolescent THC exposure in femal rats. ^[8]

Protocol

• Protocol: Kinase Assay ^[1]
• Pharmacology: Membrane fractions are prepared from brain homogenates, and FAAH activity is assayed using [^3H]anandamide (anandamide[ethanolamine-^3H], 60 Ci/mmol) as a substrate. Rat brain membranes (50 μg protein) are incubated for 30 min at 37 °C in buffer containing [^3H]anandamide and varying concentrations of URB597. At the end of the incubation period, we stopp the reactions with a mixture of chloroform/methanol and measured [^3H]ethanolamine in the aqueous phase by liquid scintillation counting.
• Protocol: Animal Study ^[5]
• Animal Models: Adult male Wistar rats (250–300 g) and C57/BL6 or FAAH-/- mice
• Formulation: sterile 0.9% sodium chloride solution
• Doses: 0.3 mg/kg
• Administration: Inject subcutaneously in a single dose 2 hours or 16 hours before killing

References

• References: [1] Mor M, et al. J Med Chem, 2004, 47(21), 4998-5008.
• References: [2] Piomelli D, et al. CNS Drug Rev, 2006, 12(1), 21-38.
• References: [3] Tham CS, et al. FEBS Lett, 2007, 581(16), 2899-2904.
• References: [4] Niforatos W, et al. Mol Pharmacol, 2007, 71(5), 1209-1216.
• References: [5] Fegley D, et al. J Pharmacol Exp Ther, 2005, 313(1), 352-358.
• References: [6] Jayamanne A, et al. Br J Pharmacol, 2006, 147(3), 281-288.
• References: [7] Bortolato M, et al. Biol Psychiatry, 2007, 62(10), 1103-1110.
• References: [8] Realini N, et al. Neuropharmacology, 2011, 60(2-3), 235-243.

Sigma Aldrich - U4133

Biochem/physiol Actions
Potent, selective fatty acid amide hydrolase (FAAH) inhibitor.

参考文献

• Mor M, et al. J Med Chem, 2004, 47(21), 4998-5008.
• Piomelli D, et al. CNS Drug Rev, 2006, 12(1), 21-38.
• Tham CS, et al. FEBS Lett, 2007, 581(16), 2899-2904.
• Niforatos W, et al. Mol Pharmacol, 2007, 71(5), 1209-1216.
• Fegley D, et al. J Pharmacol Exp Ther, 2005, 313(1), 352-358.
• Jayamanne A, et al. Br J Pharmacol, 2006, 147(3), 281-288.
• Bortolato M, et al. Biol Psychiatry, 2007, 62(10), 1103-1110.
• Realini N, et al. Neuropharmacology, 2011, 60(2-3), 235-243.