URB597

URB597, also known as KDS-4103, is a relatively selective inhibitor of the enzyme fatty acid amide hydrolase (FAAH). 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. In pre-clinical laboratory tests researchers found URB597 increased the production of endocannabinoids resulting in measurable antidepressant and analgesic effects.

Product information

CAS Number: 546141-08-6

Molecular Weight: 338.40

Formula: C20H22N2O3

Synonym:

URB-597

URB 597

KDS-4103

KDS4103

KDS 4103

Chemical Name: [3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate

Smiles: NC(=O)C1=CC(=CC=C1)C1=CC(=CC=C1)OC(=O)NC1CCCCC1

InChiKey: ROFVXGGUISEHAM-UHFFFAOYSA-N

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)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 68 mg/mL(200.94 mM). Water: Insoluble.

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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. URB597 inhibits FAAH activity in human liver microsomes with IC50 of 3 nM. 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. 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.

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. 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. 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. URB597 could reverse most depressive-like symptoms induced by adolescent THC exposure in femal rats.

References:

1. Tham CS, et al. FEBS Lett, 2007, 581(16), 2899-2904.
2. Piomelli D, et al. CNS Drug Rev, 2006, 12(1), 21-38.
3. Mor M, et al. J Med Chem, 2004, 47(21), 4998-5008.

Products are for research use only. Not for human use.