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Details

Stereochemistry ACHIRAL
Molecular Formula C20H22N2O3
Molecular Weight 338.4003
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URB-597

SMILES

NC(=O)C1=CC=CC(=C1)C2=CC(OC(=O)NC3CCCCC3)=CC=C2

InChI

InChIKey=ROFVXGGUISEHAM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
URB-597 (KDS-4103) is a highly potent and selective inhibitor of the enzyme fatty acid amide hydrolase (FAAH), which catalyzes the intracellular hydrolysis of the endocannabinoid anandamide. URB597 is one the best studied carbamate-based inhibitors. Early studies showed that the compound did not inhibit or bind related biological targets. Administration of URB597 to rats and subsequent in vivo evaluation of brain FAAH activity showed the compound elevated endogenous anandamide levels. Importantly, the compound did not produce catalepsy, hypothermia, or hyperphagia, three of the typical effects of exogenous cannabinoids. The compound did produce antinociceptive effects in the mouse hot-plate test, which were reversed by the CB1 antagonist rimonabant. These findings again support the expectation that inhibition of FAAH produces pharmacology distinct from an exogenous CB1 agonist. A more detailed study was published later showing time-course data in mice demonstrating elevation of anandamide, oleamide, and N-palmitoyl ethanolamine for 2–6 h after administration of URB597. In vivo administration of URB597 showed almost complete inhibition of FAAH by the compound, and the FAAH inhibition was still approximately 70% after 16 h. Complete recovery of CNS FAAH activity was observed 24 h after administration of URB597. In vivo administration of URB597 or the cannabinoid receptor agonist HU210 reduced both mechanical allodynia and thermal hyperalgesia in the CFA model of inflammatory pain. Effects in the inflammatory model were partially reversed by CB1 and CB2 antagonists. In a related study, the compound produced analgesic effects in the mouse CCI model (neuropathic) when administered orally. These effects were also reversed by both CB1 and CB2 antagonists.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
60.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Modulation of anxiety through blockade of anandamide hydrolysis.
2003 Jan
The discovery and development of inhibitors of fatty acid amide hydrolase (FAAH).
2011 Aug 15
Patents

Patents

Sample Use Guides

Oral administration of URB597 (1-50 mg/kg, once daily) for 4 days produced a dose-dependent reduction in nocifensive responses to thermal and mechanical stimuli
Route of Administration: Oral
The substrate N-(2-hydroxyethyl)-4-pyren-1-ylbutanamide (100 mkM) solubilized with Triton X-100 (0.2%) was incubated with rat brain microsomes. Enzyme reactions were stopped after 60 min. FAAH activity was determined directly without further sample clean-up by measuring the amount of 4-pyren-1-ylbutanoic acid released in absence and presence of a test compound (URB-597) with reversed phase HPLC and fluorescence-detection.
Name Type Language
URB-597
Common Name English
ORG-231295
Code English
CARBAMIC ACID, N-CYCLOHEXYL-, 3'-(AMINOCARBONYL)(1,1'-BIPHENYL)-3-YL ESTER
Systematic Name English
URB 597
Code English
KDS-4103
Code English
3'-(AMINOCARBONYL)(1,1'-BIPHENYL)-3-YL N-CYCLOHEXYLCARBAMATE
Systematic Name English
Code System Code Type Description
WIKIPEDIA
URB-597
Created by admin on Sat Dec 16 11:45:38 GMT 2023 , Edited by admin on Sat Dec 16 11:45:38 GMT 2023
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CAS
546141-08-6
Created by admin on Sat Dec 16 11:45:38 GMT 2023 , Edited by admin on Sat Dec 16 11:45:38 GMT 2023
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EPA CompTox
DTXSID70203046
Created by admin on Sat Dec 16 11:45:38 GMT 2023 , Edited by admin on Sat Dec 16 11:45:38 GMT 2023
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PUBCHEM
1383884
Created by admin on Sat Dec 16 11:45:38 GMT 2023 , Edited by admin on Sat Dec 16 11:45:38 GMT 2023
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FDA UNII
PX47LB88FO
Created by admin on Sat Dec 16 11:45:38 GMT 2023 , Edited by admin on Sat Dec 16 11:45:38 GMT 2023
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