ECS modulator (research)
UnscheduledURB597URB597 (KDS-4103)
[3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate
Aliases.KDS-4103 · Carbamic acid 3'-(aminocarbonyl)biphenyl-3-yl ester
The reference FAAH inhibitor. The standard pharmacological tool for studying endogenous AEA in vivo.
Updated on
Level of detail
Identifiers
- Formula
- C₂₀H₂₂N₂O₃
- Molar mass
- 338.40 g·mol⁻¹
- CAS
- 546141-08-6
- PubChem CID
- 1383884
- First described
- 2003
- Origin
- Pharmaceutical research (Piomelli)
- InChIKey
- ROFVXGGUISEHAM-UHFFFAOYSA-N
In plain terms
URB597 is an experimental drug that prevents the body from destroying its own anandamide. It has been tested in humans for pain and anxiety, but has never been marketed.
Receptors and activity
- FAAHIC50 ≈ 4,6 nM (rat)Antagonist
- CB1indirect via AEAModulator
- Agonist
- Partial agonist
- Antagonist
- Modulator
- Inverse agonist
Hover over a row for the precise value (Ki, EC50…)
Subjective signature
Hover over an axis to read its definition.
- Calm75
- Clarity45
- Sleep55
- Appetite40
- High50
Editorial estimate, not clinical.
Pharmacology
URB597 is the reference FAAH inhibitor - characterised by Kathuria, Mor, Mangieri and Piomelli (Nat Med 2003, PMID 12514735) at the University of California. Covalent mechanism: irreversible carbamylation of Ser241 in the active site of FAAH. Anxiolytic and antidepressant effect in rodent models (Bortolato et al. 2007, PMID 16968671). Human phase 2 for neuropathic pain and anxiety: abandoned in 2008 after the BIA 10-2474 incident (another FAAH inhibitor), even though URB597 itself never showed similar neurotoxicity.
Key sources.
Origin (research tool)
An irreversible covalent inhibitor of FAAH; obtained by organic synthesis (carbamylation of the Ser241 residue of the active site)
Legal framework
International
Non listé
European Union
Non listé, outil de recherche
France
Non listé, outil de recherche
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- ECS modulator (research)
- Origin
- Pharmaceutical research (Piomelli)
- Status
- Unscheduled
References
- 1.Kathuria · Nat Med 2003PMID 12514735
Structured data
- InChIKey
- ROFVXGGUISEHAM-UHFFFAOYSA-N
- SMILES
- C1CCC(CC1)NC(=O)OC2=CC=CC(=C2)C3=CC(=CC=C3)C(=O)N
- Formula
- C20H22N2O3
- Molar mass
- 338.40 g·mol⁻¹
- CAS
- 546141-08-6
- PubChem CID
- 1383884
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.