{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"ROFVXGGUISEHAM-UHFFFAOYSA-N","prefName":"URB597 (KDS-4103)","symbol":"URB597","iupacName":"[3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate","aliases":["KDS-4103","Carbamic acid 3'-(aminocarbonyl)biphenyl-3-yl ester"],"cas":"546141-08-6","pubchemCid":"1383884","chebiId":null,"smiles":"C1CCC(CC1)NC(=O)OC2=CC=CC(=C2)C3=CC(=CC=C3)C(=O)N","molecularFormula":"C20H22N2O3","molecularWeight":338.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/1383884"}},"classification":{"family":"ecs_tool","familyLabel":"Modulador del ECS (investigación)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origen (herramienta de investigación)","summaryFr":"Inhibidor covalente irreversible de la FAAH; obtenido por síntesis orgánica (carbamilación del residuo Ser241 del sitio activo)","originNote":"Investigación farmacéutica (Piomelli)","discovered":"2003"},"pharmacology":{"summaryFr":"URB597 es el inhibidor de FAAH de referencia - caracterizado por Kathuria, Mor, Mangieri y Piomelli (Nat Med 2003, PMID 12514735) en la Universidad de California. Mecanismo covalente: carbamilación irreversible de Ser241 en el sitio activo de la FAAH. Efecto ansiolítico y antidepresivo en los modelos de roedor (Bortolato et al. 2007, PMID 16968671). Fase 2 humana para dolor neuropático y ansiedad: abandonado en 2008 tras el incidente BIA 10-2474 (otro inhibidor de FAAH), aunque el propio URB597 nunca mostró una neurotoxicidad similar.","receptorSummaryFr":"Inhibidor selectivo de la FAAH (IC50 ≈ 4,6 nM rata, 3,2 nM humano) - eleva la AEA cerebral en un factor ≈ 5–10× sin efecto directo sobre CB1/CB2","binding":[{"target":"FAAH","efficacy":"antagonist","relativeActivity":95,"reported":"IC50 ≈ 4,6 nM (rat)","confidence":"medium"},{"target":"CB1","efficacy":"modulator","relativeActivity":10,"reported":"indirect via AEA","confidence":"medium"}],"references":[{"label":"Kathuria · Nat Med 2003","pmid":"12514735","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/12514735/"}]},"pharmacokinetics":null,"metabolism":null,"detection":null,"subjectiveEffects":{"profile":[{"key":"calm","label":"Calma","description":"Relajación del cuerpo y de la mente; menos ruido mental, sin somnolencia marcada.","intensity":75},{"key":"focus","label":"Claridad","description":"Atención sostenida y pensamiento claro; lucidez funcional, sin euforia.","intensity":45},{"key":"sleep","label":"Sueño","description":"Efecto sedante: favorece la conciliación del sueño y la continuidad del sueño profundo.","intensity":55},{"key":"appetite","label":"Apetito","description":"Estimulación del hambre y de la apreciación gustativa (efecto «munchies»).","intensity":40},{"key":"uplift","label":"High","description":"Euforia e intensidad sensorial; percepción del tiempo y del espacio modificada.","intensity":50}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":null},"legal":{"scheduleStatus":"unscheduled","scheduleLabel":"No listado","frScheduleStatus":null,"tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":null,"reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"No listada","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Herramienta de investigación, no listada","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Kathuria · Nat Med 2003","pmid":"12514735","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/12514735/"}],"meta":{"slug":"urb597","url":"https://es.phytogrammes.com/wiki/urb597","lastVerified":"2026-05-01","dataUpdatedAt":"2026-05-01","confidence":"medium","dataCompletenessPct":80,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}