{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"XJFUIILGVMOOHV-UHFFFAOYSA-N","prefName":"CE-178253","symbol":"CE-178253","iupacName":"1-[7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-3-(ethylamino)azetidine-3-carboxamide","aliases":["FW6JCF60XU","NCGC00485051-01","orb1740701","T68779","Q27278237"],"cas":null,"pubchemCid":"11191162","chebiId":null,"smiles":"CCNC1(CN(C1)C2=NC(=NC3=C(C(=NN32)C4=CC=CC=C4Cl)C5=CC=C(C=C5)Cl)C)C(=O)N","molecularFormula":"C24H23Cl2N7O","molecularWeight":496.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/11191162"}},"classification":{"family":"ecs_tool","familyLabel":"ECS modulator (research)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (research tool)","summaryFr":"No biosynthetic pathway: a chemically synthesised compound of the pyrazolo[1,5-a][1,3,5]triazine class.","originNote":"Entirely synthetic molecule, studied by Pfizer teams as a CB1 receptor antagonist with obesity and metabolic disorders in view (Hadcock et al., 2010).","discovered":""},"pharmacology":{"summaryFr":"CE-178253 is a synthetic antagonist of the cannabinoid receptor CB1, described as highly selective over CB2. The 2010 reference publication reports an inhibition constant of 0.33 nM at human CB1 in binding and 0.07 nM in a functional test, against more than 10 000 nM at CB2. In rats, the molecule is active by mouth: it reduces food intake, increases average oxygen consumption by 28% and 39% at 1 and 3 mg/kg, and reverses the four effects of CP-55940 in the tetrad test in a dose-dependent manner. In obese mice, 3 mg/kg per day for ten days led to an average weight loss of 18%. The same authors state that they had previously reported its efficacy in a model of parkinsonism, and suggest that selective CB1 antagonism may enhance the antiparkinsonian action of levodopa and other dopaminomimetics. No human clinical data are published in the sources consulted.","receptorSummaryFr":"Selective antagonist of the human CB1 receptor. Ki of 0.33 nM in binding and 0.07 nM in a GTPγ[35S] functional assay; the molecule also shows weak inverse agonism (intrinsic activity 21%). Very low affinity for human CB2 (Ki above 10 000 nM, a selectivity of more than 30 000-fold). Tested at 1 µM on a panel of targets (receptors, ion channels, transporters), it inhibits none of them by more than 50%, and it does not activate GPR55 at 10 µM. Ex vivo occupancy of brain CB1 receptors in rats after oral administration: about 27% at 0.3 mg/kg, 64% at 1 mg/kg, 78% at 3 mg/kg and 82% at 10 mg/kg.","binding":[{"target":"CB1","efficacy":"antagonist","relativeActivity":95,"reported":"Ki 0,33 nM en liaison sur CB1 humain ; Ki 0,07 nM en test fonctionnel GTPγ[35S] (Hadcock et coll., 2010)","confidence":"medium"},{"target":"CB2","efficacy":"antagonist","relativeActivity":5,"reported":"Ki supérieur à 10 000 nM (Hadcock et coll., 2010)","confidence":"medium"}],"references":[{"label":"Hadcock et coll., profil pharmacologique quantitatif de CE-178253, antagoniste CB1, BMC Pharmacology, 2010","pmid":"20712891","doi":"10.1186/1471-2210-10-9","url":"https://pubmed.ncbi.nlm.nih.gov/20712891/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (Convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, notice du composé CE-178253 (CID 11191162)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11191162"}]},"pharmacokinetics":null,"metabolism":null,"detection":null,"subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":3},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":3},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":3},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":2},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":2}],"doseRanges":null,"humanDataCharacterised":false},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":true,"bannerTextFr":"Aucune dose humaine caractérisée : données animales / in vitro uniquement. Profil d'effet, marge de sécurité et toxicité aiguë non documentés en clinique humaine.","toxicologyFr":null},"legal":{"scheduleStatus":"unscheduled","scheduleLabel":"Unscheduled","frScheduleStatus":"unscheduled","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 harmonised control measure at European Union level has been identified for this molecule in the sources consulted; its status falls under national legislation.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"CE-178253 is not named in any annex of the decree of 22 February 1990 (ANSM consolidated list, updated 16 February 2026); its structure meets none of the generic family definitions. It is not a tetrahydrocannabinol, and it carries none of the indole, indazole, pyrrole, pyrrolopyridine, indene or cyclohexylphenol cores, nor a benzo[c]chromene, that the family clauses target: no family clause captures it. It is therefore not classified in France. This absence of classification is not an authorisation: no marketing authorisation has been identified for this molecule in the sources consulted, and its use falls within research.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Hadcock et coll., profil pharmacologique quantitatif de CE-178253, antagoniste CB1, BMC Pharmacology, 2010","pmid":"20712891","doi":"10.1186/1471-2210-10-9","url":"https://pubmed.ncbi.nlm.nih.gov/20712891/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (Convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, notice du composé CE-178253 (CID 11191162)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11191162"}],"meta":{"slug":"ce-178253","url":"https://en.phytogrammes.com/wiki/ce-178253","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-13","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}