{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"VGUQVYZXABOXCX-UHFFFAOYSA-N","prefName":"CID16020046","symbol":"CID16020046","iupacName":"4-[4-(3-hydroxyphenyl)-3-(4-methylphenyl)-6-oxo-1,4-dihydropyrrolo[3,4-d]pyrazol-5-yl]benzoic acid","aliases":["CID 16020046","MLS000675307","SMR000314029","GTPL6577"],"cas":"834903-43-4","pubchemCid":"16020046","chebiId":null,"smiles":"CC1=CC=C(C=C1)C2=NNC3=C2C(N(C3=O)C4=CC=C(C=C4)C(=O)O)C5=CC(=CC=C5)O","molecularFormula":"C25H19N3O4","molecularWeight":425.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/16020046"}},"classification":{"family":"ecs_tool","familyLabel":"ECS modulator (research)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (research tool)","summaryFr":"No biosynthetic pathway: an organic synthetic molecule of the pyrazololactam family, built on a pyrazole ring fused to a five-membered lactam.","originNote":"Synthetic molecule: no natural source is reported in the sources consulted. The studies consulted are preclinical, in cells and in mice.","discovered":""},"pharmacology":{"summaryFr":"CID16020046 is a GPR55 antagonist, a receptor activated by lysophosphatidylinositol (LPI) and by certain cannabinoids, from the pyrazololactam chemical family. Its IC50 is 1.18 µM in the PubChem screen AID 2013. Published in 2013 as a selective antagonist of this receptor (Kargl et al., 2013), it was then used to study GPR55 in cells and in mice. It reduced inflammation in two colitis models (Stančić et al., 2015) and did not change atherosclerotic plaques in two atherosclerosis models (Montecucco et al., 2016). No human data or pharmacokinetic data have been identified in the sources consulted.","receptorSummaryFr":"GPR55 antagonist: in the PubChem assay AID 2013, its IC50 is 1.18 µM. In HEK293 cells expressing human GPR55, it blocks the calcium response and ERK activation induced by lysophosphatidylinositol (LPI) (Kargl et al., 2013). Brown et al. (2018) report that it blocks the effect of a surrogate agonist at human GPR55 and that it also antagonises rat GPR55. It is inactive in the GPR55 agonist screen (AID 1961) and in the GPR35 antagonist screen (AID 2058). In HEK293 cells expressing CB1 or CB2, it does not act as an antagonist; no affinity constant for these two receptors has been identified in the sources consulted.","binding":[{"target":"GPR55","efficacy":"antagonist","relativeActivity":40,"reported":"CI50 de 1,18 µM (criblage PubChem AID 2013, antagonistes GPR55 par imagerie)","confidence":"medium"},{"target":"CB1","efficacy":"modulator","relativeActivity":3,"reported":"aucune constante d'affinité identifiée ; pas d'antagonisme dans des cellules HEK293 exprimant CB1 (Kargl et coll., 2013)","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":3,"reported":"aucune constante d'affinité identifiée ; pas d'antagonisme dans des cellules HEK293 exprimant CB2 (Kargl et coll., 2013)","confidence":"medium"}],"references":[{"label":"Kargl et coll., antagoniste sélectif de GPR55 (plaquettes et cellules endothéliales), J Pharmacol Exp Ther 2013","pmid":"23639801","doi":"10.1124/jpet.113.204180","url":"https://pubmed.ncbi.nlm.nih.gov/23639801/"},{"label":"Brown et coll., relations structure-activité de CID16020046, antagoniste de GPR55, Pharmacology 2018","pmid":"30296786","doi":"10.1159/000493490","url":"https://pubmed.ncbi.nlm.nih.gov/30296786/"},{"label":"Stančić et coll., CID16020046 et inflammation intestinale, Neurogastroenterol Motil 2015","pmid":"26227635","doi":"10.1111/nmo.12639","url":"https://pubmed.ncbi.nlm.nih.gov/26227635/"},{"label":"Montecucco et coll., CID16020046 et activation des neutrophiles dans l'athérogenèse murine, Thromb Haemost 2016","pmid":"27465665","doi":"10.1160/TH16-02-0139","url":"https://pubmed.ncbi.nlm.nih.gov/27465665/"},{"label":"PubChem, criblage d'antagonistes GPR55 par imagerie (AID 2013), CI50 de 1,18 µM","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/bioassay/2013"},{"label":"PubChem, criblage d'agonistes GPR55 par imagerie (AID 1961), résultat inactif pour ce composé","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/bioassay/1961"},{"label":"PubChem, criblage d'antagonistes GPR35 par imagerie (AID 2058), résultat inactif pour ce composé","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/bioassay/2058"},{"label":"PubChem, composé CID 16020046, National Library of Medicine","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/16020046"},{"label":"ChEMBL, fiche CHEMBL1341792 (données d'activité du composé)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL1341792/"},{"label":"ANSM, liste consolidée des 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 (schedules de la Convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}]},"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":3},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":3}],"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 in the sources consulted; any control falls under the national law of each member state.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Not classed as a narcotic in France. CID16020046 is not named in the ANSM consolidated list of narcotics (update of 16 February 2026). Its structure does not meet any generic family definition in that list: those definitions rest on indole, indazole, pyrrole bearing a naphthyl group, pyrrolo[3,2-c]pyridine, cyclohexylphenol or naphthylidene-indene cores, none of which is present here. It is not included in the INCB Green List 2026 either. No marketing authorisation has been identified in the sources consulted.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Kargl et coll., antagoniste sélectif de GPR55 (plaquettes et cellules endothéliales), J Pharmacol Exp Ther 2013","pmid":"23639801","doi":"10.1124/jpet.113.204180","url":"https://pubmed.ncbi.nlm.nih.gov/23639801/"},{"label":"Brown et coll., relations structure-activité de CID16020046, antagoniste de GPR55, Pharmacology 2018","pmid":"30296786","doi":"10.1159/000493490","url":"https://pubmed.ncbi.nlm.nih.gov/30296786/"},{"label":"Stančić et coll., CID16020046 et inflammation intestinale, Neurogastroenterol Motil 2015","pmid":"26227635","doi":"10.1111/nmo.12639","url":"https://pubmed.ncbi.nlm.nih.gov/26227635/"},{"label":"Montecucco et coll., CID16020046 et activation des neutrophiles dans l'athérogenèse murine, Thromb Haemost 2016","pmid":"27465665","doi":"10.1160/TH16-02-0139","url":"https://pubmed.ncbi.nlm.nih.gov/27465665/"},{"label":"PubChem, criblage d'antagonistes GPR55 par imagerie (AID 2013), CI50 de 1,18 µM","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/bioassay/2013"},{"label":"PubChem, criblage d'agonistes GPR55 par imagerie (AID 1961), résultat inactif pour ce composé","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/bioassay/1961"},{"label":"PubChem, criblage d'antagonistes GPR35 par imagerie (AID 2058), résultat inactif pour ce composé","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/bioassay/2058"},{"label":"PubChem, composé CID 16020046, National Library of Medicine","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/16020046"},{"label":"ChEMBL, fiche CHEMBL1341792 (données d'activité du composé)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL1341792/"},{"label":"ANSM, liste consolidée des 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 (schedules de la Convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}],"meta":{"slug":"cid16020046","url":"https://en.phytogrammes.com/wiki/cid16020046","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."}}