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Drinabant (INN; AVE-1625) is a drug that acts as a selective CB1 receptor antagonist, which was under investigation varyingly by Sanofi-Aventis as a treatment for obesity, schizophrenia, Alzheimer's disease, Parkinson's disease, and nicotine dependence. Though initially studied as a potential treatment for a variety of different medical conditions, Sanofi-Aventis eventually narrowed down the therapeutic indications of the compound to just appetite suppression. Drinabant reached phase IIb clinical trials for this purpose in the treatment of obesity but was shortly thereafter discontinued, likel

Wikidata facts

Mass
496.059
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canonical SMILES
CS(=O)(=O)N(C1CN(C1)C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC(=CC(=C4)F)F
chemical formula
C₂₃H₂₀Cl₂F₂N₂O₂S
Commons category
Drinabant
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{{Drugbox | IUPAC_name = (±)-N-{1-[Bis(4-chlorophenyl)methyl]-3-azetidinyl}-N-(3,5-difluorophenyl)methanesulfonamide | image = Drinabant.svg | image_class = skin-invert-image | image2 = Drinabant ball-and-stick model.png | image_class2 = bg-transparent | CAS_number = 358970-97-5 | CAS_supplemental = | UNII_Ref = | UNII = 61S98RLL5I | ATC_prefix = None | ATC_suffix = | PubChem = 10278470 | ChemSpiderID = 8453947 | C = 23 | H = 20 | Cl = 2 | F = 2 | N = 2 | O = 2 | S = 1 | smiles = Fc1cc(cc(F)c1)N(C4CN(C(c2ccc(Cl)cc2)c3ccc(Cl)cc3)C4)S(=O)(=O)C | StdInChI = 1S/C23H20Cl2F2N2O2S/c1-32(30,31)29(21-11-19(26)10-20(27)12-21)22-13-28(14-22)23(15-2-6-17(24)7-3-15)16-4-8-18(25)9-5-16/h2-12,22-23H,13-14H2,1H3 | StdInChIKey = IQQBRKLVEALROM-UHFFFAOYSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_category = | routes_of_administration = }}

Drinabant (INN; AVE-1625) is a drug that acts as a selective CB1 receptor antagonist, which was under investigation varyingly by Sanofi-Aventis as a treatment for obesity, schizophrenia, Alzheimer's disease, Parkinson's disease, and nicotine dependence. Though initially studied as a potential treatment for a variety of different medical conditions, Sanofi-Aventis eventually narrowed down the therapeutic indications of the compound to just appetite suppression. Drinabant reached phase IIb clinical trials for this purpose in the treatment of obesity but was shortly thereafter discontinued, likely due to the observation of severe psychiatric side effects including anxiety, depression, and thoughts of suicide in patients treated with the now-withdrawn CB1R antagonist rimonabant.

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