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drinabant

Structure via PubChem · Public domain (PubChem)

EntityQ5307675· pop 8· linked from 584 articles

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

Chemical data

Formula
C23H20Cl2F2N2O2S
Molecular weight
497.4 g/mol
IUPAC name
N-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-N-(3,5-difluorophenyl)methanesulfonamide
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
InChIKey
IQQBRKLVEALROM-UHFFFAOYSA-N
XLogP
5.6
Polar surface area
49 Ų
H-bond donors
0
H-bond acceptors
6
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Phase 3
Molecule type
Small molecule
Indications
Alzheimer disease, schizophrenia

via ChEMBL · EBI

Wikidata facts

Mass
496.059
Show 3 more facts
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
Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

2 sections
Contents
  • See also
  • References

{{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.

Excerpted from Wikipedia’s “drinabant” article, available under the CC BY-SA 4.0 licence.

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