Drinabant

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.^[1][2][3] 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,^[4] 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severe psychiatric side effects including anxiety, depression, and thoughts of suicide in patients treated with the now-withdrawn CB1R antagonist rimonabant.^[5]

ATC code

• None

CAS Number

• 358970-97-5

PubChem CID

• 10278470

ChemSpider

• 8453947

Quick facts Clinical data, ATC code ...

Drinabant

Clinical data
ATC code	None
Identifiers
IUPAC name (±)-N-{1-[Bis(4-chlorophenyl)methyl]-3-azetidinyl}-N-(3,5-difluorophenyl)methanesulfonamide
CAS Number	358970-97-5
PubChem CID	10278470
ChemSpider	8453947
UNII	61S98RLL5I
CompTox Dashboard (EPA)	DTXSID50189455
Chemical and physical data
Formula	C23H20Cl2F2N2O2S
Molar mass	497.38 g·mol−1
3D model (JSmol)	Interactive image
SMILES Fc1cc(cc(F)c1)N(C4CN(C(c2ccc(Cl)cc2)c3ccc(Cl)cc3)C4)S(=O)(=O)C
InChI InChI=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 Key:IQQBRKLVEALROM-UHFFFAOYSA-N

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In late 2018, the drug was licensed by Opiant Pharmaceuticals, which intends to develop it for the treatment of acute cannabinoid overdose (ACO) as an injectable for administration in an emergency department setting. Opiant claims that ACO is most frequently linked to the ingestion of cannabis edibles and/or synthetic cannabinoids that are more potent and less expensive than natural cannabis extracts such as hash oil. Edibles, sold as capsules, brownies, cookies, chocolate bars and gumdrops, may pose particular risks for children, who may consume these by accident.^{[citation needed]} The existence of ACO is heavily debated. In fact, most people who die from cannabinoid ingestion have had chronic life-long heart problems or are involved in accidents from driving while intoxicated.^[6]

Rimonabant was another cannabinoid receptor antagonist developed for prescription drug use that triggered severe psychiatric side effects and was withdrawn from the market.