Drinabant

Drinabant
Clinical data
ATC code	None;
Legal status
Legal status	Development terminated;
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;

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severe psychiatric side effects including anxiety, depression, and thoughts of suicide in patients treated with the now-withdrawn rimonabant, another CB₁ antagonist that was also under development by Sanofi-Aventis.^[5]

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 edibles containing large quantities THC and synthetic cannabinoids that are more potent and less expensive than marijuana. Edibles, sold as brownies, cookies and candies, pose particular risks for children, who often consume these by accident. There are currently no approved treatments for ACO.

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was also a cannabinoid developed for prescription drug use that triggered severe psychiatric side effects and was withdrawn from the market.

References

^ Lange JH, Kruse CG (2008). "Cannabinoid CB1 receptor antagonists in therapeutic and structural perspectives". The Chemical Record. 8 (3): 156–68. doi:10.1002/tcr.20147. PMID 18563799.
^ Kwon MO, Herrling P (2005). "List of drugs in development for neurodegenerative diseases. Update September 2005". Neuro-Degenerative Diseases. 2 (2): 61–108. doi:10.1159/000089285. PMID 16909049. S2CID 2553974.
^ Gerald Litwack (14 August 2009). Anandamide. Academic Press. p. 172. ISBN 978-0-12-374782-2. Retrieved 13 May 2012.
^ Reggio, Patricia H. (2009). "Toward the design of cannabinoid CB1 receptor inverse agonists and neutral antagonists". Drug Development Research. 70 (8): 585–600. doi:10.1002/ddr.20337. ISSN 0272-4391. S2CID 83478850.
^ Lee HK, Choi EB, Pak CS (2009). "The current status and future perspectives of studies of cannabinoid receptor 1 antagonists as anti-obesity agents". Current Topics in Medicinal Chemistry. 9 (6): 482–503. doi:10.2174/156802609788897844. PMID 19689362. Archived from the original on 2013-05-22. Retrieved 2019-07-29.

[pmid18563799-1] Lange JH, Kruse CG (2008). "Cannabinoid CB1 receptor antagonists in therapeutic and structural perspectives". The Chemical Record. 8 (3): 156–68. doi:10.1002/tcr.20147. PMID 18563799.

[pmid16909049-2] Kwon MO, Herrling P (2005). "List of drugs in development for neurodegenerative diseases. Update September 2005". Neuro-Degenerative Diseases. 2 (2): 61–108. doi:10.1159/000089285. PMID 16909049. S2CID 2553974.

[Litwack2009-3] Gerald Litwack (14 August 2009). Anandamide. Academic Press. p. 172. ISBN 978-0-12-374782-2. Retrieved 13 May 2012.

[Reggio2009-4] Reggio, Patricia H. (2009). "Toward the design of cannabinoid CB1 receptor inverse agonists and neutral antagonists". Drug Development Research. 70 (8): 585–600. doi:10.1002/ddr.20337. ISSN 0272-4391. S2CID 83478850.

[pmid19689362-5] Lee HK, Choi EB, Pak CS (2009). "The current status and future perspectives of studies of cannabinoid receptor 1 antagonists as anti-obesity agents". Current Topics in Medicinal Chemistry. 9 (6): 482–503. doi:10.2174/156802609788897844. PMID 19689362. Archived from the original on 2013-05-22. Retrieved 2019-07-29.

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[2]

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[5]

See also

References