Jump to content
Wikipedia The Free Encyclopedia

Drinabant

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Drinabant
Clinical data
ATC code
  • None
Legal status
Legal status
  • Development terminated
Identifiers
  • (±)-N-{1-[Bis(4-chlorophenyl)methyl]-3-azetidinyl}-N-(3,5-difluorophenyl)methanesulfonamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C23H20Cl2F2N2O2S
Molar mass 497.38 g·mol−1
3D model (JSmol)
  • Fc1cc(cc(F)c1)N(C4CN(C(c2ccc(Cl)cc2)c3ccc(Cl)cc3)C4)S(=O)(=O)C
  • 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severe psychiatric side effects including anxiety, depression, and thoughts of suicide in patients treated with the now-withdrawn rimonabant, another CB1 antagonist that was also under development by Sanofi-Aventis.[5]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.[citation needed ] 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was also a cannabinoid developed for prescription drug use that triggered severe psychiatric side effects and was withdrawn from the market.

See also

[edit ]

References

[edit ]
  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.
  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.
  3. ^ Gerald Litwack (14 August 2009). Anandamide. Academic Press. p. 172. ISBN 978-0-12-374782-2 . Retrieved 13 May 2012.
  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.
  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年05月22日. Retrieved 2019年07月29日.
Stimulants
Amphetamines and
phenethylamines
Adrenergic agonists
Other
Cannabinoid
antagonists
GLP-1, GIP, and / or
glucagon agonists
DACRAs
5-HT2C
receptor agonists
Absorption inhibitors
Uncouplers
Others
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
Allosteric CBR Tooltip Cannabinoid receptor ligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Receptor
(ligands)
CB1 Tooltip Cannabinoid receptor type 1
Agonists
(abridged,
full list)
Inverse agonists
Antagonists
CB2 Tooltip Cannabinoid receptor type 2
Agonists
Antagonists
NAGly
(GPR18)
Agonists
Antagonists
GPR55
Agonists
Antagonists
GPR119
Agonists
Transporter
(modulators)
eCBTs Tooltip Endocannabinoid transporter
Enzyme
(modulators)
FAAH Tooltip Fatty acid amide hydrolase
MAGL
ABHD6
ABHD12
Others
  • Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272 (FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)

AltStyle によって変換されたページ (->オリジナル) /