Structure via PubChem · Public domain (PubChem)
rimonabant
Sign in to saveAlso known as A 281, SR 141716
Rimonabant (also known as SR141716; trade names Acomplia, Zimulti) is an anorectic antiobesity drug approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious neurological and psychiatric side effects; it was never approved in the United States. Rimonabant is an inverse agonist for the cannabinoid receptor CB1 and was first-in-class.
Chemical data
- Formula
- C22H21Cl3N4O
- Molecular weight
- 463.8 g/mol
- IUPAC name
- 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
- SMILES
- CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl
- InChIKey
- JZCPYUJPEARBJL-UHFFFAOYSA-N
- XLogP
- 6.5
- Polar surface area
- 50.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2006
- Admin. routes
- oral
- Indications
- obesity, cardiovascular disease, metabolic syndrome, Hepatic steatosis
via ChEMBL · EBI
Research
2,901 papers- Rimonabant Sanofi-Synthélabo.Current opinion in investigational drugs (London, England : 2000) · 2004
- Rimonabant--a selective CB1 antagonist.The Annals of pharmacotherapy · 2005
- Rimonabant for overweight or obesity.The Cochrane database of systematic reviews · 2006
- Rimonabant for the treatment of overweight and obese people.Health technology assessment (Winchester, England) · 2009
- Rimonabant for treating tobacco dependence.Vascular health and risk management · 2007
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 462.078
- Has use
- medication
Show 5 more facts
- Commons category
- Rimonabant
- chemical formula
- C₂₂H₂₁Cl₃N₄O
- World Health Organisation international non-proprietary name
- rimonabant
- canonical SMILES
- CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl
- defined daily dose
- 20
via Wikidata · CC0
~4 min read
Encyclopedic overview
7 sectionsContents
- History
- Adverse effects
- Pharmacology
- Chemistry
- Research
- See also
- References
Rimonabant (also known as SR141716; trade names Acomplia, Zimulti) is an anorectic antiobesity drug approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious neurological and psychiatric side effects; it was never approved in the United States. Rimonabant is an inverse agonist for the cannabinoid receptor CB1 and was first-in-class.
==History==
Excerpted from Wikipedia’s “rimonabant” article, available under the CC BY-SA 4.0 licence.