Rimonabant
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| Rimonabant
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| Systematic (IUPAC) name | |
| 5-(4-Chlorophenyl)-1-(2,4-dichloro-phenyl)- 4-methyl-N-(piperidin-1-yl)- 1H-pyrazole-3-carboxamide | |
| Identifiers | |
| CAS number | |
| ATC code | A08 |
| PubChem | |
| Chemical data | |
| Formula | C22H21Cl3N4O |
| Mol. mass | 463.79 g/mol |
| Pharmacokinetic data | |
| Bioavailability | Undetermined |
| Protein binding | Nearly 100% |
| Metabolism | Hepatic, CYP3A4 involved |
| Half life | Variable: 6 to 9 days with normal BMI 16 days if BMI >30 |
| Excretion | Fecal (86%) and renal (3%) |
| Therapeutic considerations | |
| Licence data |
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| Pregnancy cat. |
Not assigned. Use not recommended |
| Legal status | |
| Routes | Oral |
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WikiDoc Resources for Rimonabant | |
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Most recent articles on Rimonabant | |
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Evidence Based Medicine | |
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Clinical Trials | |
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Ongoing Trials on Rimonabant at Clinical Trials.gov Clinical Trials on Rimonabant at Google
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US National Guidelines Clearinghouse on Rimonabant
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Patient resources on Rimonabant Discussion groups on Rimonabant Patient Handouts on Rimonabant Directions to Hospitals Treating Rimonabant Risk calculators and risk factors for Rimonabant
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Causes & Risk Factors for Rimonabant | |
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Overview
Rimonabant (also known as SR141716, Acomplia, Riobant, Slimona, Rimoslim, and Zimulti)[1] is an anorectic anti-obesity drug. It is a CB1 cannabinoid receptor antagonist. Its main avenue of effect is reduction in appetite.
Rimonabant is the first selective CB1 receptor blocker to be approved for use anywhere in the world. In Europe, it is indicated for use in conjunction with diet and exercise for patients with a body mass index greater than 30 kg/m², or patients wih a BMI greater than 27 kg/m² with associated risk factors, such as type 2 diabetes or dyslipidaemia. In the UK, it has been available since the end of July 2006. As of 2007, the drug was available in 38 countries.
Approval
Despite the FDA issuing an approvable letter in February 2006 for the obesity indication and a non-approvable letter for smoking cessation, the drug did not enter the market in the United States in 2006. The French pharma firm Sanofi-Aventis disclosed that a complete response to the FDA's approvable letter was submitted on October 26, 2006, triggering a Class I (two-month) or Class II (six-month) review process. On June 13, 2007, FDA's Endocrine and Metabolic Drugs Advisory Committee (EMDAC) concluded that the French manufacturer Sanofi-Aventis failed to demonstrate the safety of rimonabant and voted against recommending the anti-obesity treatment for approval.[1] Subsequently, Sanofi-Aventis announced that it was withdrawing the new drug application (NDA) for rimonabant and that it would resubmit an application at some point in the future.
On 21 June 2006, the European Commission approved the sale of rimonabant in the then 25-member European Union. Sanofi announced that the first country in which Acomplia will be sold is the United Kingdom. Sales began in July 2006. Sanofi also announced that it projects that the drug will be sold shortly thereafter in Denmark, Ireland, Germany, Finland and Norway. It is expected in Belgium[1] and Sweden in 2007. Ordinary obesity will, according to official medical recommendations, not be enough to acquire the prescription in Sweden; there are additional requirements concerning abnormal blood lipid levels.[1]
The EU's approval was not a blanket approval, nor did it approve Acomplia for non-obesity related problems such as smoking cessation, although off-label use of the drug is still possible. The approval is in combination with diet and exercise for the treatment of obese patients (BMI greater than or equal to 30), or overweight patients (BMI greater than 27) with associated risk factors, such as type 2 diabetes or dyslipidaemia.
Side effects
Shortly after market introduction, press reports and independent studies suggest that side effects occur stronger and more commonly than shown by the manufacturer in their clinical studies. Reports of severe depression are frequent. This is deemed to result from the drug being active in the central nervous system, an area of human physiology so complex that drug effects are highly difficult to determine reliably.[1]
Because the drug has the opposite effects of cannabinoid receptor agonists such as tetrahydrocannabinol, which is neuroprotective against excitotoxicity,[1] it can be theorized that Rimonabant promotes the development of neurodegenerative diseases of the central nervous system such as Multiple sclerosis, Alzheimer's disease, Amyotrophic lateral sclerosis (ALS), Parkinson's disease, and Huntington's disease in persons who are susceptible.[1] The reported development of previously clinically silent multiple sclerosis in one patient taking Rimonabant suggests that any patients with an underlying neurological condition should not take Rimonabant, given the neuroprotective role of the endocannabinoid system in many experimental paradigms of neurological disease.
On 15 June 2007 the BBC News reported [1] that a committee advising the US FDA has voted not to recommend the drug's approval because of concerns over suicidality, depression and other related side effects associated with use of the drug.
Smoking cessation
Rimonabant may also be found to be effective in assisting some smokers to quit smoking. Sanofi-Aventis is currently conducting studies to determine the possible value of rimonabant in smoking-cessation therapy. The Studies with Rimonabant and Tobacco Use (STRATUS) Program involves more than 6,000 subjects. STRATUS is designed to explore two smoking-related therapies: first, to use rimonabant directly to aid in smoking cessation; second, to help prevent weight gain in former smokers. Initial results apparently suggest that rimonabant is effective for both uses. However, the FDA has explicitly stated to Sanofi-Aventis that without additional studies rimonabant cannot be approved in the United States for smoking cessation therapy. According to Cochrane review in 2007 Rimonabant "may increase the odds of quitting approximately 1(1/2)-fold"[1].
Addiction
Rimonabant reduced resumption of cocaine-seeking responses triggered by two of the three most common triggers of relapse in humans, priming and cues. It may also reduce ethanol and opiate seeking behavior[1].
Memory
Tetrahydrocannabinol is known to impair short-term memory. It was therefore hypothesised that Rimonabant may improve short-term memory. Indeed in animal studies it significantly improved the performance of rats to encode information in the short-term memory[1].
Blockade of Cannabis effects
Rimobants blocks the psychoactive and some of the cardiovascular effects of Δ9-Tetrahydrocannabinol in humans without affecting the pharmacokinetics[1].
References
Antiobesity preparations (A08) | |
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| Centrally acting | Phentermine - Fenfluramine - Amfepramone - Dexfenfluramine - Mazindol - Cathine - Clobenzorex - Sibutramine - Rimonabant - Taranabant |
| Peripherally acting | Orlistat |
WikiDoc Research Resources for Rimonabant | |
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| Articles on Rimonabant | Most recent articles on Rimonabant • Most cited articles on Rimonabant • Review articles on Rimonabant • Articles on Rimonabant in N Eng J Med, Lancet, BMJ |
| Media (Slides, Video, Images, MP3) on Rimonabant | Powerpoint slides on Rimonabant • Images of Rimonabant • Photos of Rimonabant • Podcasts & MP3s on Rimonabant • Videos on Rimonabant |
| Evidence Based Medicine Regarding Rimonabant | Cochrane Collaboration on Rimonabant • Bandolier on Rimonabant • TRIP on Rimonabant |
| Cost Effectiveness of Rimonabant | Cost Effectiveness of Rimonabant |
| Clinical Trials Involving Rimonabant | Ongoing Trials on Rimonabant at Clinical Trials.gov • Trial results on Rimonabant • Clinical Trials on Rimonabant at Google |
| Guidelines / Policies / Government Resources (FDA/CDC) Regarding Rimonabant | US National Guidelines Clearinghouse on Rimonabant • NICE Guidance on Rimonabant • NHS PRODIGY Guidance • FDA on Rimonabant • CDC on Rimonabant |
| Textbook Information on Rimonabant | Books and Textbook Information on Rimonabant |
| Pharmacology Resources on Rimonabant | Dosing of Rimonabant • Drug interactions with Rimonabant • Side effects of Rimonabant • Allergic reactions to Rimonabant • Overdose information on Rimonabant • Carcinogenicity information on Rimonabant • Rimonabant in pregnancy • Pharmacokinetics of Rimonabant • |
| Genetics, Pharmacogenomics, and Proteinomics of Rimonabant | Genetics of Rimonabant • Pharmacogenomics of Rimonabant • Proteomics of Rimonabant |
| Newstories on Rimonabant | Rimonabant in the news • Be alerted to news on Rimonabant • News trends on Rimonabant |
| Commentary on Rimonabant | Blogs on Rimonabant |
| Patient Resources on Rimonabant | Patient resources on Rimonabant • Discussion groups on Rimonabant • Patient Handouts on Rimonabant • Directions to Hospitals Treating Rimonabant • Risk calculators and risk factors for Rimonabant |
| Healthcare Provider Resources on Rimonabant | Symptoms of Rimonabant • Causes & Risk Factors for Rimonabant • Diagnostic studies for Rimonabant • Treatment of Rimonabant |
| Continuing Medical Education (CME) Programs on Rimonabant | CME Programs on Rimonabant |
| International Resources on Rimonabant | Rimonabant en Espanol • Rimonabant en Francais |
| Business Resources on Rimonabant | Rimonabant in the Marketplace • Patents on Rimonabant |
| Informatics Resources on Rimonabant | List of terms related to Rimonabant |
de:Rimonabant fr:Rimonabant he:רימונבאנט nl:Rimonabantfi:Rimonabantti
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Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
