chemistry

Rimonabant

Rimonabant is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Rimonabant rather than just read about it. In short: 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known as SR141716; trade names Acomplia, Zimulti) is an anorectic antiobesity drug approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious neurological and psychiatric side effects; it was never approved in the United States.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.

Key takeaways

Rimonabant belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Rimonabant to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Rimonabant from memory before moving on to harder problems.

Reference excerpt

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known as SR141716; trade names Acomplia, Zimulti) is an anorectic antiobesity drug approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious neurological and psychiatric side effects; it was never approved in the United States.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

Rimonabant was discovered and developed by Sanofi-Aventis. On 21 June 2006, the European Commission approved the sale of rimonabant in the then-25-member European Union as a prescription drug for use in conjunction with diet and exercise for patients with a body mass index (BMI) greater than 30 kg/m2, or patients with a BMI greater than 27 kg/m2 with associated risk factors, such as type 2 diabetes or dyslipidaemia. It was first in its class to be approved anywhere in the world. Rimonabant was submitted to the Food and Drug Administration (FDA) for approval in the United States in 2005; in 2007, the FDA's Endocrine and Metabolic Drugs Advisory Committee (EMDAC) concluded that Sanofi-Aventis failed to demonstrate the safety of rimonabant and voted against recommending the anti-obesity treatment for approval. The application was deemed not-approvable by FDA, and the company cancelled plans for a re-submission. The drug was approved in Brazil in April 2007. In October 2008, the European Medicines Agency recommended the suspension of Acomplia after the Committee for Medicinal Products for Human Use (CHMP) had determined that the risks of Acomplia outweighed its benefits due to the risk of serious psychiatric problems, including suicide. In November 2008 an advisory committee in Brazil recommended suspension as well, and that month Sanofi-Aventis suspended sale of the drug worldwide. The EMA approval was withdrawn in January 2009. In 2009 India prohibited the manufacture and sale of the drug.

Adverse effects Data from clinical trials submitted to regulatory authorities showed that rimonabant caused depressive disorders or mood alterations in up to 10% of subjects and suicidal ideation in around 1%, and in Europe it was contraindicated for people with any psychiatric disorder, including clinical depression. Data from a large, randomized, clinical trial (CRESCENDO) with > 9,000 patients receiving rimonabant treatment demonstrated a rate of psychiatric adverse events (anxiety, depression, depressed mood, or insomnia) of greater than 30%. Additionally, nausea and upper respiratory tract infections were very common adverse effects (occurring in more than 10% of people); common adverse effects (occurring in between 1% and 10% of people) included gastroenteritis, anxiety, irritability, insomnia and other sleep disorders, hot flushes, diarrhea, vomiting, dry or itchy skin, tendonitis, muscle cramps and spasms, fatigue, flu-like symptoms, and increased risk of falling. The FDA's advisory committee concurred with concerns raised by the review divisions. Based on human and on animal data, it appeared that the therapeutic window was narrow. EMA postmarketing surveillance data suggested that the risk of psychiatric disorders in people taking rimonabant was doubled.

Pharmacology Rimonabant is an inverse agonist of the cannabinoid CB1 receptor. Originally thought to be selective for the CB1 receptor, rimonabant was subsequently also found to act as an antagonist of the μ-opioid receptor. These properties may make this drug useful in cases of cannabinoid or opioid overdose but more research and safety testing is required.

Chemistry The chemical synthesis of rimonabant is described as follows:

Research Along with the clinical trials in obesity that generated the data submitted to regulatory authorities, rimonabant was also studied in clinical trials for diabetes, atherosclerosis, and smoking cessation.

See also Drinabant – a cannabinoid receptor antagonist developed for prescription drug use that also triggered severe psychiatric side effects.

References

Illustrations

Worked examples

Example 1 — a first encounter with Rimonabant

Start with the simplest possible case. Write down what Rimonabant claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Rimonabant before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Rimonabant ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Rimonabant

In research: Rimonabant appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Rimonabant in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Rimonabant is common in secondary-school and first-year university syllabi. It links to neighbouring topics 1-Piperidinyl compounds, 4-Chlorophenyl compounds, Anorectics, so understanding it makes those chapters shorter.
In everyday life: Look for Rimonabant outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Rimonabant in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Rimonabant means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Rimonabant out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Rimonabant in simple terms?

Why does Rimonabant matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Rimonabant?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Rimonabant.