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Rimonabant

Rimonabant structure

CAS No:
168273-06-1
Formula:
C22H21Cl3N4O
Chemical Name:
Rimonabant
Synonyms:
1H-Pyrazole-3-carboxamide,5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide;SR 141716;Rimonabant;Acomplia;A 281;N-Piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide;1-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid N-(piperidin-1-yl)amide;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide;SR 141617;Zimulti;ENP 9;948565-21-7
Categories:
Biochemical Engineering > Inhibitors

Description

Rimonabant is an inverse antagonist for the cannabinoid receptor (CB1). It acts by selectively blocking CB1 receptors found in the brain and in peripheral organs important in glucose and lipid metabolism, including adipose tissue, the liver, gastrointestinal tract, and muscle. Thus, rimonabant constitutes a therapeutic approach to obesity and cardiovascular risk factors. As an anorectic antiobesity drug, it was used as an adjunct to diet and exercise for obese or overweight patients with associ

Solid

Rimonabant is a carbohydrazide obtained by formal condensation of the carboxy group of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. It is a potent and selective cannabinoid receptor 1 (CB1R) antagonist. Besides its antagonistic properties, numerous studies have shown that, at micromolar concentrations rimonabant behaves as an inverse agonist at CB1 receptors. The drug was the first selective CB1 antagonist/inverse agonist introduced into clinical practice to treat obesity and metabolic-related disorders. It was later withdrawn from market due to CNS-related adverse effects including depression and suicidal ideation. It has a role as an anti-obesity agent, a CB1 receptor antagonist and an appetite depressant. It is a member of pyrazoles, a dichlorobenzene, a carbohydrazide, an amidopiperidine and a member of monochlorobenzenes.|Rimonabant is an anorectic anti-obesity drug produced and marketed by Sanofi-Aventis. It is an inverse agonist for the cannabinoid receptor CB1. 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. Rimonabant is approved in 38 countries including the E.U., Mexico, and Brazil. It was rejected for approval for use in the United States. This decision was made after a U.S. advisory panel recommended the medicine not be approved because it may increase suicidal thinking and depression.|A pyrazole and piperidine derivative that acts as a selective cannabinoid type-1 receptor (CB1 RECEPTOR) antagonist. It inhibits the proliferation and maturation of ADIPOCYTES, improves lipid and glucose metabolism, and regulates food intake and energy balance. It is used in the management of OBESITY.

Rimonabant Basic Attributes

Molecular Weight：

463.79

Exact Mass：

463.79

UNII：

RML78EN3XE

DSSTox ID：

DTXSID3046453

ATC Code：

A08AX01|A - Alimentary tract and metabolism

HScode：

2933990090

Characteristics

PSA：

50.2

XLogP3：

6.01

Appearance：

White or almost white crystalline powder

Density：

1.41±0.1 g/cm3(Predicted)

Melting Point：

154.7 °C

Boiling Point：

627.6ºC at 760 mmHg

Flash Point：

333.3ºC

Refractive Index：

1.668

Water Solubility：

2.00e-03 g/L

Safety Information

Precautionary statement(s)：

P260, P264, P270, P273, P314, P391, P501

Hazard Statements：

H372

Toxicity

Toxicity Summary：

Almost twice as many people discontinued rimonabant compared with placebo because of adverse events (13.8% vs. 7.2%). These consistently involved psychiatric disorders (8.5% vs. 3.2%), including depression and anxiety. Other common side effects included insomnia, nausea, vomiting, diarrhoea and fatigue.

Protein Binding：

Almost 100%

Drug Information

Drug Indication：

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.|As an adjunct to diet and exercise for the treatment of obese patients (BMI 30 kg/m2), or overweight patients (BMI 27 kg/m2) with associated risk factor(s), such as type 2 diabetes or dyslipidaemia (see section 5.1).

Pharmacology：

In the RIO-North America trial, 3040 patients were randomized to receive either placebo or one of two doses of rimonabant (5 mg or 20 mg per day). Patients taking 20 mg rimonabant had significant weigh loss, decrease in waist circumference, improved insulin sensitivity, and increases in HDL cholesterol, compared to patients on placebo.

MeSH：

Agents that increase energy expenditure and weight loss by neural and metabolic regulation. (See all compounds classified as Anti-Obesity Agents.)|Compounds that inhibit or block the activity of CANNABINOID RECEPTORS. (See all compounds classified as Cannabinoid Receptor Antagonists.)

Absorption：

Undetermined

Metabolism/Metabolites：

Hepatic, CYP3A4 involved.

Biological Half-Life：

6 to 9 days with normal BMI and 16 days if BMI is greater than 30

Mechanism of Action：

Rimonabant is a specific CB1 cannabinoid receptor antagonist. There is considerable evidence that the endocannabinoid (endogenous cannabinoid) system plays a significant role in appetitive drive and associated behaviours. It is therefore reasonable to hypothesize that the attenuation of the activity of this system would have therapeutic benefit in treating disorders that might have a component of excess appetitive drive or over-activity of the endocannabinoid system, such as obesity, ethanol and other drug abuse, and a variety of central nervous system and other disorders.

MeSH Entry Terms：

acomplia

Rimonabant Use and Manufacturing

Uses

Rimonabant is a selective antagonist of CB1 with IC50 of 13.6 nM and EC50 of 17.3 nM in hCB1 transfected HEK 293 membrane

Use Classification：

Human drugs -> Zimulti -> EMA Drug Category|Antiobesity preparations, excl. diet products -> Human pharmacotherapeutic group|Human drugs -> Acomplia -> EMA Drug Category

Computed Properties

Molecular Weight:463.8
XLogP3:6.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:462.078094
Monoisotopic Mass:462.078094
Topological Polar Surface Area:50.2
Heavy Atom Count:30
Complexity:583
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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