Rimonabant

Rimonabant

Cayman Chemical Item Number 9000484

SR141716 (CAS 168273-06-1)

Rimonabant (CAS 168273-06-1)

Description

Rimonabant, also known as SR141716, was the first selective central cannabinoid (CB₁) receptor inverse agonist (K_i = 1.8 nM) to be developed as an appetite suppressant, anti-obesity drug.¹ It is widely used as a tool to investigate CB receptor properties and the mechanisms by which CB agonists exert their pharmacological effects. In rodent models and clinical trials, rimonabant effectively induces lipolysis, reduces hepatomegaly, decreases body weight, and improves dyslipidemia by reducing triglyceride, free fatty acid, and total cholesterol levels and by increasing HDL/LDL ratios.² However, rimonabant reportedly produces adverse psychiatric and neurological effects (e.g., depression or anxiety) and therefore is not approved by the FDA for use as a weight control medication.² Rimonabant elicits antiproliferative and immunomodulatory effects (e.g., cell cycle arrest, increased expression of IκB and phosphorylated Akt, and decreased expression of NF-κB, phosphorylated ERK1/2, COX-2, and iNOS) in vitro.³

1 Rinaldi-Carmona, M., Barth, F., Héaulme, M., et al. SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett 350 240-244 (1994).

2 Leite, C.E., Mocelin, C.A., Petersen, G.O., et al. Rimonabant: An antagonist drug of the endocannabinoid system for the treatment of obesity. Pharmacol Rep 61 217-224 (2009).

3 Malfitano, A.M., Laezza, C., Pisanti, S., et al. Rimonabant (SR141716) exerts anti-proliferative and immunomodulatory effects in human peripheral blood mononuclear cells. Br J Pharmacol 153 1003-1010 (2009).

Synonyms

SR141716

Formal Name

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide

CAS Number

168273-06-1

Molecular Formula

C₂₂H₂₁Cl₃N₄O

Formula Weight

463.8

Formulation

A crystalline solid

Purity

≥98%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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Clc1ccc(cc1)c1c(C)c(nn1c1ccc(Cl)cc1Cl)C(=O)NN1CCCCC1

Background Reading

Leite, C.E., Mocelin, C.A., Petersen, G.O., et al. Rimonabant: An antagonist drug of the endocannabinoid system for the treatment of obesity. Pharmacol Rep 61 217-224 (2009).

Rinaldi-Carmona, M., Barth, F., Héaulme, M., et al. SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett 350 240-244 (1994).

Malfitano, A.M., Laezza, C., Pisanti, S., et al. Rimonabant (SR141716) exerts anti-proliferative and immunomodulatory effects in human peripheral blood mononuclear cells. Br J Pharmacol 153 1003-1010 (2009).

Size

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