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Rimonabant

Description References
Product Name
Rimonabant
CAS No.
168273-06-1
Chemical Name
Rimonabant
Synonyms
A 281;xibuqum;ACOMPLIA;Sr 141716;rimobrant;Rimonaban;RIMONABANT;Limonabant;Unii-rml78en3xe;Rimonabant base
CBNumber
CB4129374
Molecular Formula
C22H21Cl3N4O
Formula Weight
463.79
MOL File
168273-06-1.mol
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Rimonabant Property

Melting point:
154.7 °C
Density 
1.41±0.1 g/cm3(Predicted)
storage temp. 
RT
solubility 
Soluble in DMSO (up to 20 mg/ml) or in Ethanol (up to 20 mg/ml).
pka
11.31±0.20(Predicted)
form 
solid
color 
White
Stability:
Stable for 1 year from date of purchase as supplied. Protect from moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
CAS DataBase Reference
168273-06-1(CAS DataBase Reference)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H372Causes damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P314Get medical advice/attention if you feel unwell.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
9000484
Product name
Rimonabant
Purity
≥98%
Packaging
5mg
Price
$46
Updated
2024/03/01
Cayman Chemical
Product number
9000484
Product name
Rimonabant
Purity
≥98%
Packaging
10mg
Price
$61
Updated
2024/03/01
Cayman Chemical
Product number
9000484
Product name
Rimonabant
Purity
≥98%
Packaging
25mg
Price
$138
Updated
2024/03/01
Cayman Chemical
Product number
9000484
Product name
Rimonabant
Purity
≥98%
Packaging
50mg
Price
$230
Updated
2024/03/01
ApexBio Technology
Product number
B1429
Product name
Rimonabant
Packaging
10mM(in 1mL DMSO)
Price
$55
Updated
2021/12/16
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Rimonabant Chemical Properties,Usage,Production

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 associated risk factors in Europe in 2006. Nevertheless, adverse effects including suicidality, depression, and anxiety were reported, based on which rimonadant was withdrawn worldwide in 2008.
Andogenous cannabinoids are related to the pleasurable effect of nicotine, rimonabant, as a cannabinoid receptor blocker, is also being tested as a potential anti-smoking treatment.

References

[1] https://www.drugs.com/acomplia.html
[2] Leite CE, Mocelin CA, Petersen GO, Leal MB, Thiesen FV (2009) Rimonabant: an antagonist drug of the endocannabinoid system for the treatment of obesity, Pharmacol Rep., 61, 217-224

Description

Rimonabant is a first-in-class drug launched as an oral treatment for obesity, and its mechanism of action involves the selective antagonism of cannabinoid type 1 (CB1) receptor. It is specifically indicated as an adjunct to diet and exercise for the treatment of obese patients (body mass index [BMI]≥30 kg/m2), or overweight patients (BMI＞27 kg/m2) with associated risk factors such as type 2 diabetes or dyslipidemia. Additionally, rimonabant is currently under development as a treatment for nicotine dependence. The CB1 and CB2 receptors, along with their endogenous ligands, constitute the endocannabinoid system. The CB1 receptor is expressed in the brain, adipose tissue, and several peripheral organs; the CB2 receptor is predominantly expressed in immune cells. Activation of the CB1 receptor in the CNS is associated with appetite stimulation and the modulation of brain reward mechanism, whereas activation in the periphery favors metabolic processes that lead to hepatic lipogenesis and impaired glucose homeostasis. Rimonabant acts by selectively blocking the action of central and peripheral CB1 receptors, thereby reducing food intake and improving lipid and glucose metabolism.

Originator

Sanofi-Synthelabo (France)

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

Definition

ChEBI: 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.

brand name

Acomplia (Sanofi-Synthe-labo).

Synthesis

The reported preparation of rimonabant, both in small and large scale, is shown in the scheme. Lithium enolate formation of p-chlorophenyl ethyl ketone 54 with LiHMDS in THF at -78oC for 45 min followed by reaction with diethyl oxalate at -78oC and warming to room temperature over 16 h provided the lithium enolate salt of the diketoester 55. Reaction of diketoester salt 55 with 2,4-dichlorophenyl hydrazine (56) in ethanol at room temperature gave intermediate hydrazone 57 which is then cyclized in refluxing acetic acid for 24 h to obtain pyrazole ester 58. Hydrolysis of ester 58 with KOH in refluxing methanol:water mixture gave acid 59 which was then converted to the acid chloride 60 with thionyl chloride in refluxing toluene in very good yield. On scale, the synthesis of the acid chloride was performed in cyclohexane at 83oC. Reaction of acid chloride 60 with 1-aminopiperidine (61) in the presence of triethylamine at 0oC to room temperature over 3h gave rimonabant (VIII) which was isolated as the HCl salt by treating it with HCl in ether.

References

1) Rinaldi-Carmona et al. (1994) SR141716A, a potent and selective antagonist of the brain cannabinoid receptor; FEBS Lett. 350 240 2) Rinaldi-Carmona et al. (1995) Biochemical and pharmacological characterization of SR141716A, the first potent and selective cannabinoid receptor antagonist; Life Sci. 56 1941

Rimonabant Preparation Products And Raw materials

Raw materials

Preparation Products

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Rimonabant Suppliers

China 223 Europe 2 Germany 1 India 3 Japan 1 The Netherlands 1 United Kingdom 8 United States 31 Global 270
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View Lastest Price from Rimonabant manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Rimonabant 168273-06-1
Price
US $99.00-66.00/kg
Min. Order
0.0010000000474974513kg
Purity
99%
Supply Ability
5000
Release date
2024-09-18
Hebei Weibang Biotechnology Co., Ltd
Product
Rimonabant 168273-06-1
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10 mt
Release date
2024-11-11
Hong Kong Excellence Biotechnology Co., Ltd.
Product
Rimonabant 168273-06-1
Price
US $100.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
20tons
Release date
2023-10-12

168273-06-1, RimonabantRelated Search:

Phenylphosphonic dichloride Dichloromethylphenylsilane N,N-Dimethylformamide Thiophanate-methyl Chlorantraniliprole Methyl salicylate Bensulfuron methyl Methylparaben Kresoxim-methyl Benzamide METSULFURON METHYL Formamide Methyl Methyl bromide Parathion-methyl RIMONABANT CARBOXYLIC ACID RIMONABANT HYDROCHLORIDE,ACOMPLIA (RIMONABANT,RIMONABANT HCL,Rimonabant(Acomplia) Rimonabant 75000

  • ACOMPLIA
  • RIMONABANT
  • RIMONABANT(ACOMPLIA,SR141716)
  • 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidinopyrazole-3-carboxamide
  • xibuqum
  • 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
  • A 281
  • Sr 141716
  • Unii-rml78en3xe
  • Rimonabant base ,99%
  • N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-Methyl-1H-pyrazole-3-carboxyaMide
  • RiMonabant (SR141716)
  • N-piperidino-5-(4-chlorophenyl)-1(2,4-dichlorophenyl)-4-Methyl-pyrazole-3-carboxaMide
  • N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride Rimonabant(SR141716A) 158681-13-1 (HCl CAS)
  • Rimonabant base
  • 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamid
  • Limonabant
  • Rimonabant Powder
  • rimobrant
  • RimonabantQ: What is Rimonabant Q: What is the CAS Number of Rimonabant Q: What is the storage condition of Rimonabant Q: What are the applications of Rimonabant
  • Rimonaban
  • Rimonabant in methanol
  • 168273-06-1
  • C22Cl3HN4O
  • C22H21Cl3N4O
  • SR141716
  • Weight Loss