RimonabantCAS: 168273-06-1
MF: C22H21Cl3N4O
MW: 463.79
An immunomodulatory CB1 receptor inverse agonist.

Rimonabant (CAS 168273-06-1)

Rimonabant | CAS 168273-06-1 is rated 5.0 out of 5 by 1.
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Synonym: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidino-1H-pyrazole-3-carboxamide
Application: An immunomodulatory CB1 receptor inverse agonist
CAS Number: 168273-06-1
Purity: ≥98%
Molecular Weight: 463.79
Molecular Formula: C22H21Cl3N4O
* Refer to Certificate of Analysis for lot specific data (including water content).
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Rimonabant, also known as SR141716, was the first selective CB1 (cannabinoid 1) central receptor inverse agonist (Ki = 1.8 nM). 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. 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. 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.


References

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. Pharmacologiacal Reports 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. Brit J Pharmacol 153 1003-1010 (2009).

Physical State :
Solid
Solubility :
Soluble in ethanol (~20 mg/ml), DMSO (25 mg/ml), DMF (~20 mg/ml), and water (<1 mg/ml).
Storage :
Store at -20° C
Melting Point :
272.25° C (Predicted)
Boiling Point :
627.69° C (Predicted)
Refractive Index :
n20D 1.67 (Predicted)
IC50 :
CB1: IC50 = 1.35 nM; CB2: IC50 = 1.9 nM; hCB1: IC50 = 13.6 nM; hCB2: IC50 = 1.64 µM
Ki Data :
CB1: Ki= 0.19 nM (human); Rattus norvegicus: Ki= 1.1 nM; CB1: Ki= 6 nM (rat)
pK Values :
pKa: 11.31 (Predicted), pKb: 3.22 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
104850
MDL Number :
MFCD04034714
SMILES :
CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl

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Certificate of Analysis

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Rimonabant  Product Citations

See how others have used Rimonabant. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 11 total

PMID: # 30842372  Kakutani, N.|Nanayama, T.|Nomura, Y.| et al. 2019. J Toxicol Sci. 44: 201-211.

PMID: # 26365347  Wang, S. et al. 2015. Biochem. Biophys. Res. Commun. 466: 438-43.

PMID: # 20029379  Son, MH. et al. 2010. Int J Obes (Lond). 34: 547-556.

PMID: # 17223076  Yan, ZC. et al. 2007. Biochem. Biophys. Res. Commun. 354: 427-433.

PMID: # 17595161  Anavi-Goffer, S. et al. 2007. J. Biol. Chem. 282: 25100-25113.

PMID: # 17785353  Pagano, C. et al. 2007. J. Clin. Endocrinol. Metab. 92: 4810-4819.

PMID: # 16533866  Madsen, MV. et al. 2006. J. Psychopharmacol. (Oxford). 20: 622-628.

PMID: # 16144988  Wang, Y. et al. 2005. Hypertension. 46: 986-991.

PMID: # 16009704  Jbilo, O. et al. 2005. FASEB J. 19: 1567-1569.

PMID: # 10980277  Lichtman, AH. et al. 2000. Eur. J. Pharmacol. 404: 175-179.

Citations 1 to 10 of 11 total
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Rated 5 out of 5 by from Son Son, et. al. (PubMed ID 20029379) used SR141716A (code name for Rimonabant) as the benchmark to which various derivations were compared to in terms of potency. -SCBT Publication Review
Date published: 2015-03-19
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