Rimonabant free base
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MedKoo CAT#: 329640

CAS#: 158681-13-1 (HCl)

Description: Rimonabant, also known as SR141716 and A 281, is an anorectic anti-obesity drug. 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.


Price and Availability

Size Price Shipping out time Quantity
100mg USD 450 2 Weeks
200mg USD 750 2 Weeks
500mg USD 1450 2 Weeks
1g USD 1950 2 Weeks
2g USD 2950 2 Weeks
5g USD 4650 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-27. Prices are subject to change without notice.

Rimonabant free base, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 329640
Name: Rimonabant free base
CAS#: 158681-13-1 (HCl)
Chemical Formula: C22H21Cl3N4O
Exact Mass: 462.0781
Molecular Weight: 463.787
Elemental Analysis: C, 56.97; H, 4.56; Cl, 22.93; N, 12.08; O, 3.45


Related CAS #: 168273-06-1 (free base)   158681-13-1 (HCl)  

Synonym: Rimonabant free base, SR141716; SR 141716; SR-141716; A 281; A-281; A281; Rimonabant, Acomplia, Zimulti

IUPAC/Chemical Name: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide

InChi Key: JZCPYUJPEARBJL-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)

SMILES Code: O=C(C1=NN(C2=CC=C(Cl)C=C2Cl)C(C3=CC=C(Cl)C=C3)=C1C)NN4CCCCC4


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Zádor F, Lénárt N, Csibrány B, Sántha M, Molnár M, Tuka B, Samavati R, Klivényi P, Vécsei L, Marton A, Vizler C, Nagy GM, Borsodi A, Benyhe S, Páldy E. Low dosage of rimonabant leads to anxiolytic-like behavior via inhibiting expression levels and G-protein activity of kappa opioid receptors in a cannabinoid receptor independent manner. Neuropharmacology. 2015 Feb;89:298-307. PubMed PMID: 25446673.

2: Dai E, Zhang J, Zhang D, Yang L, Wang Y, Jiang X, Ye L, Li X, Liu H, Ma J, Jiang H. Rimonabant inhibits proliferation, collagen secretion and induces apoptosis in hepatic stellate cells. Hepatogastroenterology. 2014 Oct;61(135):2052-61. PubMed PMID: 25713910.

3: Wang X, Yu Q, Yue H, Zeng S, Cui F. Effect of Intermittent Hypoxia and Rimonabant on Glucose Metabolism in Rats: Involvement of Expression of GLUT4 in Skeletal Muscle. Med Sci Monit. 2015 Oct 27;21:3252-60. PubMed PMID: 26503060; PubMed Central PMCID: PMC4629628.

4: Marinho EA, Oliveira-Lima AJ, Santos R, Hollais AW, Baldaia MA, Wuo-Silva R, Yokoyama TS, Takatsu-Coleman AL, Patti CL, Longo BM, Berro LF, Frussa-Filho R. Effects of rimonabant on the development of single dose-induced behavioral sensitization to ethanol, morphine and cocaine in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Apr 3;58:22-31. doi: 10.1016/j.pnpbp.2014.11.010. Epub 2014 Dec 10. PubMed PMID: 25496830.

5: Jorgačević B, Mladenović D, Ninković M, Vesković M, Dragutinović V, Vatazević A, Vučević D, Ješić Vukićević R, Radosavljević T. Rimonabant Improves Oxidative/Nitrosative Stress in Mice with Nonalcoholic Fatty Liver Disease. Oxid Med Cell Longev. 2015;2015:842108. doi: 10.1155/2015/842108. Epub 2015 May 11. PubMed PMID: 26078820; PubMed Central PMCID: PMC4442287.

6: Zádor F, Kocsis D, Borsodi A, Benyhe S. Micromolar concentrations of rimonabant directly inhibits delta opioid receptor specific ligand binding and agonist-induced G-protein activity. Neurochem Int. 2014 Feb;67:14-22. doi: 10.1016/j.neuint.2013.12.005. Epub 2014 Feb 4. PubMed PMID: 24508403.

7: Thorsell A, Isin EM, Jurva U. Use of electrochemical oxidation and model peptides to study nucleophilic biological targets of reactive metabolites: the case of rimonabant. Chem Res Toxicol. 2014 Oct 20;27(10):1808-20. doi: 10.1021/tx500255r. Epub 2014 Sep 26. PubMed PMID: 25210840.

8: Pataky Z, Gasteyger C, Ziegler O, Rissanen A, Hanotin C, Golay A. Efficacy of rimonabant in obese patients with binge eating disorder. Exp Clin Endocrinol Diabetes. 2013 Jan;121(1):20-6. doi: 10.1055/s-0032-1329957. Epub 2012 Nov 12. PubMed PMID: 23147209.

9: Hu SS. Involvement of TRPV1 in the Olfactory Bulb in Rimonabant-Induced Olfactory Discrimination Deficit. Chin J Physiol. 2016 Feb 29;59(1):21-32. doi: 10.4077/CJP.2016.BAE366. PubMed PMID: 26875559.

10: Bergamaschi MM, Queiroz RH, Chagas MH, Linares IM, Arrais KC, de Oliveira DC, Queiroz ME, Nardi AE, Huestis MA, Hallak JE, Zuardi AW, Moreira FA, Crippa JA. Rimonabant effects on anxiety induced by simulated public speaking in healthy humans: a preliminary report. Hum Psychopharmacol. 2014 Jan;29(1):94-9. doi: 10.1002/hup.2374. Epub 2013 Dec 3. PubMed PMID: 24424711; PubMed Central PMCID: PMC4539121.

11: Johnson A, Neumann PH, Peng J, James J, Russo V, MacDonald H, Gertzberg N, Feleder C. The intracerebroventricular injection of rimonabant inhibits systemic lipopolysaccharide-induced lung inflammation. J Neuroimmunol. 2015 Sep 15;286:16-24. doi: 10.1016/j.jneuroim.2015.07.001. Epub 2015 Jul 6. PubMed PMID: 26298320; PubMed Central PMCID: PMC4548270.

12: Buckley JL, Rasmussen EB. Rimonabant's reductive effects on high densities of food reinforcement, but not palatability, in lean and obese Zucker rats. Psychopharmacology (Berl). 2014 May;231(10):2159-70. doi: 10.1007/s00213-013-3366-4. Epub 2014 Jan 8. PubMed PMID: 24398820; PubMed Central PMCID: PMC4036064.

13: Jergas B, Schulte K, Bindila L, Lutz B, Schlicker E. O-2050 facilitates noradrenaline release and increases the CB1 receptor inverse agonistic effect of rimonabant in the guinea pig hippocampus. Naunyn Schmiedebergs Arch Pharmacol. 2014 Jul;387(7):621-8. doi: 10.1007/s00210-014-0991-3. Epub 2014 May 23. PubMed PMID: 24853577.

14: Foster AJ, Prime LH, Gustafsson F, Temesi DG, Isin EM, Midlöv J, Castagnoli N Jr, Kenna JG. Bioactivation of the cannabinoid receptor antagonist rimonabant to a cytotoxic iminium ion metabolite. Chem Res Toxicol. 2013 Jan 18;26(1):124-35. doi: 10.1021/tx300418w. Epub 2012 Dec 12. PubMed PMID: 23234359.

15: Blasio A, Iemolo A, Sabino V, Petrosino S, Steardo L, Rice KC, Orlando P, Iannotti FA, Di Marzo V, Zorrilla EP, Cottone P. Rimonabant precipitates anxiety in rats withdrawn from palatable food: role of the central amygdala. Neuropsychopharmacology. 2013 Nov;38(12):2498-507. doi: 10.1038/npp.2013.153. Epub 2013 Jun 24. PubMed PMID: 23793355; PubMed Central PMCID: PMC3799070.

16: Jin SM, Oh BJ, Lee S, Choi JM, Yang SJ, Park SW, Kim KW, Kim JH, Park CY. Reduced food intake is the major contributor to the protective effect of rimonabant on islet in established obesity-associated type 2 diabetes. Yonsei Med J. 2013 Sep;54(5):1127-36. doi: 10.3349/ymj.2013.54.5.1127. PubMed PMID: 23918561; PubMed Central PMCID: PMC3743202.

17: Boomhower SR, Rasmussen EB. Haloperidol and rimonabant increase delay discounting in rats fed high-fat and standard-chow diets. Behav Pharmacol. 2014 Dec;25(8):705-16. doi: 10.1097/FBP.0000000000000058. PubMed PMID: 25000488; PubMed Central PMCID: PMC4772744.

18: Blasio A, Rice KC, Sabino V, Cottone P. Characterization of a shortened model of diet alternation in female rats: effects of the CB1 receptor antagonist rimonabant on food intake and anxiety-like behavior. Behav Pharmacol. 2014 Oct;25(7):609-17. doi: 10.1097/FBP.0000000000000059. PubMed PMID: 25011007; PubMed Central PMCID: PMC4149852.

19: Wright FL, Rodgers RJ. Low dose naloxone attenuates the pruritic but not anorectic response to rimonabant in male rats. Psychopharmacology (Berl). 2013 Mar;226(2):415-31. doi: 10.1007/s00213-012-2916-5. Epub 2012 Nov 10. PubMed PMID: 23142959.

20: Literati-Nagy Z, Tory K, Literáti-Nagy B, Bajza A, Vígh L Jr, Vígh L, Mandl J, Szilvássy Z. Synergic insulin sensitizing effect of rimonabant and BGP-15 in Zucker-obese rats. Pathol Oncol Res. 2013 Jul;19(3):571-5. doi: 10.1007/s12253-013-9620-6. Epub 2013 May 3. PubMed PMID: 23640247.