Rimonabant (SR141716)

Alias: SR141716; A 281; SR-141716; A-281; A281; SR 141716A;SR 141716; SR-141716;SR 151716A; SR-141716A; SR-151716A; SR141716A; SR151716A; Rimonabant; Acomplia; Zimulti

Cat No.:V1515 Purity: ≥98%

COA Product Data Instructions for use SDS

Rimonabant (SR141716) Chemical Structure CAS No.: 168273-06-1
Product category: Cannabinoid Receptor

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of Rimonabant (SR141716):

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Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Rimonabant (formerly known as SR-141716; A-281; A281; SR 141716A; Acomplia; Zimulti), an anorectic antiobesity drug once used in EU but withdrawn from market due to serious psychiatric side effects, is a novel, potent and selective antagonist (inverse agonist) of cannabinoid CB1 receptor. In hCB1 transfected HEK 293 membrane, it inhibits CB1 with an IC50 of 13.6 nM and an EC50 of 17.3 nM. Anorectic anti-obesity medications include rimonabant. The main result is a decrease in appetite. (Ki=1.8nM CB1, 514nM CB2) Rimonabant has demonstrated a 285-fold selectivity for CB1. For CB1-Rs, Rimonabant has a 50-fold higher affinity than for CB2-Rs, with a Ki value of 6.18nM. Furthermore, when used as a treatment on its own,rimonabant has been shown to alter ingestive behaviors.

Biological Activity I Assay Protocols (From Reference)

Targets

hCB1 ( Ki = 0.7 nM ); rCB1 ( Ki = 2.8 nM ); MmpL3; ACAT2; ACAT1

ln Vitro

In vitro activity: Rimonabant has a dose-dependent reduction in ACAT activity in isolated peritoneal macrophages and Raw264.7 macrophages with an IC50 of 2.9 μM. With an IC50 of 1.5 μM for CHO-ACAT1 and 2.2 μM for CHO-ACAT2, respectively, rimonabant approximately equally inhibits ACATactivity in both intact CHO-ACAT1 and CHO-ACAT2 cells as well as in cell-free assays. Oxysterol-induced apoptosis and foam cell formation in macrophages are two ACAT-dependent processes that are blocked by rimonabant treatment, which is consistent with ACAT inhibition. Adenylyl cyclase activity in rat brain membranes and mouse vas deferens contractions are both inhibited by cannabinoid receptor agonists; however, rimonabant counteracts these effects in a concentration-dependent way. [3] In human colorectal cancer cells (DLD-1, CaCo-2, and SW620), rimonabant induces cell death and significantly reduces cell growth. In every cell line tested, rimonabant can change the distribution of the cell cycle. Specifically, in DLD-1 cells, rimonabant causes a G2/M cell cycle arrest without causing necrosis or apoptosis. [4]

ln Vivo

Rimonabant is given intraperitoneally or orally, where it counteracts the traditional pharmacological and behavioral effects of cannabinoid receptor agonists in a potent and dose-dependent manner. In the mouse model of colon carcinogenesis induced by azoxymethane, the formation of aberrant crypt foci (ACF), a precursor to colorectal cancer, was significantly reduced by rimonabant. [4] Male obese Zucker rats that are 2 weeks to 3 months old are given 10 weeks to 6 months old of rimonabant (10 mg/kg by gavage) as a model of the metabolic syndrome and as an impaired glucose tolerance model. The serum levels of MCP-1 (monocyte chemotactic protein-1) and RANTES (Regulated upon Activation, Normal T cell Expressed and Secreted) are higher in obese Zucker rats compared to lean Zucker rats. Long-term Rimonabant treatment significantly reduces these levels, slowing weight gain in rats with the metabolic syndrome. Rimonabant reduces neutrophils and monocytes, which are markedly elevated in young, old, obese Zucker rats compared to lean Zucker rats. Rimonabant reduces platelet-bound fibrinogen, which is significantly increased in obese compared to lean Zucker rats of both ages. Obese rats' platelets are more susceptible to adhesion to fibrinogen and thrombin-induced aggregation, both of which are lessened by rimonabant therapy. [5]

Enzyme Assay

HEK 293 cells are transfected stable by human CB1 and CB2, and the cell membrane is purified. 50 mM Tris-HCl, 5 mM MgCl₂, 1 mM EDTA, 0.3% BSA, pH 7.4, 0.75 nM [³H] CP55,940, and Rimonabant are added to 0.2–8 μg of the purified membrane for incubation. In the presence of 1 μM of CP55,940, the non-specific binding is defined. In Multiscreen, the reactions are incubated for 1.5 hours at 30 °C. Manifold filtration is used to stop the reactions, and ice-cold wash buffer (50 mM Tris, pH 7.4, 0.25% BSA) is used to wash the mixture four times. Topcount measures the radioactivity bound to the filters. The IC50 is computed using non-linear regression and is defined as the concentration of rimonabant needed to inhibit 50% of the binding of [³H] CP55,940.

Cell Assay

Raw 264.7 12-well plates containing 2 × 106 cells per well are rinsed with PBS and then refed with culture media supplemented with different amounts of Rimonabant one hour before 7-ketocholesterol (7KC) is added. Equal amounts of vehicle are dispensed with in each well. Using a fluorogenic substrate (ac-DEVD-AFC) and a spectrofluorometer fitted with a microplate reader, caspase-3 and caspase 3-like activity are assessed after a 16-hour incubation.

Animal Protocol

Dissolved in two drops of Tween 80, diluted in distilled water; 20 ml/kg (mice) and 5 ml/kg (rats); i.p. injection

Male mice and male rats

References

[1]. Org Biomol Chem . 2008 Sep 21;6(18):3399-407.

[2]. Biochem Biophys Res Commun . 2010 Aug 6;398(4):671-6.

[3]. FEBS Lett . 1994 Aug 22;350(2-3):240-4.

[4]. Int J Cancer . 2009 Sep 1;125(5):996-1003.

[5]. Br J Pharmacol . 2008 Jul;154(5):1047-54.

[6]. Neuropsychopharmacology . 2007 Aug;32(8):1805-12.

[7]. Cell . 2019 Jan 24;176(3):636-648.e13.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C22H21CL3N4O

Molecular Weight

463.79

Exact Mass

462.08

Elemental Analysis

C, 56.97; H, 4.56; Cl, 22.93; N, 12.08; O, 3.45

CAS #

168273-06-1

Related CAS #

Rimonabant Hydrochloride; 158681-13-1; Rimonabant-d10; 929221-88-5

Appearance

Solid powder

SMILES

CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl

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)

Chemical Name

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide

Synonyms

SR141716; A 281; SR-141716; A-281; A281; SR 141716A;SR 141716; SR-141716;SR 151716A; SR-141716A; SR-151716A; SR141716A; SR151716A; Rimonabant; Acomplia; Zimulti

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: 25~92 mg/mL (53.9~198.4 mM)

Water: <1 mg/mL

Ethanol: ~2 mg/mL (~4.3 mM)

Solubility (In Vivo)

30% PEG400+0.5% Tween80+5%Propylene glycol: 30 mg/mL

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.1561 mL	10.7807 mL	21.5615 mL
	5 mM	0.4312 mL	2.1561 mL	4.3123 mL
	10 mM	0.2156 mL	1.0781 mL	2.1561 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
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The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

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The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

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g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT05622994	Not yet recruiting	Drug: Rimonabant	Hospital Nacional de Parapléjicos de Toledo	Pfizer	November 2022	Phase 2
NCT00358228	Completed	Drug: Rimonabant	Smoking Cessation	Sanofi	September 2002	Phase 3
NCT00464165	Completed	Drug: rimonabant	Smoking Cessation	Sanofi	November 2002	Phase 3
NCT00464256	Completed	Drug: rimonabant	Smoking Cessation	Sanofi	November 2004	Phase 3
NCT05398913	Recruiting	Drug: Rimonabant	Spinal Cord Injuries	Hospital Nacional de Parapléjicos de Toledo	May 12, 2021	Phase 1 Phase 2

Biological Data

Rimonabant selectively inhibits cholesteryl ester synthesis in macrophages. Biochem Biophys Res Commun . 2010 Aug 6;398(4):671-6.
Rimonabant inhibits oxysterol-stimulated and AcLDL-stimulated ACAT activity in macrophages. Biochem Biophys Res Commun . 2010 Aug 6;398(4):671-6.

Rimonabant decreases cell recovery and induces cell death in colon cancer cells. DLD-1, Caco-2 and SW620 cells were treated with rimonabant (0–20 μM) for 24 and 48 hr. Int J Cancer . 2009 Sep 1;125(5):996-1003.

Rimonabant affects cell cycle phase distribution in colon cancer cells. DLD-1, Caco-2 and SW620 were exposed to rimonabant for 24 hr (0–10 μM). Int J Cancer . 2009 Sep 1;125(5):996-1003.

Body weight in 3-month-old obese Zucker rats after 2 weeks of treatment with or without rimonabant (Rimo, a) compared with lean Zucker rats of the same ages, and weight gain in 6-month-old lean and obese Zucker rats after 10 weeks of treatment with or without rimonabant (Rimo, b). Br J Pharmacol . 2008 Jul;154(5):1047-54

Subthreshold doses of rimonabant (0.3 mg/kg) and donepezil (0.1 mg/kg) given in combination decreased the number of errors committed in the test phase. Neuropsychopharmacology . 2007 Aug;32(8):1805-12.

A Unique Binding Mode for Rimonabant. Cell . 2019 Jan 24;176(3):636-648.e13.