[CAS NO. 168273-06-1] Rimonabant (SR141716)

Name: Rimonabant (SR141716)
Brand: Arctom Scientific
SKU: SLK-S3021

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PRODUCTS SPECIFICATIONS [168273-06-1]

Store

Catalog

SLK-S3021

Brand

Selleck

CAS

168273-06-1

DESCRIPTION [168273-06-1]

Overview

MDL	-
Molecular Weight	463.79
Molecular Formula	C22H21Cl3N4O
SMILES	CC1=C(N(N=C1C(NN2CCCCC2)=O)C3=C(Cl)C=C(Cl)C=C3)C4=CC=C(Cl)C=C4

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume Mass	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
50 mM	0.0431 mL	0.2156 mL	0.4312 mL

Description

Rimonabant (SR141716) is a selective antagonist of with of 13.6 nM and of 17.3 nM in hCB1 transfected HEK 293 membrane. Rimonabant is also a dual inhibitor of and inhibits mycobacterial MmpL3.

Features

Efficacious to induce weight reduction and improvements in cardiometabolic risk factors, however was withdrawn in 2009 due to severe depressive disorder and anxiety.

Targets

ACAT1 ^[2]	ACAT2 ^[2]	MmpL3 ^[7]	hCB1 ^[1] (Cell-free assay)	hCB2 ^[1] (Cell-free assay)
			13.6 nM	1.64 μM

In vitro

Rimonabant dose-dependently reduces ACAT activity in Raw264.7macrophages with IC50 of 2.9 μM and isolated peritoneal macrophages. Rimonabant inhibits ACATactivity in intact CHO-ACAT1 and CHO-ACAT2 cells and in cell-free assays with approximately equal efficiency with IC50 of 1.5 μM and 2.2 μM for CHO-ACAT1 and CHO-ACAT2, respectively. Consistent with ACAT inhibition, Rimonabant treatment blocks ACAT dependent processes in macrophages, oxysterol-induced apoptosis and acetylated-LDL induced foam cell formation. Rimonabant antagonizes the inhibitory effects of cannabinoid receptor agonists on both mouse vas deferens contractions and adenylyl cyclase activity in rat brain membranes in a concentration-dependent manner. Rimonabant significantly reduces cell growth and induces cell death of human colorectal cancer cells (DLD-1, CaCo-2 and SW620). Rimonabant is able to alter cell cycle distribution in all the cell lines tested. Particularly, Rimonabant produces a G2/M cell cycle arrest in DLD-1 cells without inducing apoptosis or necrosis.

References

[1] Chu CM, et al, Org Biomol Chem, 2008, 6(18), 3399-3407
[2] Netherland C, et al, Biochem Biophys Res Commun, 2010, 398(4), 671-676.
[3] Rinaldi-Carmona M, et al, FEBS Lett, 1994, 350(2-3), 240-244.
[4] Santoro A, et al, Int J Cancer, 2009, 125(5), 996-1003.
[5] Schafer A, et al, Br J Pharmacol, 2008, 154(5), 1047-1054.
[6] Wise LE, et al, Neuropsychopharmacology, 2007, 32(8), 1805-1812.
[7] Bing Zhang, et al. Cell . 2019 Jan 24;176(3):636-648.e13.

Synonyms

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

SR 141716

Rimonabant

Acomplia

A 281

N-Piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide

1-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid N-(piperidin-1-yl)amide

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

SR 141617

Zimulti

ENP 9