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C3743

Sigma-Aldrich

CI 976

>98% (HPLC), solid

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Synonym(s):
2,2-Dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide
Empirical Formula (Hill Notation):
C23H39NO4
CAS Number:
Molecular Weight:
393.56
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

>98% (HPLC)

form

solid

solubility

DMSO: >10 mg/mL
H2O: insoluble <2 mg/mL

storage temp.

2-8°C

SMILES string

CCCCCCCCCCC(C)(C)C(=O)Nc1c(OC)cc(OC)cc1OC

InChI

1S/C23H39NO4/c1-7-8-9-10-11-12-13-14-15-23(2,3)22(25)24-21-19(27-5)16-18(26-4)17-20(21)28-6/h16-17H,7-15H2,1-6H3,(H,24,25)

Inchi Key

WAFNZAURAWBNDZ-UHFFFAOYSA-N

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This Item
N3911L9167P0043
vibrant-m

C3743

CI 976

vibrant-m

N3911

NBI 27914

vibrant-m

L9167

LWH-63 hydrochloride

vibrant-m

P0043

PNU-120596

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

form

solid

form

solid

form

solid

form

solid

solubility

DMSO: >10 mg/mL, H2O: insoluble <2 mg/mL

solubility

DMSO: >20 mg/mL at 60 °C, H2O: insoluble

solubility

DMSO: ~10 mg/mL, H2O: insoluble

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

room temp

application

CI 976 has been used as an acyl-coenzyme A: cholesterol acyltransferase (ACAT) inhibitor:
  • to analyze its anti-hepatitis C virus (HCV) activity in Huh7.5.1 cells
  • to treat Neuro-2a cells to test its effect on plasma membrane integrated density of α4-SEPβ2 or α6-SEPβ2β3 nicotinic acetylcholine receptors (nAChRs)
  • to study its effects on the anti-angiogenic activity of pyripyropenes in human umbilical vein endothelial cells

Biochem/physiol Actions

CI-976, a new trimethoxy fatty acid anilide, is a potent and specific inhibitor of liver and intestinal acyl coenzyme A; cholesterol acyltransferase (ACAT) in vitro. CI-976 decreased non-high density lipoprotein (HDL)-cholesterol and increased HDL-cholesterol in rats with pre-established dyslipidemia. High performance gel chromatographic separation of plasma lipoproteins also revealed that CI-976, but not CL 277,082, lowered low density lipoprotein (LDL)-cholesterol and elevated HDL-cholesterol.

hcodes

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Y Matsui et al.
Japanese journal of pharmacology, 85(4), 423-433 (2001-06-05)
R-755 (N-(2,6-diethylphenyl)-N'-[3-(2-methylphenyl)-6,7-dihydro-5H-cyclopenta[f[l]benzothiophen-2-yl]urea), a novel acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor, has been characterized in vitro, ex vivo and in vivo. R-755 potently inhibited ACAT activities, with IC50 values from 2.5 to 64 nM, in rabbit intestinal microsomes and several cell lines (CaCo-2
Daniel Drecktrah et al.
Molecular biology of the cell, 14(8), 3459-3469 (2003-08-20)
Recent studies have suggested that formation of Golgi membrane tubules involves the generation of membrane-associated lysophospholipids by a cytoplasmic Ca2+-independent phospholipase A2 (PLA2). Herein, we provide additional support for this idea by showing that inhibition of lysophospholipid reacylation by a
S Perrey et al.
Atherosclerosis, 155(2), 359-370 (2001-03-20)
The cholesteryl ester, foam cell-enriched vulnerable plaque is a principle pharmacological target for reducing athero-thrombosis. Acyl CoA:cholesterol Acyl Transferase (ACAT) catalyzes the esterification of free cholesterol in intestine, liver, adrenal and macrophages, leading in the latter cells to intracellular cholesteryl
Asami Hayashi et al.
Biological & pharmaceutical bulletin, 32(7), 1261-1265 (2009-07-03)
In the course of our search for anti-angiogenic substances, pyripyropenes A (1), B (2), and D (3) were re-discovered as selective anti-proliferative substances against human umbilical vein endothelial cells (HUVECs) from a marine-derived fungus of Aspergillus sp. Pyripyropenes showed potent
Y Azuma et al.
Japanese journal of pharmacology, 79(2), 151-158 (1999-04-15)
We studied the effect of NTE-122 (trans-1,4-bis[[1-cyclohexyl-3-(4-dimethylamino phenyl) ureido]methyl]cyclohexane), a novel acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor, on intracellular cholesterol esterification and the secretion of apolipoprotein B100 (apoB)-containing lipoprotein and bile acids in the human hepatoma cell line HepG2. NTE-122 markably inhibited

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