C3743
CI 976
>98% (HPLC), solid
Synonym(s):
2,2-Dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide
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About This Item
Empirical Formula (Hill Notation):
C23H39NO4
CAS Number:
Molecular Weight:
393.56
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
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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
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.
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 4
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
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
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
R A Harte et al.
Biochimica et biophysica acta, 1258(3), 241-250 (1995-10-05)
The effect of the membrane environment of acyl-CoA:cholesterol acyl transferase (ACAT), an important intracellular enzyme of cholesterol metabolism, on the properties of a range of inhibitors of varying potencies was studied. ACAT activity from rat liver was solubilised with 3%
Y Sakuma et al.
Japanese journal of pharmacology, 70(1), 35-41 (1996-01-01)
FR129169 (FR) (N-(1,2-diphenylethyl)-2-octyloxyphenylacetamide) has been found to inhibit acyl-CoA:cholesterol acyltransferase (ACAT) activities in intestinal microsomes of rats and rabbits and the liver homogenate of rats with IC50 values of around 1.0 x 10(-7) M. The inhibitory activity was 2-3 times
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