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:
12352200
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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S Murakami et al.
General pharmacology, 27(8), 1383-1386 (1996-12-01)
1. A novel ACAT (acyl-CoA: cholesterol acyltransferase) inhibitor, HL-004, exhibited a strong inhibitory effect on the hepatic and intestinal ACAT, but was less effective on the adrenal ACAT in vitro. 2. HL-004 selectively decreased serum VLDL cholesterol, and inhibited hepatic
Kimberly Chambers et al.
Journal of cell science, 118(Pt 14), 3061-3071 (2005-06-24)
Previous studies have shown that inhibition of a Golgi-complex-associated lysophospholipid acyltransferase (LPAT) activity by the drug CI-976 stimulates Golgi tubule formation and subsequent redistribution of resident Golgi proteins to the endoplasmic reticulum (ER). Here, we show that CI-976 stimulates tubule
A Tanaka et al.
Bioorganic & medicinal chemistry, 6(1), 15-30 (1998-03-21)
A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups
R E Burrier et al.
The Journal of pharmacology and experimental therapeutics, 272(1), 156-163 (1995-01-01)
Acyl CoA: cholesterol acyltransferase (ACAT) inhibitors are known to inhibit cholesterol absorption and are under investigation to reduce hypercholesterolemia. These studies examine the effect of an ACAT inhibitor 2,2-dimethyl-N-(2,4,6-trimethoxyphenyl)-dodecanamide (PD128042) on the uptake, metabolism and secretion of cholesterol by the
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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