Details
Stereochemistry | ACHIRAL |
Molecular Formula | C25H40N2O3 |
Molecular Weight | 416.5967 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCN1CCC2=C(C)C(CC(O)=O)=C(C)C(NC(=O)C(C)(C)C)=C12
InChI
InChIKey=TXIIZHHIOHVWJD-UHFFFAOYSA-N
InChI=1S/C25H40N2O3/c1-7-8-9-10-11-12-14-27-15-13-19-17(2)20(16-21(28)29)18(3)22(23(19)27)26-24(30)25(4,5)6/h7-16H2,1-6H3,(H,26,30)(H,28,29)
Molecular Formula | C25H40N2O3 |
Molecular Weight | 416.5967 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Daiichi Sankyo developed an inhibitor of acyl-coenzyme A:cholesterol acyltransferases (ACAT1 and ACAT2), pactimibe (also known as CS 505). Pactimibe has been used in trials phase II for reducing the progression of coronary artery disease and in patients with atherosclerosis. However, on October 26, 2005, the company made the decision to discontinue all ongoing clinical studies of pactimibe, because of the secondary endpoints that showed a lower effect of the drug on atherosclerosis than the standard of care alone and no beneficial effect on the frequency of cardiovascular events.
Approval Year
PubMed
Title | Date | PubMed |
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Intravascular ultrasound assessment of novel antiatherosclerotic therapies: rationale and design of the Acyl-CoA:Cholesterol Acyltransferase Intravascular Atherosclerosis Treatment Evaluation (ACTIVATE) Study. | 2006 Jul |
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Importance of acyl-coenzyme A:cholesterol acyltransferase 1/2 dual inhibition for anti-atherosclerotic potency of pactimibe. | 2006 Jul 1 |
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Pactimibe stabilizes atherosclerotic plaque through macrophage acyl-CoA:cholesterol acyltransferase inhibition in WHHL rabbits. | 2006 Jun 6 |
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Failure of ACAT inhibition to retard atherosclerosis. | 2006 Mar 23 |
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Effect of ACAT inhibition on the progression of coronary atherosclerosis. | 2006 Mar 23 |
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[New agents against atherosclerosis tested. Alarming findings, ACAT inhibitors seem to have proatherogenic effects]. | 2006 Oct 25-31 |
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ACAT inhibitor pactimibe sulfate (CS-505) reduces and stabilizes atherosclerotic lesions by cholesterol-lowering and direct effects in apolipoprotein E-deficient mice. | 2007 Feb |
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Effects of ketoconazole and quinidine on pharmacokinetics of pactimibe and its plasma metabolite, R-125528, in humans. | 2008 Aug |
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Effect of CYP2D6 polymorphism on pharmacokinetics of a novel ACAT inhibitor, pactimibe and its unique metabolite, R-125528. | 2008 Nov |
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Forkhead transcription factors (FoxOs) promote apoptosis of insulin-resistant macrophages during cholesterol-induced endoplasmic reticulum stress. | 2008 Nov |
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Substrate specificity, inhibitors and regulation of human cytochrome P450 2D6 and implications in drug development. | 2009 |
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Carotid atherosclerosis progression and ACAT inhibition. | 2009 Jul 15 |
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Impact of medical therapy on atheroma volume measured by different cardiovascular imaging modalities. | 2010 |
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Novel tetrahydroisoquinoline derivatives with inhibitory activities against acyl-CoA: cholesterol acyltransferase and lipid peroxidation. | 2010 Aug |
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Novel acyl-CoA: cholesterol acyltransferase inhibitor: indoline-based sulfamide derivatives with low lipophilicity and protein binding ratio. | 2010 Aug |
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Membrane plasmalogen composition and cellular cholesterol regulation: a structure activity study. | 2010 Jun 14 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:29:10 GMT 2023
by
admin
on
Fri Dec 15 16:29:10 GMT 2023
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Record UNII |
D874R9PZ9T
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C471
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CHEMBL478858
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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IN HEALTHY MALE VOLUNTEERS |
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Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Tmax | PHARMACOKINETIC |
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DOSE |
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Biological Half-life | PHARMACOKINETIC |
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DOSE |
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