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)
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 |
|---|---|---|
| Multiple mechanisms of hypocholesterolemic action of pactimibe, a novel acyl-coenzyme A:cholesterol acyltransferase inhibitor. | 2006 Aug 14 |
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| A bumpy road to breakthroughs. The news: it's hard to beat today's cardiac treatments. | 2006 Feb |
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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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| ACAT inhibition and the progression of coronary atherosclerosis. | 2006 Jun 15 |
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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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| CYP2D6-Mediated metabolism of a novel acyl coenzyme A:cholesterol acyltransferase inhibitor, pactimibe, and its unique plasma metabolite, R-125528. | 2008 Mar |
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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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| Novel binding mode of the acidic CYP2D6 substrates pactimibe and its metabolite R-125528. | 2008 Sep |
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| Substrate specificity, inhibitors and regulation of human cytochrome P450 2D6 and implications in drug development. | 2009 |
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| Novel indoline-based acyl-CoA: cholesterol acyltransferase inhibitor: Effects of introducing a methanesulfonamide group on physicochemical properties and biological activities. | 2009 Aug 15 |
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| Carotid atherosclerosis progression and ACAT inhibition. | 2009 Jul 15 |
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| ACAT inhibition and progression of carotid atherosclerosis in patients with familial hypercholesterolemia: the CAPTIVATE randomized trial. | 2009 Mar 18 |
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| Atherosclerosis drug fails to meet Phase III trial end point. | 2009 May |
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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 |
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| A selective ACAT-1 inhibitor, K-604, stimulates collagen production in cultured smooth muscle cells and alters plaque phenotype in apolipoprotein E-knockout mice. | 2010 Nov |
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NCI_THESAURUS |
C471
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DB12971
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C66290
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D874R9PZ9T
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DTXSID80172315
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8269
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300000036933
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C509302
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189198-30-9
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3081927
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CHEMBL478858
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
