Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D02FXU
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| Former ID |
DCL000147
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| Drug Name |
Lapaquistat acetate
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| Synonyms |
Lapaquistat acetate (USAN); TAK-475; 1-((1-(3-Acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl)acetyl)piperidine-4-acetic acid
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| Drug Type |
Small molecular drug
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| Indication | Hyperlipidaemia [ICD-11: 5C80; ICD-10: E78.5] | Discontinued in Phase 3 | [1] | |
| Company |
Takeda Chemical Industries
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| Structure |
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Download2D MOL |
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| Formula |
C33H41ClN2O9
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| Canonical SMILES |
CC(=O)OCC(C)(C)CN1C2=C(C=C(C=C2)Cl)C(OC(C1=O)CC(=O)N3CCC(CC3)CC(=O)O)C4=C(C(=CC=C4)OC)OC
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| InChI |
1S/C33H41ClN2O9/c1-20(37)44-19-33(2,3)18-36-25-10-9-22(34)16-24(25)30(23-7-6-8-26(42-4)31(23)43-5)45-27(32(36)41)17-28(38)35-13-11-21(12-14-35)15-29(39)40/h6-10,16,21,27,30H,11-15,17-19H2,1-5H3,(H,39,40)/t27-,30-/m1/s1
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| InChIKey |
CMLUGNQVANVZHY-POURPWNDSA-N
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| CAS Number |
CAS 189060-13-7
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| PubChem Compound ID | ||||
| PubChem Substance ID | ||||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Squalene synthetase (FDFT1) | Target Info | Inhibitor | [2], [3] |
| BioCyc | Cholesterol biosynthesis II (via 24,25-dihydrolanosterol) | |||
| Cholesterol biosynthesis III (via desmosterol) | ||||
| Cholesterol biosynthesis I | ||||
| Superpathway of cholesterol biosynthesis | ||||
| Epoxysqualene biosynthesis | ||||
| KEGG Pathway | Steroid biosynthesis | |||
| Metabolic pathways | ||||
| Biosynthesis of antibiotics | ||||
| Panther Pathway | Cholesterol biosynthesis | |||
| Pathwhiz Pathway | Steroid Biosynthesis | |||
| Reactome | Cholesterol biosynthesis | |||
| PPARA activates gene expression | ||||
| Activation of gene expression by SREBF (SREBP) | ||||
| WikiPathways | Statin Pathway | |||
| Regulation of Lipid Metabolism by Peroxisome proliferator-activated receptor alpha (PPARalpha) | ||||
| Activation of Gene Expression by SREBP (SREBF) | ||||
| SREBP signalling | ||||
| Cholesterol Biosynthesis | ||||
| Cholesterol biosynthesis | ||||
| References | Top | |||
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| REF 1 | ClinicalTrials.gov (NCT00532558) Efficacy of Lapaquistat Acetate on Blood Cholesterol Levels in Treating Subjects With Hypercholesterolemia. U.S. National Institutes of Health. | |||
| REF 2 | Lapaquistat acetate, a squalene synthase inhibitor, changes macrophage/lipid-rich coronary plaques of hypercholesterolaemic rabbits into fibrous le... Br J Pharmacol. 2008 Jul;154(5):949-57. | |||
| REF 3 | Protective effects of a squalene synthase inhibitor, lapaquistat acetate (TAK-475), on statin-induced myotoxicity in guinea pigs. Toxicol Appl Pharmacol. 2007 Aug 15;223(1):39-45. | |||
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