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[CAS NO. 189060-13-7] Lapaquistatacetate
| Ships within | Stock | Price | Qty | Total |
Please click "REQUEST A QUOTE" button if there is no stock, or you need other sizes or custom synthesis.
| Catalog: | HY-16274 |
| Brand: | MCE |
| CAS: | 189060-13-7 |
Overview
| MDL | - |
|---|---|
| Molecular Weight | 645.14 |
| Molecular Formula | C33H41ClN2O9 |
| SMILES | O=C(O)CC1CCN(C(C[C@@H]2C(N(CC(C)(C)COC(C)=O)C3=CC=C(Cl)C=C3[C@@H](C4=CC=CC(OC)=C4OC)O2)=O)=O)CC1 |
Summary
Lapaquistat acetate (TAK-475) is a squalene synthase inhibitor, blocking the conversion of farnesyl diphosphate (FPP) to squalene in the cholesterol biosynthesis pathway [1] . Lapaquistat acetate is effective at lowering low-density lipoprotein cholesterol , but it might cause liver damage. Lapaquistat acetate is used for hypercholesterolemia and mevalonate kinase deficiency (MKD) research [2] .
IC50 & Target
Squalene synthase [1]
In Vivo
Lapaquistat acetate (diet supplemented; 100 or 200 mg/kg; 32 weeks) decreases plasma cholesterol and triglyceride levels. It delays progression of coronary atherosclerosis and changes coronary atheromatous plaques from unstable, macrophage/lipid accumulation-rich, lesions to stable fibromuscular lesions in vivo [3] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
| Animal Model: | Male WHHLMI rabbits, aged 2 months [3] |
| Dosage: | 100 or 200 mg/kg |
| Administration: | Diet supplemented; 100 or 200 mg/kg; 32 weeks |
| Result: |
Increased collagen concentration and transformed coronary plaques into fibromuscular plaques.
Suppressed the expression of MMP-1 and PAI-1 in the plaque and increased peripheral coenzyme Q10 levels. |
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date | Phase |
|---|---|---|---|---|
| NCT00868127 | Takeda |
Hypercholesterolemia
|
December 2005 | Phase 3 |
| NCT00268697 | Takeda |
Hypercholesterolemia
|
October 2005 | Phase 3 |
| NCT00286481 | Takeda |
Hypercholesterolemia
|
March 2006 | Phase 3 |
| NCT00532311 | Takeda |
Hypercholesterolemia
|
July 2007 | Phase 3 |
| NCT00143663 | Takeda |
Dyslipidemia
|
September 2005 | Phase 3 |
| NCT00864643 | Takeda |
Hypercholesterolemia
|
September 2004 | Phase 2 |
| NCT00813527 | Takeda |
Hyperlipidemias
|
February 2006 | Phase 2 |
| NCT00249912 | Takeda |
Hypercholesterolemia
|
October 2005 | Phase 3 |
| NCT00865228 | Takeda |
Hypercholesterolemia
|
July 2007 | Phase 2 |
| NCT00251680 | Takeda |
Type 2 Diabetes
|
October 2005 | Phase 3 |
| NCT00532558 | Takeda |
Hypercholesterolemia
|
October 2007 | Phase 3 |
| NCT00263081 | Takeda |
Hypercholesterolemia
|
November 2005 | Phase 3 |
| NCT00256178 | Takeda |
Hypercholesterolemia
|
October 2005 | Phase 3 |
| NCT00487994 | Takeda |
Dyslipidemia
|
November 2004 | Phase 3 |
| NCT00143676 | Takeda |
Hypercholesterolemia
|
August 2005 | Phase 3 |
| NCT00249899 | Takeda |
Hypercholesterolemia
|
November 2005 | Phase 3 |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
DMSO : 50 mg/mL ( 77.50 mM ; Need ultrasonic)
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 1.5501 mL | 7.7503 mL | 15.5005 mL |
| 5 mM | 0.3100 mL | 1.5501 mL | 3.1001 mL |
| 10 mM | 0.1550 mL | 0.7750 mL | 1.5501 mL |
-
1.
Add each solvent one by one: 10% DMSO >> 90% corn oil
Solubility: ≥ 2.5 mg/mL (3.88 mM); Clear solution
References
- [1] Stein EA, et al. Lapaquistat acetate: development of a squalene synthase inhibitor for the treatment of hypercholesterolemia. Circulation. 2011 May 10;123(18):1974-85.
- [2] Marcuzzi A, et al. Repositioning of Tak-475 In Mevalonate Kinase Disease: Translating Theory Into Practice. Curr Med Chem. 2018;25(24):2783-2796.
- [3] M Shiomi, et al. Lapaquistat acetate, a squalene synthase inhibitor, changes macrophage/lipid-rich coronary plaques of hypercholesterolaemic rabbits into fibrous lesions. Br J Pharmacol. 2008 Jul;154(5):949-57.
Synonyms
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