A squalene synthase inhibitor and prodrug form of lapaquistat
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Lapaquistat Acetate

Item No. 46086

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[2-[(3R,5S)-1-[3-(acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-1,2,3,5-tetrahydro-2-oxo4,1-benzoxazepin-3-yl]acetyl]-4-piperidineacetic acid
CAS Number
189060-13-7
Synonyms
  • TAK-475
Molecular Formula
C33H41ClN2O9
Formula Weight
645.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1 mg/mlDMSO: Sparingly soluble: 1-10 mg/ml
SMILES
CC(OCC(C)(C)CN(C([C@H](O1)CC(N2CCC(CC2)CC(O)=O)=O)=O)C(C([C@H]1C3=C(OC)C(OC)=CC=C3)=C4)=CC=C4Cl)=O
InChi Code
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
InChi Key
CMLUGNQVANVZHY-POURPWNDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Lapaquistat acetate is a squalene synthase inhibitor (IC50 = 78 nM) and a prodrug form of lapaquistat.1 It increases LDL binding to LDL receptors in HepG2 cells at 10 µM.2 It inhibits cholesterol synthesis in rat liver (ED50 = 2.9 mg/kg) and reduces plasma non-HDL cholesterol and triglyceride levels in marmosets at 100 mg/kg.1,2 Lapaquistat acetate (60 mg/kg) reduces the hepatic triglyceride secretion rate in hypertriglyceridemic rats.2 It also reduces the development of atherosclerosis and stabilizes coronary atheromatous plaques in hypercholesterolemic rabbits.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miki, T., Kori, M., Mabuchi, H., et al. Synthesis of novel 4,1-benzoxazepine derivatives as squalene synthase inhibitors and their inhibition of cholesterol synthesis. J. Med. Chem. 45(20), 4571-4580 (2002).

    2. Nishimoto, T., Amano, Y., Tozawa, R., et al. Lipid-lowering properties of TAK-475, a squalene synthase inhibitor, in vivo and in vitro. Br. J. Pharmacol. 139(5), 911-918 (2003).

    3. Shiomi, M., Yamada, S., Amano, Y., et al. Lapaquistat acetate, a squalene synthase inhibitor, changes macrophage/lipid-rich coronary plaques of hypercholesterolaemic rabbits into fibrous lesions. Br. J. Pharmacol. 154(5), 949-957 (2008).