Lapaquistat acetate

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 525427

CAS#: 189060-13-7

Description: Lapaquistat acetate, also known as TAK475, is a cholesterol-lowering drug. It is a squalene synthase inhibitor.


Chemical Structure

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Lapaquistat acetate
CAS# 189060-13-7

Theoretical Analysis

MedKoo Cat#: 525427
Name: Lapaquistat acetate
CAS#: 189060-13-7
Chemical Formula: C33H41ClN2O9
Exact Mass: 644.25006
Molecular Weight: 645.14
Elemental Analysis: C, 61.44; H, 6.41; Cl, 5.50; N, 4.34; O, 22.32

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 189059-71-0 (free)  

Synonym: Lapaquistat acetate; TAK 475; TAK-475; TAK475.

IUPAC/Chemical Name: 2-(1-(2-((3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydrobenzo[e][1,4]oxazepin-3-yl)acetyl)piperidin-4-yl)acetic acid

InChi Key: CMLUGNQVANVZHY-POURPWNDSA-N

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

SMILES Code: O=C(O)CC1CCN(C(C[C@H]2O[C@H](C3=CC=CC(OC)=C3OC)C4=CC(Cl)=CC=C4N(CC(C)(C)COC(C)=O)C2=O)=O)CC1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 645.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ebihara T, Takeuchi T, Moriya Y, Tagawa Y, Kondo T, Moriwaki T, Asahi S. Characterization of Transporters in the Hepatic Uptake of TAK-475 M-I, a Squalene Synthase Inhibitor, in Rats and Humans. Drug Res (Stuttg). 2016 Jun;66(6):316-23. doi: 10.1055/s-0035-1569441. Epub 2016 Mar 24. PubMed PMID: 27011383.

2: Ebihara T, Teshima K, Kondo T, Tagawa Y, Moriwaki T, Asahi S. Pharmacokinetics of TAK-475, a Squalene Synthase Inhibitor, in Rats and Dogs. Drug Res (Stuttg). 2016 Jun;66(6):287-92. doi: 10.1055/s-0035-1569407. Epub 2016 Feb 2. PubMed PMID: 26839207.

3: Stein EA, Bays H, O'Brien D, Pedicano J, Piper E, Spezzi A. Lapaquistat acetate: development of a squalene synthase inhibitor for the treatment of hypercholesterolemia. Circulation. 2011 May 10;123(18):1974-85. doi: 10.1161/CIRCULATIONAHA.110.975284. Epub 2011 Apr 25. PubMed PMID: 21518985.

4: Liao JK. Squalene synthase inhibitor lapaquistat acetate: could anything be better than statins? Circulation. 2011 May 10;123(18):1925-8. doi: 10.1161/CIRCULATIONAHA.111.028571. Epub 2011 Apr 25. PubMed PMID: 21518979; PubMed Central PMCID: PMC3807098.

5: Kahlon AK, Roy S, Sharma A. Molecular docking studies to map the binding site of squalene synthase inhibitors on dehydrosqualene synthase of Staphylococcus aureus. J Biomol Struct Dyn. 2010 Oct;28(2):201-10. PubMed PMID: 20645653.

6: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Apr;30(3):231-51. PubMed PMID: 18597009.

7: Shiomi M, Yamada S, Amano Y, Nishimoto T, Ito T. 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. doi: 10.1038/bjp.2008.143. Epub 2008 Apr 21. PubMed PMID: 18587443; PubMed Central PMCID: PMC2451058.

8: Nishimoto T, Ishikawa E, Anayama H, Hamajyo H, Nagai H, Hirakata M, Tozawa R. 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. Epub 2007 May 24. PubMed PMID: 17599378.