Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

SML2168

Sigma-Aldrich

TAK-475

≥98% (HPLC)

Synonym(s):

1-[2-[(3R,5S)-1-[3-(Acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-yl]acetyl]-4-piperidineacetic acid, Lapaquistat acetate, TAK 475

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C33H41ClN2O9
CAS Number:
189060-13-7
Molecular Weight:
645.14
MDL number:
MFCD06407873
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C1[C@@H](CC(N2CCC(CC(O)=O)CC2)=O)O[C@H](C3=CC=CC(OC)=C3OC)C4=C(C=CC(Cl)=C4)N1CC(C)(C)COC(C)=O

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

Application

TAK-475 has been used:
  • as a farnesyl-diphosphate farnesyltransferase 1 (FDFT1) inhibitor to study its effects on cell signaling in pancreatic ductal adenocarcinoma cells
  • as a squalene synthase (SQS) inhibitor to stabilize HMG-CoA reductase (HMGCR)-dCat-ELuc proteins
  • as an SQS inhibitor to study its effects on the migration of prostate cancer cells

Biochem/physiol Actions

TAK-475 (Lapaquistat acetate) is a potent and selective squalene synthase inhibitor. TAK-475 effectively lowers low-density lipoprotein cholesterol in human. Clinical development of TAK-475 was discontinued due to hepatotoxicity seen in two patients receiving a high dose.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

T Ebihara et al.
Drug research, 66(6), 287-292 (2016-02-04)
The pharmacokinetics of TAK-475 (lapaquistat acetate), a squalene synthase inhibitor, was investigated in rats and dogs. After oral administration of (14)C-labeled TAK-475 ([(14)C]TAK-475) to rats and dogs at a dose of 10 mg/kg, the bioavailability (BA) was relatively low at 3.5
Evan A Stein et al.
Circulation, 123(18), 1974-1985 (2011-04-27)
Lapaquistat acetate is a squalene synthase inhibitor investigated for the treatment of hypercholesterolemia. This report summarizes the phase 2 and 3 results from the lapaquistat clinical program, which was halted at an advanced stage as a result of potential hepatic
Chao Huang et al.
Journal of extracellular vesicles, 9(1), 1692417-1692417 (2019-12-07)
Tumour metastasis suppressor KAI1/CD82 inhibits tumour cell movement. As a transmembrane protein, tetraspanin CD82 bridges the interactions between membrane microdomains of lipid rafts and tetraspanin-enriched microdomains (TEMs). In this study, we found that CD82 and other tetraspanins contain cholesterol recognition/interaction
Nobutaka Suzuki et al.
SpringerPlus, 5(1), 1429-1429 (2016-09-22)
TAK-475 (lapaquistat acetate) and its active metabolite-I (TAK-475 M-I) inhibit squalene synthase, which catalyzes the conversion of farnesyl diphosphate (FPP) to squalene. FPP is a substrate for synthesis of other mevalonate-derived isoprenoids (MDIs) such as farnesol (FOH), geranlygeranyl diphosphate (GGPP)
Ikuya Sagimori et al.
Bioorganic & medicinal chemistry, 28(3), 115298-115298 (2020-01-07)
HMG-CoA reductase (HMGCR) is the rate-limiting enzyme in the cholesterol biosynthetic pathway, and is the target of cholesterol-lowering drugs, statins. Previous studies have demonstrated that the enzyme activity is regulated by sterol-induced degradation in addition to transcriptional regulation through sterol-regulatory-element-binding
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service