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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

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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

Squalene synthase inhibitor
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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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
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
Douglas E Biancur et al.
Cell metabolism, 33(1), 199-210 (2020-11-06)
Pancreatic ductal adenocarcinoma (PDA) is a deadly cancer characterized by complex metabolic adaptations that promote survival in a severely hypoxic and nutrient-limited tumor microenvironment (TME). Modeling microenvironmental influences in cell culture has been challenging, and technical limitations have hampered the

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