SML2168

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

Properties

• 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable