General Information of Drug (ID: DMJY9CW)

Drug Name
Lapaquistat acetate
Synonyms Lapaquistat acetate (USAN); TAK-475; 1-((1-(3-Acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl)acetyl)piperidine-4-acetic acid
Indication
Disease Entry ICD 11 Status REF
Hyperlipidaemia 5C80 Discontinued in Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 645.1
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C33H41ClN2O9
IUPAC Name
2-[1-[2-[(3R,5S)-1-(3-acetyloxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-5H-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl]acetic acid
Canonical SMILES
CC(=O)OCC(C)(C)CN1C2=C(C=C(C=C2)Cl)[C@H](O[C@@H](C1=O)CC(=O)N3CCC(CC3)CC(=O)O)C4=C(C(=CC=C4)OC)OC
InChI
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
InChIKey
CMLUGNQVANVZHY-POURPWNDSA-N
Cross-matching ID
PubChem CID
9874248
CAS Number
189060-13-7
TTD ID
D02FXU

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Squalene synthetase (FDFT1) TTFQEO5 FDFT_HUMAN Inhibitor [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Hyperlipidaemia
ICD Disease Classification 5C80
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Squalene synthetase (FDFT1) DTT FDFT1 7.85E-01 -0.09 -0.38
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00532558) Efficacy of Lapaquistat Acetate on Blood Cholesterol Levels in Treating Subjects With Hypercholesterolemia. U.S. National Institutes of Health.
2 Lapaquistat acetate, a squalene synthase inhibitor, changes macrophage/lipid-rich coronary plaques of hypercholesterolaemic rabbits into fibrous le... Br J Pharmacol. 2008 Jul;154(5):949-57.