LAPAQUISTAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H39ClN2O8
Molecular Weight	603.103
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=CC([C@H]2O[C@H](CC(=O)N3CCC(CC(O)=O)CC3)C(=O)N(CC(C)(C)CO)C4=C2C=C(Cl)C=C4)=C1OC

InChI

InChIKey=HDGUKVZPMPJBFK-LEAFIULHSA-N

InChI=1S/C31H39ClN2O8/c1-31(2,18-35)17-34-23-9-8-20(32)15-22(23)28(21-6-5-7-24(40-3)29(21)41-4)42-25(30(34)39)16-26(36)33-12-10-19(11-13-33)14-27(37)38/h5-9,15,19,25,28,35H,10-14,16-18H2,1-4H3,(H,37,38)/t25-,28-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67466644 | https://www.ncbi.nlm.nih.gov/pubmed/17169251 | https://adisinsight.springer.com/drugs/800017366

LAPAQUISTAT is a squalene synthase inhibitor. It was shown to lower cholesterol levels in several animal models. It was investigated for the treatment of diabetes and hypercholesterolemia, however, its development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Lipid-lowering properties of TAK-475, a squalene synthase inhibitor, in vivo and in vitro.	2003 Jul	12839864
Squalene synthase inhibition: a novel target for the management of dyslipidemia.	2007 Jan	17169251

Patents

Name

Type

Language

LAPAQUISTAT

Official Name

English

2-(1-(2-((3R,5S)-1-(3-HYDROXY-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

Systematic Name

English

lapaquistat [INN]

Common Name

English

4-PIPERIDINEACETIC ACID, 1-(((3R,5S)-1-(3-(HYDROXY)-2,2-DIMETHYLPROPYL)-7-CHLORO-5-(2,3-DIMETHOXYPHENYL)-1,2,3,5-TETRAHYDRO-2-OXO-4,1-BENZOXAZEPIN-3-YL)ACETYL)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29703