LAPAQUISTAT

Investigational

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

Molecular Formula	C31H39ClN2O8
Molecular Weight	603.103
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Lapaquistat acetate: development of a squalene synthase inhibitor for the treatment of hypercholesterolemia.	2011-05-10	21518985
Squalene synthase inhibition: a novel target for the management of dyslipidemia.	2007-01	17169251
Lipid-lowering properties of TAK-475, a squalene synthase inhibitor, in vivo and in vitro.	2003-07	12839864
Synthesis of novel 4,1-benzoxazepine derivatives as squalene synthase inhibitors and their inhibition of cholesterol synthesis.	2002-09-26	12238936

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:40:50 GMT 2025` Edited by `admin` on `Mon Mar 31 19:40:50 GMT 2025`
Record UNII	PEZ79BV72X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAPAQUISTAT

Official 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)-

Preferred Name

English

T-91485

Code

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

Classification Tree Code System Code

NCI_THESAURUS

C29703