LAPAQUISTAT ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C33H41ClN2O9
Molecular Weight	645.14
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)COC(C)=O)C4=C2C=C(Cl)C=C4)=C1OC

InChI

InChIKey=CMLUGNQVANVZHY-POURPWNDSA-N

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

HIDE SMILES / InChI

Molecular Formula	C33H41ClN2O9
Molecular Weight	645.14
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
Synthesis of novel 4,1-benzoxazepine derivatives as squalene synthase inhibitors and their inhibition of cholesterol synthesis.	2002 Sep 26	12238936
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
Lapaquistat acetate: development of a squalene synthase inhibitor for the treatment of hypercholesterolemia.	2011 May 10	21518985

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:10:13 GMT 2023` Edited by `admin` on `Fri Dec 15 16:10:13 GMT 2023`
Record UNII	IUH3AY74O3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAPAQUISTAT ACETATE

Official Name

English

TAK-475

Code

English

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

TAK 475

Code

English

4-PIPERIDINEACETIC ACID, 1-(((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)-

Common Name

English

LAPAQUISTAT ACETATE [USAN]

Common Name

English

LAPAQUISTAT ACETATE [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29703