ENGLITAZONE

Details

Stereochemistry	MIXED
Molecular Formula	C20H19NO3S
Molecular Weight	353.435
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1NC(=O)C(CC2=CC=C3O[C@@H](CC4=CC=CC=C4)CCC3=C2)S1

InChI

InChIKey=MVDXXGIBARMXSA-PYUWXLGESA-N

InChI=1S/C20H19NO3S/c22-19-18(25-20(23)21-19)12-14-6-9-17-15(10-14)7-8-16(24-17)11-13-4-2-1-3-5-13/h1-6,9-10,16,18H,7-8,11-12H2,(H,21,22,23)/t16-,18?/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H19NO3S
Molecular Weight	353.435
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	1 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800000033 | https://www.ncbi.nlm.nih.gov/pubmed/10864893 | https://www.ncbi.nlm.nih.gov/pubmed/9179397 | https://www.ncbi.nlm.nih.gov/pubmed/2210074 | https://www.ncbi.nlm.nih.gov/pubmed/8576907 | https://www.ncbi.nlm.nih.gov/pubmed/8706692

Englitazone is a thiazolidinedione antidiabetic agent. It has insulinomimetic and insulin-enhancing actions in vitro and glucose-, insulin-, triglyceride-, and cholesterol-lowering properties in an animal model of non-insulin-dependent diabetes mellitus. It acts as a peroxisome-proliferator-activated receptor-gamma ligand. Englitazone inhibits ATP-sensitive potassium and calcium-activated non-selective cation channels in a voltage-independent manner.

Originator

Approval Year

PubMed

Title	Date	PubMed
Inhibition of phosphoenolpyruvate carboxykinase (PEPCK) gene expression by troglitazone: a peroxisome proliferator-activated receptor-gamma (PPARgamma)-independent, antioxidant-related mechanism.	2001 Oct 15	11597575
Correlation between activation of PPARγ and resistin downregulation in a mouse adipocyte cell line by a series of thiazolidinediones.	2013 Aug	23563205

Patents

Sample Use Guides

In Vitro Use Guide

Application of englitazone to the outside of CRI-G1 cells in the whole-cell recording configuration produced concentration-dependent inhibition of ATP-sensitive potassium currents with an IC50 value of 8 microM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:13:33 GMT 2023` Edited by `admin` on `Fri Dec 15 16:13:33 GMT 2023`
Record UNII	ZQW5577C3O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENGLITAZONE

Official Name

English

englitazone [INN]

Common Name

English

2,4-THIAZOLIDINEDIONE, 5-((3,4-DIHYDRO-2-(PHENYLMETHYL)-2H-1-BENZOPYRAN-6-YL)METHYL)-

Systematic Name

English

(-)-5-(((2R)-2-BENZYL-6-CHROMANYL)METHYL)-2,4-THIAZOLIDINEDIONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98241