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Details

Stereochemistry RACEMIC
Molecular Formula C19H20N2O4S.ClH
Molecular Weight 408.899
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LERIGLITAZONE HYDROCHLORIDE

SMILES

Cl.CC(O)C1=CC=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1

InChI

InChIKey=SBHOQYCDAHAMDW-UHFFFAOYSA-N
InChI=1S/C19H20N2O4S.ClH/c1-12(22)14-4-5-15(20-11-14)8-9-25-16-6-2-13(3-7-16)10-17-18(23)21-19(24)26-17;/h2-7,11-12,17,22H,8-10H2,1H3,(H,21,23,24);1H

HIDE SMILES / InChI

Molecular Formula C19H20N2O4S
Molecular Weight 372.438
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Hydroxypioglitazone (M-IV) is an active metabolite of the peroxisome proliferator-activated receptor γ (PPARγ) agonist pioglitazone. Experiments in vitro have shown that hydroxypioglitazone was more efficient than the parent drug in stimulating lipid synthesis.

Approval Year

PubMed

PubMed

TitleDatePubMed
Synthesis and biological activity of metabolites of the antidiabetic, antihyperglycemic agent pioglitazone.
1996 Dec 20
Development and validation of highly selective and robust method for simultaneous estimation of pioglitazone, hydroxypioglitazone and metformin in human plasma by LC-MS/MS: application to a pharmacokinetic study.
2013 Jul 1
A validated liquid chromatography tandem mass spectrometry method for simultaneous determination of pioglitazone, hydroxypioglitazone, and ketopioglitazone in human plasma and its application to a clinical study.
2014 Oct 15
Substance Class Chemical
Created
by admin
on Sat Dec 16 14:28:09 UTC 2023
Edited
by admin
on Sat Dec 16 14:28:09 UTC 2023
Record UNII
WN9K42SAM6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LERIGLITAZONE HYDROCHLORIDE
USAN  
Official Name English
ALL-AMBO-5-((4-(2-(5-(1-HYDROXYETHYL)PYRIDIN-2-YL)ETHOXY)PHENYL)METHYL)-1,3-THIAZOLE-2,4(3H,5H)-DIONE HYDROCLORIDE (1:1)
Common Name English
LERIGLITAZONE HYDROCHLORIDE [USAN]
Common Name English
HYDROXYPIOGLITAZONE HYDROCHLORIDE
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(5-(1-HYDROXYETHYL)-2-PYRIDINYL)ETHOXY)PHENYL)METHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(5-(1-HYDROXYETHYL)-2-PYRIDINYL)ETHOXY)PHENYL)METHYL)-, MONOHYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/16/1770
Created by admin on Sat Dec 16 14:28:09 UTC 2023 , Edited by admin on Sat Dec 16 14:28:09 UTC 2023
Code System Code Type Description
SMS_ID
100000182338
Created by admin on Sat Dec 16 14:28:09 UTC 2023 , Edited by admin on Sat Dec 16 14:28:09 UTC 2023
PRIMARY
CAS
146062-46-6
Created by admin on Sat Dec 16 14:28:09 UTC 2023 , Edited by admin on Sat Dec 16 14:28:09 UTC 2023
PRIMARY
EVMPD
SUB196366
Created by admin on Sat Dec 16 14:28:09 UTC 2023 , Edited by admin on Sat Dec 16 14:28:09 UTC 2023
PRIMARY
PUBCHEM
86748889
Created by admin on Sat Dec 16 14:28:09 UTC 2023 , Edited by admin on Sat Dec 16 14:28:09 UTC 2023
PRIMARY
NCI_THESAURUS
C174935
Created by admin on Sat Dec 16 14:28:09 UTC 2023 , Edited by admin on Sat Dec 16 14:28:09 UTC 2023
PRIMARY
FDA UNII
WN9K42SAM6
Created by admin on Sat Dec 16 14:28:09 UTC 2023 , Edited by admin on Sat Dec 16 14:28:09 UTC 2023
PRIMARY
USAN
GH-66
Created by admin on Sat Dec 16 14:28:09 UTC 2023 , Edited by admin on Sat Dec 16 14:28:09 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY