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Details

Stereochemistry RACEMIC
Molecular Formula C24H20N2O4S2
Molecular Weight 464.557
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EDAGLITAZONE

SMILES

CC1=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C4=C2C=CS4)N=C(O1)C5=CC=CC=C5

InChI

InChIKey=HAAXAFNSRADSMK-UHFFFAOYSA-N
InChI=1S/C24H20N2O4S2/c1-14-18(25-23(30-14)15-5-3-2-4-6-15)9-11-29-19-8-7-16(21-17(19)10-12-31-21)13-20-22(27)26-24(28)32-20/h2-8,10,12,20H,9,11,13H2,1H3,(H,26,27,28)

HIDE SMILES / InChI
Edaglitazone have a clear PPAR-gamma agonist profile, with predominant PPAR-gamma activity and little PPAR-alpha activity. Edaglitazone was reported to significantly improve insulin sensitivity and enhance the rate of glucose oxidation in both the presence and absence of insulin. Additional studies have shown that edaglitazone affects muscle glucose metabolism by additional mechanisms other than PPAR-gamma activation. Phase I clinical studies have revealed that edaglitazone is well-tolerated and capable of significantly improving glucose homeostasis. Edaglitazone had been in phase II clinical trials for the treatment if type 2 diabetes. However, this research has been discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
35.6 nM [EC50]
1053.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
major
yes (pharmacogenomic study)
Comment: The homozygous PM/EM ratio (AUC0-24): 3.9 (healthy subjects)
minor
minor
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Chronic and acute effects of thiazolidinediones BM13.1258 and BM15.2054 on rat skeletal muscle glucose metabolism.
1999 Nov
Novel peroxisome proliferator-activated receptor ligands for Type 2 diabetes and the metabolic syndrome.
2003 Sep
Aleglitazar, a new, potent, and balanced dual PPARalpha/gamma agonist for the treatment of type II diabetes.
2009 May 1
Comparative molecular profiling of the PPARα/γ activator aleglitazar: PPAR selectivity, activity and interaction with cofactors.
2012 Jun
Patents

Sample Use Guides

Rat: daily dose - 4.4 mg per kg body weight during 10 days.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
EDAGLITAZONE
INN  
INN  
Official Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(5-METHYL-2-PHENYL-4-OXAZOLYL)ETHOXY)BENZO(B)THIEN-7-YL)METHYL)-
Systematic Name English
BM-131258
Code English
R-483
Code English
edaglitazone [INN]
Common Name English
Edaglitazone [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C98241
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
Code System Code Type Description
CAS
213411-83-7
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL2111091
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY
PUBCHEM
9825701
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY
INN
8393
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY
DRUG BANK
DB06519
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID00870240
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY
SMS_ID
300000034258
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY
CAS
869997-64-8
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
SUPERSEDED
NCI_THESAURUS
C75189
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY
FDA UNII
8GKF7V499B
Created by admin on Fri Dec 15 16:08:49 GMT 2023 , Edited by admin on Fri Dec 15 16:08:49 GMT 2023
PRIMARY