EDAGLITAZONE

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 Search

SMILES

CC1=C(CCOC2=C3C=CSC3=C(CC4SC(=O)NC4=O)C=C2)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

Molecular Formula	C24H20N2O4S2
Molecular Weight	464.557
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12943493 | https://www.ncbi.nlm.nih.gov/pubmed/22489042 | doi: 10.2174/1568013024606440

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor gamma 118 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22489042	Agonist 2752		35.6 nM [EC50]
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22489042	Agonist 2752		1053.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: http://adisinsight.springer.com/drugs/800016463 http://en.pharmacodia.com/web/drug/1_6694.html DOI: 10.2174/1568013024606440	Primary		Phase II 1147	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087 substrate 1946	inhibitor 2438 inducer 440 substrate 1193	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 CYP2C8 1057	CYP2C19 1119 CYP2C8 810	CYP2C19 329

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	no [IC50 >100 uM]
CYP2C19 2141	inducer 1966 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	no
CYP2C9 2497	inducer 1966 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	no
CYP3A4 2633	inducer 1966 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	no
CYP1A2 2333	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	weak [IC50 125 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	yes [IC50 13 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	yes [IC50 3.1 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	yes [IC50 3.9 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	yes [IC50 5 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/	major
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/	major	yes (pharmacogenomic study) Comment: The homozygous PM/EM ratio (AUC0-24): 3.9 (healthy subjects) Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/	minor
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/	minor
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/	no

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY540286	https://www.001chemical.com/chem/213411-83-7
AA Blocks	AA0072LU	https://www.aablocks.com/goods/Goods/detail?id=AA0072LU
Acadechem	ACDC-063037	http://acadechemical.com/product/5232
Ambinter	Amb24106373	http://www.ambinter.com/reference/24106373
BioChemPartner	BCP26908	http://www.biochempartner.com/213411-83-7-BCP26908
BOC Sciences	213411-83-7	https://www.bocsci.com/edaglitazone-cas-213411-83-7-item-438790.html
ChemMol	44024156	http://www.chemmol.com/chemmol/44024156.html
ChemMol	81403586	http://www.chemmol.com/chemmol/81403586.html
DC Chemicals	DC32129	http://www.dcchemicals.com//product_show-Edaglitazone.html
Debye Scientific	DB-026273	http://www.debyesci.com/DB-026273.html
eNovation Chemicals	D676718	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676718
Finetech	FT-0714280	http://www.finetechnology-ind.com/prod/detail/pub/213411-83-7.html
iChemical	EBD2199156	http://www.ichemical.com/products/213411-83-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Molcore	MC540286	https://www.molcore.com/product/213411-83-7
MolPort	MolPort-009-684-772	https://www.molport.com/shop/molecule-link/MolPort-009-684-772
MuseChem	I006587	https://www.musechem.com/product/I006587.html
Smolecule	S526866	http://www.smolecule.com/products/s526866
Smolecule	S783852	https://www.smolecule.com/products/s783852
THE BioTek	bt-267044	https://www.thebiotek.com/product/inhibitors/bt-267044
Tocris	4784	https://www.tocris.com/products/edaglitazone_4784

PubMed

Title	Date	PubMed
Targeting peroxisome proliferator-activated receptor gamma for generation of antidiabetic drug.	2013-07	23746081
Comparative molecular profiling of the PPARα/γ activator aleglitazar: PPAR selectivity, activity and interaction with cofactors.	2012-06	22489042
Aleglitazar, a new, potent, and balanced dual PPARalpha/gamma agonist for the treatment of type II diabetes.	2009-05-01	19349176
Novel peroxisome proliferator-activated receptor ligands for Type 2 diabetes and the metabolic syndrome.	2003-09	12943493
Chronic and acute effects of thiazolidinediones BM13.1258 and BM15.2054 on rat skeletal muscle glucose metabolism.	1999-11	10578125

Patents

Sample Use Guides

In Vivo Use Guide

Rat: daily dose - 4.4 mg per kg body weight during 10 days.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:20:10 GMT 2025` Edited by `admin` on `Mon Mar 31 18:20:10 GMT 2025`
Record UNII	8GKF7V499B
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BM-131258

Preferred Name

English

EDAGLITAZONE

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

R-483

Code

English

edaglitazone [INN]

Common Name

English

Edaglitazone [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98241