EDAGLITAZONE, (-)-

Details

Stereochemistry	UNKNOWN
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=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

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 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22489042	Agonist 2678		35.6 nM [EC50]
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22489042	Agonist 2678		1053.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: http://adisinsight.springer.com/drugs/800016463 http://en.pharmacodia.com/web/drug/1_6694.html DOI: 10.2174/1568013024606440	Primary		Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 inducer 781 substrate 1737	inhibitor 1767 inducer 389 substrate 1037	inhibitor 1852 substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1478 CYP1A2 1524 CYP2C8 911	CYP2C19 991 CYP2C8 693	CYP2C19 293

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1891	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	no [IC50 >>100 uM]
CYP2C19 1553	inducer 1573 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	no
CYP2C9 1819	inducer 1573 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	no
CYP3A4 1925	inducer 1573 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	no
CYP1A2 1692	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	weak [IC50 125 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	yes [IC50 13 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	yes [IC50 3.1 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2004.12.173	yes [IC50 3.9 uM]
CYP2C8 965	inhibitor 3277 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 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/	major
CYP2C19 991	substrate 3367 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 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/	minor
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20549497/	minor
CYP2D6 1217	substrate 3367 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
BOC Sciences	213411-83-7	https://www.bocsci.com/edaglitazone-cas-213411-83-7-item-438790.html
BioChemPartner	BCP26908	http://www.biochempartner.com/213411-83-7-BCP26908
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
Finetech	FT-0714280	http://www.finetechnology-ind.com/prod/detail/pub/213411-83-7.html
MolPort	MolPort-009-684-772	https://www.molport.com/shop/molecule-link/MolPort-009-684-772
Molcore	MC540286	https://www.molcore.com/product/213411-83-7
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
eNovation Chemicals	D676718	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676718
iChemical	EBD2199156	http://www.ichemical.com/products/213411-83-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Aleglitazar, a new, potent, and balanced dual PPARalpha/gamma agonist for the treatment of type II diabetes.	2009 May 1	19349176
Comparative molecular profiling of the PPARα/γ activator aleglitazar: PPAR selectivity, activity and interaction with cofactors.	2012 Jun	22489042

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 `Sat Dec 16 10:25:54 GMT 2023` Edited by `admin` on `Sat Dec 16 10:25:54 GMT 2023`
Record UNII	59LQZ96XUU
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EDAGLITAZONE, (-)-

Common Name

English

(-)-5-((4-(2-(5-METHYL-2-PHENYL-4-OXAZOLYL)ETHOXY)BENZO(B)THIEN-7-YL)METHYL)-2,4-THIAZOLIDINEDIONE

Systematic Name

English

2,4-THIAZOLIDINEDIONE, 5-((4-(2-(5-METHYL-2-PHENYL-4-OXAZOLYL)ETHOXY)BENZO(B)THIEN-7-YL)METHYL)-, (-)-

Systematic Name

English

Code System Code Type Description

PUBCHEM

9825701

Created by admin on Sat Dec 16 10:25:54 GMT 2023 , Edited by admin on Sat Dec 16 10:25:54 GMT 2023

PRIMARY

CAS

892128-35-7

Created by admin on Sat Dec 16 10:25:54 GMT 2023 , Edited by admin on Sat Dec 16 10:25:54 GMT 2023

PRIMARY

FDA UNII

59LQZ96XUU

Created by admin on Sat Dec 16 10:25:54 GMT 2023 , Edited by admin on Sat Dec 16 10:25:54 GMT 2023

PRIMARY

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

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

Drug as perpetrator