DARGLITAZONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H20N2O4S
Molecular Weight	420.481
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(CCC(=O)C2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C(O1)C4=CC=CC=C4

InChI

InChIKey=QQKNSPHAFATFNQ-UHFFFAOYSA-N

InChI=1S/C23H20N2O4S/c1-14-18(24-22(29-14)17-5-3-2-4-6-17)11-12-19(26)16-9-7-15(8-10-16)13-20-21(27)25-23(28)30-20/h2-10,20H,11-13H2,1H3,(H,25,27,28)

HIDE SMILES / InChI

Molecular Formula	C23H20N2O4S
Molecular Weight	420.481
Charge	0
Count

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

Description
Sources: http://www.ourmed.org/wiki/Darglitazone | http://adisinsight.springer.com/drugs/800003002

Darglitazone is a member of the thiazolidinedione class of drugs and an agonist of peroxisome proliferator-activated receptor-γ (PPAR-γ), an orphan member of the nuclear receptor superfamily of transcription factors. It has a variety of insulin-sensitizing effects, such as improving glycemic and lipidemic control, and is used in the treatment of metabolic disorders such as type II diabetes. Darglitazone sodium had been in phase I clinical trials by Pfizer for the treatment of type 2 diabetes. However, this study has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: http://www.sigmaaldrich.com/catalog/product/sigma/sml0977?lang=en®ion=RU \| http://adisinsight.springer.com/drugs/800003002 \| http://www.ourmed.org/wiki/Darglitazone	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8582540 http://adisinsight.springer.com/drugs/800003002	Primary		Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
25 mg 1 times / day multiple, oral Studied dose Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8582540	unhealthy, ADULT n = 9 Health Status: unhealthy Condition: non-insulin-dependent diabetes mellitus Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/8582540	Sources: https://pubmed.ncbi.nlm.nih.gov/8582540

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY522107	https://www.001chemical.com/chem/141200-24-0
AA Blocks	AA00AEUI	https://www.aablocks.com/goods/Goods/detail?id=AA00AEUI
Aurora Fine Chemicals LLC	A24.145.171	http://online.aurorafinechemicals.com/info?ID=A24.145.171
BLD Pharm	BD01141074	http://www.bldpharm.com/products/141200-24-0.html
BOC Sciences	141200-24-0	https://www.bocsci.com/5-4-3-5-methyl-2-phenyl-1-3-oxazol-4-yl-propanoyl-phenyl-methyl-1-3-thiazolidine-2-4-dione-cas-141200-24-0-item-272827.html
BioChemPartner	BCP30326	http://www.biochempartner.com/141200-24-0-BCP30326
ChemMol	99043893	http://www.chemmol.com/chemmol/99043893.html
Chemspace	CSSB00020677381	https://chem-space.com/CSSB00020677381
Clearsynth	CS-T-73589	https://www.clearsynth.com/en/CST73589.html
Lab Network	LN01327258	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01327258
MolPort	MolPort-039-032-921	https://www.molport.com/shop/molecule-link/MolPort-039-032-921
Molcore	MC522107	https://www.molcore.com/product/141200-24-0
MuseChem	R029153	https://www.musechem.com/product/R029153.html
Smolecule	S525036	http://www.smolecule.com/products/s525036
Smolecule	S773318	https://www.smolecule.com/products/s773318
THE BioTek	bt-264511	https://www.thebiotek.com/product/inhibitors/bt-264511
THE BioTek	bt-290811	https://www.thebiotek.com/product/others/bt-290811
eNovation Chemicals	D675444	https://www.enovationchem.com/ProductDetails.asp?ProductID=D675444

PubMed

Title	Date	PubMed
Regulation of uncoupling protein-2 mRNA in L6 myotubules: II: Thyroid hormone amplifies stimulation of uncoupling protein-2 gene by thiazolidinediones and other peroxisome proliferator-activated receptor ligands in L6 myotubules: evidence for a priming effect.	2002 Nov	12588052
Discovery of a series of imidazo[4,5-b]pyridines with dual activity at angiotensin II type 1 receptor and peroxisome proliferator-activated receptor-γ.	2011 Jun 23	21557540

Patents

Sample Use Guides

In Vivo Use Guide

Non-insulin-dependent diabetes mellitus treatment: 5 mg of darglitazone was given once a day for 14 days

Route of Administration: Oral

In Vitro Use Guide

Darglitazone (1 uM) gave a robust increase (4-fold) in the steady-state LXR mRNA levels in treated fully differentiated 3T3-L1 adipocytes relative to untreated cells.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:02:01 GMT 2023` Edited by `admin` on `Sat Dec 16 18:02:01 GMT 2023`
Record UNII	AVP9C03Z3K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DARGLITAZONE

Official Name

English

CP-86325

Code

English

CP-86325-2 FREE ACID

Code

English

darglitazone [INN]

Common Name

English

2,4-THIAZOLIDINEDIONE, 5-((4-(3-(5-METHYL-2-PHENYL-4-OXAZOLYL)-1-OXOPROPYL)PHENYL)METHYL)-, (±)-

Systematic Name

English

(±)-5-(P-(3-(5-METHYL-2-PHENYL-4-OXAZOLYL)PROPIONYL)BENZYL)-2,4-THIAZOLIDINEDIONE

Common Name

English

2,4-THIAZOLIDINEDIONE, 5-((4-(3-(5-METHYL-2-PHENYL-4-OXAZOLYL)-1-OXOPROPYL)PHENYL)METHYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98241