DARGLITAZONE SODIUM

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H19N2O4S.Na
Molecular Weight	442.463
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[Na+].CC1=C(CCC(=O)C2=CC=C(CC3SC(=O)[N-]C3=O)C=C2)N=C(O1)C4=CC=CC=C4

InChI

InChIKey=AMCPCELVARAPHJ-UHFFFAOYSA-M

InChI=1S/C23H20N2O4S.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C23H20N2O4S
Molecular Weight	420.481
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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 118	Agonist 2,752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diabetes mellitus 93	Primary		Phase I 438	Unknown

Doses

Doses

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Dose	Population	Adverse events
25 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT

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Sourcing

Sourcing

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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
BioChemPartner	BCP30326	http://www.biochempartner.com/141200-24-0-BCP30326
BLD Pharm	BD01141074	http://www.bldpharm.com/products/141200-24-0.html

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PubMed

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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

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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.