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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 of DARGLITAZONE

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
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

Curator's Comment: # Pfizer

Approval Year

Doses

Doses

DosePopulationAdverse 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:
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:
PubMed

PubMed

TitleDatePubMed
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
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
Patents

Sample Use Guides

Non-insulin-dependent diabetes mellitus treatment: 5 mg of darglitazone was given once a day for 14 days
Route of Administration: Oral
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.
Name Type Language
DARGLITAZONE
INN  
INN  
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
Created by admin on Sat Dec 16 18:02:01 GMT 2023 , Edited by admin on Sat Dec 16 18:02:01 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL55624
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PRIMARY
EVMPD
SUB06912MIG
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NCI_THESAURUS
C75187
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MESH
C089948
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EPA CompTox
DTXSID3057644
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DRUG BANK
DB14034
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WIKIPEDIA
DARGLITAZONE
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INN
7092
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PUBCHEM
60870
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SMS_ID
100000083462
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CAS
141200-24-0
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FDA UNII
AVP9C03Z3K
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