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Details

Stereochemistry ACHIRAL
Molecular Formula C19H19NO6S
Molecular Weight 389.422
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDEGLITAZAR

SMILES

COC1=CC=C(C=C1)S(=O)(=O)N2C=C(CCC(O)=O)C3=CC(OC)=CC=C23

InChI

InChIKey=YMPALHOKRBVHOJ-UHFFFAOYSA-N
InChI=1S/C19H19NO6S/c1-25-14-4-7-16(8-5-14)27(23,24)20-12-13(3-10-19(21)22)17-11-15(26-2)6-9-18(17)20/h4-9,11-12H,3,10H2,1-2H3,(H,21,22)

HIDE SMILES / InChI

Molecular Formula C19H19NO6S
Molecular Weight 389.422
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Indeglitazar is orally available peroxisome proliferator-activated receptor (PPAR) pan-agonist for all three PPAR subtypes alpha (α), delta (δ) and gamma patented by Plexxikon, Inc for metabolic disorders treatment. Indeglitazar is a full agonist of PPAR alpha but only a partial agonist of PPAR gamma and delta; this may provide a better side effect profile than full activators. The molecule shows impressive pharmaceutical properties (high oral bioavailability, the long half-life, etc.) as well as promising activity in mouse and rat models of diabetes (lower blood glucose, insulin, total cholesterol, triglycerides, free fatty acids, etc.). In contrast to other PPAR agonists, which sometimes cause weight gain, Indeglitazar also caused weight loss in rodent and primate models. Although Indeglitazar was advanced to phase 2 trials in collaboration with Wyeth, increasing concerns over the potential side effects of PPAR agonists have caused Wyeth to discontinue development of this compound

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.32 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8517 ng/mL
4 mg/kg single, oral
dose: 4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDEGLITAZAR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
141900 ng × h/mL
4 mg/kg single, oral
dose: 4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDEGLITAZAR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
21.3 h
4 mg/kg single, oral
dose: 4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDEGLITAZAR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
4 mg/kg single, oral
Highest studied dose
Dose: 4 mg/kg
Route: oral
Route: single
Dose: 4 mg/kg
Sources: Page: p.264
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: unknown
Food Status: FASTED
Sources: Page: p.264
PubMed

PubMed

TitleDatePubMed
Scaffold-based discovery of indeglitazar, a PPAR pan-active anti-diabetic agent.
2009 Jan 6
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:34:28 UTC 2023
Edited
by admin
on Fri Dec 15 15:34:28 UTC 2023
Record UNII
JMC809G4ZH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDEGLITAZAR
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
3-{5-Methoxy-1-[(4-methoxyphenyl)sulfonyl]-1H-indol-3-yl}propanoic acid
Systematic Name English
indeglitazar [INN]
Common Name English
INDEGLITAZAR [USAN]
Common Name English
Indeglitazar [WHO-DD]
Common Name English
PPM-204
Code English
Classification Tree Code System Code
NCI_THESAURUS C98233
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
Code System Code Type Description
CAS
835619-41-5
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
INN
9015
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
FDA UNII
JMC809G4ZH
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL1232583
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
USAN
TT-26
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
DRUG BANK
DB07724
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
NCI_THESAURUS
C98153
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
PUBCHEM
11395145
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
SMS_ID
300000034228
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID301003567
Created by admin on Fri Dec 15 15:34:28 UTC 2023 , Edited by admin on Fri Dec 15 15:34:28 UTC 2023
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
TARGET->PARTIAL AGONIST
TARGET -> AGONIST
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ACTIVE MOIETY