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
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)
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3559683 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19116277 |
0.32 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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8517 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19116277 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
141900 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19116277 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19116277 |
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 |
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NCI_THESAURUS |
C98233
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ACTIVE MOIETY