Basic information Safety Supplier Related

Hydroxypioglitazone

Basic information Safety Supplier Related

Hydroxypioglitazone Basic information

Product Name:
Hydroxypioglitazone
Synonyms:
  • HYDROXYPIOGLITAZONE
  • Hydroxy Pioglitazone (M-IV)
  • 5-[[4-[2-[5-(1-HYDROXYETHYL)-2-PYRIDINYL]ETHOXY] PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE
  • Pioglitazone, hydroxy M-IV
  • Pioglitazone Impurity 18
  • Hydroxy Pioglitazone Solution, 100ppm
  • Pioglitazone M4 Metabolite
  • Leriglitazone
CAS:
146062-44-4
MF:
C19H20N2O4S
MW:
372.44
Product Categories:
  • Sulfur & Selenium Compounds
  • Various Metabolites and Impurities
  • Intermediates & Fine Chemicals
  • Metabolites & Impurities
  • Pharmaceuticals
Mol File:
146062-44-4.mol
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Hydroxypioglitazone Chemical Properties

Melting point:
157-1580C
Boiling point:
627.6±55.0 °C(Predicted)
Density 
1.325±0.06 g/cm3(Predicted)
storage temp. 
-20°C Freezer, Under Inert Atmosphere
solubility 
DMSO (Slightly), Methanol (Slightly, Sonicated)
pka
6.35±0.50(Predicted)
form 
Solid
color 
White to Off-White
Stability:
Hygroscopic
CAS DataBase Reference
146062-44-4
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Hydroxypioglitazone Usage And Synthesis

Description

Hydroxy pioglitazone is a major metabolite of the peroxisome proliferator-activated receptor γ (PPARγ) agonist pioglitazone (Item Nos. 71745 | 22263 | 10028). It is formed from pioglitazone by the cytochrome P450 (CYP) isoform CYP2C8 with minor contributions from CYP3A4. Hydroxy pioglitazone binds to PPARγ (Ki = 1.2 μM) and activates PPARγ in a time-resolved FRET (TR-FRET) assay (EC50 = 2.1 μM).

Chemical Properties

Off-White Solid

Uses

A metabolite of Pioglitazone (P471000).

Definition

ChEBI: Hydroxypioglitazone is a member of the class of thiazolidenediones that is the hydroxy derivative of pioglitazone. It has a role as a human xenobiotic metabolite. It is a member of thiazolidinediones, a member of pyridines and an aromatic ether. It is functionally related to a pioglitazone.

in vivo

Leriglitazone (50 mg/kg; Feed administration; 8 months) improves motor impairment in a Friedreich ataxia mouse model[2].
Leriglitazone (75 mg/kg; Feed administration; 7 months) has an improved effect in Rett mouse model[3].

Animal Model:YG8sR mice[2]
Dosage:50 mg/kg
Administration:Feed administration; 8 months
Result:Did not change the weight gain of YG8sR mice.
Improved the performance of the YG8sR mice in the case of the balance beam test.
Animal Model:Rett female mice[3]
Dosage:75 mg/kg
Administration:Feed administration; 7 months
Result:Corrected the defect of ATP concentration and lipid peroxidation in hippocampus and cerebellum.
Reduce the level of 8-OHdG, ROS, MnSOD and GPX.
Improved overall health and exploratory behavior in mice.

IC 50

PPAR-γ: 9 μM (EC50)

References

[1] SARAHA. MOSURE. Structural Basis of Altered Potency and Efficacy Displayed by a Major in Vivo Metabolite of the Antidiabetic PPARγ Drug Pioglitazone[J]. Journal of Medicinal Chemistry, 2019, 62 4: 2008-2023. DOI: 10.1021/acs.jmedchem.8b01573
[2] TIINA JAAKKOLA. Effect of rifampicin on the pharmacokinetics of pioglitazone[J]. British journal of clinical pharmacology, 2005, 61 1: 70-78. DOI: 10.1111/j.1365-2125.2005.02515.x

HydroxypioglitazoneSupplier

J & K SCIENTIFIC LTD.
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020-81960175
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