Hydroxypioglitazone

Product NameHydroxypioglitazone
CAS146062-44-4
MFC19H20N2O4S
MW372.44
EINECS
MOL File146062-44-4.mol

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

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 (K_i = 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

Hydroxypioglitazone

Chemical Properties

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