Hydroxy Pioglitazone

Names

[ Name ]:
Hydroxy Pioglitazone

[Synonym ]:
5-(4-{2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione
5-(4-{2-[5-(1-Hydroxyethyl)-2-pyridinyl]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione
2,4-Thiazolidinedione, 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-
5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
Pioglitazone Impurity 18

Biological Activity

[Description]:

Leriglitazone (Hydroxypioglitazone), a metabolite of pioglitazone.Leriglitazone (Hydroxypioglitazone) PioOH is a PPARγ agonist, stabilizes the PPARγ activation function-2 (AF-2) co-activator binding surface and enhances co-activator binding, affording slightly better transcriptional efficacy.Leriglitazone (Hydroxypioglitazone) binds to the PPARγ C-terminal ligand-binding domain (LBD) with Ki of 1.2 μM，induces transcriptional efficacy of the PPARγ (LBD) with EC50 of 680 nM[1].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR

Research Areas >> Metabolic Disease

[Target]

Ki: 1.2 μM (PPARγ LBD); EC: 680 nM (PPARγ LBD) (Leriglitazone)[1]

[References]

[1]. Mosure SA,et al. Structural Basis of Altered Potency and Efficacy Displayed by a Major in Vivo Metabolite of the Antidiabetic PPARγ Drug Pioglitazone. J Med Chem. 2019 Feb 28;62(4):2008-2023.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
627.6±55.0 °C at 760 mmHg

[ Melting Point ]:
157-158ºC

[ Molecular Formula ]:
C₁₉H₂₀N₂O₄S

[ Molecular Weight ]:
372.438

[ Flash Point ]:
333.4±31.5 °C

[ Exact Mass ]:
372.114380

[ PSA ]:
113.82000

[ LogP ]:
1.11

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.628

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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