pioglitazone   Click here for help

GtoPdb Ligand ID: 2694

Synonyms: Actos® | Glustin® | pioglitazone HCl | U-72107A
Approved drug
pioglitazone is an approved drug (FDA (1999), EMA (2000))
Compound class: Synthetic organic
Comment: Pioglitazone is a thiazolidinedione class antihyperglycemic drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 93.59
Molecular weight 356.12
XLogP 2.34
No. Lipinski's rules broken 0
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Canonical SMILES CCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)NC1=O
Isomeric SMILES CCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)NC1=O
InChI InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)
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Summary of Clinical Use Click here for help
Used in the treatment of type 2 diabetes.
In 2014, the EMA granted pioglitazone orphan designation for the treatment of adrenoleukodystrophy (ALD).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Agonist of peroxisome proliferator-activated receptor gamma receptor (PPARγ) in target tissues for insulin action. Activation of these receptors increases the transcription of insulin-responsive genes involved in the control of glucose production, transport and utilisation. This results in enhanced tissue sensitivity to insulin and reduced hepatic gluconeogenesis.
In ALD activation of PPARγ receptors by pioglitazone is postulated to reduce axonal degeneration by improving mitochondrial function in nerve cells [4].
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