Pioglitazone hydrochlorideProduct ingredient for Pioglitazone
- Name
- Pioglitazone hydrochloride
- Drug Entry
- Pioglitazone
Pioglitazone is an antihyperglycemic used as an adjunct to diet, exercise, and other antidiabetic medications to manage type 2 diabetes mellitus.4,5,6,7 It is administered as a racemic mixture, though there is no pharmacologic difference between the enantiomers and they appear to interconvert in vivo with little consequence.4 The thiazolidinedione class of medications, which also includes rosiglitazone and troglitazone, exerts its pharmacological effect primarily by promoting insulin sensitivity and the improved uptake of blood glucose4 via agonism at the peroxisome proliferator-activated receptor-gamma (PPARγ).1 PPARs are ligand-activated transcription factors that are involved in the expression of more than 100 genes and affect numerous metabolic processes, most notably lipid and glucose homeostasis.2
Thiazolidinediones, including pioglitazone, have fallen out of favor in recent years due to the presence of multiple adverse effects and warnings regarding their use (e.g. congestive heart failure, bladder cancer) and the availability of safer and more effective alternatives for patients with type 2 diabetes mellitus.9
- Accession Number
- DBSALT000555
- Structure
- Synonyms
- Pioglitazone HCl
- UNII
- JQT35NPK6C
- CAS Number
- 112529-15-4
- Weight
- Average: 392.9
Monoisotopic: 392.096140945 - Chemical Formula
- C19H21ClN2O3S
- InChI Key
- GHUUBYQTCDQWRA-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H20N2O3S.ClH/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);1H
- IUPAC Name
- 5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-4-hydroxy-2,5-dihydro-1,3-thiazol-2-one hydrochloride
- SMILES
- Cl.CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)N=C3O)C=C2)C=C1
- External Links
- PubChem Compound
- 60560
- ChemSpider
- 54590
- ChEBI
- 8229
- ChEMBL
- CHEMBL1715
- Wikipedia
- Pioglitazone
- Predicted Properties
Property Value Source Water Solubility 0.00532 mg/mL ALOGPS logP 3.46 ALOGPS logP 2.5 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 4.02 Chemaxon pKa (Strongest Basic) 5.65 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 71.78 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 97.71 m3·mol-1 Chemaxon Polarizability 38.23 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon