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
PubChem Compound
60560
ChemSpider
54590
ChEBI
8229
ChEMBL
CHEMBL1715
Wikipedia
Pioglitazone
Predicted Properties
PropertyValueSource
Water Solubility0.00532 mg/mLALOGPS
logP3.46ALOGPS
logP2.5ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)5.65ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.78 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.71 m3·mol-1ChemAxon
Polarizability38.23 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon