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E6910

Sigma-Aldrich

Pioglitazone hydrochloride

≥98% (HPLC)

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Synonym(s):
5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione monohydrochloride
Empirical Formula (Hill Notation):
C19H20N2O3S · HCl
CAS Number:
112529-15-4
Molecular Weight:
392.90
MDL number:
MFCD04975446
UNSPSC Code:
41106305
PubChem Substance ID:
329799001
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥10 mg/mL

originator

Takeda

storage temp.

room temp

SMILES string

Cl.CCc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1

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

InChI key

GHUUBYQTCDQWRA-UHFFFAOYSA-N

Gene Information

human ... PPARG(5468)

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General description

Pioglitazone hydrochloride consists of poly-morphs, form I and form II. It is an oral antidiabetic agent, that is a member of the thiazolidinedione group.

Application

Pioglitazone hydrochloride has been used:
  • to administer to mice model and treated the hepatoma cell line to study its effect on regulating insulin-degrading enzyme (IDE) in diet-induced obese (DIO) C57BL/6 mice
  • in drug preparation to analyze its effects on shortening and calcium transport in ventricular myocytes from the Goto-Kakizaki (GK) type 2 diabetic rat
  • to treat HepG2 cells with peroxisome proliferator-activated receptor γ (PPARγ) agonists to examine its effect on TOMM40-, APOE- and APOC1-mRNA levels

Biochem/physiol Actions

Pioglitazone hydrochloride is a PPARγ agonist and thiazolidinedione (TZD) anti-diabetic. Pioglitazone is a selective agonist of the nuclear receptor peroxisome proliferator-activated receptor γ (PPAR-γ) and to a lesser extent PPAR-α.
Pioglitazone hydrochloride is usually used to treat type-II diabetes. It has the ability to block hepatic gluconeogenesis.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the AMPKs and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Takeda. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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J R Colca et al.
Clinical pharmacology and therapeutics, 93(4), 352-359 (2013-03-07)
It may be possible to achieve insulin sensitivity through the recently identified mitochondrial target of thiazolidinediones (mTOT), thereby avoiding peroxisome proliferator-activated receptor-γ (PPAR-γ)-dependent side effects. In this phase IIb clinical trial, 258 patients with type 2 diabetes completed a 12-week
Peter Ochodnicky et al.
European journal of pharmacology, 730, 51-60 (2014-03-04)
Peroxisome proliferator-activated receptor γ (PPARγ) agonists have been shown to ameliorate diabetic nephropathy, but much less are known about their effects in non-diabetic nephropathies. In the present study, metabolic parameters, blood pressure, aortic endothelial function along with molecular and structural
Regulation of insulin-degrading enzyme activity by obesity-associated factors and pioglitazone in liver of diet-induced obese mice
Wei X, et al.
PLoS ONE, 9(4), e95399-e95399 (2014)
The effects of PPAR gamma on the regulation of the TOMM40-APOE-C1 genes cluster
Subramanian S, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1863(3), 810-816 (2017)
Chin-Hsiao Tseng
Gynecologic oncology, 131(1), 135-139 (2013-07-24)
The association between pioglitazone and ovarian cancer has not been studied. The reimbursement databases of all Taiwanese patients with a diagnosis of diabetes and under oral anti-diabetic agents or insulin from 1996 to 2009 were retrieved from the National Health
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