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E6910

Sigma-Aldrich

Pioglitazone hydrochloride

≥98% (HPLC), powder, hepatic gluconeogenesis blocker

Synonym(s):

5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione monohydrochloride

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About This Item

Empirical Formula (Hill Notation):
C19H20N2O3S · HCl
CAS Number:
Molecular Weight:
392.90
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.77

product name

Pioglitazone hydrochloride, ≥98% (HPLC)

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Romina Lomonaco et al.
Drugs, 73(1), 1-14 (2013-01-19)
Nonalcoholic fatty liver disease (NAFLD) is considered the most common liver disorder in the Western world. It is commonly associated with insulin resistance, obesity, dyslipidaemia, type 2 diabetes mellitus (T2DM) and cardiovascular disease. Nonalcoholic steatohepatitis (NASH) is characterized by steatosis
Andrew Grey et al.
European journal of endocrinology, 170(2), 255-262 (2013-11-13)
Preclinical studies, observational studies, and clinical trials suggest that thiazolidinediones (TZDs) reduce bone mineral density (BMD) and increase fracture risk. Most of the evidence on the skeletal effects of TZDs is from studies of rosiglitazone. We set out to investigate
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
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
Julien Lamontagne et al.
Diabetes, 62(6), 2122-2129 (2013-02-05)
Our objective was to determine if the insulin-sensitizing drug pioglitazone acutely reduces insulin secretion and causes metabolic deceleration in vivo independently of change in insulin sensitivity. We assessed glucose homeostasis by hyperinsulinemic-euglycemic and hyperglycemic clamp studies and energy expenditure by

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