CAS 111025-46-8|Pioglitazonum [INN-Latin]|pioglitazone HCl|Pioglitazone|Actos|Actost|pioglitazone|5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione|Pioglitazona [INN-Spa...

General Information

Structure

Molecular Formula

C₁₉H₂₀N₂O₃S

Molecular Mass

356.4387

Exact Mass

356.11946351

Charge

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)

InChIKey

HYAFETHFCAUJAY-UHFFFAOYSA-N

Canonic Smiles

CCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)NC1=O

Isomeric Smiles

S1C(Cc2ccc(OCCc3ncc(CC)cc3)cc2)C(=O)NC1=O

Calculated Properties

JChem

LogD (pH = 7.4)

3.23

LogD (pH = 5.5)

3.21

Log P

3.40

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.32

Polar Surface Area

68.29

Polarizability

38.35

Molar Refractivity

97.39

LOG S

-4.71

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

pioglitazone HClPioglitazonum [INN-Latin]PioglitazonePioglitazona [INN-Spanish]Pioglitazone HydrochloridePioglitazone [Ban:Inn]ActosPioglitazonepioglitazone(+-)-5-((4-(2-(5-ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione

Brand Name

ActosActostGlustin

IUPAC name

5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

IUPAC Traditional name

pioglitazone

International Nonproprietary Name (INN)

pioglitazonumpioglitazonepioglitazona

Names and Identifiers

Registration numbers

PubChem SID

4650713616096446649836649

PubChem CID

4829

CAS Number

111025-46-8

BRENDA Database

1.4.3.41.1.1.213.4.21.932.7.1.1376.2.1.32.3.1.503.4.24.351.1.1.1413.5.3.182.7.11.31

Patent number

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

MetaboLights Database

MTBLS1918MTBLS136MTBLS2267MTBLS2349MTBLS1455MTBLS2291MTBLS2825MTBLS407MTBLS1906MTBLS379

ACToR Database

111025-46-8105355-27-9

KEGG ID

C07675

SureChEMBL Database

SCHEMBL4121

PubMed Citation Links

339839681287940727842070340090303379859920797618182152323400632517628757338640973399527114522601

NURSA Database

10.1621/p5Ve2SlK4310.1621/nBNl1QIAEN10.1621/sZmbHJb4Eb10.1621/kW1GZB1BZ6

CompTox Database

DTXSID3037129

BindingDB Database

50103521

Reactom Database

R-HSA-8944104R-HSA-560517R-HSA-560493R-HSA-560491R-HSA-560472R-HSA-1183058R-HSA-560473R-HSA-381309R-HSA-560498R-HSA-1183003R-HSA-8944099R-HSA-560510

SABIO-RK Database

1496

Drug Central Database

2,179

UniProt Database

Q96B67Q9BQI4Q3ZBU2Q9NZ45O54754

KEGG DRUG Database

D08378

BKMS React Database

834436203

BRENDA Ligand Database

CHEMBL

Wikipedia Title

Chemspider ID

HMDB Database

DrugBank ID

LINCS Database

Reaxys Registry

Beilstein Number

CHEBI ID

Registration numbers

Properties

Physical Property

Solubility

mg/mL

Hydrophobicity(logP)

2.3

Product Information

Salt Data

Free Base

Safety Information

Storage Condition

-20°C

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB01132

Drug Groups

approved; investigational

Description

Pioglitazone is used for the treatment of diabetes mellitus type 2. Pioglitazone selectively stimulates nuclear receptor peroxisone proliferator-activated receptor gamma (PPAR-gamma). It modulates the transcription of the insulin-sensitive genes involved in the control of glucose and lipid metabolism in the lipidic, muscular tissues and in the liver.

Indication

Treatment of Type II diabetes mellitus

Pharmacology

Pioglitazone, a member of the drug group known as the thiazolidinediones or "insulin sensitizers", is not chemically or functionally related to the alpha-glucosidase inhibitors, the biguanides, or the sulfonylureas. Pioglitazone targets insulin resistance and, hence, is used alone or in combination with insulin, metformin, or asulfonylurea as an antidiabetic agent.

Toxicity

Hypogycemia; LD₅₀=mg/kg (orally in rat)

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Following oral administration, in the fasting state, pioglitazone is first measurable in serum within 30 minutes, with peak concentrations observed within 2 hours. Food slightly delays the time to peak serum concentration to 3 to 4 hours, but does not alter the extent of absorption.

Half Life

3-7 hours

Protein Binding

> 99%

Elimination

Following oral administration, approximately 15% to 30% of the pioglitazone dose is recovered in the urine. Renal elimination of pioglitazone is negligible, and the drug is excreted primarily as metabolites and their conjugates. It is presumed that most of the oral dose is excreted into the bile either unchanged or as metabolites and eliminated in the feces.

Distribution

* 0.63 ± 0.41 L/kg

Clearance

* apparent cl=5 - 7 L/h [oral administration]

References

• Colca JR, McDonald WG, Waldon DJ, Leone JW, Lull JM, Bannow CA, Lund ET, Mathews WR: Identification of a novel mitochondrial protein ("mitoNEET") cross-linked specifically by a thiazolidinedione photoprobe. Am J Physiol Endocrinol Metab. 2004 Feb;286(2):E252-60. Epub 2003 Oct 21. [Pubmed]

• Paddock ML, Wiley SE, Axelrod HL, Cohen AE, Roy M, Abresch EC, Capraro D, Murphy AN, Nechushtai R, Dixon JE, Jennings PA: MitoNEET is a uniquely folded 2Fe 2S outer mitochondrial membrane protein stabilized by pioglitazone. Proc Natl Acad Sci U S A. 2007 Sep 4;104(36):14342-7. Epub 2007 Aug 31. [Pubmed]

• Lincoff AM, Wolski K, Nicholls SJ, Nissen SE: Pioglitazone and risk of cardiovascular events in patients with type 2 diabetes mellitus: a meta-analysis of randomized trials. JAMA. 2007 Sep 12;298(10):1180-8. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S2590

Research Area: Metabolic Disease
Biological Activity:
Pioglitazone (Actos) is a selective peroxisome proliferator-activated receptor gamma stimulator. Pioglitazone (Actos) selectively stimulates the nuclear receptor peroxisome proliferator-activated receptor gamma (PPAR-γ) and to a lesser extent PPAR-α. Pioglitazone (Actos) modulates the transcription of the insulin-sensitive genes involved in the control of glucose and lipid metabolism in the muscle, adipose tissue, and the liver. As a result, pioglitazone (Actos) reduces insulin resistance in the liver and peripheral tissues. Pioglitazone (Actos) increases the expense of insulin-dependent glucose. Pioglitazone (Actos) decreases withdrawal of glucose from the liver. Pioglitazone (Actos) reduces quantity of glucose, insulin and glycated hemoglobin in the bloodstream. [1][2][3]References on Pioglitazone (Actos)[1] http://en.wikipedia.org/wiki/Pioglitazone, , [2] Drugs. , 2000 Aug, 60(2):333-43[3] Int J Clin Pract Suppl., 2001 Sep, (121):13-8

ChEBI

CHEBI:8228

A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.

Molecule Details

References

PubChem Literature

From Data Sources

• http://www.selleckchem.com/products/pioglitazone-actos.html

References

Bioactivity

PubChem BioAssay

Bioactivity

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Calculated Properties