112529-15-4 Usage
Description
[5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloride, also known as Pioglitazone hydrochloride, is an orally active thiazolidinedione (TZD) used in the treatment of type 2 diabetes mellitus (NIDDM). It is a euglycemic agent that potently activates the nuclear receptor peroxisome proliferator-activated receptor gamma, which is involved in the regulation of insulin resistance and adipogenesis. Pioglitazone hydrochloride is characterized by its colorless prisms and is considered safe and well-tolerated with a lower occurrence of hepatic toxicity and a low probability for drug interaction.
Uses
Used in Pharmaceutical Industry:
[5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloride is used as an antidiabetic agent for the treatment of type 2 diabetes mellitus. It helps improve glycemic control, demonstrates a beneficial effect on insulin resistance, and positively influences other clinically relevant parameters such as plasma levels of triglycerides or HDL-cholesterol.
Used in Research and Development:
In the field of pharmaceutical research and development, [5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloride serves as a key compound for studying the mechanisms of insulin resistance and the development of new treatments for diabetes and related metabolic disorders.
Originator
Takeda (Japan)
Therapeutic Function
Antidiabetic
Biochem/physiol Actions
Selective PPARγ agonist
References
1) Merck 14:7452
2) Sakamoto et al. (2000), Activation of human peroxisome proliferator-activated receptor (PPAR) subtypes by pioglitazone; Biochem. Biophys. Res. Commun., 278 704
3) Wilson et al. (2000), The PPARs: From Orphan Receptors to Drug Discovery; J. Med. Chem., 43 527
4) Shannon et al. (2017), Pioglitazone Inhibits Mitochondrial Pyruvate Metabolism and Glucose Production in Hepatocytes; FEBS J., 284 451
5) Zhao et al. (2016), The Antidepressant-Like Effects of Pioglitazone in a Chronic Mild Stress Mouse Model Are Associated With PPARγ-Mediated Alteration of Microglial Activation Phenotypes; Neuroinflamm., 13 259
Check Digit Verification of cas no
The CAS Registry Mumber 112529-15-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,5,2 and 9 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 112529-15:
(8*1)+(7*1)+(6*2)+(5*5)+(4*2)+(3*9)+(2*1)+(1*5)=94
94 % 10 = 4
So 112529-15-4 is a valid CAS Registry Number.
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
112529-15-4Relevant articles and documents
NOVEL PROCESS TO PREPARE PIOGLITAZONE VIA SEVERAL NOVEL INTERMEDIATES
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Page/Page column 0202-0203, (2014/04/03)
A novel process for preparing thiazolidinediones, preferably Pioglitazone, as described. Also described are novel intermediates involved in its synthesis and process for their preparation and use in medicine.
A PROCESS FOR THE PREPARATION OF 4-[2-(5-ETHYL-2-PYRIDYL)ETHOXY]NITROBENZENE AND PIOGLITAZONE
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Page/Page column 8, (2009/12/05)
A process for the preparation of 4-[2-(5-ethyl-2-pyridyi)ethoxy]nitrobenzene is described, which comprises the step of reacting 2-(5-ethyl-2-pyridyl)ethanol with 1-fluoro-4-nitrobenzene in acetone in the presence of an alkali metal hydroxide. The intermediate 4-[2-(5-ethyl-2-pyridyI)ethoxy]nitrobenzene is used for the preparation of pioglitazone.
NOVEL PROCESS FOR THE SYNTHESIS OF PIOGLITAZONE AND ITS SALTS THEREOF
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Page/Page column 7, (2009/01/20)
Present invention relates to an improved process for the preparation of thiazolidinedione derivatives. Further the invention provides the hydrogenation of acid addition salt of benzylidene compound with less reducing agent under low Hydrogen gas pressure to get substantially pure thiazolidinedione derivatives with improved yields.