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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, (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.
5-(4-HYDROXYBENZYL)THIAZOLIDINE-2,4-DIONE AS INTERMEDIATE FOR SYNTHESIS OF THIAZOLIDINEDIONE BASED COMPOUNDS AND PROCESS FOR PREPARING THE SAME
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Page/Page column 15; 22-23, (2009/12/28)
The present invention relates to 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by the following Chemical Formula [1], which is useful as an intermediate for synthesis of thiazolidinedione based compounds, a method for preparing the compound, and a method for preparing pioglitazone or pioglitazone hydrochloride, which is a thiazolidinedione based drug and useful in treating and preventing diabetes, using the 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by Chemical Formula [1] as an intermediate:
PROCESS FOR THE PREPARATION OF THIAZOLIDINE DERIVATIVES
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Page/Page column 13; 19, (2008/12/06)
The present invention relates to an industrially advantageous process for the preparation of thiazolidine derivatives, such as pioglitazone of formula I and its pharmaceutically acceptable salts.This invention also provides novel synthetic intermediates useful in the process for the preparation of pioglitazone.