112529-15-4 Usage
Description
Pioglitazone is a new orally active thiazolidinedione (TZD) launched in the US for the treatment of non-insulin dependent diabetes mellitus
(NIDDM). It can be synthesized in 4 steps, the last one transforming an alphabromoester
into thiazolidine with thiourea. As with other representatives in this
class, it potently activates the nuclear receptor peroxisome proliferator-activated
receptor gamma which is believed to be involved in the regulation of insulin
resistance and adipogenesis. In several obese and obese diabetic animal
models, treatment with Pioglitazone resulted in reductions in plasma glucose
and serum lipids. In clinical studies, Pioglitazone at a once daily oral dose of 15-45 mg, as monotherapy or in combination with non-TZDs or insulin, was shown
to significantly improve glycemic control in type-2 diabetes and demonstrated a
beneficial effect on insulin resistance and other clinically relevant parameters as
plasma levels of triglycerides or HDL-cholesterol. Pioglitazone is reported to be
safe and well tolerated and is said to have a lower occurrence of hepatic toxicity
as well as a low probability for drug interaction.
Chemical Properties
Colourless Prisms
Originator
Takeda (Japan)
Uses
Different sources of media describe the Uses of 112529-15-4 differently. You can refer to the following data:
1. euglycemic agent
2. Pioglitazone Hydrochloride is used as an antidiabetic.
3. Pioglitazone hydrochloride is a euglycemic agent,used as an antidiabetic.
Therapeutic Function
Antidiabetic
General Description
Pioglitazone hydrochloride is an oral antidiabetic agent used in the treatment of type 2 diabetes mellitus (also known as non-insulin-dependent diabetes mellitus (NIDDM) or adult-onset diabetes.
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
-
, (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; 18-19, (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.