146062-44-4 Usage
Description
Hydroxypioglitazone, a metabolite of Pioglitazone, is a significant derivative of the peroxisome proliferator-activated receptor γ (PPARγ) agonist pioglitazone. It is synthesized from pioglitazone through the action of cytochrome P450 (CYP) isoform CYP2C8, with minor contributions from CYP3A4. This off-white solid possesses the ability to bind to PPARγ (Ki = 1.2 μM) and activate it, as demonstrated in a time-resolved FRET (TR-FRET) assay (EC50 = 2.1 μM).
Uses
Used in Pharmaceutical Industry:
Hydroxypioglitazone is used as a therapeutic agent for the treatment of type 2 diabetes. As a PPARγ agonist, it helps regulate glucose homeostasis and improve insulin sensitivity, making it a valuable compound in the management of diabetes and related metabolic disorders.
Used in Research Applications:
In the field of medical research, Hydroxypioglitazone serves as an important tool for studying the role of PPARγ in various biological processes. Its activation of PPARγ makes it useful in investigating the molecular mechanisms underlying diabetes, obesity, and other metabolic diseases, as well as potential applications in drug discovery and development.
Used in Drug Development:
Hydroxypioglitazone is utilized in the development of novel drugs targeting PPARγ, which may have potential applications in treating not only diabetes but also other conditions related to metabolic dysfunction. Its understanding of PPARγ activation can guide the design of more effective and targeted therapies for a range of diseases.
Check Digit Verification of cas no
The CAS Registry Mumber 146062-44-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,6,0,6 and 2 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 146062-44:
(8*1)+(7*4)+(6*6)+(5*0)+(4*6)+(3*2)+(2*4)+(1*4)=114
114 % 10 = 4
So 146062-44-4 is a valid CAS Registry Number.
InChI:InChI=1/C19H20N2O4S/c1-12(22)14-4-5-15(20-11-14)8-9-25-16-6-2-13(3-7-16)10-17-18(23)21-19(24)26-17/h2-7,11-12,17,22H,8-10H2,1H3,(H,21,23,24)
146062-44-4Relevant articles and documents
PROCESS FOR PREPARING 5-[[4-[2-[5-(1-HYDROXYETHYL)-2-PYRIDINYL]ETHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE AND SALTS THEREOF
-
, (2018/07/29)
The disclosure provides a process of making the compound of Formula I, and pharmaceutically acceptable salts thereof: and the process of making the intermediate of Formula III: wherein PG is as defined as set forth in the specification.
Synthesis and biological activity of metabolites of the antidiabetic, antihyperglycemic agent pioglitazone
Tanis, Steven P.,Parker, Timothy T.,Colca, Jerry R.,Fisher, Roberta M.,Kletzein, Rolf F.
, p. 5053 - 5063 (2007/10/03)
Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4- thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible clinical development. Metabolites 6-9 have been identified after dosing of rats and dogs. Ketone 10 has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 6-9 and the putative metabolite ketone 10. These entities have been compared in the KKA(y) mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in vivo assay. When 6-10 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9 roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).
Thiazolidinedione derivatives, production and use thereof
-
, (2008/06/13)
A thiazolidinedione compound of the formula STR1 wherein X,Q are as defined in the specification. The compounds are used for treating diabetes.
