155141-29-0 Usage
Description
Rosiglitazone maleate is a thiazolidinedione compound that belongs to a novel class of thiazolidine diones. It is primarily used as an anti-diabetic agent and acts as a potent and selective agonist of peroxisome proliferator-activated receptor-g (PPARγ). Rosiglitazone maleate has been shown to reduce fatty acid uptake, ameliorate lipid metabolism, and improve insulin resistance in animal models of type II diabetes. It also significantly improves the differentiation of C3H10T1/2 stem cells into adipocytes and has been used as an oral hypoglycemic agent in the treatment of type 2 diabetes in humans for many years.
Uses
Used in Pharmaceutical Industry:
Rosiglitazone maleate is used as an insulin sensitizer for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It helps in improving blood sugar control and reducing the exogenous dose of insulin needed to achieve glycemic control in patients with type II diabetes.
Used in Antidiabetic Drug Development:
Rosiglitazone maleate is used as a thiazole alkanes antidiabetic drug, which is part of the thiazolidinediones (TZDs) group. It acts as a potent and selective PPARγ ligand, activating PPARγ1 and PPARγ2 with EC50 values of approximately 30 nM and 100 nM, respectively. This activation helps in normalizing glucose metabolism and improving insulin sensitivity.
Used in Research and Development:
Rosiglitazone maleate is used as a reference compound for the development of new drugs targeting PPARγ. Its potent agonist activity and selectivity make it a valuable tool for studying the role of PPARγ in various diseases and for developing new therapeutic strategies.
Used in Cell Differentiation Studies:
Rosiglitazone maleate is used to promote the differentiation of C3H10T1/2 stem cells into adipocytes. This application helps in understanding the role of PPARγ in adipose tissue differentiation and its potential implications in the treatment of obesity and related metabolic disorders.
Chemical Properties:
Rosiglitazone maleate is a white to off-white solid with a Kd value of approximately 43 nM for PPARγ. It does not induce the activity of P4503A4, unlike troglitazone, and has been shown to block estrogen synthesis by interfering with androgen binding to aromatase without affecting aromatase mRNA or protein expression.
Originator
SmithKline Beecham (US)
Indications
Rosiglitazone maleate is an antihyperglycemic agent in the thiazolidinedione class. It is indicated for the treatment of patients with type 2 diabetes mellitus.
References
1) Cantello et al. (1994), [[omega-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents; J. Med. Chem., 37 3977
2) Lehmann et al. (1995) An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor gamma (PPARgamma); J. Biol. Chem., 270 12953
3) Wilson et al. (1996), The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones; J. Med. Chem., 39 665
4) Haruya et al. (2012), PPARγ agonists induce a white-to-brown fat conversion through stabilization of PRDM16 protein; Cell Metab., 15 395
5) Ruiz-Ojeda et al. (2016), Cell Models and their Application for Studying Adipogenic Differentiation in Relation to Obesity: A Review; Int. J. Mol. Sci., 17 E1040
Check Digit Verification of cas no
The CAS Registry Mumber 155141-29-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,5,1,4 and 1 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 155141-29:
(8*1)+(7*5)+(6*5)+(5*1)+(4*4)+(3*1)+(2*2)+(1*9)=110
110 % 10 = 0
So 155141-29-0 is a valid CAS Registry Number.
InChI:InChI=1/C18H19N3O3S.C4H4O4/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15;5-3(6)1-2-4(7)8/h2-9,15H,10-12H2,1H3,(H,20,22,23);1-2H,(H,5,6)(H,7,8)/b;2-1-
155141-29-0Relevant articles and documents
Process for the Preparation of Intermediates of Rosiglitazone, Rosiglitazone and New Polymorphic Forms Thereof
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Page/Page column 5-6, (2009/09/28)
The invention relates to a polymorphic form of 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzylidene)-2,4-thiazolidinedione (Formula (I)): to a process for its preparation and to the use of such compound for preparing rosiglitazone in the form of a free base or a salt thereof. The invention also relates to a polymorphic form of rosiglitazone in the form of a free base, to a process for its preparation and to the use of such polymorph for preparing a salt of rosiglitazone. The invention also relates to a process of preparing a polymorphic form of a rosiglitazone salt.
A PROCESS FOR THE CRYSTALLIZATION OF ROSIGLITAZONE AND ITS DERIVATIVES FROM MIXED SOLVENTS
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Page/Page column 20, (2008/06/13)
Crystallization of rosiglitazone of formula (I), its penultimate of formula (II), or salts with acids of formula (III), wherein HX stands for a mineral or carboxylic acid, is carried out from mixed organic solvents, consisting of mixtures of carboxylic acids, particularly formic acid, acetic acid or propionic acid, with aliphatic alcohols, particularly methanol, ethanol, 1-propanol, 2- propanol, butanols or amyl alcohols.
PROCESS
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Page/Page column 15, (2008/06/13)
The present invention relates to processes for the preparation of rosiglitazone, rosiglitazone prepared thereby and pharmaceutical compositions and therapeutic uses thereof, and methods of treatment employing the same.
