Rosiglitazone

Rosiglitazone Basic information
Description References
Product Name:Rosiglitazone
Synonyms:5-(4-[2-(METHYL-PYRIDIN-2-YL-AMINO)-ETHOXY]-BENZYL)-THIAZOLIDINE-2,4-DIONE;5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]-phenyl]methyl]-2,4-thiazolidine-dione;ROSIGLITAZONE;Rosiglitazone free base;Rosiglitazone and its intermediates;ROSIGLITAZONE 99%;RosiglitazoneBase/Hcl/Maleate;5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzylidine]-2,4-thiazolidinedione
CAS:122320-73-4
MF:C18H19N3O3S
MW:357.43
EINECS:924-121-1
Product Categories:AVANDIA;Inhibitor;Rosiglitazone;API's;Active Pharmaceutical Ingredients
Mol File:122320-73-4.mol
Rosiglitazone Structure
Rosiglitazone Chemical Properties
Melting point 153-155 C
Boiling point 585.0±35.0 °C(Predicted)
density 1.315±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: ≥10mg/mL
pka6.34±0.50(Predicted)
form powder
color White to Off-White
Merck 14,8265
CAS DataBase Reference122320-73-4(CAS DataBase Reference)
IARC3 (Vol. 108) 2016
Safety Information
Hazard Codes Xi
Risk Statements 36/38
Safety Statements 26-37/39
WGK Germany 3
RTECS XJ5813850
HS Code 2934100000
Hazardous Substances Data122320-73-4(Hazardous Substances Data)
MSDS Information
Rosiglitazone Usage And Synthesis
DescriptionRosiglitazone is a type of thiazolidinedione antidiabetics. Thiazolidinedione are agonists for peroxisome-proliferator–activated receptor γ (PPAR-γ). PPAR-γ receptors are ligand-activated nuclear transcription factors that modulate gene expression, lowering blood glucose primarily by increasing insulin sensitivity in peripheral tissues.
Rosiglitazone is widely used to lower blood glucose levels in patients with type 2 diabetes mellitus. Rosiglitazone functionalizes by makes the cells of the body more sensitive to the naturally produced insulin in body. It shouldn’t be used if the patient is injecting or inhaling insulin. Using rosiglitazone with insulin could increase the risk of heart failure. Patients having heart failure with symptoms or moderate to severe heart failure should not use Rosiglitazone.
References[1] http://www.nejm.org/doi/full/10.1056/NEJMoa072761#t=article
[2] http://circ.ahajournals.org/content/128/8/785
[3] https://www.drugs.com/cdi/rosiglitazone.html

UsesA potent and selective PPARγ agonist.
Usesantidiabetic
UsesRosiglitazone is an insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ).
IndicationsRosiglitazone is approved for use as monotherapy and in conjunction with metformin, though it is sometimes combined with a sulfonylurea or insulin. It is usually taken once or twice a day with or without food. Rosiglitazone may cause a modest increase in lowdensity lipoprotein and triglyceride concentrations, but it is unclear whether this effect has any clinical significance or persists in the long term.
DefinitionChEBI: Rosiglitazone is an aminopyridine and a member of thiazolidinediones. It has a role as an insulin-sensitizing drug, a ferroptosis inhibitor and an EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor. It is a conjugate acid of a rosiglitazone(1-).
Brand nameAvandia (GlaxoSmithKline).
General DescriptionRosiglitazone is 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, and is availableas the maleate salt in tablets containing the drug alone(Avandia) or in combination products with metformin(Avandamet) or with glimepiride (Avandaryl). The2-aminopyridine moiety allows for salt formation; the marketedformulations contain the 1:1 salt with maleic acid, inwhich the pyridine nitrogen accepts a proton, forming the2-aminopyridinium species.
General DescriptionRosiglitazone, (±)-5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione(Avandia), is a white to off-white solid with pKavalues of 6.8 and 6.1. Rosiglitazone is readily soluble inethanol and a buffered aqueous solution with pH of 2.3; solubilitydecreases with increasing pH in the physiologicalrange. The molecule has a single chiral center and is presentas a racemate. Even so, the enantiomers are functionally indistinguishablebecause of rapid interconversion.
Biological Activityrosiglitazone is a potent agonist of peroxisome proliferator-activated receptor γ (pparγ), a subfamily of the nuclear-receptor superfamily which is predominately expressed in adipose tissue and regulates gene expression responding to ligand binding. belonging to the thiazolidinedione (tzd) class, rosiglitazone, like other tzd members, binds to pparγ dna as heterodimers and activate transcription of various metabolic regulators involved in the differentiation of stem cells into adipocytes and increased expression of genes regulating the metabolism of glucose and lipid. rosiglitazone is used to treat patients with type ii diabetes mellitus for its strong ability to improve insulin sensitization through its effects either on fatty acid uptake and storage in adipose tissue or on adiokines.peter j. cox, david a. ryan, frank j. hollis, ann-marie harris, ann k. miller, marika vousden and hugh cowley. absorption, disposition, and metabolism of rosiglitazone, a potent thiazolidinedione insulin sensitizer, in humans. drug metabolism and disposition 2000; 28 (7): 772-780adie vilioen and alan sinclair. safety and efficacy of rosiglitazone in the elderly diabetic patient. vascular health and risk management 2009: 5 389-395
Biochem/physiol ActionsRosiglitazone is a potent agonist for PPARγ with an EC50 of 43 nM for the human receptor. It is antidiabetic, working as an insulin sensitizer by binding to the PPARγ receptors in fat cells and making the cells more responsive to insulin.
Clinical UseAlthough rosiglitazone is extensively biotransformed—playing the major role in both transformations, and some involvementof CYP2C9.21,47 The sulfate conjugate M10 is thepredominant circulating metabolite by 4-hour postdose. Theextraordinarily high plasma protein binding of this metabolite(and the N-demethylated sulfate conjugate M4) in humans accountsfor the lengthy residence time of the radioactivity in thebody, despite the relatively short pharmacokinetic half-life(4–4.5 hours) of rosiglitazone itself.
storage+4°C
ROSIGLITAZONE MALEATE ROSIGLITAZONE D-TARTRATE ROSIGLITAZONE-D3 Methyl N-Desmethyl rosiglitazone-d4 ROSIGLITAZONE-5-SULFOXY,5-Hydroxy Rosiglitazone Sulfate DESMETHYL ROSIGLITAZONE-D4 ROSIGLITAZONE, [BENZYL-14C] AKOS 92116 5-HYDROXY ROSIGLITAZONE 5-Hydroxy rosiglitazone sulphate potassium salt ROSIGLITAZONE, [3H] 5-Hydroxy Rosiglitazone -D-Glucuronide,5-Hydroxy Rosiglitazone b-D-Glucuronide rosiglitazone sodium ROSIGLITAZONE HYDROCHLORIDE 99%,Rosiglitazone hydrochloride PHENYL VALERATE Ethoxy 5-Hydroxy rosiglitazone-d4

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