Rosiglitazone

Bezeichnung:Rosiglitazone

CAS-Nr122320-73-4

Englisch Name:Rosiglitazone

CBNumberCB7133275

SummenformelC18H19N3O3S

Molgewicht357.43

MOL-Datei122320-73-4.mol

Rosiglitazone physikalisch-chemischer Eigenschaften

Schmelzpunkt	153-155 C
Siedepunkt	585.0±35.0 °C(Predicted)
Dichte	1.315±0.06 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	DMSO: ≥10mg/mL
pka	6.34±0.50(Predicted)
Aggregatzustand	powder
Farbe	White to Off-White
Merck	14,8265
CAS Datenbank	122320-73-4(CAS DataBase Reference)
IARC	3 (Vol. 108) 2016

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/38
S-Sätze:	26-37/39
WGK Germany	3
RTECS-Nr.	XJ5813850
HS Code	2934100000
Giftige Stoffe Daten	122320-73-4(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Rosiglitazone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Verwenden
A potent and selective PPARγ agonist.
Verwenden
antidiabetic
Verwenden
Rosiglitazone is an insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ).
Indications
Rosiglitazone 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.
Definition
ChEBI: 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-).
Trademarks
Avandia (GlaxoSmithKline).
Allgemeine Beschreibung
Rosiglitazone 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.
Allgemeine Beschreibung
Rosiglitazone, (±)-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.
Biologische Aktivität
rosiglitazone 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 Actions
Rosiglitazone 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 Use
Although 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.
Lager
+4°C

Rosiglitazone Upstream-Materialien And Downstream Produkte

Rosiglitazone Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

122320-73-4, Rosiglitazone Verwandte Suche:

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