Rosuvastatin

Bezeichnung:Rosuvastatin

CAS-Nr287714-41-4

Englisch Name:Rosuvastatin

CBNumberCB8793779

SummenformelC22H28FN3O6S

Molgewicht481.54

MOL-Datei287714-41-4.mol

Rosuvastatin physikalisch-chemischer Eigenschaften

Schmelzpunkt	161.9 °C
Siedepunkt	745.6±70.0 °C(Predicted)
Dichte	1.368±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Store in freezer, under -20°C
Löslichkeit	DMSO (Slightly), Methanol (Slightly), Water (Slightly)
Aggregatzustand	Solid
pka	4.25±0.10(Predicted)
Farbe	White to Pale Beige
BCS Class	3
CAS Datenbank	287714-41-4(CAS DataBase Reference)
EPA chemische Informationen	6-Heptenoic acid, 7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-, (3R,5S,6E)- (287714-41-4)

Sicherheit

Giftige Stoffe Daten

287714-41-4(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Rosuvastatin Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Rosuvastatin is the most recent FDA-approved statin (doses 5–40 mg) for the treatment of dyslipidemia. Rosuvastatin, which has a structure similar to other synthetic statins, has a long halflife (20–24 hours) similar to atorvastatin and hydrophilicity comparable to pravastatin. Consequently, rosuvastatin is minimally metabolized and has no significant cytochrome P450 drug interactions. The efficacy of rosuvastatin is superior to that of other statins. Compared to atorvastatin, rosuvastatin provides approximately an 8% additional lowering of LDL-C on an equivalent dose level. This provides modestly more efficacy than a doubling of the dose of atorvastatin. Rosuvastatin also increases HDL-C slightly more than atorvastatin, especially at the highest doses.
Verwenden
Rosuvastatin Calcium is a competitive inhibitor of HMG-CoA reductase with IC50 of 11 nM.
Definition
ChEBI: Rosuvastatin is a dihydroxy monocarboxylic acid that is (6E)-7-{4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl} hept-6-enoic acid carrying two hydroxy substituents at positions 3 and 5 (the 3R,5S-diastereomer). It has a role as an antilipemic drug, an anti-inflammatory agent, a CETP inhibitor, a cardioprotective agent, a xenobiotic and an environmental contaminant. It is a member of pyrimidines, a sulfonamide, a dihydroxy monocarboxylic acid, a statin (synthetic) and a member of monofluorobenzenes. It derives from a hept-6-enoic acid. It is a conjugate acid of a rosuvastatin(1-).
synthetische
Rosuvastatin synthesis: Reduction to the 5-hydroxymethyl derivative proceeds smoothly with diisobutylaluminum hydride (DIBALH) in toluene at -10 °C. The hydroxymethyl group is then converted to the bromo derivative, which upon reaction with triphenylphosphine affords the Wittig reagent. The latter is treated with tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate and provides the protected rosuvastatin ester. Removal of the dioxane protecting group by HCl, ester hydrolysis with NaOH and precipitation with CaCl2 gives rosuvastatin.
Kleemann A; Cardiovascular Drugs. Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2017). NY, NY: John Wiley & Sons. Online Posting Date: January 15, 2008
Trademarks
Crestor (AstraZeneca).
Allgemeine Beschreibung
Rosuvastatin, 7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl-methylsulfonyl-amino)-pyrimidin-5-yl]-3,5-dihydroxy-hept-6-enoic acid (Crestor), is oneof the more recently introduced statins in the United States.As with all statins, there is a concern of rhabdomyolysis andas such, the FDA has mandated that a warning about thisside effect, as well as a kidney toxicity warning, be added tothe product label (http://www.fda.gov/CDER/Drug/advisory/crestor_3_2005.htm). This should not come as a surprisebecause of the relationship in the chemical architectureto cerivastatin, which was withdrawn from the market as aresult of its adverse side effects.
Clinical Use
HMG CoA reductase inhibitor:
Hyperlipidaemia
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Anti-arrhythmics: concentration possibly increased by dronedarone - reduce dose of rosuvastatin.
Antibacterials: erythromycin reduces concentration of rosuvastatin; increased risk of myopathy with daptomycin and fusidic acid - avoid.
Anticoagulants: effect of coumarins and phenindione enhanced.
Antifungals: concentration increased by itraconazole - reduce dose of rosuvastatin.
Antivirals: increased risk of myopathy with atazanavir, darunavir, dasabuvir, fosamprenavir, indinavir, ledipasvir, lopinavir, paritaprevir, ritonavir, saquinavir and tipranavir - reduce dose of rosuvastatin, avoid with fosamprenavir, indinavir, ledipasvir, ritonavir and saquinavir.
Ciclosporin: increased risk of myopathy - avoid.
Clopidogrel: concentration of rosuvastatin increased, maximum rosuvastatin dose is 20 mg in normal renal function.
Colchicine: possible increased risk of myopathy.
Cytotoxics: concentration increased by eltrombopag - reduce dose of rosuvastatin.
Lipid-lowering agents: increased risk of myopathy with ezetimibe, fibrates, gemfibrozil (avoid) and nicotinic acid - reduce dose of rosuvastatin.
Teriflunomide: concentration increased by teriflunomide - reduce dose of rosuvastatin.
Stoffwechsel
Rosuvastatin undergoes limited metabolism in the liver mainly by the cytochrome P450 isoenzyme CYP2C9 (approximately 10%).
Approximately 90% of the rosuvastatin dose is excreted unchanged in the faeces (consisting of absorbed and non-absorbed active substance) and the remaining part is excreted in urine.

Rosuvastatin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

287714-41-4, Rosuvastatin Verwandte Suche:

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