Ranolazine

Bezeichnung:Ranolazine

CAS-Nr95635-55-5

Englisch Name:Ranolazine

CBNumberCB5195172

SummenformelC24H33N3O4

Molgewicht427.54

MOL-Datei95635-55-5.mol

Ranolazine physikalisch-chemischer Eigenschaften

Schmelzpunkt	119-1200C
Siedepunkt	624.1±55.0 °C(Predicted)
Dichte	1.174±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	14.06±0.20(Predicted)
Farbe	White
CAS Datenbank	95635-55-5(CAS DataBase Reference)

Sicherheit

HS Code	2933595960
Giftige Stoffe Daten	95635-55-5(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Ranolazine Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Ranolazine is an orally available, extended release drug for the treatment of chronic angina in patients who have failed to respond to prior angina therapy. Chronic stable angina (CSA) is a common symptom of coronary artery disease wherein plaques in the coronary vasculature restrict blood flow to the heart, which in turn leads to insufficient oxygenation of the heart, typically during physical exertion or emotional stress. A vast majority of the existing anti-anginal and anti-ischemic therapies aim to correct the imbalance between myocardial oxygen demand and supply through mechanisms that produce reductions in heart rate or blood pressure.
Chemische Eigenschaften
White Solid
Originator
Roche Bioscience (US)
Verwenden
antianginal, antiischemic
Definition
ChEBI: N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide is an aromatic amide obtained by formal condensation of the carboxy group of 2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetic acid with the amino group of 2,6-dimethylaniline. It is a monocarboxylic acid amide, an aromatic amide, a N-alkylpiperazine, a secondary alcohol and a monomethoxybenzene.
Trademarks
Ranexa (Sensus).
Allgemeine Beschreibung
Ranolazine, N-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl]acetamide (Ranexa), is an antianginal medication thatwas approved by the Food and Drug Administration (FDA)in January 2006 for the treatment of chronic angina.Ranolazine is believed to elicit its effects by altering thetranscellular late sodium current. This, in turn, alters thesodium-dependent calcium channels during myocardial ischemia.Thus, ranolazine indirectly prevents the calciumoverload that is associated with cardiac ischemia.Ranolazine is metabolized by the cytochrome CYP3A enzymesin the liver.
Clinical Use
Add on therapy for angina
Synthese
Two syntheses, one from the inventors at Roche and other from a group in Hungary, of Ranolazine have been described in the patent literature. The original synthesis is highlighted in the Scheme. Reaction of 2,6-dimethylaniline 46 with chloroacetyl chloride (47) in the presence of triethylamine for 4h at 0oC gave amide 48 in 82% yield. This chloro amide 48 was reacted with piperazine in refluxing ethanol for 2 h to give piperazinyl amide 50. Reaction of amide 50 with epoxide intermediate 53, prepared by reacting 2-methoxy phenol 51 with epichlorohydrin, in refluxing isopropanol for 3 h followed by treatment with HCl/methanol gave ranolazine dihydrochloride (VII) in 73% yield.
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Anti-arrhythmics: avoid with disopyramide.
Antibacterials: concentration possibly increased by clarithromycin and telithromycin - avoid concomitant use; concentration reduced by rifampicin - avoid.
Antifungals: concentration increased by ketoconazole and possibly itraconazole, posaconazole and voriconazole - avoid.
Antivirals: concentration possibly increased by atazanavir, darunavir, fosamprenavir, indinavir, lopinavir, ritonavir, saquinavir and tipranavir - avoid.
Beta-blockers: avoid with sotalol.
Ciclosporin: concentration of both drugs possibly increased.
Grapefruit juice: concentration of ranolazine possibly increased - avoid.
Statins: concentration of simvastatin increased - maximum dose of simvastatin is 20 mg.
Tacrolimus: concentration of tacrolimus increased.
Stoffwechsel
Extensively metabolised in the gastrointestinal tract and liver. Four main metabolites have been identified.
Approximately 75% of a dose is excreted in the urine with the remainder in the faeces.

Ranolazine Upstream-Materialien And Downstream Produkte

Ranolazine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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