Ebastine

Bezeichnung:Ebastine

CAS-Nr90729-43-4

Englisch Name:Ebastine

CBNumberCB8271800

SummenformelC32H39NO2

Molgewicht469.66

MOL-Datei90729-43-4.mol

Ebastine physikalisch-chemischer Eigenschaften

Schmelzpunkt	80-82°C
Siedepunkt	596.3±50.0 °C(Predicted)
Dichte	1.09±0.1 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	Slightly soluble in chloroform, methanol.
Aggregatzustand	solid
pka	8.19±0.10(Predicted)
Farbe	white
Merck	14,3484
CAS Datenbank	90729-43-4(CAS DataBase Reference)

Sicherheit

WGK Germany	3
RTECS-Nr.	EL8140000
HS Code	2933.39.9200

Gefahreninformationscode (GHS)

Ebastine Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Ebastine is a new once-daily histamine Hl-receptor antagonist with no sedative effects or autonomic impairment at therapeutic doses. It is reported to be effective in the treatment of hay fever, perennial rhinitis, and uticaria. Ebastine's antihistamine activity is attributed to its carboxylic acid metabolite carebastine.
Chemische Eigenschaften
White to Off-White Powder
Originator
Almirall (Spain)
Verwenden
A nonsedating type histamine H1-receptor antagonist. Antihistaminic
Verwenden
Ebastine is a second-generation H1 receptor antagonist that is indicated mainly for allergic rhinitis and chronic idiopathic urticaria. It is available in 10 and 20 mg tablets and as fast-dissolving tablets, as well as in pediatric syrup. It has a recommended flexible daily dose of 10 or 20 mg, depending on disease severity.
Definition
ChEBI: Ebastine is an organic molecular entity.
Manufacturing Process
(a) A mixture of 4-hydroxypiperidine (40.4 g; 0.4 moles), p-tert-butyl-ω- chlorobutyrophenone (105 g, 0.44 moles), sodium bicarbonate (67.2 g; 0.8 moles) and a crystal of potassium iodide in methyl isobutyl ketone (1 liter) was boiled under reflux for 24 hours. After cooling, the reaction mixture waswashed with water, dried (Na2SO4) and the solvent removed in vacuum. The residue was salified with the stoichiometric amount of fumaric acid in a mixture of acetone and ethanol to give 1-[3-(4-tert-butylbenzoyl)propyl]-4- hydroxypiperidine fumarate (148 g), melting point 163-165°C. This compound was converted into the free base, and 1-[3-(4-tert-butylbenzoyl)propyl]-4- hydroxypiperidine was obtained and recrystallized from a mixture of diethyl ether and petroleum ether (boiling point 50-70°C). 102 g were obtained (yield 84%), melting point 63-65°C.
(b) A mixture of 1-[3-(tert-butylbenzoyl)propyl]-4-hydroxypiperidine (60.68 g; 0.2 moles) and sodium carbonate (42.4 g; 0.4 moles) in methyl isobutyl ketone (500 ml) was heated to the boiling point and a solution of diphenylmethyl bromide (49.42 g; 0.2 moles) in methyl isobutyl ketone (75 ml) was slowly added in 1.5 hours. The resulting mixture was boiled under reflux for another 12 hours, and then another solution of diphenylmethyl bromide (24.71 g; 0.1 moles) in methyl isobutyl ketone (50 ml) was added and the mixture boiled under reflux again for 12 hours. Another solution of diphenylmethyl bromide in the same quantity was added and after refluxing for 12 additional hours the reaction mixture was cooled, washed with water, dried (Na2SO4) and the solvent removed in vacuum.
The residual oil was treated with the stoichiometric amount of fumaric acid in ethanol and 4-diphenylmethoxy-1-[3-(4-tert-butylbenzoyl)propyl]piperidine fumarate crystallized. After recrystallisation from ethanol the pure compound was obtained (88 g; yield 75%), melting point 197-198°C.
Trademarks
Kestine (Rhone-Poulenc Rorer);Ebastel.
Therapeutic Function
Antihistaminic, Antiallergic, Calcium entry blocker
Allgemeine Beschreibung
Ebastine is metabolised by cytochrome P450 3A (CYP3A4) to carebastine. It is used to treat allergic rhinitis and chronic idiopathic urticaria.
Biochem/physiol Actions
Ebastine is a non-sedating histamine H1 receptor antagonist, which inhibits allergen-induced bronchospasm in conscious guinea pigs. Unlike other compounds in this category, ebastine does not prolong the QT interval at up to five times the recommended therapeutic dose.

Ebastine Upstream-Materialien And Downstream Produkte

Ebastine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

90729-43-4, Ebastine Verwandte Suche:

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