LEVOBUNOLOL

Bezeichnung:LEVOBUNOLOL

CAS-Nr47141-42-4

Englisch Name:LEVOBUNOLOL

CBNumberCB5210167

SummenformelC17H25NO3

Molgewicht291.39

MOL-Datei47141-42-4.mol

LEVOBUNOLOL physikalisch-chemischer Eigenschaften

Schmelzpunkt	209-211°C
storage temp.	-20°C Freezer, Under Inert Atmosphere
CAS Datenbank	47141-42-4(CAS DataBase Reference)

Sicherheit

Toxizität

LD50 in male, female rats, mice (mg/kg): 700, 800, 1530, 1220 orally; 25, 28, 78, 84 i.v.; LD50 in male, female hamsters, dogs (mg/kg): 435, 500, 100, 100 orally (Kaplan, 1980)

LEVOBUNOLOL Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
White Solid
Originator
Betagan,Allergan,India
Verwenden
Levobunolol hydrochloride is an antiglaucoma agent in ophthalmie solutions.
Verwenden
As a non-selective adrenoceptor antagonist, Levobunolol is used as an anticonvulsant.
Definition
ChEBI: A cyclic ketone that is 3,4-dihydronaphthalen-1-one substituted at position 5 by a 3-(tert-butylamino)-2-hydroxypropoxy group (the S-enantiomer). A non-selective beta-adrenergic antagonist used (as its hydrochlo ide salt) for treatment of glaucoma.
Manufacturing Process
9.62 g (59 mmoles) 5-hydroxy-3,4-dihydro-1(2H)-naphthalenone, 67 ml toluene, 0.36 g (1.1 mmoles) tetra-n-butylammonium bromide, 4.51 g (68 mmoles) 85% potassium hydroxide and 20 ml (254 mmoles) (R)-(-)- epichlorhydrine were placed in an appropriate flask fitted with efficient mechanical stirring, and the mixture was heated under reflux for two hours. The mixture was allowed to cool to 30°C, 50 ml toluene and 50 ml water were added and the mixture was vigorously stirred. The organic phase was removed and the aqueous phase extracted with 25 ml toluene. The combined organic phases were concentrated at reduced pressure, 31 ml (300 mmoles) tert-butylamine, 45 ml ethanol and 3 ml deionized water were added, and the solution was heated under reflux for one hour. The mixture was allowed to cool to 40°C and the volatile products were distilled at reduced pressure. Toluene (9 ml) was added to the residue and volatiles were distilled at reduced pressure. (S)-5-(2,3-Epoxypropoxy)-3,4-dihydro-1(2H)- naphthalenone with an optical purity greater than 95% was obtained. Toluene (75 ml) was added to the product, and then, 10 ml of 35% (w/v) hydrochloric acid and 110 ml water, and the mixture was stirred for fifteen minutes. The organic phase was decanted and the aqueous one was extracted with 50 ml toluene. The aqueous phase was basified by addition of a solution of 5.1 g sodium hydroxide in 150 ml water and extracted twice with toluene (100 and 50 ml, respectively). The combined organic extracts were dried with anhydrous sodium sulfate, decolorized with active charcoal and filtered.
To the above toluenic solution containing levobunolol as free base, 16 ml ethanol and the stoichiometric amount of hydrogen chloride were added. The stirred mixture was cooled below 10°C and kept at this temperature for one hour. The precipitated solid was filtered, washed with toluene, recrystallized twice from 43 ml ethanol and dried to give 10.0 g (51% yield) of (-)-3,4- dihydro-5-(3-(tert-butylamino)-2-hydroxypropoxy)-1(2H)-naphthalenone hydrochloride (levobunolol hydrochloride) having a rotary power at 25°C below -19°.
Trademarks
Akbeta(Akorn); Betagan(Allergan).
Therapeutic Function
Beta-adrenergic blocker

LEVOBUNOLOL Upstream-Materialien And Downstream Produkte

LEVOBUNOLOL Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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