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HomeProduct name listLevobunolol hydrochloride

Levobunolol hydrochloride

  • CAS NO.:27912-14-7
  • Empirical Formula: C17H26ClNO3
  • Molecular Weight: 327.85
  • MDL number: MFCD03425587
  • EINECS: 248-725-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-09-04 15:51:00
Levobunolol hydrochloride Structural

What is Levobunolol hydrochloride?

Description

Levobunolol hydrochloride is a non-selective β-adrenergic blocker useful in the treatment of glaucoma. Worldwide, it represents the sixth B-blocker to be launched for this indication.

Originator

Warner Lambert (USA)

The Uses of Levobunolol hydrochloride

Anti-adrenergic (β-receptor).

The Uses of Levobunolol hydrochloride

A non-selective ?-adrenoceptor antagonist used as an anticonvulsant.

What are the applications of Application

Levobunolol, Hydrochloride is a β-adrenoceptor antagonist

Definition

ChEBI: A hydrochloride obtained by combining equimolar amounts of levobunolol and hydrochloric acid. A non-selective beta-adrenergic antagonist used 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°.

brand name

Akbeta(Akorn); Betagan(Allergan);VISTAGEN LIQUIFILM.

Therapeutic Function

Beta-adrenergic blocker

Veterinary Drugs and Treatments

Levobunolol HCl is a beta1- and beta2-blocking agent similar to timolol and metipranolol above but without the potential for myocardial depression or airway constriction noted rarely in veterinary medicine and occasionally in human patients. Levobunolol is used in humans with glaucoma responsive to beta adrenergic blocking agents but who suffer cardiac and respiratory side effects associated with timolol. Levobunolol HCl and then carteolol HCl would be suitable Beta blocking agents for feline patients with glaucoma and asthma, although carbonic anhydrase inhibitors should be used in such cases prior to adding a Beta blocking agent.

Properties of Levobunolol hydrochloride

Melting point: 209-211°
alpha  24589 -19.6±0.7° (c = 2.90 in methanol)
storage temp.  Amber Vial, Refrigerator, Under inert atmosphere
solubility  DMSO (Slightly), Methanol (Slightly), Water (Sparingly)
form  Solid
color  White to Off-White
Stability: Light Sensitive

Safety information for Levobunolol hydrochloride

Computed Descriptors for Levobunolol hydrochloride

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