Levobunolol

Structural formula
General
Non-proprietary name	Levobunolol
other names	( S ) -5- [3- (1,1-Dimethylamino) -2-hydroxypropoxy] -3,4-dihydro-1 (2 H ) -naphthalenone
Molecular formula	C 17 H 25 NO 3 (levobunolol) ; C 17 H 25 NO 3 HCl (levobunolol hydrochloride ) ;
External identifiers / databases
PubChem	39468
ChemSpider	36089
DrugBank	DB01210
Wikidata	Q408556
Drug information
ATC code	S01 ED03
Drug class	Beta blockers
properties
Molar mass	291.39 g mol −1 (levobunolol) ; 327.85 g mol −1 (levobunolol HCl) ;
Physical state	firmly
Melting point	209–211 ° C (levobunolol · HCl)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	78 mg kg −1 ( LD 50 , mouse , iv , levobunolol HCl) ; 1220 mg kg −1 ( LD 50 , mouse , oral , levobunolol HCl) ; 25 mg kg −1 ( LD 50 , rat , iv , levobunolol HCl) ; 100 mg kg −1 ( LD 50 , rat , oral , levobunolol HCl) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Levobunolol is a drug from the group of β-receptor blockers , which is used in the form of eye drops to treat increased pressure in the eye (ocular hypertension) and chronic wide-angle glaucoma .

Clinical information

Application areas (indications)

Levobunolol-containing eye drops are used to treat glaucoma (wide-angle glaucoma = open-angle glaucoma); with increased intraocular pressure; after eye surgery associated with ocular hypertension; Glaucoma in benzalkonium chloride - allergy . As soon as the intraocular pressure is well adjusted, one application per day is sufficient. Contact lenses must be removed before each application and only reinserted 15 minutes after use.

Special dosage instructions

If the intraocular pressure cannot be reduced sufficiently, a combination with pilocarpine or other miotics and / or epinephrine or dipivefrine and / or systemically applied carbonic anhydrase inhibitors such as acetazolamide is possible.

Contraindications (contraindications)

Bronchial asthma (also in the anamnesis ); chronic obstructive pulmonary disease (COPD); Sinus bradycardia ; 2nd and 3rd degree AV block ; Heart failure ; cardiogenic shock .

Drug interactions

With simultaneous systemic or local use of steroids, the pressure values must be carefully and continuously monitored.

Special patient groups

Pulse rate should be monitored in patients with a history of severe heart disease. In previous eye operations, the intraocular pressure should be checked carefully and at frequent frequency. Regular monitoring of intraocular pressure and cornea is indicated. Blood sugar tests in diabetics are indicated.

Other Information

Chemical and pharmaceutical information

Manufacturing

Levobunolol is made from 5-hydroxy-1-tetralone. Alkylation of the phenolic hydroxy group gives 5- (2,3-epoxypropxy) -1-tetralone. This is followed by the ring opening of the epoxide with tert- butylamine to form the racemic amino alcohol. The resolution of the amino alcohol with ( R , R ) -tartaric acid yields the enantiomerically pure levobunolol.

History

Levobunolol was patented by Warner Lambert in 1970 and is marketed as a beta sympatholytic and antihypertensive agent for the treatment of glaucoma by the international pharmaceutical company Allergan, Inc. under the trade name Vistagan ^® .

Trade names

Levobunolol is commercially available in Germany, Austria and Switzerland under the name Vistagan.

Individual evidence

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 946, ISBN 978-0-911910-00-1 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ ^A ^b ^c ^d ^e Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.
↑ ^a ^b ^c ^d FDA professional information for levobunolol at Drugs.com .
↑ Entry on levobunolol. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.

[Merckedex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 946, ISBN 978-0-911910-00-1 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[A._Kleemann-3] A ^b ^c ^d ^e Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.

[fi-4] FDA professional information for levobunolol at Drugs.com .

[RÖMPP_Online-5] Entry on levobunolol. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.