LEVOBUNOLOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H25NO3
Molecular Weight	291.3853
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)NC[C@H](O)COC1=C2CCCC(=O)C2=CC=C1

InChI

InChIKey=IXHBTMCLRNMKHZ-LBPRGKRZSA-N

InChI=1S/C17H25NO3/c1-17(2,3)18-10-12(19)11-21-16-9-5-6-13-14(16)7-4-8-15(13)20/h5-6,9,12,18-19H,4,7-8,10-11H2,1-3H3/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H25NO3
Molecular Weight	291.3853
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.allergan.com/assets/pdf/betagan_pi
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11572462 | https://www.drugs.com/pro/levobunolol.html | https://www.ncbi.nlm.nih.gov/pubmed/3019819 | https://www.ncbi.nlm.nih.gov/pubmed/17459374

Levobunolol is a non-cardioselective beta-adrenoceptor blocking agent, equipotent at both beta1 and beta2 adrenergic receptors. Levobunolol is greater than 60 times more potent than its dextro isomer in its beta-blocking activity, yet equipotent in its potential for direct myocardial depression. Accordingly, the levo isomer, levobunolol, is used. Levobunolol does not have significant local anesthetic (membrane-stabilizing) or intrinsic sympathomimetic activity. Levobunolol, sold under the brand name Betagan, has been shown to be an active agent in lowering elevated as well as normal intraocular pressure (IOP) whether or not accompanied by glaucoma. Levobunolol is contraindicated in those individuals with bronchial asthma or with a history of bronchial asthma, or severe chronic obstructive pulmonary disease sinus bradycardia; second and third-degree atrioventricular block; overt cardiac failure cardiogenic shock; or hypersensitivity to any component of these products.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11572462	Antagonist 2849		0.76 nM [Ki]
Beta-1 adrenergic receptor 163 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11572462	Antagonist 2849		32.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ocular hypertension 52 Sources: http://www.allergan.com/assets/pdf/betagan_pi	Primary		Approved 8583	BETAGAN Approved Use BETAGAN ® ophthalmic solution has been shown to be effective in lowering intraocular pressure and may be used in patients with chronic open-angle glaucoma or ocular hypertension. Launch Date 1985
Chronic open-angle glaucoma 6 Sources: http://www.allergan.com/assets/pdf/betagan_pi	Primary		Approved 8583	BETAGAN Approved Use BETAGAN ® ophthalmic solution has been shown to be effective in lowering intraocular pressure and may be used in patients with chronic open-angle glaucoma or ocular hypertension. Launch Date 1985

C_max

Value	Dose	Co-administered	Analyte	Population
3.72 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/336256	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:		LEVOBUNOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.65 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/336256	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:		DIHYDROBUNOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/336256	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:		LEVOBUNOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
7.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/336256	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:		DIHYDROBUNOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
0.5 % 1 times / day steady, ophthalmic Recommended Dose: 0.5 %, 1 times / day Route: ophthalmic Route: steady Dose: 0.5 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019219s029lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019219s029lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019219s029lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6438	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6438
ZINC	ZINC000003830339	http://zinc15.docking.org/substances/ZINC000003830339

PubMed

Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
Efficacy and patient tolerability of travoprost BAK-free solution in patients with open-angle glaucoma and ocular hypertension.	2010-08-09	20714366
A new mode of dimerization of allosteric enzymes with ACT domains revealed by the crystal structure of the aspartate kinase from Cyanobacteria.	2010-06-04	20398676
Effects of topical 0.5% levobunolol alone or in association with 2% dorzolamide compared with a fixed combination of 0.5% timolol and 2% dorzolamide on intraocular pressure and heart rate in dogs without glaucoma.	2010	20960417
Comparison of effects of topical levobunolol to a combination of timolol-dorzolamide on intraocular pressure and pulse rate of healthy dogs.	2009-09	19626454
Aerobic exercise and intraocular pressure in normotensive and glaucoma patients.	2009-08-13	19678955
Retrospective cohort study of 163 pediatric glaucoma patients.	2009-06	19491991
[Cytotoxicity of antiglaucoma ophthalmic solutions for human corneal endothelial cells].	2009-05	19489448
Effect of latanoprost and timolol on the histopathology of the human conjunctiva.	2009-02	18971237
Poly (epsilon-caprolactone) microparticles containing Levobunolol HCl prepared by a multiple emulsion (W/O/W) solvent evaporation technique: effects of some formulation parameters on microparticle characteristics.	2009-02	18608798
Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery.	2009	19668590
Miscellaneous.	2008-10	21593974
Recent advances in pharmacotherapy of glaucoma.	2008-10	20040958
An in vivo confocal microscopy and impression cytology analysis of preserved and unpreserved levobunolol-induced conjunctival changes.	2008-05-10	18465723
Daily cost of glaucoma medications in China.	2007-12-20	18091176
Membrane electrodes for determination of some beta-blocker drugs.	2007-09-01	17760336
Levobetaxolol hydrochloride: a review of its pharmacology and use in the treatment of chronic open-angle glaucoma and ocular hypertension.	2007-06	19668496
Vasodilatory mechanism of levobunolol on vascular smooth muscle cells.	2007-06	17459374
Myocilin mutations among primary open angle glaucoma patients of Kanyakumari district, South India.	2007-04-02	17417611
Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells.	2007-03	17389174
Allergic contact dermatitis due to levobunolol with cross-sensitivity to befunolol.	2007-01	17177718
Contact dermatitis to levobunolol eyedrops superimposed on IgE-mediated rhinoconjunctivitis.	2006-12	17201244
Drops and falls.	2006-11	17047012
Allergic contact dermatitis due to levobunolol in an ophthalmic preparation.	2006-07	16848829
Beta-blocker eye drops.	2006-06-13	16764382
The management of glaucoma and intraocular hypertension: current approaches and recent advances.	2006-06	18360593
Transdermal delivery of beta-blockers.	2006-05	16640500
Effects of antiglaucoma drugs on cellular proliferation in cultured human corneal keratocytes.	2006-03	16602276
Effects of antiglaucoma drugs on calcium mobility in cultured corneal endothelial cells.	2006-02	16568722
Allergic contact dermatitis due to beta-blockers in eye drops: a retrospective analysis of multicentre surveillance data 1993-2004.	2006	17106597
Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro.	2005-03	15725891
Reversal of disc cupping after intraocular pressure reduction in topographic image series.	2004-10	15354070
Study of effects of antiglaucoma eye drops on N-methyl-D-aspartate-induced retinal damage.	2004-09-04	16365790
[Cost-effectivity analysis of the most used antiglaucoma drugs].	2004-08	15306964
Effects of carteolol hydrochloride on the in vitro production of LPS-induced proinflammatory cytokines by murine macrophage.	2004-06	15279728
Inhibition of endothelin-1 and KCL-induced increase of [CA2+]i by antiglaucoma drugs in cultured A7r5 vascular smooth-muscle cells.	2004-06	15279725
Binding affinities of ocular hypotensive beta-blockers levobetaxolol, levobunolol, and timolol at endogenous guinea pig beta-adrenoceptors.	2004-04	15117564
Deposits in artificial corneas: risk factors and prevention.	2004-04	15068437
Stereoselectivity for interactions of agonists and antagonists at mouse, rat and human beta3-adrenoceptors.	2004-01-26	14744619
[Osmotic resistance of red blood cells membranes in Vermox and "AKbeta" vitamin complex treatment of experimental trichinosis in rats].	2004	16865965
The effect of once-daily levobunolol on intraocular pressure in normal-tension glaucoma.	2003-12-26	15692777
Bilateral nongranulomatous anterior uveitis associated with bimatoprost.	2003-11	14670442
Short-term effects of topical levobunolol on the human retinal circulation.	1997	9373479
Syncope, bradycardia, and atrioventricular block associated with topical ophthalmic levobunolol.	1994-03	8122621
A comparison of the ocular hypotensive efficacy and systemic safety of 0.5% levobunolol and 2% carteolol.	1994	8145982
A comparison of the ocular tolerability of a single dose of timolol and levobunolol in healthy normotensive volunteers.	1993-04	8484654
Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy.	1987-12	2892662
Comparison of ophthalmic beta-blocking agents.	1987-06	2891463
Levobunolol for the long-term treatment of glaucoma.	1986	3019819
l-Bunolol and propranolol: oral and intravenous beta-adrenoceptor blocking activity in rats compared to dogs and humans.	1978-01	22739

Patents

Sample Use Guides

In Vivo Use Guide

The recommended starting dose is one to two drops of BETAGAN (Levobunolol) ophthalmic solution 0.5% in the affected eye(s) once a day. Typical dosing with BETAGAN® 0.25% is one to two drops twice daily. In patients with more severe or uncontrolled glaucoma, BETAGAN® 0.5% can be administered b.i.d. As with any new medication, careful monitoring of patients is advised. Dosages above one drop of BETAGAN® 0.5% b.i.d. are not generally more effective.

Route of Administration: Topical

In Vitro Use Guide

The ability of levobunolol to relax ciliary artery rings pre-contracted with other agents, including phenylephrine and in Ca2+-free media was determined by isometric tension recording method. The pre-contraction was maintained for 20 min, then levobunolol was applied every 10 min in a cumulative manner. Levobunolol at 30 mkM and at 100 mkM significantly reduced the contractile response to phenylephrine.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:28:47 GMT 2025` Edited by `admin` on `Wed Apr 02 08:28:47 GMT 2025`
Record UNII	G6317AOI7K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVOBUNOLOL

Official Name

English

BUNOLOL, (-)-

Preferred Name

English

LEVOBUNOLOL [MI]

Common Name

English

LEVOBUNOLOL [VANDF]

Common Name

English

BUNOLOL, (S)-

Common Name

English

(-)-(S)-5-(3-(TERT-BUTYLAMINO)-2-HYDROXYPROPOXY)-3,4-DIHYDRO-1(2H)-NAPHTHALENONE

Systematic Name

English

levobunolol [INN]

Common Name

English

Levobunolol [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175556