Identification
- Summary
Levobunolol is a beta-adrenergic antagonist used for the reduction of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.
- Brand Names
- Betagan
- Generic Name
- Levobunolol
- DrugBank Accession Number
- DB01210
- Background
A nonselective beta-adrenoceptor antagonist used in the treatment of glaucoma.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Levobunolol (DB01210)
- Weight
- Average: 291.3853
Monoisotopic: 291.183443671 - Chemical Formula
- C17H25NO3
- Synonyms
- (-)-Bunolol
- (S)-5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-1(2H)-naphthalenone
- Levobunolol
- Levobunololum
Pharmacology
- Indication
For lowering intraocular pressure (IOP) and may be used in patients with chronic open-angle glaucoma or ocular hypertension.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Ocular hypertension •••••••••••• ••••••••• •••••••• • ••••• Management of Open-angle glaucoma •••••••••••• ••••••••• •••••••• • ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Levobunolol is an ophthalmic beta-blocker, equally effective at β(1)- and β(2)-receptor sites. Levobunolol reduces both elevated and normal IOP in patients with or without glaucoma. In patients with elevated IOP, levobunolol reduces mean IOP by approximately 25-40% from baseline. As the drug is a nonselective &beta-adrenergic blocking agent, it can produce both systemic pulmonary and cardiovascular effects following topical application to the eye. These effects include adverse pulmonary effects (eg. bronchoconstriction, increased airway resistance), and a decrease in blood pressure and heart rate.
- Mechanism of action
Levobunolol's mechanism of action in reducing IOP is not clearly defined, but is believed to be due to a reduction of the production of aqueous humor via blockage of endogenous catecholamine-stimulated increases in cyclic adenosine monophosphate (AMP) concentrations within the ciliary processes.
Target Actions Organism ABeta-1 adrenergic receptor antagonistHumans ABeta-2 adrenergic receptor antagonistHumans - Absorption
80%
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic
- Route of elimination
Not Available
- Half-life
20 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Bradycardia, hypotension, bronchospasm, and acute cardiac failure, LD50=700 mg/kg (orally in rat).
- Pathways
Pathway Category Levobunolol Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAvanafil The risk or severity of hypotension can be increased when Avanafil is combined with Levobunolol. Clobazam The serum concentration of Levobunolol can be increased when it is combined with Clobazam. Clozapine The serum concentration of Levobunolol can be increased when it is combined with Clozapine. Desvenlafaxine The serum concentration of Levobunolol can be increased when it is combined with Desvenlafaxine. Dipyridamole The risk or severity of hypotension can be increased when Dipyridamole is combined with Levobunolol. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Levobunolol hydrochloride O90S49LDHH 27912-14-7 DNTDOBSIBZKFCP-YDALLXLXSA-N - International/Other Brands
- Akbeta
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Betagan Solution / drops 5 mg/1mL Ophthalmic Physicians Total Care, Inc. 1986-07-24 2012-06-30 US 
Betagan Solution / drops 5 mg/1mL Ophthalmic Allergan, Inc. 1986-07-24 Not applicable US Betagan Solution / drops 5 mg/1mL Ophthalmic Physicians Total Care, Inc. 1986-07-24 2010-06-30 US Betagan Solution 2.5 mg/1mL Ophthalmic Allergan, Inc. 2006-03-03 2006-03-03 US Betagan 0.5% Ophthalmic Sol Liquid 0.5 % Ophthalmic Allergan 1985-12-31 2020-02-21 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-levobunolol Ophthalmic Solution USP 0.25% Liquid 0.25 % Ophthalmic Apotex Corporation 2000-02-21 Not applicable Canada Apo-levobunolol Ophthalmic Solution USP 0.5% Liquid 0.5 % Ophthalmic Apotex Corporation 2000-02-21 Not applicable Canada Levobunolol Hydrochloride Solution / drops 5 mg/1mL Ophthalmic Physicians Total Care, Inc. 1995-02-23 Not applicable US Levobunolol Hydrochloride Solution 5 mg/1mL Ophthalmic Sandoz Inc 1997-01-30 2017-08-31 US Levobunolol Hydrochloride Solution 2.5 mg/1mL Ophthalmic Apotex Corporation 2000-08-03 2006-02-03 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Probeta - Liq Oph Levobunolol hydrochloride (0.5 %) + Dipivefrin hydrochloride (0.1 %) Liquid Ophthalmic Allergan 1996-08-30 2012-07-16 Canada
Categories
- ATC Codes
- S01ED03 — Levobunolol
- Drug Categories
- Adrenergic Agents
- Adrenergic Antagonists
- Adrenergic beta-Antagonists
- Agents causing hyperkalemia
- Alcohols
- Amines
- Amino Alcohols
- Antiglaucoma Preparations and Miotics
- Autonomic Agents
- Beta-adrenergic Agents
- Bradycardia-Causing Agents
- Bunolol
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Hypotensive Agents
- Naphthalenes
- Neurotransmitter Agents
- Ophthalmologicals
- Peripheral Nervous System Agents
- Phenoxypropanolamines
- Propanolamines
- Propanols
- Sensory Organs
- Sympatholytics
- Tetrahydronaphthalenes
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Tetralins
- Sub Class
- Not Available
- Direct Parent
- Tetralins
- Alternative Parents
- Aryl alkyl ketones / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aromatic homopolycyclic compound / Aryl alkyl ketone / Aryl ketone / Ether / Hydrocarbon derivative / Ketone
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- cyclic ketone, aromatic ether, propanolamine (CHEBI:6438)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- G6317AOI7K
- CAS number
- 47141-42-4
- InChI Key
- IXHBTMCLRNMKHZ-LBPRGKRZSA-N
- InChI
- 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
- IUPAC Name
- 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one
- SMILES
- CC(C)(C)NC[C@H](O)COC1=CC=CC2=C1CCCC2=O
References
- General References
- Ishibashi T, Yokoi N, Kinoshita S: Comparison of the effects of topical levobunolol and timolol solution on the human ocular surface. Cornea. 2003 Nov;22(8):709-15. [Article]
- Ogasawara H, Yoshida A, Fujio N, Konno S, Ishiko S: [Effect of topical levobunolol on retinal, optic nerve head, and choroidal circulation in normal volunteers]. Nippon Ganka Gakkai Zasshi. 1999 Jul;103(7):544-50. [Article]
- Leung M, Grunwald JE: Short-term effects of topical levobunolol on the human retinal circulation. Eye (Lond). 1997;11 ( Pt 3):371-6. [Article]
- Dong Y, Ishikawa H, Wu Y, Yoshitomi T: Vasodilatory mechanism of levobunolol on vascular smooth muscle cells. Exp Eye Res. 2007 Jun;84(6):1039-46. Epub 2007 Jan 27. [Article]
- Gonzalez JP, Clissold SP: Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1987 Dec;34(6):648-61. [Article]
- Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [Article]
- Novack GD: Levobunolol for the long-term treatment of glaucoma. Gen Pharmacol. 1986;17(4):373-7. [Article]
- External Links
- Human Metabolome Database
- HMDB0015341
- KEGG Compound
- C07914
- PubChem Compound
- 39468
- PubChem Substance
- 46507518
- ChemSpider
- 36089
- 1813
- ChEBI
- 6438
- ChEMBL
- CHEMBL1201237
- ZINC
- ZINC000003830339
- Therapeutic Targets Database
- DAP000303
- PharmGKB
- PA164747027
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Levobunolol
- FDA label
- Download (850 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Alcon Laboratories
- Allergan Inc.
- Apotex Inc.
- Bausch & Lomb Inc.
- Dispensing Solutions
- Falcon Pharmaceuticals Ltd.
- Novex Pharma
- Pacific Pharma Lp
- Pharmedix
- Physicians Total Care Inc.
- Prescript Pharmaceuticals
- Dosage Forms
Form Route Strength Liquid Ophthalmic 0.5 % Solution Ophthalmic 2.5 mg/1mL Solution Ophthalmic 5 mg/1mL Solution / drops Ophthalmic 2.5 mg/1mL Solution / drops Ophthalmic 5 mg/1mL Liquid Ophthalmic 0.25 % Liquid Ophthalmic 0.50 % Liquid Ophthalmic Solution Ophthalmic 0.25 % Solution Ophthalmic 0.5 % Solution / drops Ophthalmic 1 MG/ML Solution / drops Ophthalmic 2.5 MG/ML Solution / drops Ophthalmic 5 MG/ML Solution / drops Ophthalmic 0.5 % - Prices
Unit description Cost Unit Levobunolol HCl 0.5% Solution 15ml Bottle 50.25USD bottle Levobunolol HCl 0.5% Solution 10ml Bottle 33.58USD bottle Levobunolol HCl 0.25% Solution 10ml Bottle 32.59USD bottle Levobunolol HCl 0.5% Solution 5ml Bottle 17.26USD bottle Levobunolol HCl 0.25% Solution 5ml Bottle 16.45USD bottle Betagan 0.5% Solution 6.39USD ml Betagan 0.5% eye drops 6.1USD ml Betagan 0.25% eye drops 4.9USD ml Betagan 0.5 % Solution 3.7USD ml Levobunolol 0.5% eye drops 3.24USD ml Levobunolol 0.25% eye drops 2.83USD ml Pms-Levobunolol 0.5 % Solution 1.63USD ml Ratio-Levobunolol 0.5 % Solution 1.63USD ml Sandoz Levobunolol 0.5 % Solution 1.63USD ml Ratio-Levobunolol 0.25 % Solution 1.23USD ml Sandoz Levobunolol 0.25 % Solution 1.23USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 209-211 °C Not Available logP 2.40 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.251 mg/mL ALOGPS logP 2.06 ALOGPS logP 2.18 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 14.09 Chemaxon pKa (Strongest Basic) 9.75 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 58.56 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 83.28 m3·mol-1 Chemaxon Polarizability 33.38 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9923 Blood Brain Barrier - 0.8738 Caco-2 permeable - 0.6105 P-glycoprotein substrate Substrate 0.8227 P-glycoprotein inhibitor I Inhibitor 0.5712 P-glycoprotein inhibitor II Non-inhibitor 0.5691 Renal organic cation transporter Non-inhibitor 0.8179 CYP450 2C9 substrate Non-substrate 0.7696 CYP450 2D6 substrate Substrate 0.8547 CYP450 3A4 substrate Non-substrate 0.5554 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8378 Ames test Non AMES toxic 0.8825 Carcinogenicity Non-carcinogens 0.9039 Biodegradation Not ready biodegradable 0.9972 Rat acute toxicity 2.1253 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9613 hERG inhibition (predictor II) Inhibitor 0.593
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-08gi-9540000000-243680d4a0d98a06ee5e Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00dl-1090000000-fdc4623f08e214b0f4a8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0390000000-44fa266952c4b03a4b62 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-02mi-9480000000-681f260c36c4c701b68b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-2900000000-129c8fa8a24cfd237d56 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9400000000-98fa47d4b29eae956eb7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01ow-1900000000-0411e04c2eaafbbfdb59 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 181.6464731 predictedDarkChem Lite v0.1.0 [M-H]- 181.3032731 predictedDarkChem Lite v0.1.0 [M-H]- 166.227 predictedDeepCCS 1.0 (2019) [M+H]+ 181.3011731 predictedDarkChem Lite v0.1.0 [M+H]+ 181.6194731 predictedDarkChem Lite v0.1.0 [M+H]+ 168.585 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.0441731 predictedDarkChem Lite v0.1.0 [M+Na]+ 181.7462731 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.67815 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Receptor signaling protein activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51322.1 Da
References
- Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [Article]
- Harris A, Malinovsky V, Martin B: Correlates of acute exercise-induced ocular hypotension. Invest Ophthalmol Vis Sci. 1994 Oct;35(11):3852-7. [Article]
- Chidlow G, Melena J, Osborne NN: Betaxolol, a beta(1)-adrenoceptor antagonist, reduces Na(+) influx into cortical synaptosomes by direct interaction with Na(+) channels: comparison with other beta-adrenoceptor antagonists. Br J Pharmacol. 2000 Jun;130(4):759-66. [Article]
- Sharif NA, Xu SX, Crider JY, McLaughlin M, Davis TL: Levobetaxolol (Betaxon) and other beta-adrenergic antagonists: preclinical pharmacology, IOP-lowering activity and sites of action in human eyes. J Ocul Pharmacol Ther. 2001 Aug;17(4):305-17. [Article]
- Brooks AM, Gillies WE: Ocular beta-blockers in glaucoma management. Clinical pharmacological aspects. Drugs Aging. 1992 May-Jun;2(3):208-21. [Article]
- Gonzalez JP, Clissold SP: Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1987 Dec;34(6):648-61. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Quast U, Vollmer KO: Binding of beta-adrenoceptor antagonists to rat and rabbit lung: special reference to levobunolol. Arzneimittelforschung. 1984;34(5):579-84. [Article]
- Sharif NA, Xu SX, Crider JY, McLaughlin M, Davis TL: Levobetaxolol (Betaxon) and other beta-adrenergic antagonists: preclinical pharmacology, IOP-lowering activity and sites of action in human eyes. J Ocul Pharmacol Ther. 2001 Aug;17(4):305-17. [Article]
- Harris A, Malinovsky V, Martin B: Correlates of acute exercise-induced ocular hypotension. Invest Ophthalmol Vis Sci. 1994 Oct;35(11):3852-7. [Article]
- Brooks AM, Gillies WE: Ocular beta-blockers in glaucoma management. Clinical pharmacological aspects. Drugs Aging. 1992 May-Jun;2(3):208-21. [Article]
- Gonzalez JP, Clissold SP: Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1987 Dec;34(6):648-61. [Article]
- Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [Article]
- Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
- Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55