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Identification
Name Levobunolol
Accession Number DB01210 (APRD00165)
Type small molecule
Groups approved
Description

A nonselective beta-adrenoceptor antagonist used in the treatment of glaucoma. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Levobunolol HCl
  • Levobunololum [INN-Latin]
Synonyms
Levobunolol HCl
Levobunololum [INN-Latin]
Salts Not Available
Brand names
Name Company
Akbeta
Betagan
Brand mixtures Not Available
Categories
  • Adrenergic beta-Antagonists
  • Sympatholytics
  • EENT Drugs
CAS number 47141-42-4
Weight Average: 291.3853
Monoisotopic: 291.183443671
Chemical Formula C17H25NO3
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Naphthalenes
Substructures
  • Hydroxy Compounds
  • Naphthalenes
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Amino Alcohols
  • Aromatic compounds
  • Anisoles
  • Benzoyl Derivatives
  • Alcohols and Polyols
  • Cyclohexenes and Derivatives
  • Phenyl Esters
  • Ketones
Pharmacology
Indication For lowering intraocular pressure (IOP) and may be used in patients with chronic open-angle glaucoma or ocular hypertension.
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.
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
Toxicity Bradycardia, hypotension, bronchospasm, and acute cardiac failure, LD50=700 mg/kg (orally in rat).
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Akorn inc
  • Allergan pharmaceutical
  • Bausch and lomb pharmaceuticals inc
  • Falcon pharmaceuticals ltd
  • Novex pharma
Packagers
Dosage forms
Form Route Strength
Liquid Ophthalmic
Solution Ophthalmic
Prices
Unit description Cost Unit
Levobunolol HCl 0.5% Solution 15ml Bottle 50.25 USD bottle
Levobunolol HCl 0.5% Solution 10ml Bottle 33.58 USD bottle
Levobunolol HCl 0.25% Solution 10ml Bottle 32.59 USD bottle
Levobunolol HCl 0.5% Solution 5ml Bottle 17.26 USD bottle
Levobunolol HCl 0.25% Solution 5ml Bottle 16.45 USD bottle
Betagan 0.5% Solution 6.39 USD ml
Betagan 0.5% eye drops 6.1 USD ml
Betagan 0.25% eye drops 4.9 USD ml
Betagan 0.5 % Solution 3.7 USD ml
Levobunolol 0.5% eye drops 3.24 USD ml
Levobunolol 0.25% eye drops 2.83 USD ml
Pms-Levobunolol 0.5 % Solution 1.63 USD ml
Ratio-Levobunolol 0.5 % Solution 1.63 USD ml
Sandoz Levobunolol 0.5 % Solution 1.63 USD ml
Ratio-Levobunolol 0.25 % Solution 1.23 USD ml
Sandoz Levobunolol 0.25 % Solution 1.23 USD ml
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Patents Not Available
Properties
State solid
Melting point 209-211oC
Experimental Properties
Property Value Source
logP 2.1 PhysProp
Predicted Properties
Property Value Source
water solubility 2.51e-01 g/l ALOGPS
logP 2.06 ALOGPS
logP 2.18 ChemAxon Molconvert
logS -3.1 ALOGPS
pKa 16.52 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 58.56 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 83.28 ChemAxon Molconvert
polarizability 33.38 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. 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. Pubmed
  2. 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. Pubmed
  3. Leung M, Grunwald JE: Short-term effects of topical levobunolol on the human retinal circulation. Eye. 1997;11 ( Pt 3):371-6. Pubmed
  4. 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. Pubmed
  5. Gonzalez JP, Clissold SP: Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1987 Dec;34(6):648-61. Pubmed
  6. Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. Pubmed
  7. Novack GD: Levobunolol for the long-term treatment of glaucoma. Gen Pharmacol. 1986;17(4):373-7. Pubmed
External Links
Resource Link
KEGG Compound C07914 Link_out
PubChem Compound 39468 Link_out
PubChem Substance 46507518 Link_out
ChemSpider 36089 Link_out
ChEBI 6438 Link_out
ChEMBL 6438 Link_out
Therapeutic Targets Database DAP000303 Link_out
Drug Product Database 2241575 Link_out
RxList http://www.rxlist.com/cgi/generic/levobunolol.htm Link_out
Drugs.com http://www.drugs.com/cdi/levobunolol-drops.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Levobunolol Link_out
ATC Codes
  • S01ED03
AHFS Codes
  • 52:92.00
PDB Entries Not Available
FDA label show (850 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Food Interactions Not Available
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: antagonist

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 30-fold greater affinity than it does norepinephrine

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Quast U, Vollmer KO: Binding of beta-adrenoceptor antagonists to rat and rabbit lung: special reference to levobunolol. Arzneimittelforschung. 1984;34(5):579-84. Pubmed
  3. 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. Pubmed
  4. Harris A, Malinovsky V, Martin B: Correlates of acute exercise-induced ocular hypotension. Invest Ophthalmol Vis Sci. 1994 Oct;35(11):3852-7. Pubmed
  5. Brooks AM, Gillies WE: Ocular beta-blockers in glaucoma management. Clinical pharmacological aspects. Drugs Aging. 1992 May-Jun;2(3):208-21. Pubmed
  6. Gonzalez JP, Clissold SP: Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1987 Dec;34(6):648-61. Pubmed
  7. Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. Pubmed

2. Beta-1 adrenergic receptor

Pharmacological action: yes
Actions: antagonist

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 equal affinity

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. Pubmed
  2. Harris A, Malinovsky V, Martin B: Correlates of acute exercise-induced ocular hypotension. Invest Ophthalmol Vis Sci. 1994 Oct;35(11):3852-7. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. Brooks AM, Gillies WE: Ocular beta-blockers in glaucoma management. Clinical pharmacological aspects. Drugs Aging. 1992 May-Jun;2(3):208-21. Pubmed
  6. Gonzalez JP, Clissold SP: Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1987 Dec;34(6):648-61. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:46