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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H25NO3
Molecular Weight 291.3859
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOBUNOLOL

SMILES

CC(C)(C)NC[C@@]([H])(COc1cccc2c1CCCC2=O)O

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 291.3859
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.76 nM [Ki]
32.6 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

5.03798399E11
Primary
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

5.03798399E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.65 ng/mL
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
3.72 ng/mL
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.08 μg × min/mL
410 μg single, intravenous
dose: 410 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LEVOBUNOLOL blood
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.1 h
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
42 min
410 μg single, intravenous
dose: 410 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LEVOBUNOLOL blood
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
6.1 h
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
Doses

Doses

DosePopulationAdverse 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:
unhealthy, adult
Health Status: unhealthy
Condition: glaucoma
Age Group: adult
Sex: unknown
Sources:
PubMed

PubMed

TitleDatePubMed
l-Bunolol and propranolol: oral and intravenous beta-adrenoceptor blocking activity in rats compared to dogs and humans.
1978 Jan
Levobunolol for the long-term treatment of glaucoma.
1986
Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy.
1987 Dec
Comparison of ophthalmic beta-blocking agents.
1987 Jun
A comparison of the ocular tolerability of a single dose of timolol and levobunolol in healthy normotensive volunteers.
1993 Apr
A comparison of the ocular hypotensive efficacy and systemic safety of 0.5% levobunolol and 2% carteolol.
1994
Syncope, bradycardia, and atrioventricular block associated with topical ophthalmic levobunolol.
1994 Mar
Short-term effects of topical levobunolol on the human retinal circulation.
1997
Bilateral nongranulomatous anterior uveitis associated with bimatoprost.
2003 Nov
[Osmotic resistance of red blood cells membranes in Vermox and "AKbeta" vitamin complex treatment of experimental trichinosis in rats].
2004
Binding affinities of ocular hypotensive beta-blockers levobetaxolol, levobunolol, and timolol at endogenous guinea pig beta-adrenoceptors.
2004 Apr
Deposits in artificial corneas: risk factors and prevention.
2004 Apr
[Cost-effectivity analysis of the most used antiglaucoma drugs].
2004 Aug
Stereoselectivity for interactions of agonists and antagonists at mouse, rat and human beta3-adrenoceptors.
2004 Jan 26
Effects of carteolol hydrochloride on the in vitro production of LPS-induced proinflammatory cytokines by murine macrophage.
2004 Jun
Inhibition of endothelin-1 and KCL-induced increase of [CA2+]i by antiglaucoma drugs in cultured A7r5 vascular smooth-muscle cells.
2004 Jun
Reversal of disc cupping after intraocular pressure reduction in topographic image series.
2004 Oct
The effect of once-daily levobunolol on intraocular pressure in normal-tension glaucoma.
2005 Jan-Feb
Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro.
2005 Mar
Study of effects of antiglaucoma eye drops on N-methyl-D-aspartate-induced retinal damage.
2005 Nov-Dec
Allergic contact dermatitis due to beta-blockers in eye drops: a retrospective analysis of multicentre surveillance data 1993-2004.
2006
Contact dermatitis to levobunolol eyedrops superimposed on IgE-mediated rhinoconjunctivitis.
2006 Dec
Effects of antiglaucoma drugs on calcium mobility in cultured corneal endothelial cells.
2006 Feb
Allergic contact dermatitis due to levobunolol in an ophthalmic preparation.
2006 Jul
The management of glaucoma and intraocular hypertension: current approaches and recent advances.
2006 Jun
Effects of antiglaucoma drugs on cellular proliferation in cultured human corneal keratocytes.
2006 Mar
Transdermal delivery of beta-blockers.
2006 May
Beta-blocker eye drops.
2006 May 30-Jun 5
Drops and falls.
2006 Nov
Myocilin mutations among primary open angle glaucoma patients of Kanyakumari district, South India.
2007 Apr 2
Allergic contact dermatitis due to levobunolol with cross-sensitivity to befunolol.
2007 Jan
Membrane electrodes for determination of some beta-blocker drugs.
2007 Jul-Aug
Levobetaxolol hydrochloride: a review of its pharmacology and use in the treatment of chronic open-angle glaucoma and ocular hypertension.
2007 Jun
Vasodilatory mechanism of levobunolol on vascular smooth muscle cells.
2007 Jun
Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells.
2007 Mar
Daily cost of glaucoma medications in China.
2007 Oct-Nov
An in vivo confocal microscopy and impression cytology analysis of preserved and unpreserved levobunolol-induced conjunctival changes.
2008 May-Jun
Miscellaneous.
2008 Oct
Recent advances in pharmacotherapy of glaucoma.
2008 Oct
Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery.
2009
Aerobic exercise and intraocular pressure in normotensive and glaucoma patients.
2009 Aug 13
Effect of latanoprost and timolol on the histopathology of the human conjunctiva.
2009 Feb
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 Feb
Retrospective cohort study of 163 pediatric glaucoma patients.
2009 Jun
[Cytotoxicity of antiglaucoma ophthalmic solutions for human corneal endothelial cells].
2009 May
Comparison of effects of topical levobunolol to a combination of timolol-dorzolamide on intraocular pressure and pulse rate of healthy dogs.
2009 Sep
Efficacy and patient tolerability of travoprost BAK-free solution in patients with open-angle glaucoma and ocular hypertension.
2010 Aug 9
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 Fall
A new mode of dimerization of allosteric enzymes with ACT domains revealed by the crystal structure of the aspartate kinase from Cyanobacteria.
2010 Jun 4
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Patents

Sample Use Guides

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
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 Sat Jun 26 10:46:40 UTC 2021
Edited
by admin
on Sat Jun 26 10:46:40 UTC 2021
Record UNII
G6317AOI7K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOBUNOLOL
INN   MI   VANDF   WHO-DD  
INN  
Official 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
BUNOLOL, (-)-
Common Name English
Classification Tree Code System Code
NDF-RT N0000175556
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
WHO-VATC QS01ED03
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
NDF-RT N0000000161
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
NCI_THESAURUS C29705
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
WHO-ATC S01ED03
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
Code System Code Type Description
INN
4706
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
DRUG CENTRAL
431
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
DRUG BANK
DB01210
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
EPA CompTox
47141-42-4
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
RXCUI
1813
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY RxNorm
IUPHAR
570
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
MERCK INDEX
M6784
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1201237
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
WIKIPEDIA
LEVOBUNOLOL
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
EVMPD
SUB08463MIG
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
MESH
D002040
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
NCI_THESAURUS
C62043
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
CAS
47141-42-4
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
LACTMED
Levobunolol
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
PUBCHEM
39468
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
FDA UNII
G6317AOI7K
Created by admin on Sat Jun 26 10:46:40 UTC 2021 , Edited by admin on Sat Jun 26 10:46:40 UTC 2021
PRIMARY
Related Record Type Details
TARGET->ANTAGONIST
Levobunolol (LB) is the levo-rotatory isomer of bunolol, a potent, nonselective antagonist of beta-adrenergic receptors.
TARGET->ANTAGONIST
Levobunolol (LB) is the levo-rotatory isomer of bunolol, a potent, nonselective antagonist of beta-adrenergic receptors.
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY