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
Synonyms
  • (-)-Bunolol
  • (S)-5-(3-((1,1-Dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-1(2H)-naphthalenone
  • Levobunolol
  • Levobunololum
Product Ingredients
IngredientUNIICASInChI Key
Levobunolol HydrochlorideO90S49LDHH27912-14-7DNTDOBSIBZKFCP-YDALLXLXSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BetaganSolution / drops5 mg/mLOphthalmicAllergan1986-07-24Not applicableUs
Betagan 0.5% Ophthalmic SolLiquid5 mgOphthalmicAllergan1985-12-31Not applicableCanada
Betagan Oph Soln 0.25%Liquid0.25 %OphthalmicAllergan1990-12-31Not applicableCanada
Levobunolol HydrochlorideSolution / drops5 mg/mLOphthalmicPacific Pharma1997-07-15Not applicableUs
Levobunolol Hydrochloride Ophthalmic SolutionLiquid0.50 %OphthalmicAlcon, Inc.Not applicableNot applicableCanada
Levobunolol Hydrochloride Ophthalmic SolutionLiquid0.25 %OphthalmicBausch & Lomb Inc1997-09-242003-07-14Canada
Levobunolol Hydrochloride Ophthalmic SolutionLiquid0.25 %OphthalmicAlcon, Inc.Not applicableNot applicableCanada
Levobunolol Hydrochloride Ophthalmic SolutionLiquid0.50 %OphthalmicBausch & Lomb Inc1997-09-242003-07-14Canada
Sandoz LevobunololLiquid0.5 %OphthalmicSandoz Canada Incorporated2000-08-21Not applicableCanada
Sandoz LevobunololLiquid0.25 %OphthalmicSandoz Canada Incorporated2000-08-21Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-levobunolol Ophthalmic Solution USP 0.25%Liquid0.25 %OphthalmicApotex Corporation2000-02-21Not applicableCanada
Apo-levobunolol Ophthalmic Solution USP 0.5%Liquid0.5 %OphthalmicApotex Corporation2000-02-21Not applicableCanada
Levobunolol HydrochlorideSolution / drops2.5 mg/mLOphthalmicBauch & Lomb Incorporated1994-03-042016-10-13Us
Levobunolol HydrochlorideSolution5 mg/mLOphthalmicSandoz1997-01-30Not applicableUs
Levobunolol HydrochlorideSolution / drops5 mg/mLOphthalmicPhysicians Total Care, Inc.1995-02-23Not applicableUs
Levobunolol HydrochlorideSolution / drops5 mg/mLOphthalmicBauch & Lomb Incorporated1994-03-04Not applicableUs
Novo-levobunolol - Liq 0.25%Liquid0.25 %OphthalmicNovopharm Limited1996-07-302015-10-26Canada
Novo-levobunolol - Liq 0.5%Liquid0.5 %OphthalmicNovopharm Limited1996-07-302015-10-26Canada
PMS-levobunololLiquid0.5 %OphthalmicPharmascience Inc1998-08-312016-10-28Canada
PMS-levobunololLiquid0.25 %OphthalmicPharmascience IncNot applicableNot applicableCanada
International/Other Brands
Akbeta
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Probeta - Liq OphLevobunolol Hydrochloride (0.5 %) + Dipivefrin Hydrochloride (0.1 %)LiquidOphthalmicAllergan1996-08-302012-07-16Canada
Categories
UNII
G6317AOI7K
CAS number
47141-42-4
Weight
Average: 291.3853
Monoisotopic: 291.183443671
Chemical Formula
C17H25NO3
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[[email protected]](O)COC1=CC=CC2=C1CCCC2=O

Pharmacology

Indication

For lowering intraocular pressure (IOP) and may be used in patients with chronic open-angle glaucoma or ocular hypertension.

Structured Indications
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.

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Human
ABeta-2 adrenergic receptor
antagonist
Human
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
PathwayCategory
Levobunolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Levobunolol.Experimental
AceclofenacAceclofenac may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
AcemetacinAcemetacin may decrease the antihypertensive activities of Levobunolol.Approved, Experimental, Investigational
AcepromazineAcepromazine may increase the hypotensive activities of Levobunolol.Approved, Vet Approved
AceprometazineAceprometazine may increase the hypotensive activities of Levobunolol.Approved
AcetohexamideLevobunolol may increase the hypoglycemic activities of Acetohexamide.Investigational, Withdrawn
AcetylcholineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Acetylcholine.Approved
AcetyldigitoxinLevobunolol may increase the bradycardic activities of Acetyldigitoxin.Approved
AcetyldigoxinLevobunolol may increase the bradycardic activities of Acetyldigoxin.Experimental
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved
AdapaleneAdapalene may decrease the antihypertensive activities of Levobunolol.Approved
AlaproclateThe serum concentration of Levobunolol can be increased when it is combined with Alaproclate.Experimental
AlclofenacAlclofenac may decrease the antihypertensive activities of Levobunolol.Approved, Withdrawn
AlfentanilAlfentanil may increase the bradycardic activities of Levobunolol.Approved, Illicit
AlimemazineAlimemazine may increase the hypotensive activities of Levobunolol.Approved, Vet Approved
AlminoprofenAlminoprofen may decrease the antihypertensive activities of Levobunolol.Experimental
AmbenoniumAmbenonium may increase the bradycardic activities of Levobunolol.Approved
AmiodaroneAmiodarone may increase the bradycardic activities of Levobunolol.Approved, Investigational
AmobarbitalThe serum concentration of Levobunolol can be decreased when it is combined with Amobarbital.Approved, Illicit
AmodiaquineThe metabolism of Levobunolol can be decreased when combined with Amodiaquine.Approved, Investigational
AndrographolideAndrographolide may decrease the antihypertensive activities of Levobunolol.Investigational
AnisodamineAnisodamine may decrease the antihypertensive activities of Levobunolol.Investigational
AntipyrineAntipyrine may decrease the antihypertensive activities of Levobunolol.Approved
ApocyninApocynin may decrease the antihypertensive activities of Levobunolol.Investigational
ApremilastApremilast may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
ArecolineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Arecoline.Experimental
AzapropazoneAzapropazone may decrease the antihypertensive activities of Levobunolol.Withdrawn
AzelastineAzelastine may decrease the antihypertensive activities of Levobunolol.Approved
BalsalazideBalsalazide may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
BarbexacloneThe serum concentration of Levobunolol can be decreased when it is combined with Barbexaclone.Experimental
BarbitalThe serum concentration of Levobunolol can be decreased when it is combined with Barbital.Illicit
BendazacBendazac may decrease the antihypertensive activities of Levobunolol.Experimental
BenorilateBenorilate may decrease the antihypertensive activities of Levobunolol.Experimental
BenoxaprofenBenoxaprofen may decrease the antihypertensive activities of Levobunolol.Withdrawn
BenzydamineBenzydamine may decrease the antihypertensive activities of Levobunolol.Approved
BethanecholThe risk or severity of adverse effects can be increased when Levobunolol is combined with Bethanechol.Approved
BevoniumBevonium may decrease the antihypertensive activities of Levobunolol.Experimental
BL-1020BL-1020 may increase the hypotensive activities of Levobunolol.Investigational
BromfenacBromfenac may decrease the antihypertensive activities of Levobunolol.Approved
BromocriptineLevobunolol may increase the vasoconstricting activities of Bromocriptine.Approved, Investigational
BucillamineBucillamine may decrease the antihypertensive activities of Levobunolol.Investigational
BufexamacBufexamac may decrease the antihypertensive activities of Levobunolol.Experimental
BumadizoneBumadizone may decrease the antihypertensive activities of Levobunolol.Experimental
BupivacaineThe serum concentration of Bupivacaine can be increased when it is combined with Levobunolol.Approved, Investigational
CabergolineLevobunolol may increase the vasoconstricting activities of Cabergoline.Approved
CarbacholThe risk or severity of adverse effects can be increased when Levobunolol is combined with Carbachol.Approved
Carbaspirin calciumCarbaspirin calcium may decrease the antihypertensive activities of Levobunolol.Experimental, Investigational
CarbutamideLevobunolol may increase the hypoglycemic activities of Carbutamide.Experimental
CarprofenCarprofen may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the antihypertensive activities of Levobunolol.Experimental
CelecoxibCelecoxib may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
CevimelineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Cevimeline.Approved
ChloroquineThe metabolism of Levobunolol can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorproethazineChlorproethazine may increase the hypotensive activities of Levobunolol.Experimental
ChlorpromazineChlorpromazine may increase the hypotensive activities of Levobunolol.Approved, Vet Approved
ChlorpropamideLevobunolol may increase the hypoglycemic activities of Chlorpropamide.Approved
Choline magnesium trisalicylateCholine magnesium trisalicylate may decrease the antihypertensive activities of Levobunolol.Approved
ClonixinClonixin may decrease the antihypertensive activities of Levobunolol.Approved
CoumaphosCoumaphos may increase the bradycardic activities of Levobunolol.Vet Approved
CurcuminCurcumin may decrease the antihypertensive activities of Levobunolol.Investigational
CymarinLevobunolol may increase the bradycardic activities of Cymarin.Experimental
DapoxetineThe serum concentration of Levobunolol can be increased when it is combined with Dapoxetine.Investigational
DecamethoniumDecamethonium may increase the bradycardic activities of Levobunolol.Approved
DemecariumDemecarium may increase the bradycardic activities of Levobunolol.Approved
DeslanosideLevobunolol may increase the bradycardic activities of Deslanoside.Approved
DesvenlafaxineThe serum concentration of Levobunolol can be increased when it is combined with Desvenlafaxine.Approved
DichlorvosDichlorvos may increase the bradycardic activities of Levobunolol.Vet Approved
DiclofenacDiclofenac may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved
DifenpiramideDifenpiramide may decrease the antihypertensive activities of Levobunolol.Experimental
DiflunisalDiflunisal may decrease the antihypertensive activities of Levobunolol.Approved
DigitoxinLevobunolol may increase the bradycardic activities of Digitoxin.Approved, Investigational
DigoxinLevobunolol may increase the bradycardic activities of Digoxin.Approved
Digoxin Immune Fab (Ovine)Levobunolol may increase the bradycardic activities of Digoxin Immune Fab (Ovine).Approved
DiltiazemDiltiazem may increase the hypotensive activities of Levobunolol.Approved
DipyridamoleDipyridamole may increase the bradycardic activities of Levobunolol.Approved
DisopyramideDisopyramide may increase the bradycardic activities of Levobunolol.Approved
DistigmineDistigmine may increase the bradycardic activities of Levobunolol.Experimental
DronedaroneDronedarone may increase the bradycardic activities of Levobunolol.Approved
DroxicamDroxicam may decrease the antihypertensive activities of Levobunolol.Withdrawn
DuvelisibDuvelisib may decrease the antihypertensive activities of Levobunolol.Investigational
E-6201E-6201 may decrease the antihypertensive activities of Levobunolol.Investigational
EchothiophateEchothiophate may increase the bradycardic activities of Levobunolol.Approved
EdrophoniumEdrophonium may increase the bradycardic activities of Levobunolol.Approved
EpibatidineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Epibatidine.Experimental
EpirizoleEpirizole may decrease the antihypertensive activities of Levobunolol.Approved
EtanerceptEtanercept may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
EthenzamideEthenzamide may decrease the antihypertensive activities of Levobunolol.Experimental
EtodolacEtodolac may decrease the antihypertensive activities of Levobunolol.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
EtoperidoneThe serum concentration of Levobunolol can be increased when it is combined with Etoperidone.Withdrawn
EtoricoxibEtoricoxib may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
ExisulindExisulind may decrease the antihypertensive activities of Levobunolol.Investigational
FelbinacFelbinac may decrease the antihypertensive activities of Levobunolol.Experimental
FenbufenFenbufen may decrease the antihypertensive activities of Levobunolol.Approved
FenoprofenFenoprofen may decrease the antihypertensive activities of Levobunolol.Approved
FentanylFentanyl may increase the bradycardic activities of Levobunolol.Approved, Illicit, Investigational, Vet Approved
FenthionFenthion may increase the bradycardic activities of Levobunolol.Vet Approved
FentiazacFentiazac may decrease the antihypertensive activities of Levobunolol.Experimental
FeprazoneFeprazone may decrease the antihypertensive activities of Levobunolol.Experimental
Ferulic acidFerulic acid may decrease the antihypertensive activities of Levobunolol.Experimental
FingolimodLevobunolol may increase the bradycardic activities of Fingolimod.Approved, Investigational
FloctafenineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Floctafenine.Approved, Withdrawn
FlunixinFlunixin may decrease the antihypertensive activities of Levobunolol.Vet Approved
FlunoxaprofenFlunoxaprofen may decrease the antihypertensive activities of Levobunolol.Experimental
FluoxetineThe serum concentration of Levobunolol can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FluphenazineFluphenazine may increase the hypotensive activities of Levobunolol.Approved
FlurbiprofenFlurbiprofen may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
Gallamine TriethiodideGallamine Triethiodide may increase the bradycardic activities of Levobunolol.Approved
GitoformateLevobunolol may increase the bradycardic activities of Gitoformate.Experimental
GlibornurideLevobunolol may increase the hypoglycemic activities of Glibornuride.Investigational, Withdrawn
GliclazideLevobunolol may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideLevobunolol may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideLevobunolol may increase the hypoglycemic activities of Glipizide.Approved
GliquidoneLevobunolol may increase the hypoglycemic activities of Gliquidone.Approved, Investigational
GlisoxepideLevobunolol may increase the hypoglycemic activities of Glisoxepide.Approved, Investigational
GlyburideLevobunolol may increase the hypoglycemic activities of Glyburide.Approved
GTS-21The risk or severity of adverse effects can be increased when Levobunolol is combined with GTS-21.Investigational
GuacetisalGuacetisal may decrease the antihypertensive activities of Levobunolol.Experimental
HexobarbitalThe serum concentration of Levobunolol can be decreased when it is combined with Hexobarbital.Approved
HigenamineHigenamine may decrease the antihypertensive activities of Levobunolol.Investigational
Huperzine AHuperzine A may increase the bradycardic activities of Levobunolol.Investigational
HydroxychloroquineThe metabolism of Levobunolol can be decreased when combined with Hydroxychloroquine.Approved
IbuprofenIbuprofen may decrease the antihypertensive activities of Levobunolol.Approved
IbuproxamIbuproxam may decrease the antihypertensive activities of Levobunolol.Withdrawn
IcatibantIcatibant may decrease the antihypertensive activities of Levobunolol.Approved
Imidazole salicylateImidazole salicylate may decrease the antihypertensive activities of Levobunolol.Experimental
IndalpineThe serum concentration of Levobunolol can be increased when it is combined with Indalpine.Investigational, Withdrawn
IndobufenIndobufen may decrease the antihypertensive activities of Levobunolol.Investigational
IndomethacinIndomethacin may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
IndoprofenIndoprofen may decrease the antihypertensive activities of Levobunolol.Withdrawn
IpidacrineIpidacrine may increase the bradycardic activities of Levobunolol.Experimental
IsoflurophateIsoflurophate may increase the bradycardic activities of Levobunolol.Approved, Investigational, Withdrawn
IsoxicamIsoxicam may decrease the antihypertensive activities of Levobunolol.Withdrawn
KebuzoneKebuzone may decrease the antihypertensive activities of Levobunolol.Experimental
KetoprofenKetoprofen may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved
KetorolacKetorolac may decrease the antihypertensive activities of Levobunolol.Approved
Lanatoside CLevobunolol may increase the bradycardic activities of Lanatoside C.Experimental
LeflunomideLeflunomide may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
LevomilnacipranThe serum concentration of Levobunolol can be increased when it is combined with Levomilnacipran.Approved
LidocaineThe serum concentration of Lidocaine can be increased when it is combined with Levobunolol.Approved, Vet Approved
LisofyllineLisofylline may decrease the antihypertensive activities of Levobunolol.Investigational
LobelineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Lobeline.Investigational
LonazolacLonazolac may decrease the antihypertensive activities of Levobunolol.Experimental
LornoxicamLornoxicam may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
LoxoprofenLoxoprofen may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
LumiracoxibLumiracoxib may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the antihypertensive activities of Levobunolol.Approved
MalathionMalathion may increase the bradycardic activities of Levobunolol.Approved, Investigational
MasoprocolMasoprocol may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
Meclofenamic acidMeclofenamic acid may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the antihypertensive activities of Levobunolol.Approved
MefloquineMefloquine may increase the bradycardic activities of Levobunolol.Approved
MeloxicamMeloxicam may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved
MemantineMemantine may increase the bradycardic activities of Levobunolol.Approved, Investigational
MepivacaineThe serum concentration of Mepivacaine can be increased when it is combined with Levobunolol.Approved, Vet Approved
MesalazineMesalazine may decrease the antihypertensive activities of Levobunolol.Approved
MesoridazineMesoridazine may increase the hypotensive activities of Levobunolol.Approved, Investigational
MetahexamideLevobunolol may increase the hypoglycemic activities of Metahexamide.Experimental
MetamizoleMetamizole may decrease the antihypertensive activities of Levobunolol.Investigational, Withdrawn
MethacholineLevobunolol may increase the bronchoconstrictory activities of Methacholine.Approved
Methanesulfonyl FluorideMethanesulfonyl Fluoride may increase the bradycardic activities of Levobunolol.Investigational
MethohexitalThe serum concentration of Levobunolol can be decreased when it is combined with Methohexital.Approved
MethotrimeprazineMethotrimeprazine may increase the hypotensive activities of Levobunolol.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Levobunolol.Approved, Investigational
MethylergometrineLevobunolol may increase the vasoconstricting activities of Methylergometrine.Approved
MethylphenobarbitalThe serum concentration of Levobunolol can be decreased when it is combined with Methylphenobarbital.Approved
MetildigoxinLevobunolol may increase the bradycardic activities of Metildigoxin.Experimental
MetoclopramideMetoclopramide may increase the bradycardic activities of Levobunolol.Approved, Investigational
MidodrineLevobunolol may increase the bradycardic activities of Midodrine.Approved
MilnacipranThe serum concentration of Levobunolol can be increased when it is combined with Milnacipran.Approved
MinaprineMinaprine may increase the bradycardic activities of Levobunolol.Approved
MizoribineMizoribine may decrease the antihypertensive activities of Levobunolol.Investigational
MofebutazoneMofebutazone may decrease the antihypertensive activities of Levobunolol.Experimental
MoricizineMoricizine may increase the hypotensive activities of Levobunolol.Approved, Investigational, Withdrawn
Mycophenolate mofetilMycophenolate mofetil may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the antihypertensive activities of Levobunolol.Approved
NabumetoneNabumetone may decrease the antihypertensive activities of Levobunolol.Approved
NafamostatNafamostat may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
NaftifineNaftifine may decrease the antihypertensive activities of Levobunolol.Approved
NaproxenNaproxen may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved
NefazodoneThe serum concentration of Levobunolol can be increased when it is combined with Nefazodone.Approved, Withdrawn
NeostigmineNeostigmine may increase the bradycardic activities of Levobunolol.Approved, Vet Approved
NepafenacNepafenac may decrease the antihypertensive activities of Levobunolol.Approved
NicotineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Nicotine.Approved
NifedipineNifedipine may increase the hypotensive activities of Levobunolol.Approved
NifenazoneNifenazone may decrease the antihypertensive activities of Levobunolol.Experimental
Niflumic AcidNiflumic Acid may decrease the antihypertensive activities of Levobunolol.Approved
NimesulideNimesulide may decrease the antihypertensive activities of Levobunolol.Approved, Investigational, Withdrawn
NitroaspirinNitroaspirin may decrease the antihypertensive activities of Levobunolol.Investigational
OleandrinLevobunolol may increase the bradycardic activities of Oleandrin.Experimental, Investigational
OlopatadineOlopatadine may decrease the antihypertensive activities of Levobunolol.Approved
OlsalazineOlsalazine may decrease the antihypertensive activities of Levobunolol.Approved
OrgoteinOrgotein may decrease the antihypertensive activities of Levobunolol.Vet Approved
OuabainLevobunolol may increase the bradycardic activities of Ouabain.Approved
OxaprozinOxaprozin may decrease the antihypertensive activities of Levobunolol.Approved
OxyphenbutazoneOxyphenbutazone may decrease the antihypertensive activities of Levobunolol.Approved, Withdrawn
ParaoxonParaoxon may increase the bradycardic activities of Levobunolol.Experimental
ParecoxibParecoxib may decrease the antihypertensive activities of Levobunolol.Approved
ParoxetineThe serum concentration of Levobunolol can be increased when it is combined with Paroxetine.Approved, Investigational
ParthenolideParthenolide may decrease the antihypertensive activities of Levobunolol.Investigational
PentobarbitalThe serum concentration of Levobunolol can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PerazinePerazine may increase the hypotensive activities of Levobunolol.Investigational
PerphenazinePerphenazine may increase the hypotensive activities of Levobunolol.Approved
PeruvosideLevobunolol may increase the bradycardic activities of Peruvoside.Experimental
PhenobarbitalThe serum concentration of Levobunolol can be decreased when it is combined with Phenobarbital.Approved
PhenylbutazonePhenylbutazone may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved
PhysostigminePhysostigmine may increase the bradycardic activities of Levobunolol.Approved
PilocarpineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Pilocarpine.Approved
PimecrolimusPimecrolimus may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
PirfenidonePirfenidone may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
PiroxicamPiroxicam may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
PirprofenPirprofen may decrease the antihypertensive activities of Levobunolol.Experimental
PranoprofenPranoprofen may decrease the antihypertensive activities of Levobunolol.Experimental, Investigational
PrimaquineThe metabolism of Levobunolol can be decreased when combined with Primaquine.Approved
PrimidoneThe serum concentration of Levobunolol can be decreased when it is combined with Primidone.Approved, Vet Approved
ProchlorperazineProchlorperazine may increase the hypotensive activities of Levobunolol.Approved, Vet Approved
ProglumetacinProglumetacin may decrease the antihypertensive activities of Levobunolol.Experimental
PromazinePromazine may increase the hypotensive activities of Levobunolol.Approved, Vet Approved
PromethazinePromethazine may increase the hypotensive activities of Levobunolol.Approved
PropacetamolPropacetamol may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
PropafenoneThe serum concentration of Levobunolol can be increased when it is combined with Propafenone.Approved
PropericiazinePropericiazine may increase the hypotensive activities of Levobunolol.Approved
PropiopromazinePropiopromazine may increase the hypotensive activities of Levobunolol.Vet Approved
PropyphenazonePropyphenazone may decrease the antihypertensive activities of Levobunolol.Experimental
ProquazoneProquazone may decrease the antihypertensive activities of Levobunolol.Experimental
ProscillaridinLevobunolol may increase the bradycardic activities of Proscillaridin.Experimental
PTC299PTC299 may decrease the antihypertensive activities of Levobunolol.Investigational
PyridostigminePyridostigmine may increase the bradycardic activities of Levobunolol.Approved
RegorafenibRegorafenib may increase the bradycardic activities of Levobunolol.Approved
RemifentanilRemifentanil may increase the bradycardic activities of Levobunolol.Approved
ReserpineReserpine may increase the hypotensive activities of Levobunolol.Approved, Investigational
ResveratrolResveratrol may decrease the antihypertensive activities of Levobunolol.Approved, Experimental, Investigational
RifampicinThe serum concentration of Levobunolol can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Levobunolol can be decreased when it is combined with Rifapentine.Approved
RifaximinThe serum concentration of Levobunolol can be decreased when it is combined with Rifaximin.Approved, Investigational
RivastigmineLevobunolol may increase the bradycardic activities of Rivastigmine.Approved, Investigational
RofecoxibRofecoxib may decrease the antihypertensive activities of Levobunolol.Investigational, Withdrawn
SalicylamideSalicylamide may decrease the antihypertensive activities of Levobunolol.Approved
Salicylic acidSalicylic acid may decrease the antihypertensive activities of Levobunolol.Approved, Vet Approved
SalsalateSalsalate may decrease the antihypertensive activities of Levobunolol.Approved
SecobarbitalThe serum concentration of Levobunolol can be decreased when it is combined with Secobarbital.Approved, Vet Approved
SemapimodSemapimod may decrease the antihypertensive activities of Levobunolol.Investigational
SeratrodastSeratrodast may decrease the antihypertensive activities of Levobunolol.Approved
SerrapeptaseSerrapeptase may decrease the antihypertensive activities of Levobunolol.Investigational
SertralineThe serum concentration of Levobunolol can be increased when it is combined with Sertraline.Approved
SRT501SRT501 may decrease the antihypertensive activities of Levobunolol.Investigational
SufentanilSufentanil may increase the bradycardic activities of Levobunolol.Approved, Investigational
SulfasalazineSulfasalazine may decrease the antihypertensive activities of Levobunolol.Approved
SulindacSulindac may decrease the antihypertensive activities of Levobunolol.Approved
SuprofenSuprofen may decrease the antihypertensive activities of Levobunolol.Approved, Withdrawn
SuxibuzoneSuxibuzone may decrease the antihypertensive activities of Levobunolol.Experimental
TacrineTacrine may increase the bradycardic activities of Levobunolol.Investigational, Withdrawn
TarenflurbilTarenflurbil may decrease the antihypertensive activities of Levobunolol.Investigational
TenidapTenidap may decrease the antihypertensive activities of Levobunolol.Experimental
TenoxicamTenoxicam may decrease the antihypertensive activities of Levobunolol.Approved
TepoxalinTepoxalin may decrease the antihypertensive activities of Levobunolol.Vet Approved
TeriflunomideTeriflunomide may decrease the antihypertensive activities of Levobunolol.Approved
ThiamylalThe serum concentration of Levobunolol can be decreased when it is combined with Thiamylal.Approved, Vet Approved
ThiazinamThiazinam may increase the hypotensive activities of Levobunolol.Experimental
ThiethylperazineThiethylperazine may increase the hypotensive activities of Levobunolol.Withdrawn
ThiopentalThe serum concentration of Levobunolol can be decreased when it is combined with Thiopental.Approved, Vet Approved
ThioproperazineThioproperazine may increase the hypotensive activities of Levobunolol.Approved
ThioridazineThioridazine may increase the hypotensive activities of Levobunolol.Approved, Withdrawn
Tiaprofenic acidTiaprofenic acid may decrease the antihypertensive activities of Levobunolol.Approved
TinoridineTinoridine may decrease the antihypertensive activities of Levobunolol.Investigational
TolazamideLevobunolol may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideLevobunolol may increase the hypoglycemic activities of Tolbutamide.Approved
Tolfenamic AcidTolfenamic Acid may decrease the antihypertensive activities of Levobunolol.Approved
TolmetinTolmetin may decrease the antihypertensive activities of Levobunolol.Approved
TranilastTranilast may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
TribenosideTribenoside may decrease the antihypertensive activities of Levobunolol.Experimental
TrichlorfonTrichlorfon may increase the bradycardic activities of Levobunolol.Vet Approved
TrifluoperazineTrifluoperazine may increase the hypotensive activities of Levobunolol.Approved
TriflupromazineTriflupromazine may increase the hypotensive activities of Levobunolol.Approved, Vet Approved
TriptolideTriptolide may decrease the antihypertensive activities of Levobunolol.Investigational
TubocurarineTubocurarine may increase the bradycardic activities of Levobunolol.Approved
ValdecoxibValdecoxib may decrease the antihypertensive activities of Levobunolol.Investigational, Withdrawn
VareniclineThe risk or severity of adverse effects can be increased when Levobunolol is combined with Varenicline.Approved, Investigational
VenlafaxineThe serum concentration of Levobunolol can be increased when it is combined with Venlafaxine.Approved
VerapamilVerapamil may increase the hypotensive activities of Levobunolol.Approved
ZaltoprofenZaltoprofen may decrease the antihypertensive activities of Levobunolol.Approved, Investigational
ZileutonZileuton may decrease the antihypertensive activities of Levobunolol.Approved, Investigational, Withdrawn
ZimelidineThe serum concentration of Levobunolol can be increased when it is combined with Zimelidine.Withdrawn
ZomepiracZomepirac may decrease the antihypertensive activities of Levobunolol.Withdrawn
Food Interactions
Not Available

References

General References
  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:14576520]
  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:10443129]
  3. Leung M, Grunwald JE: Short-term effects of topical levobunolol on the human retinal circulation. Eye (Lond). 1997;11 ( Pt 3):371-6. [PubMed:9373479]
  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:17459374]
  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:2892662]
  6. Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [PubMed:2891463]
  7. Novack GD: Levobunolol for the long-term treatment of glaucoma. Gen Pharmacol. 1986;17(4):373-7. [PubMed:3019819]
External Links
Human Metabolome Database
HMDB0015341
KEGG Compound
C07914
PubChem Compound
39468
PubChem Substance
46507518
ChemSpider
36089
ChEBI
6438
ChEMBL
CHEMBL1201237
Therapeutic Targets Database
DAP000303
PharmGKB
PA164747027
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Levobunolol
ATC Codes
S01ED03 — Levobunolol
AHFS Codes
  • 52:40.08 — Beta-adrenergic Agents
FDA label
Download (850 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
LiquidOphthalmic5 mg
SolutionOphthalmic5 mg/mL
Solution / dropsOphthalmic2.5 mg/mL
Solution / dropsOphthalmic5 mg/mL
LiquidOphthalmic0.25 %
LiquidOphthalmic0.50 %
LiquidOphthalmic0.5 %
LiquidOphthalmic
SolutionOphthalmic0.25 %
SolutionOphthalmic0.5 %
Prices
Unit descriptionCostUnit
Levobunolol HCl 0.5% Solution 15ml Bottle50.25USD bottle
Levobunolol HCl 0.5% Solution 10ml Bottle33.58USD bottle
Levobunolol HCl 0.25% Solution 10ml Bottle32.59USD bottle
Levobunolol HCl 0.5% Solution 5ml Bottle17.26USD bottle
Levobunolol HCl 0.25% Solution 5ml Bottle16.45USD bottle
Betagan 0.5% Solution6.39USD ml
Betagan 0.5% eye drops6.1USD ml
Betagan 0.25% eye drops4.9USD ml
Betagan 0.5 % Solution3.7USD ml
Levobunolol 0.5% eye drops3.24USD ml
Levobunolol 0.25% eye drops2.83USD ml
Pms-Levobunolol 0.5 % Solution1.63USD ml
Ratio-Levobunolol 0.5 % Solution1.63USD ml
Sandoz Levobunolol 0.5 % Solution1.63USD ml
Ratio-Levobunolol 0.25 % Solution1.23USD ml
Sandoz Levobunolol 0.25 % Solution1.23USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)209-211 °CNot Available
logP2.40HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.251 mg/mLALOGPS
logP2.06ALOGPS
logP2.18ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.28 m3·mol-1ChemAxon
Polarizability33.38 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9923
Blood Brain Barrier-0.8738
Caco-2 permeable-0.6105
P-glycoprotein substrateSubstrate0.8227
P-glycoprotein inhibitor IInhibitor0.5712
P-glycoprotein inhibitor IINon-inhibitor0.5691
Renal organic cation transporterNon-inhibitor0.8179
CYP450 2C9 substrateNon-substrate0.7696
CYP450 2D6 substrateSubstrate0.8547
CYP450 3A4 substrateNon-substrate0.5554
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8378
Ames testNon AMES toxic0.8825
CarcinogenicityNon-carcinogens0.9039
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.1253 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9613
hERG inhibition (predictor II)Inhibitor0.593
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Tetralin / Aryl alkyl ketone / Aryl ketone / Alkyl aryl ether / 1,2-aminoalcohol / Ketone / Secondary alcohol / Secondary aliphatic amine / Ether / Secondary amine
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
cyclic ketone, aromatic ether, propanolamine (CHEBI:6438)

Targets

Kind
Protein
Organism
Human
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
  1. Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [PubMed:2891463]
  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:7928182]
  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:10864881]
  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:11572462]
  5. Brooks AM, Gillies WE: Ocular beta-blockers in glaucoma management. Clinical pharmacological aspects. Drugs Aging. 1992 May-Jun;2(3):208-21. [PubMed:1351412]
  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:2892662]
Kind
Protein
Organism
Human
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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  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:6147147]
  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:11572462]
  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:7928182]
  5. Brooks AM, Gillies WE: Ocular beta-blockers in glaucoma management. Clinical pharmacological aspects. Drugs Aging. 1992 May-Jun;2(3):208-21. [PubMed:1351412]
  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:2892662]
  7. Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [PubMed:2891463]

Drug created on June 13, 2005 07:24 / Updated on January 19, 2018 10:55