Levobunolol

Levobunolol
Systematic (IUPAC) name

(S)-5-{[3-(tert-Butylamino)-2-hydroxypropyl]oxy}-3,4-dihydronaphthalen-1(2H)-one
Clinical data
Trade names	Betagan
AHFS/Drugs.com	monograph
MedlinePlus	a686011
Pregnancy category	C
Legal status	US: ℞-only
Routes of administration	Topical (eye drops)
Pharmacokinetic data
Biological half-life	20 hours
Identifiers
CAS Number	47141-42-4^Y
ATC code	S01ED03
PubChem	CID 39468
IUPHAR/BPS	570
DrugBank	DB01210^Y
ChemSpider	36089^Y
UNII	G6317AOI7K^Y
KEGG	D08115^Y
ChEBI	CHEBI:6438^Y
ChEMBL	CHEMBL1201237^N
Chemical data
Formula	C₁₇H₂₅NO₃
Molar mass	291.385 g/mol
SMILES O=C2c1cccc(OC[C@@H](O)CNC(C)(C)C)c1CCC2
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^Y Key:IXHBTMCLRNMKHZ-LBPRGKRZSA-N^Y
^NY (what is this?) (verify)

Levobunolol (AK-Beta, Liquifilm, Betegan) is a non-selective beta blocker. It is used topically to manage glaucoma.

References

Ishibashi T, Yokoi N, Kinoshita S (2003). "Comparison of the effects of topical levobunolol and timolol solution on the human ocular surface.". Cornea 22 (8): 709–15. doi:10.1097/00003226-200311000-00001. PMID 14576520.
Ogasawara H, Yoshida A, Fujio N, Konno S, Ishiko S (1999). "[Effect of topical levobunolol on retinal, optic nerve head, and choroidal circulation in normal volunteers]". Nippon Ganka Gakkai Zasshi 103 (7): 544–50. PMID 10443129.
Leung M, Grunwald J (1997). "Short-term effects of topical levobunolol on the human retinal circulation.". Eye 11 (3): 371–6. doi:10.1038/eye.1997.78. PMID 9373479.

Drugs used for glaucoma preparations and miosis (S01E)

Sympathomimetics

Parasympathomimetics

muscarinic	Aceclidine Pilocarpine

muscarinic/nicotinic	Acetylcholine Carbachol

Acetylcholinesterase inhibitors	Demecarium Ecothiopate Stigmine (Fluostigmine Neostigmine Physostigmine) Paraoxon

Carbonic anhydrase inhibitors/
(sulfonamides)

Beta blocking agents

Prostaglandin analogues (F_2α)

Other agents

Adrenergics

Receptor ligands

α₁

Agonists 6-FNE Amidephrine Anisodamine Anisodine Buspirone Cirazoline Corbadrine Dipivefrine Dopamine Ephedrine Epinephrine Etilefrine Ethylnorepinephrine Indanidine Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetrahydrozoline Tiamenidine Xylometazoline

Antagonists Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Arotinolol Atiprosin Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone) Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride) Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Nefazodone Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin Silodosin Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Trazodone Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine) Trimazosin Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Urapidil WB-4101 Zolertine

α₂

Agonists (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz Lofexidine Medetomidine Methamphetamine Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rilmenidine Romifidine Talipexole Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil Xylazine Xylometazoline

Antagonists 1-PP Adimolol Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine) Azapirones (e.g., buspirone, tandospirone) BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine

Agonists Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Cimaterol Clenbuterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Ephedrine Epinephrine Etafedrine Etilefrine Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine Levosalbutamol Mabuterol Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol Zilpaterol Zinterol

Antagonists Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

Reuptake inhibitors

NET

Selective norepinephrine reuptake inhibitors Amedalin Atomoxetine (tomoxetine) Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Viloxazine

Norepinephrine-dopamine reuptake inhibitors Amineptine Bupropion Fencamine Fencamfamine Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine

Serotonin-norepinephrine reuptake inhibitors Bicifadine BTS-54505 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN-5652 Milnacipran N-Methyl-PPPA PPPA Sibutramine Venlafaxine WY-45233

Serotonin-norepinephrine-dopamine reuptake inhibitors (S)-Duloxetine 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Diclofensine DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 Indatraline JNJ-7925476 JZ-IV-10 Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 SEP-228431 SEP-228432 Tedatioxetine Tesofensine

Tricyclic antidepressants Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine

Tetracyclic antidepressants Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline

Others Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine) Arylcyclohexylamines (e.g., ketamine, phencyclidine) CP-39,332 EXP-561 Fezolamine Ginkgo biloba Indeloxazine Loxapine Nefazodone Nefopam Opioids (e.g., methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol) Pridefine Tedatioxetine Teniloxazine Tofenacin Tropanes (e.g., cocaine) Ziprasidone

VMATs

Amiodarone
Amphetamines (e.g., amphetamine, methamphetamine, MDMA)
Bietaserpine
Deserpidine
Efavirenz
GBR-12935
Ibogaine
Ketanserin
Lobeline
Reserpine
Rose bengal
Tetrabenazine
Vanoxerine (GBR-12909)

Releasing agents

Morpholines Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine

Oxazolines 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines (also amphetamines, cathinones, etc) 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Bupropion Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) 5-MAPDI (IMP) Iofetamine (123I) Lisdexamfetamine Lophophine MBDB MDA MDEA MDMA Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine

Piperazines 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP pFPP

Others 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine (Levopropylhexedrine) Tuaminoheptane

Enzyme inhibitors

PAH

3,4-Dihydroxystyrene

AAAD

DBH

PNMT

CGS-19281A
SKF-64139
SKF-7698

MAO

Nonselective Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine

MAO-A selective Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids Harmine Harmaline Tetrahydroharmine Harman Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone

MAO-B selective Ladostigil Lazabemide Milacemide Mofegiline Pargyline Rasagiline Safinamide Selegiline (also D-Deprenyl)

Others

L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
L-DOPS (Droxidopa)

Cofactors

Ferrous Iron (Fe²⁺)
S-Adenosyl-L-Methionine
Vitamin B₃ (Niacin
Nicotinamide → NADPH)
Vitamin B₆ (Pyridoxine
Pyridoxamine
Pyridoxal → Pyridoxal Phosphate)
Vitamin B₉ (Folic acid → Tetrahydrofolic acid)
Vitamin C (Ascorbic acid)
Zinc (Zn²⁺)

Neurotoxins

Others

Activity enhancers BPAP PPAP

Release blockers Bethanidine Bretylium Guanadrel Guanazodine Guanethidine Guanoxan

See also:: Dopaminergics; Melatonergics; Serotonergics; List of adrenergic drugs

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