CHEBI:6439 - levobunolol hydrochloride

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ChEBI Name levobunolol hydrochloride
ChEBI ID CHEBI:6439
Definition A hydrochloride obtained by combining equimolar amounts of levobunolol and hydrochloric acid. A non-selective β-adrenergic antagonist used for treatment of glaucoma.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information eMolecules:3714906
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Formulae C17H25NO3.HCl
C17H26ClNO3
Net Charge 0
Average Mass 327.84600
Monoisotopic Mass 327.16012
InChI InChI=1S/C17H25NO3.ClH/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;1H/t12-;/m0./s1
InChIKey DNTDOBSIBZKFCP-YDALLXLXSA-N
SMILES Cl.CC(C)(C)NC[C@H](O)COc1cccc2C(=O)CCCc12
Roles Classification
Biological Role(s): beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
Application(s): beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
antiglaucoma drug
Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing levobunolol hydrochloride (CHEBI:6439) has part levobunolol(1+) (CHEBI:72567)
levobunolol hydrochloride (CHEBI:6439) has role β-adrenergic antagonist (CHEBI:35530)
levobunolol hydrochloride (CHEBI:6439) has role antiglaucoma drug (CHEBI:39456)
levobunolol hydrochloride (CHEBI:6439) is a hydrochloride (CHEBI:36807)
IUPAC Name
5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydronaphthalen-1(2H)-one hydrochloride
Synonyms Sources
(−)-3,4-dihydro-5-(3-(tert-butylamino)-2-hydroxypropoxy)-1(2H)-naphthalenone hydrochloride ChemIDplus
(−)-5-(3-(tert-butylamino)-2-hydroxypropoxy)-3,4-dihydro-1(2H)-naphthalenone hydrochloride ChemIDplus
(2S)-N-(tert-butyl)-2-hydroxy-3-[(5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]propan-1-aminium chloride IUPAC
levobunolol HCl ChemIDplus
levobunolol hydrochloride KEGG COMPOUND
levobunolol monohydrochloride ChEBI
Brand Name Source
Betagan KEGG DRUG
Manual Xrefs Databases
CN101342163 Patent
D01025 KEGG DRUG
DBSALT000251 DrugBank
JP2008094780 Patent
US5733938 Patent
US6159458 Patent
WO2007034140 Patent
WO2008002929 Patent
View more database links
Registry Number Type Source
27912-14-7 CAS Registry Number ChemIDplus
Citations
Baker MM, Belal TS (2018)
Validated HPLC-DAD Method for the Simultaneous Determination of Six Selected Drugs Used in the Treatment of Glaucoma.
Journal of AOAC International 101, 993-1000 [PubMed:28859698]
[show Abstract]
Lin L, Wang Y, Chen Y, Liu M (2014)
Bradyarrhythmias secondary to topical levobunolol hydrochloride solution.
Clinical interventions in aging 9, 1741-1745 [PubMed:25342892]
[show Abstract]
Karataş A, Sonakin O, Kiliçarslan M, Baykara T (2009)
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.
Journal of microencapsulation 26, 63-74 [PubMed:18608798]
[show Abstract]
Ramadan NK, Zaazaa HE (2007)
Membrane electrodes for determination of some beta-blocker drugs.
Journal of AOAC International 90, 987-994 [PubMed:17760336]
[show Abstract]
Ishibashi T, Yokoi N, Kinoshita S (2003)
Comparison of the effects of topical levobunolol and timolol solution on the human ocular surface.
Cornea 22, 709-715 [PubMed:14576520]
[show Abstract]
Halper LK, Johnson-Pratt L, Dobbins T, Hartenbaum D (2002)
A comparison of the efficacy and tolerability of 0.5% timolol maleate ophthalmic gel-forming solution QD and 0.5% levobunolol hydrochloride BID in patients with ocular hypertension or open-angle glaucoma.
Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 18, 105-113 [PubMed:12002664]
[show Abstract]
Vold SD, Wiggins DA, Jackimiec J (2000)
Cost analysis of glaucoma medications.
Journal of glaucoma 9, 150-153 [PubMed:10782624]
[show Abstract]
Walters TR, Maloney S, Slater D, Liss C, Wilson H, Hartenbaum D (1998)
Efficacy and tolerability of 0.5% timolol maleate ophthalmic gel-forming solution QD compared with 0.5% levobunolol hydrochloride BID in patients with open-angle glaucoma or ocular hypertension.
Clinical therapeutics 20, 1170-1178 [PubMed:9916610]
[show Abstract]
Bloom AH, Grunwald JE, DuPont JC (1997)
Effect of one week of levobunolol HCl 0.5% on the human retinal circulation.
Current eye research 16, 191-196 [PubMed:9088734]
[show Abstract]
Leung M, Grunwald JE (1997)
Short-term effects of topical levobunolol on the human retinal circulation.
Eye (London, England) 11 ( Pt 3), 371-376 [PubMed:9373479]
[show Abstract]
Tang M, Chen L, Wei W, Yang L, Wang T, Liu Z, Hu X, Sun H, Luo H (1997)
The effect of levobunolol hydrochloride on the calcium and potassium channels in isolated ventricular myocytes of guinea pig.
Journal of Tongji Medical University = Tong ji yi ke da xue xue bao 17, 90-93 [PubMed:9639797]
[show Abstract]
Hyung SM, Kim DM, Hong C, Lee J, Youn DH (1994)
Effects of postoperative mitomycin C on glaucoma filtration surgery in rabbits treated preoperatively with antiglaucoma medications.
Ophthalmic surgery 25, 704-714 [PubMed:7898865]
[show Abstract]
Stubbs GM (1994)
Betagan drops.
The Medical journal of Australia 161, 576 [PubMed:7968772]
Síp L, Růzicková E (1992)
[Levobunolol HCl--a beta-blocker produced by the firm Allergan].
Ceskoslovenska oftalmologie 48, 370-373 [PubMed:1486629]
[show Abstract]
Fry LL (1992)
Comparison of the postoperative intraocular pressure with Betagan, Betoptic, Timoptic, Iopidine, Diamox, Pilopine Gel, and Miostat.
Journal of cataract and refractive surgery 18, 14-19 [PubMed:1346539]
[show Abstract]
Derick RJ, Robin AL, Tielsch J, Wexler JL, Kelley EP, Stoecker JF, Novack GD, Coleman AL (1992)
Once-daily versus twice-daily levobunolol (0.5%) therapy. A crossover study.
Ophthalmology 99, 424-429 [PubMed:1565455]
[show Abstract]
Egorov EA, Shmeleva IA (1992)
[Results of the clinical study of a new adrenergic beta blocker levobunolol hydrochloride in healthy subjects and in patients with glaucoma].
Vestnik oftalmologii 108, 24-25 [PubMed:1481323]
[show Abstract]
Follmann P, Varga M, Daróczy J (1989)
The effect of timolol, betaxolol and levobunolol on the surface of rabbit cornea.
International ophthalmology 13, 81-84 [PubMed:2663750]
[show Abstract]
Liu GS, Trope GE, Basu PK (1989)
Ultrastructural effects of topical betoptic, betagan, and timoptic on the rabbit corneal endothelium.
Journal of ocular pharmacology 5, 329-342 [PubMed:2628505]
[show Abstract]
Allen RC, Robin AL, Long D, Novack GD, Lue JC, Kaplan G (1988)
A combination of levobunolol and dipivefrin for the treatment of glaucoma.
Archives of ophthalmology (Chicago, Ill. : 1960) 106, 904-907 [PubMed:3291837]
[show Abstract]
Boozman FW, Carriker R, Foerster R, Allen RC, Novack GD, Batoosingh AL (1988)
Long-term evaluation of 0.25% levobunolol and timolol for therapy for elevated intraocular pressure.
Archives of ophthalmology (Chicago, Ill. : 1960) 106, 614-618 [PubMed:3282501]
[show Abstract]
Seamone C, LeBlanc R, Saheb N, Novack G (1988)
Efficacy of twice-daily levobunolol in the treatment of elevated intraocular pressure.
Canadian journal of ophthalmology. Journal canadien d'ophtalmologie 23, 168-170 [PubMed:3293726]
[show Abstract]
Tang-Liu DD, Shackleton M, Richman JB (1988)
Ocular metabolism of levobunolol.
Journal of ocular pharmacology 4, 269-278 [PubMed:3058836]
[show Abstract]
Trope GE, Liu GS, Basu PK (1988)
Toxic effects of topically administered Betagan, Betoptic, and Timoptic on regenerating corneal epithelium.
Journal of ocular pharmacology 4, 359-366 [PubMed:3246571]
[show Abstract]
Tierney DW (1987)
Betaxolol and levobunolol: new beta-blocking antiglaucoma agents.
Journal of the American Optometric Association 58, 722-727 [PubMed:2895783]
[show Abstract]
Bensinger RE, Keates EU, Gofman JD, Novack GD, Duzman E (1985)
Levobunolol. A three-month efficacy study in the treatment of glaucoma and ocular hypertension.
Archives of ophthalmology (Chicago, Ill. : 1960) 103, 375-378 [PubMed:3883971]
[show Abstract]
Last Modified
15 May 2024