LEVOBUNOLOL HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H25NO3.ClH
Molecular Weight	327.846
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)(C)NC[C@H](O)COC1=CC=CC2=C1CCCC2=O

InChI

InChIKey=DNTDOBSIBZKFCP-YDALLXLXSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H25NO3
Molecular Weight	291.3853
Charge	0
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.allergan.com/assets/pdf/betagan_pi
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11572462	Antagonist 2778		0.76 nM [Ki]
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11572462	Antagonist 2778		32.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ocular hypertension 50 Sources: http://www.allergan.com/assets/pdf/betagan_pi	Primary		Approved 8429	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
Chronic open-angle glaucoma 6 Sources: http://www.allergan.com/assets/pdf/betagan_pi	Primary		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
2.65 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/336256	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/336256	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

Value	Dose	Co-administered	Analyte	Population
3.08 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3323465	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

T_1/2

Value	Dose	Analyte	Population
7.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/336256	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3323465	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/336256	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019219s029lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: glaucoma Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019219s029lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019219s029lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6438	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6438
ZINC	ZINC000003830339	http://zinc15.docking.org/substances/ZINC000003830339

PubMed

Title	Date	PubMed
Cardiovascular considerations in using topical, oral, and intravenous drugs for the treatment of glaucoma and ocular hypertension: focus on beta-adrenergic blockade.	2001 Nov-Dec	11975823
Timolol may inhibit aqueous humor secretion by cAMP-independent action on ciliary epithelial cells.	2001 Sep	11502564
Allergic reactions to brimonidine in patients treated for glaucoma.	2002 Feb	11865954
Noninvasive assessment of aqueous humor turnover in the mouse eye.	2003 Feb	12556404
Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs.	2003 Oct	12898280
[Osmotic resistance of red blood cells membranes in Vermox and "AKbeta" vitamin complex treatment of experimental trichinosis in rats].	2004	16865965
[Cost-effectivity analysis of the most used antiglaucoma drugs].	2004 Aug	15306964
Effects of carteolol hydrochloride on the in vitro production of LPS-induced proinflammatory cytokines by murine macrophage.	2004 Jun	15279728
Inhibition of endothelin-1 and KCL-induced increase of [CA2+]i by antiglaucoma drugs in cultured A7r5 vascular smooth-muscle cells.	2004 Jun	15279725
Study of effects of antiglaucoma eye drops on N-methyl-D-aspartate-induced retinal damage.	2005 Nov-Dec	16365790
The management of glaucoma and intraocular hypertension: current approaches and recent advances.	2006 Jun	18360593
Recent advances in pharmacotherapy of glaucoma.	2008 Oct	20040958
Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery.	2009	19668590
Effect of latanoprost and timolol on the histopathology of the human conjunctiva.	2009 Feb	18971237
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	18608798
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	20960417

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Fri Dec 15 15:24:46 UTC 2023` Edited by `admin` on `Fri Dec 15 15:24:46 UTC 2023`
Record UNII	O90S49LDHH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVOBUNOLOL HYDROCHLORIDE

Official Name

English

LEVOBUNOLOL HCL

Common Name

English

LEVOBUNOLOL HYDROCHLORIDE [VANDF]

Common Name

English

NSC-759158

Code

English

LEVOBUNOLOL HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

(-)-(S)-5-(3-(TERT-BUTYLAMINO)-2-HYDROXYPROPOXY)-3,4-DIHYDRO-1(2H)-NAPHTHALENONE HYDROCHLORIDE

Systematic Name

English

BETAGAN

Brand Name

English

1(2H)-NAPHTHALENONE, 5-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)-3,4-DIHYDRO-, HYDROCHLORIDE, (-)-(S)

Common Name

English

LEVOBUNOLOL HYDROCHLORIDE [JAN]

Common Name

English

W-7000A

Code

English

AKBETA

Brand Name

English

Levobunolol hydrochloride [WHO-DD]

Common Name

English

LEVOBUNOLOL HYDROCHLORIDE [MI]

Common Name

English

W 7000A

Code

English

LEVOBUNOLOL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

LEVOBUNOLOL HYDROCHLORIDE [USAN]

Common Name

English

LEVOBUNOLOL HYDROCHLORIDE [USP-RS]

Common Name

English

LEVOBUNOLOL HYDROCHLORIDE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29576