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
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
| 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 |
DescriptionCurator'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
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 |
|---|---|---|---|
Target ID: CHEMBL210 |
0.76 nM [Ki] | ||
Target ID: CHEMBL213 |
32.6 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BETAGAN Approved UseBETAGAN ® 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 Date5.03798399E11 |
|||
| Primary | BETAGAN Approved UseBETAGAN ® 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 Date5.03798399E11 |
Cmax
| 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 |
T1/2
| Value | Dose | Co-administered | 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| The effects of beta-blockers on ocular blood flow in patients with primary open angle glaucoma: a color Doppler imaging study. | 2001 Jan-Mar |
|
| Comparative effects of antiglaucoma drugs on voltage-dependent calcium channels. | 2001 Jul |
|
| 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 |
|
| 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. | 2002 Apr |
|
| Topical beta blockers and atrioventricular block in the elderly. | 2002 Oct-Dec |
|
| Noninvasive assessment of aqueous humor turnover in the mouse eye. | 2003 Feb |
|
| The effect of topical glaucoma medications evaluated by perimetry. | 2003 Jun |
|
| [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 |
|
| [Cost-effectivity analysis of the most used antiglaucoma drugs]. | 2004 Aug |
|
| 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 |
|
| Study of effects of antiglaucoma eye drops on N-methyl-D-aspartate-induced retinal damage. | 2005 Nov-Dec |
|
| 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 |
|
| Beta-blocker eye drops. | 2006 May 30-Jun 5 |
|
| Miscellaneous. | 2008 Oct |
|
| 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 |
|
| 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 |
|
| Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
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
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admin
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Sat Jun 26 10:46:40 UTC 2021
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| Record UNII |
G6317AOI7K
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| Record Status |
Validated (UNII)
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| Record Version |
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NDF-RT |
N0000175556
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WHO-VATC |
QS01ED03
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NDF-RT |
N0000000161
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NCI_THESAURUS |
C29705
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NCI_THESAURUS |
C29576
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WHO-ATC |
S01ED03
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DB01210
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570
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M6784
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CHEMBL1201237
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LEVOBUNOLOL
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SUB08463MIG
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47141-42-4
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Levobunolol
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39468
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET->ANTAGONIST |
Levobunolol (LB) is the levo-rotatory isomer of bunolol, a potent, nonselective antagonist of beta-adrenergic receptors.
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TARGET->ANTAGONIST |
Levobunolol (LB) is the levo-rotatory isomer of bunolol, a potent, nonselective antagonist of beta-adrenergic receptors.
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SALT/SOLVATE -> PARENT | |||
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RACEMATE -> ENANTIOMER |
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ACTIVE MOIETY |
