Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H25NO3 |
Molecular Weight | 291.3853 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)NC[C@H](O)COC1=CC=CC2=C1CCCC2=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
DescriptionSources: http://www.allergan.com/assets/pdf/betagan_piCurator'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
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 |
---|---|---|---|
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11572462 |
0.76 nM [Ki] | ||
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11572462 |
32.6 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 Date1985 |
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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 Date1985 |
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 |
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A comparison of the ocular hypotensive efficacy and systemic safety of 0.5% levobunolol and 2% carteolol. | 1994 |
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Short-term effects of topical levobunolol on the human retinal circulation. | 1997 |
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[Effect of topical levobunolol on retinal, optic nerve head, and choroidal circulation in normal volunteers]. | 1999 Jul |
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Levobetaxolol (Betaxon) and other beta-adrenergic antagonists: preclinical pharmacology, IOP-lowering activity and sites of action in human eyes. | 2001 Aug |
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Contact dermatitis to topical drugs for glaucoma. | 2001 Dec |
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Commercially available ocular hypotensive products: preservative concentration, stability, storage, and in-life utilization. | 2001 Dec |
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Timolol may inhibit aqueous humor secretion by cAMP-independent action on ciliary epithelial cells. | 2001 Sep |
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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 |
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Spectrophotometric determination of beta-adrenergic blocking agents in pharmaceutical formulations. | 2002 Jul 1 |
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[Cost-effectivity analysis of the most used antiglaucoma drugs]. | 2004 Aug |
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Inhibition of endothelin-1 and KCL-induced increase of [CA2+]i by antiglaucoma drugs in cultured A7r5 vascular smooth-muscle cells. | 2004 Jun |
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Reversal of disc cupping after intraocular pressure reduction in topographic image series. | 2004 Oct |
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The effect of once-daily levobunolol on intraocular pressure in normal-tension glaucoma. | 2005 Jan-Feb |
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Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro. | 2005 Mar |
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Effects of antiglaucoma drugs on cellular proliferation in cultured human corneal keratocytes. | 2006 Mar |
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Beta-blocker eye drops. | 2006 May 30-Jun 5 |
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Membrane electrodes for determination of some beta-blocker drugs. | 2007 Jul-Aug |
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Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells. | 2007 Mar |
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Miscellaneous. | 2008 Oct |
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Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery. | 2009 |
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Aerobic exercise and intraocular pressure in normotensive and glaucoma patients. | 2009 Aug 13 |
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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 |
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Retrospective cohort study of 163 pediatric glaucoma patients. | 2009 Jun |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.allergan.com/assets/pdf/betagan_pi
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17459374
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.
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NDF-RT |
N0000175556
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QS01ED03
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C29705
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C29576
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S01ED03
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LEVOBUNOLOL
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Levobunolol
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ACTIVE MOIETY
METABOLITE (PARENT)
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