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
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
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 |
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 |
---|---|---|---|---|
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 |
|||
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 |
---|---|---|
Ocular levobunolol. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. | 1987 Dec |
|
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 |
|
Timolol may inhibit aqueous humor secretion by cAMP-independent action on ciliary epithelial cells. | 2001 Sep |
|
Cost analysis of glaucoma medications: a 3-year review. | 2002 Aug |
|
Allergic reactions to brimonidine in patients treated for glaucoma. | 2002 Feb |
|
Spectrophotometric determination of beta-adrenergic blocking agents in pharmaceutical formulations. | 2002 Jul 1 |
|
Medical therapy cost considerations for glaucoma. | 2003 Jul |
|
Comparison of the effects of topical levobunolol and timolol solution on the human ocular surface. | 2003 Nov |
|
[Osmotic resistance of red blood cells membranes in Vermox and "AKbeta" vitamin complex treatment of experimental trichinosis in rats]. | 2004 |
|
Stereoselectivity for interactions of agonists and antagonists at mouse, rat and human beta3-adrenoceptors. | 2004 Jan 26 |
|
Effects of carteolol hydrochloride on the in vitro production of LPS-induced proinflammatory cytokines by murine macrophage. | 2004 Jun |
|
Allergic contact dermatitis due to beta-blockers in eye drops: a retrospective analysis of multicentre surveillance data 1993-2004. | 2006 |
|
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 |
|
Transdermal delivery of beta-blockers. | 2006 May |
|
Beta-blocker eye drops. | 2006 May 30-Jun 5 |
|
Allergic contact dermatitis due to levobunolol with cross-sensitivity to befunolol. | 2007 Jan |
|
Levobetaxolol hydrochloride: a review of its pharmacology and use in the treatment of chronic open-angle glaucoma and ocular hypertension. | 2007 Jun |
|
Vasodilatory mechanism of levobunolol on vascular smooth muscle cells. | 2007 Jun |
|
Daily cost of glaucoma medications in China. | 2007 Oct-Nov |
|
Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery. | 2009 |
|
Retrospective cohort study of 163 pediatric glaucoma patients. | 2009 Jun |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:24:46 GMT 2023
by
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on
Fri Dec 15 15:24:46 GMT 2023
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Record UNII |
O90S49LDHH
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29576
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NCI_THESAURUS |
C29705
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C29153
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m6784
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Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |