Levobetaxolol

Identification

Generic Name
Levobetaxolol
DrugBank Accession Number
DB09351
Background

Levobetaxolol is a beta-blocker used to lower the pressure in the eye to treat conditions such as glaucoma. It was marketed as a 0.5% ophthalmic solution of levobetaxolol hydrochloride under the trade name Betaxon but has been discontinued.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 307.434
Monoisotopic: 307.214743798
Chemical Formula
C18H29NO3
Synonyms
  • (S)-betaxolol
  • Levobetaxolol

Pharmacology

Indication

Used in the treatment of open-angle glaucoma and ocular hypertension Label.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Levobetaxolol is a selective β1 adrenergic receptor antagonist Label. It acts to lower intraocular pressure. Levobataxolol is condsidered to be the more active component of the betaxolol racemate.

Mechanism of action

The exact mechanism by which levobetaxolol lowers intraocular pressure is not known. It it thought that antagonism of β-adrenergic receptors may reduce the production of aqueous humour stimulated via the cyclic adenosine monophosphate-protein kinase A pathway 1. It is also thought that the vasoconstriction produced by antagonism of β adrenergic receptors reduces blood flow to the eye and therefore the ultrafiltration responsible for aqueous humour production. β1 selective antagonists are less effective than non-selective β adrenergic receptor antagonists because β2 receptors make up the bulk of the population in the eye. They do, however, come with the benefit of reduced respiratory complications.

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Humans
Absorption

Levobetaxolol is applied topically to the eye but some does reach systemic circulaton with a Tmax of 3 h Label.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

The mean half life of levobetaxolol is 20 h Label.

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe metabolism of Levobetaxolol can be increased when combined with Abatacept.
AbirateroneThe metabolism of Levobetaxolol can be decreased when combined with Abiraterone.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Levobetaxolol.
AcebutololThe metabolism of Levobetaxolol can be decreased when combined with Acebutolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Levobetaxolol.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Levobetaxolol hydrochloride8MR4W4O06J116209-55-3CHDPSNLJFOQTRK-LMOVPXPDSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tyrosols and derivatives. These are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Tyrosols and derivatives
Direct Parent
Tyrosols and derivatives
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Dialkyl ethers / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aromatic homomonocyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
betaxolol (CHEBI:59254)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
75O9XHA4TU
CAS number
93221-48-8
InChI Key
NWIUTZDMDHAVTP-KRWDZBQOSA-N
InChI
InChI=1S/C18H29NO3/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3/t17-/m0/s1
IUPAC Name
(2S)-1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-[(propan-2-yl)amino]propan-2-ol
SMILES
CC(C)NC[C@H](O)COC1=CC=C(CCOCC2CC2)C=C1

References

General References
  1. Goodman, Louis Sanford, Brunton, Laurence L. Chabner, Bruce. Knollman, Bjorn C. (2011). Goodman and Gilman's the pharmacological basis of therapeutics, Pharmacological basis of therapeutics (12th ed.). New York: McGraw-Hill. [ISBN:9780071624428]
PubChem Compound
60657
PubChem Substance
310265224
ChemSpider
54669
BindingDB
25752
RxNav
353497
ChEBI
59254
ChEMBL
CHEMBL1201274
ZINC
ZINC000001530567
Wikipedia
Levobetaxolol
FDA label
Download (73.8 KB)
MSDS
Download (389 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentGlaucoma / Ocular Hypertension1
3CompletedTreatmentOcular Hypertension / Ocular Hypertension, Primary Open-angle Glaucoma (POAG)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0298 mg/mLALOGPS
logP3ALOGPS
logP2.54Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)14.09Chemaxon
pKa (Strongest Basic)9.67Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area50.72 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity88.64 m3·mol-1Chemaxon
Polarizability37.06 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0596-9420000000-9c1f8bedf0982e6e1fb8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-4089000000-68a78506bcdcab4488e2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0avu-1922000000-7d6fb89e821f0d9b8e62
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-5490000000-c70bf86d9e2ab4ce4019
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2900000000-2473f0f6808144d2b30a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9410000000-67d5bf7172dd808cad0f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0079-1900000000-4798ddc72940acab4673
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-185.0702788
predicted
DarkChem Lite v0.1.0
[M-H]-176.86511
predicted
DeepCCS 1.0 (2019)
[M+H]+185.0108788
predicted
DarkChem Lite v0.1.0
[M+H]+179.22313
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.0531788
predicted
DarkChem Lite v0.1.0
[M+Na]+185.31627
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [Article]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
  3. Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [Article]

Drug created at November 27, 2015 23:43 / Updated at February 02, 2024 22:54