Identification

Name
Levobetaxolol
Accession Number
DB09351
Type
Small Molecule
Groups
Approved, Investigational
Description

Levobetaxolol is a drug used to lower the pressure in the eye in treating 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. Levobetaxolol is a beta-adrenergic receptor inhibitor (beta blocker).

Structure
Thumb
Synonyms
  • (S)-betaxolol
Product Ingredients
IngredientUNIICASInChI Key
Levobetaxolol hydrochloride8MR4W4O06J116209-55-3CHDPSNLJFOQTRK-LMOVPXPDSA-N
Categories
UNII
75O9XHA4TU
CAS number
93221-48-8
Weight
Average: 307.434
Monoisotopic: 307.214743798
Chemical Formula
C18H29NO3
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

Pharmacology

Indication

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

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
Human
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limonene(4R)-limonene may decrease the antihypertensive activities of Levobetaxolol.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Levobetaxolol.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Levobetaxolol.
AcebutololThe risk or severity of hyperkalemia can be increased when Acebutolol is combined with Levobetaxolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Levobetaxolol.
AcemetacinAcemetacin may decrease the antihypertensive activities of Levobetaxolol.
AcepromazineLevobetaxolol may increase the orthostatic hypotensive activities of Acepromazine.
AceprometazineAceprometazine may increase the hypotensive activities of Levobetaxolol.
AcetohexamideLevobetaxolol may increase the hypoglycemic activities of Acetohexamide.
AcetylcholineThe risk or severity of adverse effects can be increased when Levobetaxolol is combined with Acetylcholine.
Food Interactions
Not Available

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]
External Links
PubChem Compound
60657
PubChem Substance
310265224
ChemSpider
54669
BindingDB
25752
ChEBI
59254
ChEMBL
CHEMBL1201274
Wikipedia
Levobetaxolol
FDA label
Download (73.8 KB)
MSDS
Download (389 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentGlaucoma / Ocular Hypertension1

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Tyrosol derivative / Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Dialkyl ether / Secondary amine / Secondary aliphatic amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
betaxolol (CHEBI:59254)

Targets

Kind
Protein
Organism
Human
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
Human
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. [PubMed:27836712]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [PubMed:14732961]
  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 . [PubMed:17125412]

Drug created on November 27, 2015 16:43 / Updated on August 02, 2018 07:53