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
Structure for Levobetaxolol (DB09351)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ABeta-1 adrenergic receptor antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Levobetaxolol can be increased when combined with Abatacept. Abiraterone The metabolism of Levobetaxolol can be decreased when combined with Abiraterone. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Levobetaxolol. Acebutolol The metabolism of Levobetaxolol can be decreased when combined with Acebutolol. Aceclofenac Aceclofenac may decrease the antihypertensive activities of Levobetaxolol. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Levobetaxolol hydrochloride 8MR4W4O06J 116209-55-3 CHDPSNLJFOQTRK-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
- 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
- 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);">
Phase Status Purpose Conditions Count 3 Completed Treatment Glaucoma / Ocular Hypertension 1 3 Completed Treatment Ocular 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
Property Value Source Water Solubility 0.0298 mg/mL ALOGPS logP 3 ALOGPS logP 2.54 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 14.09 Chemaxon pKa (Strongest Basic) 9.67 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 50.72 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 88.64 m3·mol-1 Chemaxon Polarizability 37.06 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0596-9420000000-9c1f8bedf0982e6e1fb8 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-4089000000-68a78506bcdcab4488e2 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0avu-1922000000-7d6fb89e821f0d9b8e62 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-5490000000-c70bf86d9e2ab4ce4019 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-2900000000-2473f0f6808144d2b30a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-9410000000-67d5bf7172dd808cad0f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0079-1900000000-4798ddc72940acab4673 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.0702788 predictedDarkChem Lite v0.1.0 [M-H]- 176.86511 predictedDeepCCS 1.0 (2019) [M+H]+ 185.0108788 predictedDarkChem Lite v0.1.0 [M+H]+ 179.22313 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.0531788 predictedDarkChem Lite v0.1.0 [M+Na]+ 185.31627 predictedDeepCCS 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
- 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]
- Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
- 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