Identification
- Summary
Betaxolol is a cardioselective beta blocking agent commonly used to treat hypertension and elevated intraocular pressure (when administered ophthalmically).
- Brand Names
- Betoptic, Betoptic Pilo, Betoptic S
- Generic Name
- Betaxolol
- DrugBank Accession Number
- DB00195
- Background
A cardioselective beta-1-adrenergic antagonist with no partial agonist activity.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Betaxolol (DB00195)
- Weight
- Average: 307.4278
Monoisotopic: 307.214743799 - Chemical Formula
- C18H29NO3
- Synonyms
- 1-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-2-propanol
- 1-(isopropylamino)-3-[p-(cyclopropylmethoxyethyl)phenoxy]-2-propanol
- Betaxolol
- Bétaxolol
- Betaxololum
Pharmacology
- Indication
For the management of hypertension.
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.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Elevated intraocular pressure Combination Product in combination with: Pilocarpine (DB01085) ••• ••••• •••••••••••• •••••••• •• •••••••••• •••••••••• Used in combination to treat Elevated intraocular pressure Combination Product in combination with: Pilocarpine (DB01085) ••• ••••• •••••••••••• •••••••• •• •••••••••• •••••••••• Management of Hypertension •••••••••••• - 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
Betaxolol is a competitive, beta(1)-selective (cardioselective) adrenergic antagonist. Betaxolol is used to treat hypertension, arrhythmias, coronary heart disease, glaucoma, and is also used to reduce non-fatal cardiac events in patients with heart failure. Activation of beta(1)-receptors (located mainly in the heart) by epinephrine increases the heart rate and the blood pressure, and the heart consumes more oxygen. Drugs such as betaxolol that block these receptors therefore have the reverse effect: they lower the heart rate and blood pressure and hence are used in conditions when the heart itself is deprived of oxygen. They are routinely prescribed in patients with ischemic heart disease. In addition, beta(1)-selective blockers prevent the release of renin, which is a hormone produced by the kidneys which leads to constriction of blood vessels. Betaxolol is lipophilic and exhibits no intrinsic sympathomimetic activity (ISA) or membrane stabilizing activity.
- Mechanism of action
Betaxolol selectively blocks catecholamine stimulation of beta(1)-adrenergic receptors in the heart and vascular smooth muscle. This results in a reduction of heart rate, cardiac output, systolic and diastolic blood pressure, and possibly reflex orthostatic hypotension. Betaxolol can also competitively block beta(2)-adrenergic responses in the bronchial and vascular smooth muscles, causing bronchospasm.
Target Actions Organism ABeta-1 adrenergic receptor antagonistHumans UBeta-2 adrenergic receptor antagonistHumans - Absorption
Absorption of an oral dose is complete. There is a small and consistent first-pass effect resulting in an absolute bioavailability of 89% ± 5% that is unaffected by the concomitant ingestion of food or alcohol.
- Volume of distribution
Not Available
- Protein binding
50%
- Metabolism
Primarily hepatic. Approximately 15% of the dose administered is excreted as unchanged drug, the remainder being metabolites whose contribution to the clinical effect is negligible.
- Route of elimination
Not Available
- Half-life
14-22 hours
- 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
Oral LD50s are 350 to 400 mg betaxolol/kg in mice and 860 to 980 mg/kg in rats. Predicted symptoms of overdose include bradycardia, congestive heart failure, hypotension, bronchospasm, and hypoglycemia.
- Pathways
Pathway Category Betaxolol Action Pathway Drug action - 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 softwareAbaloparatide The risk or severity of adverse effects can be increased when Betaxolol is combined with Abaloparatide. Abametapir The serum concentration of Betaxolol can be increased when it is combined with Abametapir. Abatacept The metabolism of Betaxolol can be increased when combined with Abatacept. Abiraterone The serum concentration of Betaxolol can be increased when it is combined with Abiraterone. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Betaxolol. - Food Interactions
- No food interactions are expected.
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 Betaxolol hydrochloride 6X97D2XT0O 63659-19-8 CHDPSNLJFOQTRK-UHFFFAOYSA-N - International/Other Brands
- Betaxon
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Betoptic Solution / drops 5.6 mg/1mL Ophthalmic Alcon 2006-10-30 Not applicable US 
Betoptic Liq Liquid 0.5 % Ophthalmic Alcon, Inc. 1986-12-31 1997-07-31 Canada 
Betoptic S Suspension / drops 2.8 mg/1mL Ophthalmic Novartis Pharmaceuticals Corporation 1996-01-15 Not applicable US Betoptic S Suspension / drops 2.8 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1996-01-15 2024-08-31 US Betoptic S Suspension 0.25 % w/v Ophthalmic Novartis 1994-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Betaxolol Tablet, film coated 10 mg/1 Oral Marlex Pharmaceuticals Inc 2016-07-01 Not applicable US Betaxolol Tablet, film coated 20 mg/1 Oral Golden State Medical Supply, Inc. 2008-06-27 2013-11-25 US Betaxolol Tablet, film coated 20 mg/1 Oral PuraCap Laboratories LLC 2016-08-22 Not applicable US Betaxolol Tablet, film coated 10 mg/1 Oral Epic Pharma LLC 2010-07-20 Not applicable US Betaxolol Solution / drops 5 mg/1mL Ophthalmic Akorn 2003-04-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Betoptic Pilo Betaxolol hydrochloride (2.5 mg/1mL) + Pilocarpine hydrochloride (17.5 mg/1mL) Kit Ophthalmic ALCON LABORATORIES, INC. 2006-09-26 Not applicable US Betoptic/pilo Betaxolol hydrochloride (0.25 %) + Pilocarpine hydrochloride (1.75 %) Suspension Ophthalmic Alcon, Inc. Not applicable Not applicable Canada
Categories
- ATC Codes
- S01ED02 — Betaxolol
- S01ED — Beta blocking agents
- S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- C07AB — Beta blocking agents, selective
- C07A — BETA BLOCKING AGENTS
- C07 — BETA BLOCKING AGENTS
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic Antagonists
- Adrenergic beta-1 Receptor Antagonists
- Adrenergic beta-Antagonists
- Agents causing hyperkalemia
- Alcohols
- Amines
- Amino Alcohols
- Antiarrhythmic agents
- Antiglaucoma Preparations and Miotics
- Antihypertensive Agents
- Antihypertensive Agents Indicated for Hypertension
- Autonomic Agents
- Beta Blocking Agents, Selective
- Beta-adrenergic Agents
- Beta-Blockers (Beta1 Selective)
- Bradycardia-Causing Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Hypotensive Agents
- Neurotransmitter Agents
- Ophthalmologicals
- Peripheral Nervous System Agents
- Phenoxypropanolamines
- Propanolamines
- Propanols
- QTc Prolonging Agents
- Sensory Organs
- Sympatholytics
- 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
- propanolamine (CHEBI:3082)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- O0ZR1R6RZ2
- CAS number
- 63659-18-7
- InChI Key
- NWIUTZDMDHAVTP-UHFFFAOYSA-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
- IUPAC Name
- 1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-[(propan-2-yl)amino]propan-2-ol
- SMILES
- CC(C)NCC(O)COC1=CC=C(CCOCC2CC2)C=C1
References
- Synthesis Reference
Ramesh Joshi, Muthukrishnan Murugan, Dinesh Garud, Sanjay Borikar, Mukund Gurjar, "PROCESS FOR PREPARATION OF S-(-)-BETAXOLOL AND SALTS THEREOF." U.S. Patent US20060004109, issued January 05, 2006.
US20060004109- General References
- Canotilho J, Castro RA: The structure of betaxolol studied by infrared spectroscopy and natural bond orbital theory. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Aug;76(3-4):395-400. doi: 10.1016/j.saa.2010.03.038. Epub 2010 Apr 4. [Article]
- External Links
- Human Metabolome Database
- HMDB0014341
- KEGG Compound
- C06849
- PubChem Compound
- 2369
- PubChem Substance
- 46506041
- ChemSpider
- 2279
- BindingDB
- 50405521
- 1520
- ChEBI
- 3082
- ChEMBL
- CHEMBL423
- Therapeutic Targets Database
- DAP000305
- PharmGKB
- PA448611
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Betaxolol
- FDA label
- Download (111 KB)
- MSDS
- Download (38.8 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 4 Completed Other Cardiac Failure / Cardiovascular Disease (CVD) / Heart Failure / Heart Failure With Preserved Ejection Fraction (HFpEF) / Heart Failure, Diastolic 2 3 Completed Treatment Glaucoma / Ocular Hypertension 2 3 Completed Treatment Ocular Hypertension / Ocular Hypertension, Primary Open-angle Glaucoma (POAG) 1 3 Unknown Status Treatment Open Angle Glaucoma (OAG) 1 1 Completed Prevention Development of Side Effects From Betaxolol 1
Pharmacoeconomics
- Manufacturers
- Akorn inc
- Bausch and lomb pharmaceuticals inc
- Novex pharma
- Wockhardt ltd
- Alcon laboratories inc
- Epic pharma llc
- Kvk tech inc
- Sanofi aventis us llc
- Alcon inc
- Packagers
- Alcon Laboratories
- Apotex Inc.
- Dispensing Solutions
- Falcon Pharmaceuticals Ltd.
- GD Searle LLC
- Golden State Medical Supply Inc.
- Kaiser Foundation Hospital
- KVK-Tech Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Novex Pharma
- Pharmedix
- Physicians Total Care Inc.
- Sanofi-Aventis Inc.
- Dosage Forms
Form Route Strength Tablet, film coated Oral Solution / drops Ophthalmic 5 mg/1mL Tablet, film coated Oral 10 mg/1 Tablet, coated Oral 10 mg/1 Tablet, coated Oral 20 mg/1 Solution / drops Ophthalmic 0.25 % Solution / drops Ophthalmic 0.5 % Solution / drops Ophthalmic 2.5 mg Solution / drops Ophthalmic 5 MG/ML Solution / drops Ophthalmic 5.6 mg/1mL Liquid Ophthalmic 0.5 % Kit Ophthalmic Suspension Ophthalmic 0.25 % w/v Suspension / drops Ophthalmic 2.5 mg/1ml Suspension / drops Ophthalmic 2.8 mg/1mL Suspension Ophthalmic 2.8 mg/ml Solution Ophthalmic 0.25 % w/v Suspension Ophthalmic Suspension Ophthalmic 2.5 mg/ml Solution Ophthalmic 0.5 % w/v Suspension Ophthalmic 0.25 % Suspension Ophthalmic Solution / drops; suspension / drops Ophthalmic 5 mg/mL Solution Ophthalmic 2.500 mg Solution / drops Ophthalmic 0.5 % W/V Tablet, coated Oral 20 MG Tablet, film coated Oral 20 mg/1 Tablet, film coated Oral 20 MG Solution / drops Ophthalmic Solution Ophthalmic 0.5 % - Prices
Unit description Cost Unit Betoptic-S 0.25% Suspension 15ml Bottle 195.44USD bottle Betoptic-S 0.25% Suspension 10ml Bottle 130.29USD bottle Betaxolol HCl 0.5% Solution 15ml Bottle 104.31USD bottle Betoptic-S 0.25% Suspension 5ml Bottle 51.99USD bottle Betoptic s 0.25% eye drops 9.79USD ml Betaxolol hcl 0.5% eye drop 6.82USD ml Betoptic S 0.25 % Suspension 2.54USD ml Kerlone 20 mg tablet 2.35USD tablet Betaxolol 20 mg tablet 1.86USD tablet Kerlone 10 mg tablet 1.63USD tablet Betaxolol HCl 10 mg tablet 1.29USD tablet Betaxolol 10 mg tablet 1.24USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5540918 No 1996-07-30 2014-01-30 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 70-72 °C PhysProp water solubility 451 mg/L Not Available logP 2.81 RECANATINI,M (1992) Caco2 permeability -4.81 ADME Research, USCD pKa 9.4 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 37.05 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
Property Value Probability Human Intestinal Absorption + 0.9903 Blood Brain Barrier - 0.8906 Caco-2 permeable + 0.8866 P-glycoprotein substrate Substrate 0.7683 P-glycoprotein inhibitor I Non-inhibitor 0.7967 P-glycoprotein inhibitor II Non-inhibitor 0.8547 Renal organic cation transporter Non-inhibitor 0.8206 CYP450 2C9 substrate Non-substrate 0.8106 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Non-substrate 0.7221 CYP450 1A2 substrate Inhibitor 0.8972 CYP450 2C9 inhibitor Inhibitor 0.5241 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9249 CYP450 3A4 inhibitor Non-inhibitor 0.9647 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9741 Ames test Non AMES toxic 0.8765 Carcinogenicity Non-carcinogens 0.9304 Biodegradation Not ready biodegradable 0.9395 Rat acute toxicity 2.1620 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7663 hERG inhibition (predictor II) Non-inhibitor 0.7498
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.5620788 predictedDarkChem Lite v0.1.0 [M-H]- 176.53958 predictedDeepCCS 1.0 (2019) [M+H]+ 191.1622788 predictedDarkChem Lite v0.1.0 [M+H]+ 178.89758 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.4250788 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.99074 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
References
- McLean AJ, Zeng FY, Behan D, Chalmers D, Milligan G: Generation and analysis of constitutively active and physically destabilized mutants of the human beta(1)-adrenoceptor. Mol Pharmacol. 2002 Sep;62(3):747-55. [Article]
- Rudoy CA, Van Bockstaele EJ: Betaxolol, a selective beta(1)-adrenergic receptor antagonist, diminishes anxiety-like behavior during early withdrawal from chronic cocaine administration in rats. Prog Neuropsychopharmacol Biol Psychiatry. 2007 Jun 30;31(5):1119-29. Epub 2007 Apr 19. [Article]
- Satoh N, Suzuki J, Bessho H, Kitada Y, Narimatsu A, Tobe A: Effects of betaxolol on cardiohemodynamics and coronary circulation in anesthetized dogs: comparison with atenolol and propranolol. Jpn J Pharmacol. 1990 Oct;54(2):113-9. [Article]
- Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Rait JL: Systemic effects of topical ophthalmic beta-adrenoceptor antagonists. Aust N Z J Ophthalmol. 1999 Feb;27(1):57-64. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Zateyshchikov DA, Minushkina LO, Brovkin AN, Savel'eva EG, Zateyshchikova AA, Manchaeva BB, Nikitin AG, Sidorenko BA, Nosikov VV: Association of CYP2D6 and ADRB1 genes with hypotensive and antichronotropic action of betaxolol in patients with arterial hypertension. Fundam Clin Pharmacol. 2007 Aug;21(4):437-43. doi: 10.1111/j.1472-8206.2007.00518.x. [Article]
- Zisaki A, Miskovic L, Hatzimanikatis V: Antihypertensive drugs metabolism: an update to pharmacokinetic profiles and computational approaches. Curr Pharm Des. 2015;21(6):806-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55