You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameBetaxolol
Accession NumberDB00195  (APRD00245)
TypeSmall Molecule
GroupsApproved
Description

A cardioselective beta-1-adrenergic antagonist with no partial agonist activity. [PubChem]

Structure
Thumb
Synonyms
1-(4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-2-propanol
1-(Isopropylamino)-3-[P-(cyclopropylmethoxyethyl)phenoxy]-2-propanol
Betaxololum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Betaxolol Hydrochloridesolution/ drops5.6 mg/mLophthalmicSandoz Inc2000-05-15Not applicableUs
Betoptic Liqliquid0.5 %ophthalmicAlcon Canada Inc1986-12-311997-07-31Canada
Betoptic Ssuspension/ drops2.8 mg/mLophthalmicAlcon Laboratories, Inc.1996-01-15Not applicableUs
Betoptic S Oph Sus 0.25%suspension.25 %ophthalmicAlcon Canada Inc1994-12-31Not applicableCanada
Novo-betaxololliquid0.5 %ophthalmicNovopharm LimitedNot applicableNot applicableCanada
Sandoz Betaxololsolution0.5 %ophthalmicSandoz Canada Incorporated1998-11-27Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Betaxololtablet, film coated10 mg/1oralGolden State Medical Supply, Inc.2008-06-27Not applicableUs
Betaxololtablet, film coated10 mg/1oralPhysicians Total Care, Inc.2003-10-07Not applicableUs
Betaxololtablet, film coated20 mg/1oralEpic Pharma LLC2010-07-20Not applicableUs
Betaxololtablet, film coated10 mg/1oralEpic Pharma LLC2010-07-20Not applicableUs
Betaxololsolution/ drops5 mg/mLophthalmicAkorn, Inc.2003-04-01Not applicableUs
Betaxololtablet, film coated20 mg/1oralGolden State Medical Supply, Inc.2008-06-27Not applicableUs
Betaxolol Hydrochloridetablet, coated10 mg/1oralKvk Tech, Inc.2011-11-02Not applicableUs
Betaxolol Hydrochloridetablet, coated20 mg/1oralKvk Tech, Inc.2011-11-02Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BetaxonNot Available
BetopticNot Available
KerloneNot Available
Brand mixtures
NameLabellerIngredients
Betoptic/piloAlcon Canada Inc
Salts
Name/CASStructureProperties
Betaxolol Hydrochloride
63659-19-8
Thumb
  • InChI Key: CHDPSNLJFOQTRK-UHFFFAOYNA-N
  • Monoisotopic Mass: 343.191421538
  • Average Mass: 343.889
DBSALT000328
Categories
UNIIO0ZR1R6RZ2
CAS number63659-18-7
WeightAverage: 307.4278
Monoisotopic: 307.214743799
Chemical FormulaC18H29NO3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentTyrosols and derivatives
Alternative Parents
Substituents
  • Tyrosol derivative
  • Phenol ether
  • Alkyl aryl ether
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the management of hypertension.
PharmacodynamicsBetaxolol 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 actionBetaxolol 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.
Related Articles
AbsorptionAbsorption 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 distributionNot Available
Protein binding50%
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 eliminationNot Available
Half life14-22 hours
ClearanceNot Available
ToxicityOral 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.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Betaxolol Action PathwayDrug actionSMP00299
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9903
Blood Brain Barrier-0.8906
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.7683
P-glycoprotein inhibitor INon-inhibitor0.7967
P-glycoprotein inhibitor IINon-inhibitor0.8547
Renal organic cation transporterNon-inhibitor0.8206
CYP450 2C9 substrateNon-substrate0.8106
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.7221
CYP450 1A2 substrateInhibitor0.8972
CYP450 2C9 inhibitorInhibitor0.5241
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9249
CYP450 3A4 inhibitorNon-inhibitor0.9647
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9741
Ames testNon AMES toxic0.8765
CarcinogenicityNon-carcinogens0.9304
BiodegradationNot ready biodegradable0.9395
Rat acute toxicity2.1620 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7663
hERG inhibition (predictor II)Non-inhibitor0.7498
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Dosage forms
FormRouteStrength
Solution/ dropsophthalmic5 mg/mL
Tablet, film coatedoral10 mg/1
Tablet, film coatedoral20 mg/1
Solution/ dropsophthalmic5.6 mg/mL
Tablet, coatedoral10 mg/1
Tablet, coatedoral20 mg/1
Liquidophthalmic0.5 %
Suspension/ dropsophthalmic2.8 mg/mL
Suspensionophthalmic.25 %
Suspensionophthalmic
Solutionophthalmic0.5 %
Prices
Unit descriptionCostUnit
Betoptic-S 0.25% Suspension 15ml Bottle195.44USD bottle
Betoptic-S 0.25% Suspension 10ml Bottle130.29USD bottle
Betaxolol HCl 0.5% Solution 15ml Bottle104.31USD bottle
Betoptic-S 0.25% Suspension 5ml Bottle51.99USD bottle
Betoptic s 0.25% eye drops9.79USD ml
Betaxolol hcl 0.5% eye drop6.82USD ml
Betoptic S 0.25 % Suspension2.54USD ml
Kerlone 20 mg tablet2.35USD tablet
Betaxolol 20 mg tablet1.86USD tablet
Kerlone 10 mg tablet1.63USD tablet
Betaxolol HCl 10 mg tablet1.29USD tablet
Betaxolol 10 mg tablet1.24USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5540918 No1994-01-302014-01-30Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point70-72 °CPhysProp
water solubility451 mg/LNot Available
logP2.81RECANATINI,M (1992)
Caco2 permeability-4.81ADME Research, USCD
pKa9.4Not 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
Polarizability37.05 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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
  1. 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. [PubMed:20418154 ]
External Links
ATC CodesC07AB05S01ED52S01ED02
AHFS Codes
  • 52:92.00
PDB EntriesNot Available
FDA labelDownload (111 KB)
MSDSDownload (38.8 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Betaxolol can be increased when it is combined with Abiraterone.
AcepromazineAcepromazine may increase the hypotensive activities of Betaxolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Betaxolol is combined with Acetylcholine.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Betaxolol.
AlfuzosinBetaxolol may increase the orthostatic hypotensive activities of Alfuzosin.
AmifostineBetaxolol may increase the hypotensive activities of Amifostine.
AmiodaroneAmiodarone may increase the bradycardic activities of Betaxolol.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Betaxolol.
BortezomibThe metabolism of Betaxolol can be decreased when combined with Bortezomib.
BretyliumBretylium may increase the bradycardic activities of Betaxolol.
BrimonidineBrimonidine may increase the antihypertensive activities of Betaxolol.
BupivacaineThe serum concentration of Bupivacaine can be increased when it is combined with Betaxolol.
ButabarbitalThe serum concentration of Betaxolol can be decreased when it is combined with Butabarbital.
ButethalThe serum concentration of Betaxolol can be decreased when it is combined with Butethal.
CabergolineBetaxolol may increase the vasoconstricting activities of Cabergoline.
CarbacholThe risk or severity of adverse effects can be increased when Betaxolol is combined with Carbachol.
CarbamazepineThe metabolism of Betaxolol can be increased when combined with Carbamazepine.
CeritinibBetaxolol may increase the bradycardic activities of Ceritinib.
ChloroquineThe metabolism of Betaxolol can be decreased when combined with Chloroquine.
ChlorpropamideBetaxolol may increase the hypoglycemic activities of Chlorpropamide.
Cyproterone acetateThe serum concentration of Betaxolol can be decreased when it is combined with Cyproterone acetate.
DeferasiroxThe serum concentration of Betaxolol can be increased when it is combined with Deferasirox.
DiazoxideDiazoxide may increase the hypotensive activities of Betaxolol.
DigoxinBetaxolol may increase the bradycardic activities of Digoxin.
DipivefrinDipivefrin may increase the atrioventricular blocking (AV block) activities of Betaxolol.
DipyridamoleDipyridamole may increase the bradycardic activities of Betaxolol.
DisopyramideDisopyramide may increase the bradycardic activities of Betaxolol.
DronedaroneDronedarone may increase the bradycardic activities of Betaxolol.
DuloxetineBetaxolol may increase the orthostatic hypotensive activities of Duloxetine.
EsmololEsmolol may increase the bradycardic activities of Betaxolol.
FingolimodBetaxolol may increase the bradycardic activities of Fingolimod.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Betaxolol.
FluvoxamineThe metabolism of Betaxolol can be decreased when combined with Fluvoxamine.
HeptabarbitalThe serum concentration of Betaxolol can be decreased when it is combined with Heptabarbital.
HexobarbitalThe serum concentration of Betaxolol can be decreased when it is combined with Hexobarbital.
InfliximabInfliximab may decrease the antihypertensive activities of Betaxolol.
IvabradineBetaxolol may increase the bradycardic activities of Ivabradine.
LacosamideBetaxolol may increase the atrioventricular blocking (AV block) activities of Lacosamide.
LevodopaBetaxolol may increase the orthostatic hypotensive activities of Levodopa.
LidocaineThe serum concentration of Lidocaine can be increased when it is combined with Betaxolol.
MepivacaineThe serum concentration of Mepivacaine can be increased when it is combined with Betaxolol.
MethacholineThe risk or severity of adverse effects can be increased when Betaxolol is combined with Methacholine.
MethohexitalThe serum concentration of Betaxolol can be decreased when it is combined with Methohexital.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Betaxolol.
MexiletineThe metabolism of Betaxolol can be decreased when combined with Mexiletine.
MidodrineBetaxolol may increase the bradycardic activities of Midodrine.
MolsidomineMolsidomine may increase the hypotensive activities of Betaxolol.
MoxonidineMoxonidine may increase the hypotensive activities of Betaxolol.
NicorandilNicorandil may increase the hypotensive activities of Betaxolol.
NifedipineNifedipine may increase the hypotensive activities of Betaxolol.
ObinutuzumabBetaxolol may increase the hypotensive activities of Obinutuzumab.
OctreotideOctreotide may increase the bradycardic activities of Betaxolol.
OrciprenalineBetaxolol may decrease the activities of Orciprenaline.
Peginterferon alfa-2bThe serum concentration of Betaxolol can be increased when it is combined with Peginterferon alfa-2b.
PentobarbitalThe serum concentration of Betaxolol can be decreased when it is combined with Pentobarbital.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Betaxolol.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Betaxolol.
PrazosinBetaxolol may increase the orthostatic hypotensive activities of Prazosin.
PrimidoneThe serum concentration of Betaxolol can be decreased when it is combined with Primidone.
PropafenoneThe serum concentration of Betaxolol can be increased when it is combined with Propafenone.
QuinineQuinine may increase the hypotensive activities of Betaxolol.
RegorafenibRegorafenib may increase the bradycardic activities of Betaxolol.
ReserpineReserpine may increase the hypotensive activities of Betaxolol.
RisperidoneBetaxolol may increase the hypotensive activities of Risperidone.
RituximabBetaxolol may increase the hypotensive activities of Rituximab.
RivastigmineRivastigmine may increase the bradycardic activities of Betaxolol.
RuxolitinibRuxolitinib may increase the bradycardic activities of Betaxolol.
SecobarbitalThe serum concentration of Betaxolol can be decreased when it is combined with Secobarbital.
SufentanilSufentanil may increase the bradycardic activities of Betaxolol.
TacrineTacrine may increase the bradycardic activities of Betaxolol.
TadalafilTadalafil may increase the antihypertensive activities of Betaxolol.
TeriflunomideThe serum concentration of Betaxolol can be decreased when it is combined with Teriflunomide.
TheophyllineBetaxolol may decrease the activities of Theophylline.
TofacitinibTofacitinib may increase the bradycardic activities of Betaxolol.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Betaxolol.
TreprostinilTreprostinil may increase the hypotensive activities of Betaxolol.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Betaxolol.
VardenafilVardenafil may increase the antihypertensive activities of Betaxolol.
VemurafenibThe serum concentration of Betaxolol can be increased when it is combined with Vemurafenib.
YohimbineYohimbine may decrease the antihypertensive activities of Betaxolol.
Food InteractionsNot Available

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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
References
  1. 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. [PubMed:12181453 ]
  2. 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. [PubMed:17513029 ]
  3. 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. [PubMed:2077180 ]
  4. Lesar TS: Comparison of ophthalmic beta-blocking agents. Clin Pharm. 1987 Jun;6(6):451-63. [PubMed:2891463 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
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 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Rait JL: Systemic effects of topical ophthalmic beta-adrenoceptor antagonists. Aust N Z J Ophthalmol. 1999 Feb;27(1):57-64. [PubMed:10080340 ]

Enzymes

Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23