Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:35 UTC
HMDB IDHMDB0014341
Secondary Accession Numbers
  • HMDB14341
Metabolite Identification
Common NameBetaxolol
DescriptionBetaxolol is only found in individuals that have used or taken this drug. It is a cardioselective beta-1-adrenergic antagonist with no partial agonist activity. [PubChem]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.
Structure
Data?1582753167
Synonyms
ValueSource
1-(4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-2-propanolChEBI
1-(Isopropylamino)-3-[p-(cyclopropylmethoxyethyl)phenoxy]-2-propanolChEBI
BetaxololumChEBI
BetopticHMDB
BetoptimaHMDB
KerloneHMDB
Lorex brand OF betaxolol hydrochlorideHMDB
OxodalHMDB
Synthelabo brand OF betaxolol hydrochlorideHMDB
Betaxolol alconHMDB
Boots brand OF betaxolol hydrochlorideHMDB
Hydrochloride, betaxololHMDB
Synthélabo brand OF betaxolol hydrochlorideHMDB
Alcon brand OF betaxolol hydrochlorideHMDB
Allphar brand OF betaxolol hydrochlorideHMDB
Betaxolol hydrochlorideHMDB
KerlonHMDB
Searle brand OF betaxolol hydrochlorideHMDB
Alcon, betaxololHMDB
Schwarz brand OF betaxolol hydrochlorideHMDB
Chemical FormulaC18H29NO3
Average Molecular Weight307.4278
Monoisotopic Molecular Weight307.214743799
IUPAC Name1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-[(propan-2-yl)amino]propan-2-ol
Traditional Name1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-(isopropylamino)propan-2-ol
CAS Registry Number63659-18-7
SMILES
CC(C)NCC(O)COC1=CC=C(CCOCC2CC2)C=C1
InChI Identifier
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
InChI KeyNWIUTZDMDHAVTP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassTyrosols and derivatives
Direct ParentTyrosols and derivatives
Alternative Parents
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
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point70 - 72 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.03 g/LNot Available
LogP2.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity88.64 m³·mol⁻¹ChemAxon
Polarizability37.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.32431661259
DarkChem[M-H]-171.86331661259
DeepCCS[M+H]+178.89830932474
DeepCCS[M-H]-176.5430932474
DeepCCS[M-2H]-209.42630932474
DeepCCS[M+Na]+184.99130932474
AllCCS[M+H]+178.032859911
AllCCS[M+H-H2O]+175.132859911
AllCCS[M+NH4]+180.732859911
AllCCS[M+Na]+181.532859911
AllCCS[M-H]-177.432859911
AllCCS[M+Na-2H]-178.132859911
AllCCS[M+HCOO]-179.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BetaxololCC(C)NCC(O)COC1=CC=C(CCOCC2CC2)C=C12880.5Standard polar33892256
BetaxololCC(C)NCC(O)COC1=CC=C(CCOCC2CC2)C=C12329.7Standard non polar33892256
BetaxololCC(C)NCC(O)COC1=CC=C(CCOCC2CC2)C=C12384.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Betaxolol,1TMS,isomer #1CC(C)NCC(COC1=CC=C(CCOCC2CC2)C=C1)O[Si](C)(C)C2377.8Semi standard non polar33892256
Betaxolol,1TMS,isomer #2CC(C)N(CC(O)COC1=CC=C(CCOCC2CC2)C=C1)[Si](C)(C)C2530.3Semi standard non polar33892256
Betaxolol,2TMS,isomer #1CC(C)N(CC(COC1=CC=C(CCOCC2CC2)C=C1)O[Si](C)(C)C)[Si](C)(C)C2566.4Semi standard non polar33892256
Betaxolol,2TMS,isomer #1CC(C)N(CC(COC1=CC=C(CCOCC2CC2)C=C1)O[Si](C)(C)C)[Si](C)(C)C2581.2Standard non polar33892256
Betaxolol,2TMS,isomer #1CC(C)N(CC(COC1=CC=C(CCOCC2CC2)C=C1)O[Si](C)(C)C)[Si](C)(C)C2835.7Standard polar33892256
Betaxolol,1TBDMS,isomer #1CC(C)NCC(COC1=CC=C(CCOCC2CC2)C=C1)O[Si](C)(C)C(C)(C)C2601.2Semi standard non polar33892256
Betaxolol,1TBDMS,isomer #2CC(C)N(CC(O)COC1=CC=C(CCOCC2CC2)C=C1)[Si](C)(C)C(C)(C)C2779.7Semi standard non polar33892256
Betaxolol,2TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CCOCC2CC2)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3032.5Semi standard non polar33892256
Betaxolol,2TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CCOCC2CC2)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2967.7Standard non polar33892256
Betaxolol,2TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CCOCC2CC2)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3018.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Betaxolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9650000000-21779d64a7615ec0e9a72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betaxolol GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9312000000-df9b051547c498753dc82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betaxolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betaxolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betaxolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betaxolol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betaxolol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betaxolol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol LC-ESI-qTof , Positive-QTOFsplash10-0900-0619000000-76032f7e5f2fbe4058152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0009000000-287e15a62fc0a0a17ccc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol LC-ESI-QTOF , positive-QTOFsplash10-0a4i-1309000000-627420cbd67d8ac1e4ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol LC-ESI-QTOF , positive-QTOFsplash10-05fr-6900000000-e23f35ab4359c86dd9662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol LC-ESI-QTOF , positive-QTOFsplash10-0ab9-9800000000-0fec1fdb5cce29edc7de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol LC-ESI-QTOF , positive-QTOFsplash10-0a6u-9600000000-35b64bf771f1c210f29d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol , positive-QTOFsplash10-0900-0619000000-76032f7e5f2fbe4058152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol , positive-QTOFsplash10-0a4i-0209000000-891e6fe5f7380d1b79242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 40V, Positive-QTOFsplash10-0ab9-9800000000-1581f085d3cf2606d2732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 30V, Positive-QTOFsplash10-05fr-6900000000-e23f35ab4359c86dd9662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 30V, Positive-QTOFsplash10-05fr-7900000000-8b3da8b26492a31a57382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 40V, Positive-QTOFsplash10-0ab9-9800000000-0fec1fdb5cce29edc7de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 50V, Positive-QTOFsplash10-0a6u-9600000000-35b64bf771f1c210f29d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 40V, Positive-QTOFsplash10-0ab9-9800000000-4b362234f6e0f5887b6b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 30V, Positive-QTOFsplash10-05fr-7900000000-9eedd696217b0ff2828c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 10V, Positive-QTOFsplash10-0a4i-0009000000-287e15a62fc0a0a17ccc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 20V, Positive-QTOFsplash10-0a4i-1309000000-627420cbd67d8ac1e4ad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 35V, Positive-QTOFsplash10-0a4i-4619000000-272c3925c0851728b34d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betaxolol 50V, Positive-QTOFsplash10-0a6u-9600000000-f3652f7252879767f20b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betaxolol 10V, Positive-QTOFsplash10-0a4i-9468000000-e0c4ef86da5c09da058b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betaxolol 20V, Positive-QTOFsplash10-0ab9-9330000000-7f5e684c54e1c0fb87952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betaxolol 40V, Positive-QTOFsplash10-0a4i-9100000000-17c55a2f167c8a3bb3972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betaxolol 10V, Negative-QTOFsplash10-0a4i-4739000000-e28598a9072550f2eacf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betaxolol 20V, Negative-QTOFsplash10-0006-3900000000-c8a3a97284187523ea6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betaxolol 40V, Negative-QTOFsplash10-05fu-9500000000-639170036a85595085932016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00195 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00195 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00195
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2279
KEGG Compound IDC06849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBetaxolol
METLIN IDNot Available
PubChem Compound2369
PDB IDNot Available
ChEBI ID3082
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 ]

Enzymes

General function:
Involved in monooxygenase 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
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 ]
General function:
Involved in monooxygenase activity
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 N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
46458.3
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 ]