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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:46:29 UTC
HMDB IDHMDB0015520
Secondary Accession Numbers
  • HMDB15520
Metabolite Identification
Common NameOxprenolol
DescriptionOxprenolol is only found in individuals that have used or taken this drug. It is a non-selective beta blocker with some intrinsic sympathomimetic activity. It is used for the treatment of angina pectoris, abnormal heart rhythms, anxiety, and high blood pressure. Oxprenolol is a lipophilic beta blocker which passes the blood-brain barrier more easily than water-soluble beta blockers. As such, it is associated with a higher incidence of CNS-related side effects than beta blockers with more hydrophilic molecules such as atenolol, sotalol, and nadolol (Wikipedia ). Like other beta-adrenergic antagonists, oxprenolol competes with adrenergic neurotransmitters such as catecholamines for binding at sympathetic receptor sites. Like propranolol and timolol, oxprenolol binds at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting the effects of the catecholamines epinephrine and norepinephrine and decreasing heart rate, cardiac output, and systolic and diastolic blood pressure. It also blocks beta-2 adrenergic receptors located in bronchiole smooth muscle, causing vasoconstriction. By binding beta-2 receptors in the juxtaglomerular apparatus, oxprenolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production. Oxprenolol, therefore, inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.
Structure
Data?1582753306
Synonyms
ValueSource
(+)-1-(O-(Allyloxy)phenoxy)-3-(isopropylamino)propan-2-olHMDB
(+-)-OxprenololHMDB
(1)-1-(O-(Allyloxy)phenoxy)-3-(isopropylamino)propan-2-olHMDB
1-(Isopropylamino)-2-hydroxy-3-(O-(allyloxy)phenoxy)propaneHMDB
1-(O-(Allyloxy)phenoxy)-3-(isopropylamino)-2-propanolHMDB
1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)-2-propanolHMDB
DL-OxprenololHMDB
OsprenololoHMDB
CoretalHMDB
Trasicor, slowHMDB
KoretalHMDB
Slow trasicorHMDB
TrasicorHMDB
Oxprenolol hydrochlorideHMDB
Hydrochloride, oxprenololHMDB
TevacorHMDB
Chemical FormulaC15H23NO3
Average Molecular Weight265.348
Monoisotopic Molecular Weight265.167793607
IUPAC Name1-[2-(prop-2-en-1-yloxy)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol
Traditional Nameoxprenolol
CAS Registry Number6452-71-7
SMILES
CC(C)NCC(O)COC1=C(OCC=C)C=CC=C1
InChI Identifier
InChI=1S/C15H23NO3/c1-4-9-18-14-7-5-6-8-15(14)19-11-13(17)10-16-12(2)3/h4-8,12-13,16-17H,1,9-11H2,2-3H3
InChI KeyCEMAWMOMDPGJMB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary 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 DescriptorsNot Available
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.68 g/LNot Available
LogP2.10HANSCH,C ET AL. (1995)
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.68 g/LALOGPS
logP2.44ALOGPS
logP2.17ChemAxon
logS-2.6ALOGPS
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 Count9ChemAxon
Refractivity76 m³·mol⁻¹ChemAxon
Polarizability30.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M+H]+ExperimentalCBM161.730932474
DarkChem[M+H]+PredictedNot Available160.5731661259
DarkChem[M-H]-PredictedNot Available159.43731661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Oxprenolol,1TMS,#11934.169https://arxiv.org/abs/1905.12712
Oxprenolol,1TMS,#22086.541https://arxiv.org/abs/1905.12712
Oxprenolol,1TBDMS,#12147.81https://arxiv.org/abs/1905.12712
Oxprenolol,1TBDMS,#22357.1147https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-9830000000-ffc434fb823de100db4d2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9140000000-20b54606cade12365e822017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-006t-7920000000-1fed9f62e7ece1c8e9512017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-3090000000-9ca7ccd0c0daba3c30402017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-9110000000-b81a2c636a97b7a75df02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-9000000000-996746df1ffa4553b2db2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fr-9000000000-cc715f4401a8ea6f3c132017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fr-9000000000-7a6e78af4d59990c16da2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ab9-9000000000-986953ff107cdee4fc242017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-05fr-9000000000-cc715f4401a8ea6f3c132021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00di-9000000000-969719220e2b72646ef62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-3090000000-9ca7ccd0c0daba3c30402021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-9110000000-b81a2c636a97b7a75df02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - -1V, Positivesplash10-006t-7920000000-d6e482916b84d26317de2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0ab9-9000000000-986953ff107cdee4fc242021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-05fr-9000000000-7a6e78af4d59990c16da2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3290000000-5fdffee3a1deff8383012016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9340000000-2ef2cda6debfabf11f4e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9100000000-fecbd33075dfbb13f4a42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1690000000-8d2a9f42673ab60f9f762016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-2910000000-b2d35105403e4589696c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-dd301346a7a467bd9fe52016-08-03View 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 DB01580 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01580 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01580
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxprenolol
METLIN IDNot Available
PubChem Compound4631
PDB IDNot Available
ChEBI ID113756
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. McDevitt DG: Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs. Eur Heart J. 1987 Dec;8 Suppl M:9-14. [PubMed:2897304 ]

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 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Campbell CA, Parratt JR, Kane KA, Bullock G: Effects of prolonged administration of oxprenolol on severity of ischaemic arrhythmias, enzyme leakage, infarct size, and intracellular cardiac muscle action potentials. J Cardiovasc Pharmacol. 1984 May-Jun;6(3):369-77. [PubMed:6202960 ]
  4. Lemmer B: [Pharmacological basis for the therapy of cardiovascular disease with beta-adrenoceptor blocking drugs (author's transl)]. Herz. 1982 Jun;7(3):168-78. [PubMed:6124492 ]
  5. Abrahamsson T: The beta 1- and beta 2-adrenoceptor stimulatory effects of alprenolol, oxprenolol and pindolol: a study in the isolated right atrium and uterus of the rat. Br J Pharmacol. 1986 Apr;87(4):657-64. [PubMed:2871880 ]
  6. 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Sekut L, Champion BR, Page K, Menius JA Jr, Connolly KM: Anti-inflammatory activity of salmeterol: down-regulation of cytokine production. Clin Exp Immunol. 1995 Mar;99(3):461-6. [PubMed:7882570 ]
  4. Fujita H, Tanaka J, Maeda N, Sakanaka M: Adrenergic agonists suppress the proliferation of microglia through beta 2-adrenergic receptor. Neurosci Lett. 1998 Feb 6;242(1):37-40. [PubMed:9509999 ]
  5. Prinz M, Hausler KG, Kettenmann H, Hanisch U: beta-adrenergic receptor stimulation selectively inhibits IL-12p40 release in microglia. Brain Res. 2001 Apr 27;899(1-2):264-70. [PubMed:11311890 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular weight:
62564.0
References
  1. Dudley AJ, Bleasby K, Brown CD: The organic cation transporter OCT2 mediates the uptake of beta-adrenoceptor antagonists across the apical membrane of renal LLC-PK(1) cell monolayers. Br J Pharmacol. 2000 Sep;131(1):71-9. [PubMed:10960071 ]