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Identification
NameOxprenolol
Accession NumberDB01580
TypeSmall Molecule
GroupsApproved
Description

A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety. [PubChem]

Structure
Thumb
Synonyms
Oxprenolol
Oxprenololum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Slow Trasicor Tab 160mgtablet (extended-release)160 mgoralNovartis Pharmaceuticals Canada Inc1981-12-312005-08-02Canada
Slow Trasicor Tab 80mgtablet (extended-release)80 mgoralNovartis Pharmaceuticals Canada Inc1981-12-312005-08-02Canada
Trasicor Tab 20mgtablet20 mgoralNovartis Pharmaceuticals Canada Inc1980-12-311999-08-04Canada
Trasicor Tab 40mgtablet40 mgoralNovartis Pharmaceuticals Canada Inc1980-12-312008-01-22Canada
Trasicor Tab 80mgtablet80 mgoralNovartis Pharmaceuticals Canada Inc1980-12-312009-02-25Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
TrasacorNot Available
TrasicorNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Oxprenolol hydrochloride
ThumbNot applicableDBSALT001070
Categories
UNII519MXN9YZR
CAS number6452-71-7
WeightAverage: 265.348
Monoisotopic: 265.167793607
Chemical FormulaC15H23NO3
InChI KeyInChIKey=CEMAWMOMDPGJMB-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-[2-(prop-2-en-1-yloxy)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol
SMILES
CC(C)NCC(O)COC1=CC=CC=C1OCC=C
Taxonomy
DescriptionThis compound 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
ClassBenzene and substituted derivatives
Sub ClassPhenol ethers
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenol ether
  • Alkyl aryl ether
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.
PharmacodynamicsOxprenolol is a non-selective beta blocker with some intrinsic sympathomimetic activity. 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 hydrophilic ligands such as atenolol, sotalol and nadolol. Oxprenolol is an potent beta-blocker and should not be administered to asthmatics because it can cause irreversible airway failure and inflammation.
Mechanism of actionLike 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.
Related Articles
AbsorptionOral bioavailability is 20-70%.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half life1-2 hours
ClearanceNot Available
ToxicitySymptoms of overdose include abdominal irritation, central nervous system depression, coma, extremely slow heartbeat, heart failure, lethargy, low blood pressure, and wheezing.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Oxprenolol Action PathwayDrug actionSMP00304
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9817
Blood Brain Barrier-0.9759
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.6618
P-glycoprotein inhibitor INon-inhibitor0.5567
P-glycoprotein inhibitor IINon-inhibitor0.8945
Renal organic cation transporterNon-inhibitor0.8698
CYP450 2C9 substrateNon-substrate0.8122
CYP450 2D6 substrateNon-substrate0.5424
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9209
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8958
Ames testNon AMES toxic0.9367
CarcinogenicityNon-carcinogens0.9206
BiodegradationNot ready biodegradable0.9593
Rat acute toxicity2.5730 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9351
hERG inhibition (predictor II)Non-inhibitor0.7501
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tablet (extended-release)oral160 mg
Tablet (extended-release)oral80 mg
Tabletoral20 mg
Tabletoral40 mg
Tabletoral80 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.10HANSCH,C ET AL. (1995)
Caco2 permeability-4.68ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.68 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76 m3·mol-1ChemAxon
Polarizability30.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot 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 ]
External Links
ATC CodesC07AA02C07BA02C07CA02
AHFS Codes
  • 24:24.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
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. 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 ]
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. 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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Quaternary ammonium group 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-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
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 ]
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Drug created on August 29, 2007 08:53 / Updated on April 10, 2014 18:14