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Identification
Name Oxprenolol
Accession Number DB01580
Type small molecule
Groups approved
Description

A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(+-)-oxprenolol
(+)-1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)propan-2-ol
(1)-1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)propan-2-ol
1-(Isopropylamino)-2-hydroxy-3-(o-(allyloxy)phenoxy)propane
1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)-2-propanol
1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)-2-propanol
DL-oxprenolol
Osprenololo [dcit]
Oxprenololum [inn-latin]
Salts Not Available
Brand names
Name Company
Coretal
Laracor
Slow-pren
Trasacor
Trasicor
Brand mixtures Not Available
Categories
  • Anti-anxiety Agents
  • Antihypertensive Agents
  • Adrenergic beta-Antagonists
  • Sympatholytics
  • Vasodilator Agents
  • Anti-Arrhythmia Agents
CAS number 6452-71-7
Weight Average: 265.348
Monoisotopic: 265.167793607
Chemical Formula C15H23NO3
InChI Key InChIKey=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
Plain Text
IUPAC Name
{2-hydroxy-3-[2-(prop-2-en-1-yloxy)phenoxy]propyl}(propan-2-yl)amine
SMILES
CC(C)NCC(O)COC1=CC=CC=C1OCC=C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Ethers
  • Catechols
  • Anisoles
  • Phenyl Esters
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Amino Alcohols
  • Catechols
  • Aromatic compounds
  • Anisoles
  • Alcohols and Polyols
  • Phenyl Esters
Pharmacology
Indication Used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.
Pharmacodynamics Oxprenolol 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 action 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.
Absorption Oral bioavailability is 20-70%.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Hepatic.
Route of elimination Not Available
Half life 1-2 hours
Clearance Not Available
Toxicity Symptoms 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
Pathway Name SMPDB ID
Smp00304 Oxprenolol Pathway SMP00304
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers Not Available
Dosage forms
Form Route Strength
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 2.10 HANSCH,C ET AL. (1995)
Caco2 permeability -4.68 ADME Research, USCD
Predicted Properties
Property Value Source
water solubility 6.80e-01 g/l ALOGPS
logP 2.44 ALOGPS
logP 2.17 ChemAxon
logS -2.6 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 ChemAxon
rotatable bond count 9 ChemAxon
refractivity 76 ChemAxon
polarizability 30.31 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. McDevitt DG: Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs. Eur Heart J. 1987 Dec;8 Suppl M:9-14. Pubmed
External Links
Resource Link
PubChem Compound 4631 Link_out
PubChem Substance 46508996 Link_out
ChemSpider 4470 Link_out
BindingDB 50240370 Link_out
Therapeutic Targets Database DAP000485 Link_out
PharmGKB PA10284 Link_out
Drug Product Database 402575 Link_out
Wikipedia http://en.wikipedia.org/wiki/Oxprenolol Link_out
ATC Codes
  • C07AA02
AHFS Codes
  • 24:24.00
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Acetohexamide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Chlorpropamide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Clonidine Increased hypertension when clonidine stopped
Dihydroergotamine Ischemia with risk of gangrene
Dihydroergotoxine Ischemia with risk of gangrene
Disopyramide The beta-blocker, oxprenolol, may increase the toxicity of disopyramide.
Epinephrine Hypertension, then bradycardia
Ergonovine Ischemia with risk of gangrene
Ergotamine Ischemia with risk of gangrene
Fenoterol Antagonism
Formoterol Antagonism
Gliclazide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Glipizide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Glisoxepide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Glyburide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Glycodiazine The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Ibuprofen Risk of inhibition of renal prostaglandins
Indomethacin Risk of inhibition of renal prostaglandins
Insulin The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Insulin Glargine The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Isoproterenol Antagonism
Lidocaine The beta-blocker increases the effect and toxicity of lidocaine
Methyldopa Possible hypertensive crisis
Methysergide Ischemia with risk of gangrene
Orciprenaline Antagonism
Pipobroman Antagonism
Pirbuterol Antagonism
Piroxicam Risk of inhibition of renal prostaglandins
Practolol Antagonism
Prazosin Risk of hypotension at the beginning of therapy
Repaglinide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Salbutamol Antagonism
Salmeterol Antagonism
Terazosin Increased risk of hypotension. Initiate concomitant therapy cautiously.
Terbutaline Antagonism
Tolazamide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Tolbutamide The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Verapamil Increased effect of both drugs
Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.
  • Take without regard to meals.
Targets

1. Beta-1 adrenergic receptor

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-2 adrenergic receptor

Pharmacological action: unknown
Actions: antagonist

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

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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
  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
Enzymes

1. Cytochrome P450 2D6

Actions: inhibitor

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

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
Transporters

1. Solute carrier family 22 member 2

Actions: inhibitor

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

UniProt ID: O15244 Link_out
Gene: SLC22A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 cell monolayers. Br J Pharmacol. 2000 Sep;131(1):71-9. Pubmed
Comments
Drug created on August 29, 2007 08:53 / Updated on February 08, 2013 16:20