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Details

Stereochemistry RACEMIC
Molecular Formula C15H23NO3
Molecular Weight 265.348
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXPRENOLOL

SMILES

CC(C)NCC(O)COC1=CC=CC=C1OCC=C

InChI

InChIKey=CEMAWMOMDPGJMB-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Oxprenolol is clinically a well-established beta blocker that shares with other members of this group the ability to control a variety of disorders, in particular, hypertension and angina. Pharmacologically it is a nonselective beta blocker that possesses partial agonist activity (intrinsic sympathomimetic activity). Pharmacokinetically, oxprenolol behaves as a moderately lipophilic agent. Oxprenolol undergoes first pass metabolism with only 30% of an oral dose reaching the systemic circulation. The drug is approximately 80% protein bound and is eliminated primarily by glucuronidation in the liver. Less than 4% of oxprenolol is excreted unchanged in the urine. Oxprenolol may reduce the heart rate and prolong the effective and functional atrioventricular nodal refractory period. Oxprenolol has less negative inotropic and chronotropic effects than propranolol. Plasma renin activity is reduced; however, changes in plasma aldosterone level are not significant. Long term metabolic effects require further study. Chest pain (angina), high blood pressure (hypertension), irregular heart beats and anxiety are indications for Oxprenolol usage. To date Oxprenolol is discontinued by FDA.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
Condition Info

Condition Info

PMID

PMID

TitleDatePMID
Use of oxprenolol in cardiac arrhythmias associated with acute myocardial ischaemia.
1971 Jan 30
Idioventricular tachycardia elicited by the combined administration of trasicor and lidocain.
1972
Prevention of isoproterenol-induced cardiac hypertrophy by beta-blocking agents in the rat.
1976
Effect of beta-blockade during bowling competitions.
1976 Dec
Inappropriate antihypertensive therapy in the elderly.
1976 Dec 18
[Experimental anti-arrhythmic effects of a new beta-adrenergic receptor blocking agent, dl-l-(tert. butylamino)-3-[(2-propinyloxy)phenoxy]2-propanol hydrochloride (dl Kö 1400-Cl)].
1976 Jul
Severe hypertension produced by interaction of phenylpropanolamine with methyldopa and oxprenolol.
1976 Jul 31
Raynaud's phenomenon as side effect of beta-blockers in hypertension.
1976 Jun 19
[The role of reduction of the heart rate in the favorable effect of the beta blockers on myocardial ischemia due to isoprenalin in patients with angina pectoris].
1977 Nov 5
Therapy of extrapyramidal side effects, with particular reference to persistent dyskinesia and lithium tremor.
1978
Antiarrhythmic effect of oxprenolol on halothane-epinephrine and coronary ligation induced ventricular arrhythmias in beagle dogs.
1978 Aug
Two patients with schizophrenic-like psychosis after treatment with beta-adrenergic blockers.
1979 Mar 24
Comparison of the activity and plasma levels of oxprenolol, slow release oxprenolol, long acting propranolol and sotalol.
1980 Jun
Effect of prazosin and oxprenolol on plasma renin activity and blood pressure in patients with essential hypertension.
1981
Slow release oxprenolol in angina pectoris: study comparing oxprenolol, once daily, with propranolol, four times daily.
1981 May
Mediation of renin release in essential hypertension by alpha-adrenoreceptors.
1981 Nov-Dec
Interaction between oxprenolol and indomethacin on blood pressure in essential hypertensive patients.
1982
The acute and chronic effect of oxprenolol and propranolol on peripheral blood flow in hypertensive patients.
1982 Nov
Beta-adrenoreceptor antagonists and diplopia.
1982 Oct 9
Some functional changes in experimentally induced cardiac overload.
1983
Oxprenolol hydrochloride: pharmacology, pharmacokinetics, adverse effects and clinical efficacy.
1983 Mar-Apr
Clinical responses to oxprenolol in the elderly.
1983 Nov 10
Increased plasma vasopressin and serum uric acid in the low renin type of essential hypertension.
1984
Cardiovascular risk and risk factors in a randomized trial of treatment based on the beta-blocker oxprenolol: the International Prospective Primary Prevention Study in Hypertension (IPPPSH). The IPPPSH Collaborative Group.
1985 Aug
Predictors of blood pressure increases after withdrawal of antihypertensive therapy.
1985 Dec
Effect of oxprenolol on ventricular arrhythmias: the European Infarction Study experience.
1985 Nov
Interference by sulphinpyrazone with the antihypertensive effects of oxprenolol.
1986
Potentiation of haloperidol-induced catalepsy by beta-adrenoceptor antagonists in mice.
1986 Sep
Haemodynamic, metabolic, and lymphocyte beta 2-adrenoceptor changes following chronic beta-adrenoceptor antagonism.
1987
Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs.
1987 Dec
Beta-2-adrenoceptor-mediated hypokalemia and its abolishment by oxprenolol.
1987 Dec
A nonsteady-state agonist antagonist interaction model using plasma potassium concentrations to quantify the beta-2 selectivity of beta blockers.
1989 Apr
Cardioprotection by beta-blockers: molecular and structural aspects in experimental hypertension.
1990
Beta-blockade in the primary prevention of coronary heart disease in hypertensive patients. Review of present evidence.
1991 Dec
Atypical beta-adrenergic receptor in 3T3-F442A adipocytes. Pharmacological and molecular relationship with the human beta 3-adrenergic receptor.
1991 Oct 25
Oxprenolol-loaded bioadhesive microspheres: preparation and in vitro/in vivo characterization.
2003 Nov-Dec
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.
2004 May
Cutaneous vasculitis induced by carvedilol.
2007 Aug
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.
2007 Oct 16
Patent

Sample Use Guides

In Vivo Use Guide
Chest pain (angina): 80-160 mg a day taken in 2 to 3 doses. The maximum daily dose is 320 mg. High blood pressure (hypertension): 80-160 mg a day given in 2 to 3 doses. The maximum daily dose is 320 mg. Irregular heart beats: 20-80 mg taken 2 or 3 times a day. The maximum daily dose is 240 mg. Anxiety: The starting dose is 40 mg taken twice a day. A single dose of Trasicor (40-80 mg) may be taken for anxiety during a specific stressful situation.
Route of Administration: Oral
In Vitro Use Guide
Oxprenolol had biphasic actions on the rat sarcolemmal Ca2+ pump activities; the lower concentrations (1 and 10 microM) were stimulatory, but the higher concentrations (100 and 1000 microM) were inhibitory.
Name Type Language
OXPRENOLOL
INN   MI   WHO-DD  
INN  
Official Name English
2-PROPANOL, 1-(O-ALLYLOXYPHENOXY)-3-ISOPROPYLAMINO-
Common Name English
OXPRENOLOL [INN]
Common Name English
OXPRENOLOL [MI]
Common Name English
OXPRENOLOL [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC C07BA02
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
WHO-VATC QC07CA02
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
WHO-ATC C07AA02
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
WHO-VATC QC07BA02
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
WHO-ATC C07CA02
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
WHO-VATC QC07AA02
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
Code System Code Type Description
PUBCHEM
4631
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY SWITZERF
RXCUI
7801
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY RxNorm
EVMPD
SUB09555MIG
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
DRUG BANK
DB01580
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
NCI_THESAURUS
C66276
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
MESH
D010096
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
ChEMBL
CHEMBL546
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
CAS
6452-71-7
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
ECHA (EC/EINECS)
229-257-9
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
IUPHAR
7255
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
MERCK INDEX
M8321
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY Merck Index
EPA CompTox
6452-71-7
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
INN
2506
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY
WIKIPEDIA
OXPRENOLOL
Created by admin on Tue Mar 06 12:13:09 UTC 2018 , Edited by admin on Tue Mar 06 12:13:09 UTC 2018
PRIMARY