OXPRENOLOL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H23NO3.ClH
Molecular Weight	301.809
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)NCC(O)COC1=C(OCC=C)C=CC=C1

InChI

InChIKey=COAJXCLTPGGDAJ-UHFFFAOYSA-N

InChI=1S/C15H23NO3.ClH/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;1H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6356863/
Curator's Comment: Description was created based on several sources, including: https://www.medicines.org.uk/emc/PIL.27982.latest.pdf https://www.ncbi.nlm.nih.gov/pubmed/6344036

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

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor beta 87 Target ID: CHEMBL2094118 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D08318	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Chest pain (angina) 2 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1501220376572.pdf	Primary	Approved 8429	TRASICOR Approved Use Trasicor is used to treat high blood pressure and to reduce or prevent chest pain (angina). It is also used to treat some heart disorders such as irregular heart beat and to relieve the symptoms of anxiety. Launch Date 1983
Hypertension 567 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1501220376572.pdf	Primary	Approved 8429	TRASICOR Approved Use Trasicor is used to treat high blood pressure and to reduce or prevent chest pain (angina). It is also used to treat some heart disorders such as irregular heart beat and to relieve the symptoms of anxiety. Launch Date 1983
Irregular heart beats 2 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1501220376572.pdf	Primary	Approved 8429	TRASICOR Approved Use Trasicor is used to treat high blood pressure and to reduce or prevent chest pain (angina). It is also used to treat some heart disorders such as irregular heart beat and to relieve the symptoms of anxiety. Launch Date 1983
Anxiety 267 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1501220376572.pdf	Primary	Approved 8429	TRASICOR Approved Use Trasicor is used to treat high blood pressure and to reduce or prevent chest pain (angina). It is also used to treat some heart disorders such as irregular heart beat and to relieve the symptoms of anxiety. Launch Date 1983

AUC

Value	Dose	Co-administered	Analyte	Population
60.7 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7712670	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		(S)-(-)-OXPRENOLOL blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
73.1 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7712670	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		(R)-(+)-OXPRENOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
108.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7712670	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		(S)-(-)-OXPRENOLOL blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
111.6 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7712670	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		(R)-(+)-OXPRENOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
20 mg single, intravenous Highest studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10124	healthy, 21 - 29 years n = 6 Health Status: healthy Age Group: 21 - 29 years Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/10124	Sources: https://pubmed.ncbi.nlm.nih.gov/10124
480 mg 1 times / day multiple, oral Studied dose Dose: 480 mg, 1 times / day Route: oral Route: multiple Dose: 480 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (severe, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
160 mg 1 times / day multiple, oral (starting) Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	Disc. AE: Weakness, Headache... AEs leading to discontinuation/dose reduction: Weakness (6 patients) Headache (6 patients) Malaise (6 patients) Fatigue (6 patients) Bad dreams (6 patients) Fluid retention (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
160 mg 2 times / day multiple, oral Dose: 160 mg, 2 times / day Route: oral Route: multiple Dose: 160 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	Disc. AE: Weakness, Headache... AEs leading to discontinuation/dose reduction: Weakness (2 patients) Headache (2 patients) Malaise (2 patients) Fatigue (2 patients) Bad dreams (2 patients) Fluid retention (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6820501	unhealthy n = 1 Health Status: unhealthy Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6820501	Sources: https://pubmed.ncbi.nlm.nih.gov/6820501

AEs

AE	Significance	Dose	Population
Headache	severe, 1 patient Disc. AE	480 mg 1 times / day multiple, oral Studied dose Dose: 480 mg, 1 times / day Route: oral Route: multiple Dose: 480 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Fluid retention	1 patient Disc. AE	160 mg 1 times / day multiple, oral (starting) Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Bad dreams	6 patients Disc. AE	160 mg 1 times / day multiple, oral (starting) Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Fatigue	6 patients Disc. AE	160 mg 1 times / day multiple, oral (starting) Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Headache	6 patients Disc. AE	160 mg 1 times / day multiple, oral (starting) Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Malaise	6 patients Disc. AE	160 mg 1 times / day multiple, oral (starting) Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Weakness	6 patients Disc. AE	160 mg 1 times / day multiple, oral (starting) Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Fluid retention	1 patient Disc. AE	160 mg 2 times / day multiple, oral Dose: 160 mg, 2 times / day Route: oral Route: multiple Dose: 160 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Bad dreams	2 patients Disc. AE	160 mg 2 times / day multiple, oral Dose: 160 mg, 2 times / day Route: oral Route: multiple Dose: 160 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Fatigue	2 patients Disc. AE	160 mg 2 times / day multiple, oral Dose: 160 mg, 2 times / day Route: oral Route: multiple Dose: 160 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Headache	2 patients Disc. AE	160 mg 2 times / day multiple, oral Dose: 160 mg, 2 times / day Route: oral Route: multiple Dose: 160 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Malaise	2 patients Disc. AE	160 mg 2 times / day multiple, oral Dose: 160 mg, 2 times / day Route: oral Route: multiple Dose: 160 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Weakness	2 patients Disc. AE	160 mg 2 times / day multiple, oral Dose: 160 mg, 2 times / day Route: oral Route: multiple Dose: 160 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6352119	unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: https://pubmed.ncbi.nlm.nih.gov/6352119

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY565286	https://www.001chemical.com/chem/6452-71-7
1PlusChem LLC	1P00E94W
ABI Chem	AC1L1ILM
AK Scientific	7348AE
AbMole Bioscience	M7583	http://www.abmole.com/products/oxprenolol.html
Alfa Chemistry	ACM6452739
Ambinter	Amb17619037	http://www.ambinter.com/reference/17619037
Angene	AGN-PC-0TCWD7
Aronis	BBC/665
AstaTech	C16157
BLD Pharm	BD8165
BOC Sciences	6452-71-7
BOC Sciences	6452-73-9
BOC Sciences	97399-56-9
BlocksMatrix Scientific	47901
Chem Scene	CS-0013185
ChemMol	99051084	http://www.chemmol.com/chemmol/99051084.html
ChemMol	99137585	http://www.chemmol.com/chemmol/99137585.html
ChemTik	CTK5J5288
Compound Cloud	4631
Compound Cloud	71172
Glentham Life Sciences	GP4555	http://www.glentham.com/products/product/GP4555/
Hairui	HR140534
HongKong Chemhere	SCD02223
KeyOrganics	KS-1152
MedChem Express	HY-B1486
MolPort	MolPort-001-770-529
Molcore	MC565286	https://www.molcore.com/product/6452-71-7
MuseChem	I008525
MuseChem	R010732
Norris Pharm	NSZB-A026223
NovoSeek	4631
Princeton BioMolecular Research	PBMR221643
Smolecule	S538406	http://www.smolecule.com/products/s538406
THE BioTek	bt-278059	https://www.thebiotek.com/product/inhibitors/bt-278059
Tetrahedron	TS30187
Tetrahedron	TS74732
TimTec	SBB058171
TimTec	ST51015083
Toronto Research Chemicals	O870500
Wonderchem	WD06IK1
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0462A
ZINC	ZINC000001542924	http://zinc15.docking.org/substances/ZINC000001542924
ZINC	ZINC000001999544	http://zinc15.docking.org/substances/ZINC000001999544
eMolecules	109716541
eMolecules	1988305
eMolecules	3715166
mcule	MCULE-3209868387	https://mcule.com/MCULE-3209868387/

PubMed

Title	Date	PubMed
Use of oxprenolol in cardiac arrhythmias associated with acute myocardial ischaemia.	1971 Jan 30	5100496
Idioventricular tachycardia elicited by the combined administration of trasicor and lidocain.	1972	4115168
Prevention of isoproterenol-induced cardiac hypertrophy by beta-blocking agents in the rat.	1976	146398
Effect of beta-blockade during bowling competitions.	1976 Dec	12713
Inappropriate antihypertensive therapy in the elderly.	1976 Dec 18	63799
[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	11153
Severe hypertension produced by interaction of phenylpropanolamine with methyldopa and oxprenolol.	1976 Jul 31	953565
Raynaud's phenomenon as side effect of beta-blockers in hypertension.	1976 Jun 19	6109
[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	918610
Therapy of extrapyramidal side effects, with particular reference to persistent dyskinesia and lithium tremor.	1978	32149
Antiarrhythmic effect of oxprenolol on halothane-epinephrine and coronary ligation induced ventricular arrhythmias in beagle dogs.	1978 Aug	32416
Two patients with schizophrenic-like psychosis after treatment with beta-adrenergic blockers.	1979 Mar 24	35266
Comparison of the activity and plasma levels of oxprenolol, slow release oxprenolol, long acting propranolol and sotalol.	1980 Jun	7398733
Effect of prazosin and oxprenolol on plasma renin activity and blood pressure in patients with essential hypertension.	1981	7023672
Mediation of renin release in essential hypertension by alpha-adrenoreceptors.	1981 Nov-Dec	6173514
Interaction between oxprenolol and indomethacin on blood pressure in essential hypertensive patients.	1982	7049707
Beta-adrenoreceptor antagonists and diplopia.	1982 Oct 9	6126700
Some functional changes in experimentally induced cardiac overload.	1983	6230880
Oxprenolol hydrochloride: pharmacology, pharmacokinetics, adverse effects and clinical efficacy.	1983 Mar-Apr	6344036
Clinical responses to oxprenolol in the elderly.	1983 Nov 10	6356866
Increased plasma vasopressin and serum uric acid in the low renin type of essential hypertension.	1984	6367368
Effect of oxprenolol on ventricular arrhythmias: the European Infarction Study experience.	1985 Nov	2413097
Interference by sulphinpyrazone with the antihypertensive effects of oxprenolol.	1986	3519237
Haemodynamic, metabolic, and lymphocyte beta 2-adrenoceptor changes following chronic beta-adrenoceptor antagonism.	1987	2885202
Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs.	1987 Dec	2897304
A nonsteady-state agonist antagonist interaction model using plasma potassium concentrations to quantify the beta-2 selectivity of beta blockers.	1989 Apr	2565392
Cardioprotection by beta-blockers: molecular and structural aspects in experimental hypertension.	1990	1974839
Oxprenolol-loaded bioadhesive microspheres: preparation and in vitro/in vivo characterization.	2003 Nov-Dec	14594666
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.	2004 May	15060759
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.	2007 Oct 16	17925438

Patents

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 HYDROCHLORIDE

Official Name

English

Oxprenolol hydrochloride [WHO-DD]

Common Name

English

1-(O-Allyloxyphenoxy)-3-isopropylamino-2-propanol hydrochloride

Common Name

English

TRASICOR

Brand Name

English

OXPRENOLOL HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

OXPRENOLOL HYDROCHLORIDE [JAN]

Common Name

English

OXPRENOLOL HYDROCHLORIDE [MI]

Common Name

English

BA-39,089

Code

English

2-PROPANOL, 1-(O-ALLYLOXYPHENOXY)-3-ISOPROPYLAMINO-, HYDROCHLORIDE

Common Name

English

OXPRENOLOL HYDROCHLORIDE [USP-RS]

Common Name

English

OXPRENOLOL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

BA-39089

Code

English

OXPRENOLOL HYDROCHLORIDE [USP IMPURITY]

Common Name

English

OXPRENOLOL HYDROCHLORIDE [USAN]

Common Name

English

OXPRENOLOL HCL

Common Name

English

OXPRENOLOL HYDROCHLORIDE [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29576