OXPRENOLOL SUCCINATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H27NO6
Molecular Weight	365.4208
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XJPXSBZDTNCWRT-UHFFFAOYSA-N

InChI=1S/C19H27NO6/c1-4-11-24-16-7-5-6-8-17(16)25-13-15(12-20-14(2)3)26-19(23)10-9-18(21)22/h4-8,14-15,20H,1,9-13H2,2-3H3,(H,21,22)

HIDE SMILES / InChI

Molecular Formula	C19H27NO6
Molecular Weight	365.4208
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 89 Target ID: CHEMBL2094118 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D08318	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Chest pain (angina) 3 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1501220376572.pdf	Primary	Approved 8583	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 575 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1501220376572.pdf	Primary	Approved 8583	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 3 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1501220376572.pdf	Primary	Approved 8583	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 275 Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1501220376572.pdf	Primary	Approved 8583	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 Health Status: healthy Age Group: 21 - 29 years Sex: M+F 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 Health Status: unhealthy 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Fluid retention	1 patient Disc. AE	160 mg 1 times / day multiple, oral 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Bad dreams	6 patients Disc. AE	160 mg 1 times / day multiple, oral 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Fatigue	6 patients Disc. AE	160 mg 1 times / day multiple, oral 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Headache	6 patients Disc. AE	160 mg 1 times / day multiple, oral 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Malaise	6 patients Disc. AE	160 mg 1 times / day multiple, oral 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6352119
Weakness	6 patients Disc. AE	160 mg 1 times / day multiple, oral 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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 Health Status: unhealthy Age Group: 22 - 70 years Sex: M+F 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
AbMole Bioscience	M7583	http://www.abmole.com/products/oxprenolol.html
AK Scientific	7348AE
Alfa Chemistry	ACM6452739
Ambinter	Amb17619037	http://www.ambinter.com/reference/17619037
Angene	AGN-PC-0TCWD7
Aronis	BBC/665
AstaTech	C16157
BLD Pharm	BD8165
BlocksMatrix Scientific	47901
BOC Sciences	6452-71-7
BOC Sciences	6452-73-9
BOC Sciences	97399-56-9
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
eMolecules	109716541
eMolecules	1988305
eMolecules	3715166
Glentham Life Sciences	GP4555	http://www.glentham.com/products/product/GP4555/
Hairui	HR140534
HongKong Chemhere	SCD02223
KeyOrganics	KS-1152
mcule	MCULE-3209868387	https://mcule.com/MCULE-3209868387/
MedChem Express	HY-B1486
Molcore	MC565286	https://www.molcore.com/product/6452-71-7
MolPort	MolPort-001-770-529
MuseChem	I008525
MuseChem	R010732
Norris Pharm	NSZB-A026223
NovoSeek	4631
Princeton BioMolecular Research	PBMR221643
Smolecule	S538406	http://www.smolecule.com/products/s538406
Tetrahedron	TS30187
Tetrahedron	TS74732
THE BioTek	bt-278059	https://www.thebiotek.com/product/inhibitors/bt-278059
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

PubMed

Title	Date	PubMed
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.	2007-10-16	17925438
Cutaneous vasculitis induced by carvedilol.	2007-08	17659030
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.	2004-05	15060759
Oxprenolol-loaded bioadhesive microspheres: preparation and in vitro/in vivo characterization.	2003-11-05	14594666
Beta-blockade in the primary prevention of coronary heart disease in hypertensive patients. Review of present evidence.	1991-12	1683615
Atypical beta-adrenergic receptor in 3T3-F442A adipocytes. Pharmacological and molecular relationship with the human beta 3-adrenergic receptor.	1991-10-25	1682311
Cardioprotection by beta-blockers: molecular and structural aspects in experimental hypertension.	1990	1974839
A nonsteady-state agonist antagonist interaction model using plasma potassium concentrations to quantify the beta-2 selectivity of beta blockers.	1989-04	2565392
Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs.	1987-12	2897304
Beta-2-adrenoceptor-mediated hypokalemia and its abolishment by oxprenolol.	1987-12	2826064
Haemodynamic, metabolic, and lymphocyte beta 2-adrenoceptor changes following chronic beta-adrenoceptor antagonism.	1987	2885202
Potentiation of haloperidol-induced catalepsy by beta-adrenoceptor antagonists in mice.	1986-09	2879054
Interference by sulphinpyrazone with the antihypertensive effects of oxprenolol.	1986	3519237
Predictors of blood pressure increases after withdrawal of antihypertensive therapy.	1985-12	2856766
Effect of oxprenolol on ventricular arrhythmias: the European Infarction Study experience.	1985-11	2413097
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.	1985-08	2864374
Increased plasma vasopressin and serum uric acid in the low renin type of essential hypertension.	1984	6367368
Clinical responses to oxprenolol in the elderly.	1983-11-10	6356866
Oxprenolol hydrochloride: pharmacology, pharmacokinetics, adverse effects and clinical efficacy.	1983-03-01	6344036
Some functional changes in experimentally induced cardiac overload.	1983	6230880
The acute and chronic effect of oxprenolol and propranolol on peripheral blood flow in hypertensive patients.	1982-11	7138753
Beta-adrenoreceptor antagonists and diplopia.	1982-10-09	6126700
Interaction between oxprenolol and indomethacin on blood pressure in essential hypertensive patients.	1982	7049707
Mediation of renin release in essential hypertension by alpha-adrenoreceptors.	1981-11-01	6173514
Slow release oxprenolol in angina pectoris: study comparing oxprenolol, once daily, with propranolol, four times daily.	1981-05	7223659
Effect of prazosin and oxprenolol on plasma renin activity and blood pressure in patients with essential hypertension.	1981	7023672
Comparison of the activity and plasma levels of oxprenolol, slow release oxprenolol, long acting propranolol and sotalol.	1980-06	7398733
Two patients with schizophrenic-like psychosis after treatment with beta-adrenergic blockers.	1979-03-24	35266
Antiarrhythmic effect of oxprenolol on halothane-epinephrine and coronary ligation induced ventricular arrhythmias in beagle dogs.	1978-08	32416
Therapy of extrapyramidal side effects, with particular reference to persistent dyskinesia and lithium tremor.	1978	32149
[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].	1977-11-05	918610
Inappropriate antihypertensive therapy in the elderly.	1976-12-18	63799
Effect of beta-blockade during bowling competitions.	1976-12	12713
Severe hypertension produced by interaction of phenylpropanolamine with methyldopa and oxprenolol.	1976-07-31	953565
[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)].	1976-07	11153
Raynaud's phenomenon as side effect of beta-blockers in hypertension.	1976-06-19	6109
Prevention of isoproterenol-induced cardiac hypertrophy by beta-blocking agents in the rat.	1976	146398
Idioventricular tachycardia elicited by the combined administration of trasicor and lidocain.	1972	4115168
Use of oxprenolol in cardiac arrhythmias associated with acute myocardial ischaemia.	1971-01-30	5100496

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 19:05:38 GMT 2025` Edited by `admin` on `Wed Apr 02 19:05:38 GMT 2025`
Record UNII	4KUK5H8PWH
Record Status	`Validated (UNII)`
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Name

Type

Language

OXPRENOLOL SUCCINATE

Common Name

English

4-[1-[(2-Allyloxyphenoxy)methyl]-2-(isopropylamino)ethoxy]-4-oxo-butanoic acid

Preferred Name

English

Code System Code Type Description

FDA UNII

4KUK5H8PWH

Created by admin on Wed Apr 02 19:05:38 GMT 2025 , Edited by admin on Wed Apr 02 19:05:38 GMT 2025

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					519MXN9YZR

OXPRENOLOL

METABOLITE ACTIVE -> PRODRUG

Amount:

Related Record Type Details


					519MXN9YZR

OXPRENOLOL

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: 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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

AUC

T1/2

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

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

T_1/2