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
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
Molecular Formula | C15H23NO3 |
Molecular Weight | 265.348 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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
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.
Originator
Sources: Drug Discovery: A History. W. Sneader. John Wiley & Sons, 2005 pp 468
Curator's Comment: https://books.google.ru/books?id=Cb6BOkj9fK4C&pg=PA193&lpg=PA193&dq=Oxprenolol+first+discovered&source=bl&ots=NOemB0BehV&sig=ozflVDgEzprG_g-hgUfTYdJeoPw&hl=ru&sa=X&ved=0ahUKEwiv1pLbl6jQAhUHiCwKHTGTDusQ6AEIIzAB#v=onepage&q=Oxprenolol&f=false
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094118 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D08318 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TRASICOR Approved UseTrasicor 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 Date4.41331188E11 |
|||
Primary | TRASICOR Approved UseTrasicor 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 Date4.41331188E11 |
|||
Primary | TRASICOR Approved UseTrasicor 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 Date4.41331188E11 |
|||
Primary | TRASICOR Approved UseTrasicor 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 Date4.41331188E11 |
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 |
T1/2
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 |
healthy, 21 - 29 years n = 6 Health Status: healthy Age Group: 21 - 29 years Sex: M+F Population Size: 6 Sources: |
|
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (severe, 1 patient) Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
Disc. AE: Weakness, Headache... AEs leading to discontinuation/dose reduction: Weakness (6 patients) Sources: Headache (6 patients) Malaise (6 patients) Fatigue (6 patients) Bad dreams (6 patients) Fluid retention (1 patient) |
160 mg 2 times / day multiple, oral Dose: 160 mg, 2 times / day Route: oral Route: multiple Dose: 160 mg, 2 times / day Sources: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
Disc. AE: Weakness, Headache... AEs leading to discontinuation/dose reduction: Weakness (2 patients) Sources: Headache (2 patients) Malaise (2 patients) Fatigue (2 patients) Bad dreams (2 patients) Fluid retention (1 patient) |
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: |
unhealthy n = 1 |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
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: |
unhealthy, 22 - 70 years n = 58 Health Status: unhealthy Condition: Hypertensive patients Age Group: 22 - 70 years Sex: M+F Population Size: 58 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Prevention of isoproterenol-induced cardiac hypertrophy by beta-blocking agents in the rat. | 1976 |
|
Inappropriate antihypertensive therapy in the elderly. | 1976 Dec 18 |
|
Raynaud's phenomenon as side effect of beta-blockers in hypertension. | 1976 Jun 19 |
|
Therapy of extrapyramidal side effects, with particular reference to persistent dyskinesia and lithium tremor. | 1978 |
|
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 |
|
Some functional changes in experimentally induced cardiac overload. | 1983 |
|
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 |
|
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 |
|
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 |
|
Oxprenolol-loaded bioadhesive microspheres: preparation and in vitro/in vivo characterization. | 2003 Nov-Dec |
|
Cutaneous vasculitis induced by carvedilol. | 2007 Aug |
|
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. | 2007 Oct 16 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6152393
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
Edited
Fri Dec 15 16:16:57 UTC 2023
by
admin
on
Fri Dec 15 16:16:57 UTC 2023
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Record UNII |
F4XSI7SNIU
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Record Status |
Validated (UNII)
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Record Version |
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C29576
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203131
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Trasicor
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SUB03578MIG
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ACTIVE MOIETY |