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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

Molecular Formula C15H23NO3
Molecular Weight 265.348
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRASICOR
Primary
TRASICOR
Primary
TRASICOR
Primary
TRASICOR

AUC

ValueDoseCo-administeredAnalytePopulation
60.7 μg × min/mL
80 mg single, oral
(S)-(-)-OXPRENOLOL blood
Homo sapiens
73.1 μg × min/mL
80 mg single, oral
(R)-(+)-OXPRENOLOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
108.4 min
80 mg single, oral
(S)-(-)-OXPRENOLOL blood
Homo sapiens
111.6 min
80 mg single, oral
(R)-(+)-OXPRENOLOL plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
519MXN9YZR
Record Status Validated (UNII)
Record Version