Oxprenolol

Oxprenolol

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	AU: C
Routes of administration	By mouth
ATC code	C07AA02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	20-70%
Metabolism	Liver
Elimination half-life	1-2hours
Excretion	Kidney Lactic (in lactiferous females)
Identifiers
IUPAC name (RS)-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol
CAS Number	6452-71-7 Y
PubChem CID	4631
IUPHAR/BPS	7255
DrugBank	DB01580 N
ChemSpider	4470 Y
UNII	519MXN9YZR
KEGG	D08318 Y
ChEMBL	ChEMBL546 Y
CompTox Dashboard (EPA)	DTXSID1043835
ECHA InfoCard	100.026.598
Chemical and physical data
Formula	C15H23NO3
Molar mass	265.353 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES O(c1ccccc1OC\C=C)CC(O)CNC(C)C
InChI 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 Y Key:CEMAWMOMDPGJMB-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Oxprenolol (brand names Trasacor, Trasicor, Coretal, Laracor, Slow-Pren, Captol, Corbeton, Slow-Trasicor, Tevacor, Trasitensin, Trasidex) is a non-selective beta blocker with some intrinsic sympathomimetic activity. It is used for the treatment of angina pectoris, abnormal heart rhythms and high blood pressure.

Oxprenolol is a lipophilic beta blocker which passes the blood–brain barrier more easily than water-soluble beta blockers. As such, it is associated with a higher incidence of CNS-related side effects than beta blockers with more hydrophilic molecules such as atenolol, sotalol and nadolol.

Oxprenolol is a potent beta blocker and should not be administered to asthmatics under any circumstances due to their low beta levels as a result of depletion due to other asthma medication, and because it can cause irreversible, often fatal, airway failure and inflammation.

Pharmacology

Pharmacodynamics

Oxprenolol is a beta blocker. In addition, it has been found to act as an antagonist of the serotonin 5-HT_1A and 5-HT_1B receptors with respective K_i values of 94.2 nM and 642 nM in rat brain tissue.

Chemistry

Stereochemistry

Oxprenolol is a chiral compound, the beta blocker is used as a racemate, e. g. a 1:1 mixture of (R)-(+)-oxprenolol and (S)-(–)-oxprenolol. Analytical methods (HPLC) for the separation and quantification of (R)-(+)-oxprenolol and (S)-(–)-oxprenolol in urine and in pharmaceutical formulations have been described in the literature.

(R)-(+)-Oxprenolol (top) and (S)-(–)-oxprenolol