Oxprenolol

Oxprenolol

Systematic (IUPAC) name
(RS)-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	AU: C
Routes of administration	oral
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	20-70%
Metabolism	Hepatic
Biological half-life	1-2hours
Excretion	Renal Lactic (In lactiferous females)
Identifiers
CAS Number	6452-71-7
ATC code	C07AA02 (WHO)
PubChem	CID 4631
IUPHAR/BPS	7255
DrugBank	DB01580
ChemSpider	4470
UNII	519MXN9YZR
KEGG	D08318
ChEMBL	CHEMBL546
Chemical data
Formula	C15H23NO3
Molar mass	265.348
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 Key:CEMAWMOMDPGJMB-UHFFFAOYSA-N
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Oxprenolol (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 hydrophilic ligands such as atenolol, sotalol and nadolol.^[1]

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.^[2]

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.^[3]

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

References

1. McDevitt DG (1987). "Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs". Eur. Heart J. 8. Suppl M: 9–14. doi:10.1093/eurheartj/8.suppl_M.9. PMID 2897304.
2. I P Williams and F J Millard (1980). "Severe asthma after inadvertent ingestion of oxprenolol". Thorax 35 (2): 160. doi:10.1136/thx.35.2.160. PMC 471246. PMID 7376124.
3. Abounassif, Mohammed A.; Hefnawy, Mohammed M.; Mostafa, Gamal A. E. (2011). "Separation and quantitation of oxprenolol in urine and pharmaceutical formulations by HPLC using a Chiralpak IC and UV detection". Monatshefte für Chemie - Chemical Monthly 143 (3): 365. doi:10.1007/s00706-011-0605-4.