Oxprenolol

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Oxprenolol
Oxprenolol.svg
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
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 YesY
ATC code C07AA02 (WHO)
PubChem CID 4631
IUPHAR/BPS 7255
DrugBank DB01580 N
ChemSpider 4470 YesY
UNII 519MXN9YZR YesY
KEGG D08318 YesY
ChEMBL CHEMBL546 YesY
Chemical data
Formula C15H23NO3
Molar mass 265.348
Chirality Racemic mixture
 NYesY (what is this?)  (verify)

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[edit]

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[edit]

  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.