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Oxprenolol

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Oxprenolol
200px
Systematic (IUPAC) name
(RS)-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
  • AU: C
  • (Prescription only)
oral
Pharmacokinetic data
Bioavailability 20-70%
Metabolism Hepatic
Half-life 1-2hours
Excretion Renal
Lactic (In lactiferous females)
Identifiers
6452-71-7 7pxY
C07AA02
PubChem CID 4631
DrugBank DB01580 7pxN
ChemSpider 4470 7pxY
UNII 519MXN9YZR 7pxY
KEGG D08318 7pxY
ChEMBL CHEMBL546 7pxY
Chemical data
Formula C15H23NO3
265.348
 14pxN (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

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]

File:(±)-Oxoprenolol Structural Formulae V.2.svg
(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. PMID 2897304. doi:10.1093/eurheartj/8.suppl_M.9. 
  2. ^ I P Williams and F J Millard (1980). "Severe asthma after inadvertent ingestion of oxprenolol". Thorax 35 (2): 160. PMC 471246. PMID 7376124. doi:10.1136/thx.35.2.160. 
  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.