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 cat.
Legal status
  • Prescription only
Routes oral
Pharmacokinetic data
Bioavailability 20-70%
Metabolism Hepatic
Half-life 1-2hours
Excretion Renal
Lactic (In lactiferous females)
Identifiers
CAS number 6452-71-7 YesY
ATC code C07AA02
PubChem CID 4631
DrugBank DB01580
ChemSpider 4470 YesY
UNII 519MXN9YZR YesY
KEGG D08318 YesY
ChEMBL CHEMBL546 YesY
Chemical data
Formula C15H23NO3 
Mol. mass 265.348
 N (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.