Oxprenolol

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Oxprenolol
Oxprenolol.svg
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy
category
  • AU:C
Routes of
administration
By mouth
ATC code
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
  • (RS)-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.026.598 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H23NO3
Molar mass 265.353 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • O(c1ccccc1OC\C=C)CC(O)CNC(C)C
  • 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 Yes check.svgY
  • Key:CEMAWMOMDPGJMB-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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.

Contents

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. [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]

Pharmacology

Pharmacodynamics

Oxprenolol is a beta blocker. In addition, it has been found to act as an antagonist of the serotonin 5-HT1A and 5-HT1B receptors with respective Ki values of 94.2 nM and 642 nM in rat brain tissue. [3]

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. [4]

(R)-(+)-Oxprenolol (top) and (S)-(-)-oxprenolol (+-)-Oxoprenolol Structural Formulae V.2.svg
(R)-(+)-Oxprenolol (top) and (S)-(–)-oxprenolol

Related Research Articles

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References

  1. McDevitt DG (December 1987). "Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs". European Heart Journal. 8. 8 Suppl M: 9–14. doi:10.1093/eurheartj/8.suppl_M.9. PMID   2897304.
  2. Williams IP, Millard FJ (February 1980). "Severe asthma after inadvertent ingestion of oxprenolol". Thorax. 35 (2): 160. doi:10.1136/thx.35.2.160. PMC   471246 . PMID   7376124.
  3. Langlois M, Brémont B, Rousselle D, Gaudy F (January 1993). "Structural analysis by the comparative molecular field analysis method of the affinity of beta-adrenoreceptor blocking agents for 5-HT1A and 5-HT1B receptors". European Journal of Pharmacology. 244 (1): 77–87. doi:10.1016/0922-4106(93)90061-d. PMID   8093601.
  4. Abounassif MA, Hefnawy MM, Mostafa GA (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): 365–371. doi:10.1007/s00706-011-0605-4. S2CID   95959906.