Chemistry:Oxprenolol

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Oxprenolol, sold under the brand name Trasicor among others, is a non-selective beta blocker with some intrinsic sympathomimetic activity. It was used for the treatment of angina pectoris, abnormal heart rhythms, and high blood pressure.[1]

Medical uses

Oxprenolol has been used in the treatment of angina pectoris, abnormal heart rhythms, and high blood pressure.

It has been used to treat anxiety as well.[2][3]

Contraindications

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.[4]

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.[5]

Pharmacokinetics

Oxprenolol is a lipophilic beta blocker which passes the blood–brain barrier more easily than hydrophilic 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.[6] The brain-to-blood ratio of oxprenolol in humans has been found to be 50:1.[7] For comparison, the brain-to-blood ratio of the highly lipophilic propranolol was 15:1 to 26:1 and of the hydrophilic atenolol was 0.2:1.[7]

Chemistry

The experimental log P of oxprenolol is 2.10.[8][9]

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.[10]

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

Society and culture

Brand names

Brand names of oxprenolol include Trasacor, Trasicor, Coretal, Laracor, Slow-Pren, Captol, Corbeton, Slow-Trasicor, Tevacor, Trasitensin, and Trasidex.

References

  1. ↑ "Oxprenolol". https://drugs.ncats.io/drug/519MXN9YZR. 
  2. ↑ "The Use of β-Adrenergic Receptor Antagonists in Psychiatry: A Review". J Acad Consult Liaison Psychiatry 62 (4): 404–412. 2021. doi:10.1016/j.jaclp.2020.12.009. PMID 34210401. 
  3. ↑ "Beta-blockers for the treatment of anxiety disorders: A systematic review and meta-analysis". J Affect Disord 368: 90–99. January 2025. doi:10.1016/j.jad.2024.09.068. PMID 39271062. 
  4. ↑ "Severe asthma after inadvertent ingestion of oxprenolol". Thorax 35 (2): 160. February 1980. doi:10.1136/thx.35.2.160. PMID 7376124. 
  5. ↑ "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. January 1993. doi:10.1016/0922-4106(93)90061-d. PMID 8093601. 
  6. ↑ "Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs". European Heart Journal. 8 8 Suppl M: 9–14. December 1987. doi:10.1093/eurheartj/8.suppl_M.9. PMID 2897304. 
  7. ↑ 7.0 7.1 "Lipophilicity, hydrophilicity, and the central nervous system side effects of beta blockers". Pharmacotherapy 7 (4): 87–91. 1987. doi:10.1002/j.1875-9114.1987.tb04029.x. PMID 2891122. 
  8. ↑ "Oxprenolol". https://pubchem.ncbi.nlm.nih.gov/compound/4631. 
  9. ↑ "Oxprenolol". https://go.drugbank.com/drugs/DB01580. 
  10. ↑ "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. 2011. doi:10.1007/s00706-011-0605-4. 



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