Oxprenolol

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Oxprenolol
Oxprenolol.svg
Clinical data
Trade names Trasicor, others
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 1–2 hours
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
   (verify)

Oxprenolol, sold under the brand name Trasicor among others, 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

Medical uses

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

It has been used to treat anxiety as well. [1] [2]

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. [3]

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. [4]

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. [5] The brain-to-blood ratio of oxprenolol in humans has been found to be 50:1. [6] 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. [6]

Chemistry

The experimental log P of oxprenolol is 2.10. [7] [8]

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. [9]

(R)-(+)-Oxprenolol (top) and (S)-(-)-oxprenolol (+-)-Oxoprenolol Structural Formulae V.2.svg
(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. ↑ Boyce TG, Ballone NT, Certa KM, Becker MA (2021). "The Use of β-Adrenergic Receptor Antagonists in Psychiatry: A Review". J Acad Consult Liaison Psychiatry. 62 (4): 404–412. doi:10.1016/j.jaclp.2020.12.009. PMID   34210401.
  2. ↑ Archer C, Wiles N, Kessler D, Turner K, Caldwell DM (January 2025). "Beta-blockers for the treatment of anxiety disorders: A systematic review and meta-analysis". J Affect Disord. 368: 90–99. doi: 10.1016/j.jad.2024.09.068 . PMID   39271062.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. 1 2 Drayer DE (1987). "Lipophilicity, hydrophilicity, and the central nervous system side effects of beta blockers". Pharmacotherapy. 7 (4): 87–91. doi:10.1002/j.1875-9114.1987.tb04029.x. PMID   2891122.
  7. ↑ https://pubchem.ncbi.nlm.nih.gov/compound/4631
  8. ↑ https://go.drugbank.com/drugs/DB01580
  9. ↑ 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.
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