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Oxprenolol

From Wikipedia, the free encyclopedia
Non-selective beta blocker
Pharmaceutical compound
Oxprenolol
Clinical data
Trade namesTrasicor, others
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability20–70%
MetabolismLiver
Eliminationhalf-life1–2 hours
ExcretionKidney
Lactic (in lactiferous females)
Identifiers
  • (RS)-1-[2-(allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.026.598Edit this at Wikidata
Chemical and physical data
FormulaC15H23NO3
Molar mass265.353 g·mol−1
3D model (JSmol)
ChiralityRacemic 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 checkY
  • Key:CEMAWMOMDPGJMB-UHFFFAOYSA-N checkY
  (verify)

Oxprenolol, sold under the brand nameTrasicor among others, is anon-selectivebeta blocker with some intrinsicsympathomimetic activity. It is used for the treatment ofangina pectoris, abnormalheart rhythms, andhigh blood pressure.

Medical uses

[edit]

Oxprenolol is used in the treatment ofangina pectoris, abnormalheart rhythms, andhigh blood pressure.

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

Contraindications

[edit]

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

[edit]

Pharmacodynamics

[edit]

Oxprenolol is abeta blocker. In addition, it has been found to act as anantagonist of theserotonin5-HT1A and5-HT1B receptors with respective Ki values of 94.2 nM and 642 nM in rat brain tissue.[4]

Pharmacokinetics

[edit]

Oxprenolol is alipophilic beta blocker which passes theblood–brain barrier more easily thanhydrophilic beta blockers. As such, it is associated with a higher incidence ofCNS-related side effects than beta blockers with more hydrophilic molecules such asatenolol,sotalol, andnadolol.[5] Thebrain-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 lipophilicpropranolol was 15:1 to 26:1 and of the hydrophilic atenolol was 0.2:1.[6]

Chemistry

[edit]

The experimentallog P of oxprenolol is 2.10.[7][8]

Stereochemistry

[edit]

Oxprenolol is a chiral compound, the beta blocker is used as aracemate, 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

Society and culture

[edit]

Brand names

[edit]

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

References

[edit]
  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. ^abDrayer 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.
β, non-selective
β1-selective
β2-selective
α1- + β-selective
5-HT1ARTooltip 5-HT1A receptoragonists
GABAARTooltip GABAA receptorPAMsTooltip positive allosteric modulators
Gabapentinoids
(α2δVDCCblockers)
Antidepressants
Sympatholytics
(Antiadrenergics)
Others
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
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