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Pharmaceutisch Weekblad

, Volume 6, Issue 4, pp 150–156 | Cite as

Effects of methoxy groups in the N1-substituent of sulfonamides on the pathways of elimination in man

The acetylation-deacetylation equilibrium and mechanisms of renal excretion of sulfisomidine, sulfamethomidine and sulfadimethoxine
  • T. B. Vree
  • Y. A. Hekster
  • M. W. Tijhuis
  • M. Baakman
  • M. J. M. Oosterbaan
  • E. F. S. Termond
Original Articles

Abstract

Sulfisomidine, sulfamethomidine, sulfadimethoxine and their corresponding N4-acetyl derivatives were administered to man. The percentages of acetylation and deacetylation and those of protein binding, the half-lives of elimination and the apparent and true renal clearance values were measured. No acetylation phenotype could be demonstrated in these compounds. Methoxy substitution in the N1-pyrimidine group of sulfisomidine affects predominantly the renal clearance value and mechanism of the parent compound but has no influence on the renal clearance of the N4-acetyl derivatives.

The renal clearance value of sulfisomidine is 232±33 ml/min, of sulfamethomidine 21.60±16.4 ml/min and of sulfadimethoxine 10.87±10.44 ml/min. The renal clearance values of the corresponding N4-acetylsulfonamide derivatives are 314±91 ml/min, 342±63 ml/min and 202±65 ml/min respectively.

Tubular reabsorption, caused by methoxy substitution in the N1-pyrimidine ring, lowers the rate of elimination and increases the half-life. The half-life of sulfisomidine is 8.5±0.5 h, of sulfamethomidine 27.8±5.3 h and of sulfadimethoxine 34.6±10.4 h.

Keywords

Public Health Sulfonamide Internal Medicine Methoxy Parent Compound 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Royal Dutch Association for Advancement of Pharmacy 1984

Authors and Affiliations

  • T. B. Vree
    • 1
  • Y. A. Hekster
    • 1
  • M. W. Tijhuis
    • 1
  • M. Baakman
    • 1
  • M. J. M. Oosterbaan
    • 1
  • E. F. S. Termond
    • 1
  1. 1.Department of Clinical Pharmacy, Sint Radboud HospitalUniversity of NijmegenGA NijmegenThe Netherlands

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