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Relationship between pKa and Uricosuric Activity in Phenylbutazone Analogues

Nature volume 182, pages 1162–1163 (1958)Cite this article

Abstract

DRUGS which increase the urinary excretion of uric acid are of considerable value in the treatment of gout. Although it is fairly well established that these agents act by interfering with the reabsorption of uric acid by the renal tubular cells, the structural features required for this activity have not been defined. In the course of studies with one such drug, phenyl-butazone, a relationship between chemical structure and uricosuric activity was noted. It was found that modifications in phenylbutazone, resulting in increased acidity of the molecule, are associated with enhanced uricosuric activity. However, changes which decrease the acidity of the drug are accompanied by loss of this activity.

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References

  1. Flexser, L. A., Hammett, L. P., and Dingwall, A., J. Amer. Chem. Soc., 57, 2106 (1935).

    Article  Google Scholar 

  2. Burns, J. J., Yü, T. F., Ritterband, A., Perel, J. M., Gutman, A. B., and Brodie, B. B., J. Pharm. Exp. Therap., 119, 418 (1957).

    CAS  Google Scholar 

  3. Yü, T. F., Burns, J. J., Paton, B. C., Gutman, A. B., and Brodie, B. B., J. Pharm. Exp. Therap., 123, 63 (1958).

    Google Scholar 

  4. Burns, J. J., Rose, R. K., Goodwin, S., Reichenthal, J., Horning, E. C., and Brodie, B. B., J. Pharm. Exp. Therap., 113, 481 (1955).

    CAS  Google Scholar 

  5. Gutman, A. B., and Yü, T. F., Lancet, ii, 1258 (1957).

  6. Ogryzlo, M. A., and Harrison, J., Ann. Rheumatic Dis., 16, 425 (1957).

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. The Laboratory of Chemical Pharmacology, National Heart Institute, Bethesda, Maryland

    J. J. BURNS, T. F. YÜ, PETER DAYTON, LAWRENCE BERGER, ALEXANDER B. GUTMAN & BERNARD B. BRODIE

  2. The Departments of Medicine, The Mount Sinai Hospital,

    J. J. BURNS, T. F. YÜ, PETER DAYTON, LAWRENCE BERGER, ALEXANDER B. GUTMAN & BERNARD B. BRODIE

  3. Columbia University College of Physicians and Surgeons, New York

    J. J. BURNS, T. F. YÜ, PETER DAYTON, LAWRENCE BERGER, ALEXANDER B. GUTMAN & BERNARD B. BRODIE

  4. The Research Service, Third (New York University) Medical Division, Goldwater Memorial Hospital, New York

    J. J. BURNS, T. F. YÜ, PETER DAYTON, LAWRENCE BERGER, ALEXANDER B. GUTMAN & BERNARD B. BRODIE

Authors
  1. J. J. BURNS
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  2. T. F. YÜ
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  3. PETER DAYTON
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  4. LAWRENCE BERGER
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  5. ALEXANDER B. GUTMAN
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  6. BERNARD B. BRODIE
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BURNS, J., YÜ, T., DAYTON, P. et al. Relationship between pKa and Uricosuric Activity in Phenylbutazone Analogues. Nature 182, 1162–1163 (1958). https://doi.org/10.1038/1821162a0

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