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Research ArticleArticle

Isolation, Purification, and Structural Characterization of Flunixin Glucuronide in the Urine of Greyhound Dogs

Thomas C. Brady, Albert J. Kind, Walter H. Hyde, Mark Favrow and Dennis W. Hill
Drug Metabolism and Disposition April 1998, 26 (4) 294-298;
Thomas C. Brady
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Albert J. Kind
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Walter H. Hyde
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Mark Favrow
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Dennis W. Hill
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Abstract

A urinary metabolite of flunixin in greyhound dogs was isolated and purified by a gradient-elution solid-phase extraction technique. The purified metabolite was shown to be hydrolyzed to free flunixin by strong base and by β-glucuronidase, suggesting the presence of a C1-β-glucuronide ester of flunixin. The metabolite was further characterized by positive-ion, tandem MS with electrospray ionization. Mass spectral data showed the presence of a protonated molecular ion (M+1) at m/z 473, which was consistent with the molecular weight of protonated flunixin glucuronide, and a product ion atm/z 297, which was consistent with the molecular weight of protonated flunixin. Collisionally induced dissociation of them/z 297 product ion showed a fragmentation pattern consistent with that of standard flunixin. These data support the contention that this metabolite of flunixin in greyhound urine is the C1-β-glucuronide of flunixin. Acyl glucuronide metabolites of some organic acid drugs have been shown to bind covalently to tissue proteins in vitro, in vivo, and ex vivo. The presence of this metabolite may, therefore, have pharmacokinetic and pharmacodynamic implications for flunixin in greyhound dogs, as well as in other animal species in which the acyl glucuronide of flunixin is a metabolite.

Footnotes

  • Send reprint requests to: Dr. Dennis W. Hill, Microchemistry Laboratory, U-193, University of Connecticut, 3113 Horsebarn Road, Storrs, CT 06269-4193.

  • ↵1 Laboratory of origin for this work.

  • Abbreviations used are::
    TEA
    triethylamine
    DAD
    diode-array detection
    CID
    collision-induced dissociation
    DFU
    drug-free urine
    SPE
    solid-phase extraction
    ELISA
    enzyme-linked immunosorbent assay
    • Received April 9, 1997.
    • Accepted December 16, 1997.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition
Vol. 26, Issue 4
1 Apr 1998
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Research ArticleArticle

Isolation, Purification, and Structural Characterization of Flunixin Glucuronide in the Urine of Greyhound Dogs

Thomas C. Brady, Albert J. Kind, Walter H. Hyde, Mark Favrow and Dennis W. Hill
Drug Metabolism and Disposition April 1, 1998, 26 (4) 294-298;

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Research ArticleArticle

Isolation, Purification, and Structural Characterization of Flunixin Glucuronide in the Urine of Greyhound Dogs

Thomas C. Brady, Albert J. Kind, Walter H. Hyde, Mark Favrow and Dennis W. Hill
Drug Metabolism and Disposition April 1, 1998, 26 (4) 294-298;
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