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Research ArticleArticle

DETECTION OF CARBOXYLIC ACIDS AND INHIBITION OF HIPPURIC ACID FORMATION IN RATS TREATED WITH 3-BUTENE-1,2-DIOL, A MAJOR METABOLITE OF 1,3-BUTADIENE

Christopher L. Sprague and Adnan A. Elfarra
Drug Metabolism and Disposition August 2003, 31 (8) 986-992; DOI: https://doi.org/10.1124/dmd.31.8.986
Christopher L. Sprague
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Adnan A. Elfarra
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  • CORRECTION TO “DETECTION OF CARBOXYLIC ACIDS AND INHIBITION OF HIPPURIC ACID FORMATION IN RATS TREATED WITH 3-BUTENE-1,2-DIOL, A MAJOR METABOLITE OF 1,3-BUTADIENE” - September 01, 2003

Abstract

Epidemiological studies have indicated that 1,3-butadiene exposure is associated with an increased risk of leukemia. In human liver microsomes, 1,3-butadiene is rapidly oxidized to butadiene monoxide, which can then be hydrolyzed to 3-butene-1,2-diol (BDD). In this study, BDD and several potential metabolites were characterized in the urine of male B6C3F1 mice and Sprague-Dawley rats after BDD administration (i.p.). Rats given 1420 μmol kg-1 BDD excreted significantly greater amounts of BDD relative to rats administered 710 μmol kg-1 BDD. Rats administered 1420 or 2840 μmol kg-1 BDD excreted significantly greater amounts of BDD per kilogram of body weight than mice given an equivalent dose. Trace amounts of 1-hydroxy-2-butanone and the carboxylic acid metabolites, crotonic acid, propionic acid, and 2-ketobutyric acid, were detected in mouse and rat urine after BDD administration. Because of the identification of the carboxylic acid metabolites and because of the known ability of carboxylic acids to conjugate coenzyme A, which is critical for hippuric acid formation, the effect of BDD treatment on hippuric acid concentrations was investigated. Rats given 1420 or 2272 μmol kg-1 BDD had significantly elevated ratios of benzoic acid to hippuric acid in the urine after treatment compared with control urine. However, this effect was not observed in mice administered 1420 or 2840 μmol kg-1 BDD. Collectively, the results demonstrate species differences in the urinary excretion of BDD and show that BDD administration in rats inhibits hippuric acid formation. The detection of 1-hydroxy-2-butanone and the carboxylic acids also provides insight regarding pathways of BDD metabolism in vivo.

Footnotes

  • ↵1 Abbreviations used are: BD, 1,3-butadiene; BMO, butadiene monoxide; BDD, 3-butene-1,2-diol; HBO, 1-hydroxy-2-butanone; ADH, alcohol dehydrogenase; GC/MS, gas chromatography/mass spectrometry; HPLC, high-performance liquid chromatography; BSTFA, N,O-bis(trimethylsilyl)trifluoroacetamide; TMCS, trimethylchlorosilane; HMVK, hydroxymethylvinylketone.

  • This research was supported by National Institutes of Health Grant ES06841. C.L.S. was supported by a chemistry-biology interface training grant from the National Institutes of Health (GM08505-08).

    • Received January 27, 2003.
    • Accepted April 25, 2003.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 31 (8)
Drug Metabolism and Disposition
Vol. 31, Issue 8
1 Aug 2003
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DETECTION OF CARBOXYLIC ACIDS AND INHIBITION OF HIPPURIC ACID FORMATION IN RATS TREATED WITH 3-BUTENE-1,2-DIOL, A MAJOR METABOLITE OF 1,3-BUTADIENE
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Research ArticleArticle

DETECTION OF CARBOXYLIC ACIDS AND INHIBITION OF HIPPURIC ACID FORMATION IN RATS TREATED WITH 3-BUTENE-1,2-DIOL, A MAJOR METABOLITE OF 1,3-BUTADIENE

Christopher L. Sprague and Adnan A. Elfarra
Drug Metabolism and Disposition August 1, 2003, 31 (8) 986-992; DOI: https://doi.org/10.1124/dmd.31.8.986

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Research ArticleArticle

DETECTION OF CARBOXYLIC ACIDS AND INHIBITION OF HIPPURIC ACID FORMATION IN RATS TREATED WITH 3-BUTENE-1,2-DIOL, A MAJOR METABOLITE OF 1,3-BUTADIENE

Christopher L. Sprague and Adnan A. Elfarra
Drug Metabolism and Disposition August 1, 2003, 31 (8) 986-992; DOI: https://doi.org/10.1124/dmd.31.8.986
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