19F nuclear magnetic resonance analysis of trifluoroethanol metabolites in the urine of the Sprague-Dawley rat

Barry S. Selinsky, Daniel Rusyniak, Joseph O. Warsheski, A. P. Joseph

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

2,2,2-Trifluoroethanol (TFE) is a common industrial solvent and a known metabolite of the inhalation anesthetics fluroxene (2,2,2-trifluoroethyl vinyl ether) and halothane (2-bromo-2-chloro-1,1,1-trifluoroethane). The water-soluble metabolites of TFE were identified in the urine of Sprague-Dawley rats using 19F NMR spectroscopy. In rats dosed with 0.21 g TFE/kg body weight, approximately one-half of the administered TFE was excreted as the trifluoroethyl glucuronide. The remaining TFE was oxidized, primarily to trifluoroacetaldehyde hydrate, with a small percentage of the aldehyde oxidized further to trifluoroacetate. One additional fluorinated compound was found; after investigation, this was identified as a Schiff's base compound resulting from the addition of trifluoroacetaldehyde to urea. The time-dependent excretion of TFE metabolites was measured as a function of ethanol induction of hepatic enzymes. This study demonstrates the utility of 19F NMR for the analysis of drug metabolism in laboratory animals. In addition, the resistance of trifluoroacetaldehyde hydrate to further oxidation, coupled with its reactivity with common cellular amines, indicates the potential toxicity of this metabolite to mammalian tissues.

Original languageEnglish (US)
Pages (from-to)2229-2238
Number of pages10
JournalBiochemical Pharmacology
Volume42
Issue number11
DOIs
StatePublished - Nov 6 1991
Externally publishedYes

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Trifluoroethanol
Metabolites
Sprague Dawley Rats
Rats
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
Urine
Inhalation Anesthetics
Trifluoroacetic Acid
Enzyme Induction
Schiff Bases
Glucuronides
Laboratory Animals
Halothane
Metabolism
Aldehydes
Nuclear magnetic resonance spectroscopy
Amines
Toxicity
Urea

ASJC Scopus subject areas

  • Pharmacology

Cite this

19F nuclear magnetic resonance analysis of trifluoroethanol metabolites in the urine of the Sprague-Dawley rat. / Selinsky, Barry S.; Rusyniak, Daniel; Warsheski, Joseph O.; Joseph, A. P.

In: Biochemical Pharmacology, Vol. 42, No. 11, 06.11.1991, p. 2229-2238.

Research output: Contribution to journalArticle

Selinsky, Barry S. ; Rusyniak, Daniel ; Warsheski, Joseph O. ; Joseph, A. P. / 19F nuclear magnetic resonance analysis of trifluoroethanol metabolites in the urine of the Sprague-Dawley rat. In: Biochemical Pharmacology. 1991 ; Vol. 42, No. 11. pp. 2229-2238.
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