Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 34, 2004 - Issue 3
91
Views
16
CrossRef citations to date
0
Altmetric
Research Article

Use of 19F-nuclear magnetic resonance and gas chromatography-electron capture detection in the quantitative analysis of fluorine-containing metabolites in urine of sevoflurane-anaesthetized patients

, , , , &
Pages 301-316 | Received 07 Jul 2003, Published online: 22 Sep 2008

Reference

  • ANSELME, J. P., 1963, A convenient synthesis of phenyldiazomethane. Journal of Organic Chemistry, 28, 592–593.
  • BAXTER, P. J., GARTON, K. and KHARASCH, E. D., 1998, Mechanistic aspects of carbon monoxide formation from volatile anesthetics. Anesthesiology, 89, 929–941.
  • BITO, H. and IKEDA, K., 1994, Long duration, low-flow sevoflurane anaesthesia using two carbon dioxide absorbents. Quantification of degradation products in the circuit. Anesthesiology, 81, 340–345.
  • COHEN, E. N., TRUDELL, J. R., EDMUNDS, H. N. and WATSON, E., 1975, Urinary metabolites of halothane in man. Anesthesiology, 43, 392–401.
  • FIESER, L. F. and FIESER, M., 1967, Reagents for Organic Synthesis (New York: Wiley).
  • FISCHER, B., NUDELMAN, A., RUSE, M., HERZIG, J., GOTTLIEB, H. E. and KEINAN, E., 1984, A novel method for stereoselective glucuronidation. Journal of Organic Chemistry, 49, 4988–4993.
  • FRINK, E. J., JR, ISNER, R. J., MALAN, T. P., JR, MORGAN, S. E., BROWN, E. A. and BROWN, B. R., 1994, Sevofiurane degradation product concentrations with soda lime during prolonged anaesthesia. Journal of Clinical Anaesthesia, 6, 239–242.
  • FRINK, E. J., JR, MALAN, T. P., MORGAN, S. E., BROWN, E. A., MALCOMSON, M. and BROWN, B. R., 1992, Quantification of the degradation products of sevoflurane in two CO2 absorbents during low-flow anaesthesia in surgical patients. Anesthesiology, 77, 1064–1069.
  • HARRIS, J. W. and ANDERS, M. W., 1991, Metabolism of the hydrochlorofiuorocarbon 1,2-dichloro-1,1-difiuoroethane. Chemical Research in Toxicology, 4, 180–186.
  • HINSBERG, 0., 1890, Ueber die bildung von saureestern und saureamiden bei gegenwart von wasser und alkali. Berichte Devt Chemische Ges, 23, 2962–2965.
  • HOLADAY, D. A. and SMITH, F. R., 1981, Clinical characteristics and biotransformation of sevoflurane in healthy human volunteers. Anesthesiology, 54, 100–106.
  • IYER, R. A. and ANDERS, M. W., 1996, Cysteine conjugate 13-lyase dependent biotransformation of the cysteine S-conjugates of the sevoflurane degradation product compound A in human, nonhuman primate, and rat kidney cytosol and mitochondria. Anesthesiology, 85, 1454–1461.
  • IYER, R. A. and ANDERS, M. W., 1997, Cysteine conjugate 13-lyase dependent biotransformation of the cysteine S-conjugates of the sevoflurane degradation product 2-(fluoromethoxy)-1,1,3,3,3-pentafluoro-1-propene (compound A). Chemical Research in Toxicology, 10, 811–819.
  • IYER, R. A., FRINK, E. J., EBERT, T. J. and ANDERS, M. W., 1998, Cysteine conjugate 13-lyase dependent metabolism of compound A (2-[fluoromethoxy]-1,1,3,3,3-pentafluoro-1-propene) in human subjects anaesthetised with sevoflurane and in rats given compound A. Anesthesiology, 88, 611–618.
  • JIAXIANG, N., SATO, N., Fuji', K. and YUGE, 0., 1993, Urinary excretion of hexafluoroisopropanol glucuronide and fluoride in patients after sevoflurane anaesthesia. Journal of Pharmacy and Pharmacology, 45, 67–69.
  • JIN, L., BAILLIE, T., DAVIS, M. R. and KHARASCH, E. D., 1995, Nephrotoxicity of sevoflurane compound A [fluoromethy1-2,2-difluoro-1-(trifluoromethyl)vinyl ether] in rats. Biochemical and Biophysical Research Communication, 210, 498–506.
  • JIN, L., DAVIS, M. R., KHARASCH, E. D., Doss, G. A. and BAILLIE, T. A., 1996, Identification in rat bile of glutathione conjugates of fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether, a nephrotoxic degradate of the anesthetic agent sevoflurane. Chemical Research in Toxicology, 9, 555–561.
  • KHARASCH, E. D., ARMSTRONG, A. S., GUNN, K., ARTRU, A., Cox, K., KAROL, M. D. and LANNI, C., 1995a, Clinical sevoflurane metabolism and disposition II. The role of cytochrome P450 2E1 in fluoride and hexafluoroisopropanol formation. Anesthesiology, 82, 1379–1388.
  • KHARASCH, E. D. and JUBERT, C., 1999b, Compound A uptake and metabolism to mercapturic acids and 3,3,3-trifluoro-2-fluoromethoxypropanoic acid during low flow sevoflurane anaesthesia. Anesthesiology, 91, 1267–1278.
  • KHARASCH, E. D., JUBERT, C., SPRACKLIN, D. K. and HOFFMAN, G. M., 1999a, Dose dependent metabolism of fluoromethy1-2,2-difluoro-1-(trifluoromethyl)vinyl Ether (Compound A), an anesthetic degradation product, to mercapturic acid and 3,3,3-trifluoro-2-(fluoromethoxy) propanoic acid in rats. Toxicology and Applied Pharmacology, 160, 49–59.
  • KHARASCH, E. D., KAROL, M. D., LANNI, C. and SAWCHUK, R., 1995b, Clinical sevoflurane metabolism and disposition I. Sevoflurane and metabolic pharmacokinetics. Anesthesiology, 82, 1369–1378.
  • KIKUCHI, H., MORIO, M., FUJII, K., MUKAIDA, K., HORIBE, M., DAVIDKOVA, T. I., KAWACHI, S. and SATO, N., 1987, Clinical evaluation and metabolism of sevoflurane in patients. Hiroshima Journal of Medical Sciences, 36, 93–97.
  • MARTINO, R., MALET-MARTINO, M. and GILARD, V., 2000, Fluorine nuclear magnetic resonance, a privileged tool for metabolic studies of fluoropyrimidine drugs. Current Drug Metabolism, 1, 271–303.
  • MARTIS, L., LYNCH, S., NAPOLI, M. D. and WooDs, E. F., 1981, Biotransformation of sevoflurane in dogs and rats. Anaesthesia and Analgesia, 60, 186–191.
  • MORGAN, S. E., FRINK, E. J. and GANDOLFI, J., 1994, A simplified gas chromatographic method for quantifying the sevoflurane metabolite hexafluoroisopropanol. Anesthesiology, 80, 201–205.
  • ORHAN, H., VERMEULEN, N. P. E., SAHIN, G. and COMMANDEUR, J. N. M., 2001, Characterisation of thioether compounds formed from potentially nephrotoxic alkaline degradation products of enflurane. Anesthesiology, 95, 165–175.
  • ROOSEBOOM, M., COMMANDEUR, J. N. M., FLOOR, G. C., RETTIE, A. E. and VERMEULEN, N. P. E., 2001, Selenoxidation by flavin-containing monooxygenases as a novel pathways for 13-elimination of selenocysteine Se-conjugates. Chemical Research in Toxicology, 14, 127–134.
  • SPRACKLIN, D. and KHARASCH, E. D., 1996, Evidence for the metabolism of fluoromethy1-2,2-difluoro-1-(trifluoromethyl)vinyl ether (compound A) by cysteine conjugate 13-lyase in rats. Chemical Research in Toxicology, 9, 696–702.
  • UTTAMSINGH, V., IYER, R. A., BAGGS, R. B. and ANDERS, M. W., 1998, Fate and toxicity of 2-(fluoromethoxy)-1,1,3,3,3-pentafluoro-1-propene (compound A)-derived mercapturates in male, Fischer 344 rats. Anesthesiology, 89, 1174–1183.
  • VAN WELIE, R. T. H., VAN DICK, R. G. J. M., VERMEULEN, N. P. E. and VAN SITTERT, N. J., 1992, Mercapturic acids and protein and DNA adducts as biomarkers of electrophilic chemicals. Critical Reviews in Toxicology, 22, 271–306.
  • WARK, H., EARL, J., OVERTON, J. and CHEUNG, H. T. A., 1990, A urinary cysteine-halothane metabolite: Validation and measurement in children. British Journal of Anaesthesia, 64, 469–473.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.