Direct nuclear magnetic resonance spectroscopic analysis of 13C-labeled antipyrine metabolites in human urine

Drug Metabolism and Disposition

Volumn 29, Issue 6, 2001, Pages 903-907

  Akira, Kazuki ^a   Negishi, Eiji ^a   Imachi, Misako ^b   Hashimoto, Takao ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b Bruker Japan Co Ltd ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHENAZONE; PHENAZONE DERIVATIVE;

ADULT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIAGNOSTIC VALUE; DRUG METABOLISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; JAPAN; MALE; NORMAL HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SIGNAL NOISE RATIO;

ADULT; ANTIPYRINE; CARBON ISOTOPES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALE;

EID: 0035001548     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. 13C labeling and NMR spectroscopy. Drug Metab Dispos 27:1248-1253.
2. 13C-labelled benzoic acid and hippuric acid coupled with nuclear magnetic resonance spectroscopy. J Pharm Pharmacol 49:1242-1247.
3. 13C-labeled ketoprofen glucuronides in human urine by nuclear magnetic resonance spectroscopy. Anal Chim Acta 334:67-74.
4. 13C labeling and nuclear magnetic resonance spectroscopy. Drug Metab Dispos 26:457-464.
5. 13C-labeling and nuclear magnetic resonance spectroscopy to pharmacokinetic research: measurement of metabolic rate of benzoic acid to hippuric acid in the rat. Anal Biochem 210:86-90
6. Ali HA, el Yazigi A, Sieck JO, Ali MA, Raines DA, Saour J, Ernst P, Khan B and Dossing M (1995) Antipyrine clearance and metabolite excretion in patients with chronic hepatitis C. J Hepatol 22:17-21.
7. 13C label-nuclear magnetic resonance (NMR) tracer techniques to clinical chemistry. Metabolic rate of benzoic acid to hippuric acid. Yakugaku Zasshi 110:586-590.
8. 13C-labeling for pharmacokinetic research in man: detection of benzoic acid conversion to hippuric acid. Biol Pharm Bull 18:643-647.
9. Bassmann H, Bottcher J and Schuppel R (1985) Isolation and characterization of the four antipyrne glucuronides and determination of their urinary excretion pattern in man by a reversed-phase h.p.l.c. assay. Xenobiotica 15:941-952.
10. Bottcher J, Bassmann H and Schuppel R (1982a) Quantitation and urinary pattern of 4.4′-dihydroxy-antipyrine, 4-hydroxy-antipyrine and 3-hydrosymethyl-antipyrine, as main metabolites of antipyrine in man and rat. J Pharm Pharmacol 34:168-175.
11. Bottcher J, Bassmann H and Schuppel R (1984) Quantitation of norantipyrine sulphate and norantipyrine glucuronide as major metabolites of antipyrine in man and rat. J Pharm Pharmacol 36:391-398.
12. Bottcher J, Bassmann H, Schuppel R and Lehmann WD (1982b) Preparative isolation and purification of urinary conjugates in antipyrine metabolism in man and rat. Naunyn-Schmiedeberg's Arch Pharmacol 321:226-233.
13. Danhof M, de Groot-van der Vis E and Breimer DD ( 1979) Assay of antipyrine and its primary metabolites in plasma, saliva and urine by high-performance liquid chromatography and some preliminary results in man. Pharmacology 18:210-223
14. Hartleb M (1991) Drugs and the liver part II: the role of the antipyrine test in drug metabolism studies. Biopharm Drug Dispos 12:559-570.
15. Malet-Martino MC and Martino R ( 1992) Magnetic resonance spectroscopy: a powerful tool for drug metabolism studies. Biochimie (Paris) 74:785-800).
16. Mikati MA, Szabo GK and Pylilo RJ (1988) Improved high-performance liquid Chromatographic assay of antipyrine, hydroxymethylantipyrne, 4-hydroxyantipyrine and norantipyrine in urine. J Chromatogr 433:305-311.
17. Moreau J, Palette C, Cordonnier P, Naline E, Advenier C and Pays M (1992) Separation and identification of the 4-hydroxyantipyrine sulphoconjugate. J Chromatogr 576:103-109.
18. 13NMR Spectroscopy (Levy GC ed) vol 4, pp 179-196. John Wiley & Sons. New York.
19. Nicholson JK and Wilson ID (1987) High resolution nuclear magnetic resonance spectroscopy of biological samples as an aid to drug development. Prog Drug Res 31:427-479.
20. Ohashi K, Sakamoto K, Sudo T, Tateishi T, Harada K, Fujimura A, Ebihara A and Tanaka E (1991) The effect of diltiazem on hepatic drug oxidation assessed by antipyrine and trimethadione. J Clin Pharmacol 31:1132-1136.
21. Palette C, Cordonnier P, Naline E, Adventer C and Pays M (1991) High-performance liquid chromatographic method for the determination of the three main oxidative and 3-carboxylic antipyrine metabolites in human urine. J Chromatogr 563:103-113.
22. Palette C, Cordonnier P, Tillequin F, Koch M, Advenier C and Pays M (1994) Isolation and purification of three glucuronides of antipyrine. Proposal for an original analytical method for quantitation of sulpho-and glucuroconjugated metabolites. Biomed Chromatogr 8:77-84.
23. Robertz Vaupel GM, Lindecken KD, Edeki T, Funke C, Belwon S and Dengler HJ (1992) Disposition of antipyrine in patients with extensive metastatic liver disease. Eur J Clin Pharmacol 42:465-469.
24. Sharer JE and Wrighton SA (1996) Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine-Drug Metab Dispos 24:487-494
25. 13C NMR spectroscopy. Prog Nucl Magn Reson Spectrosc 11:79-93.
26. St. Peter JV and Awni WM (1991) Quantifying hepatic function in the presence of liver disease with phenazone (antipyrine) and its metabolites. Clin Pharmacokinet 20:50-65.
27. Teunissen MWE, Meerburg-Van Der Torren JE, Vermeulen NPE and Breimer DD (1983) Automated high-performance liquid chromatographic determination of antipyrine and its main metabolites in plasma, saliva and urine, including 4.4′-dihydroxyantipyrine. J Chromatogr 278:367-378.
28. 14C in the pyrazolone ring or in the N-methyl group. Xenobiotica 13:155-162.
29. 14C]antipyrine metabolites in rat and dog urine. J Chromatogr B 666:139-147.
30. Yang BB. Hounslow NJ, Sedman AJ and Forgue ST (1996) Effects of atorvastatin. an HMG-CoA reductase inhibitor, on hepatic oxidative metabolism of antipyrine. J Clin Pharmacol 36:356-360.