Identification of phenacetin metabolites in human urine after administration of phenacetin-C2H3: Measurement of futile metabolic deacetylation via HPLC/MS-SPE-NMR and HPLC-ToF MS

Xenobiotica

Volumn 36, Issue 7, 2006, Pages 615-629

  Nicholls, A W ^a,e   Wilson, I D ^b   Godejohann, M ^c   Nicholson, J K ^d   Shockcor, J P ^a,f  

^a Metabometrix Ltd   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c Bruker GmbH   (Germany)

^d IMPERIAL COLLEGE LONDON   (United Kingdom)

^e GLAXOSMITHKLINE   (United Kingdom)

^f Waters Inc   (United States)

Author keywords

Acetaminophen; Futile deacetylation; Mass spectrometry (MS); Nuclear magnetic resonance (NMR) spectroscopy; Phenacetin; Solid phase extraction (SPE)

Indexed keywords

CYSTEINE DERIVATIVE; DRUG METABOLITE; PARACETAMOL GLUCURONIDE; PARACETAMOL SULFATE; PHENACETIN;

ADULT; ARTICLE; CONJUGATION; DEACETYLATION; DRUG IDENTIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MALE; MEASUREMENT; NORMAL HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLID PHASE EXTRACTION; TIME OF FLIGHT MASS SPECTROMETRY; URINALYSIS;

ACETYLATION; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PHENACETIN; RATS; URINE;

EID: 33746792830     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.1080/00498250600711113     Document Type: Article

References (19)

1. Brodie BB, Axelrod J. 1949. The fate of acetaphenetidin (phenacetin) in man and its metabolites in biological materials. Journal of Pharmacology and Experimental Therapeutics 97:58-67.
2. Buckalew VM Jr. 1996. Habitual use of acetaminophen as a risk factor for chronic renal failure: A comparison with phenacetin. American Journal of Kidney Diseases 28:S7-13.
3. Duggin GG. 1980. Mechanisms in the development of analgesic nephropathy. Kidney International 18:553-561.
4. Duggin GG. 1993. The biochemistry and pharmacology of antipyretic-analgesics. In: Stewart JH, editor. Analgesic and NSAID-induced kidney disease. Oxford: Oxford Medical. pp 5-16.
5. Gloor FJ. 1993. Historical introduction. In: Stewart JH, editor. Analgesic and NSAID-induced kidney disease. Oxford: Oxford Medical. pp 1-3.
6. Goldstein RS, Schnellmann RG. 1996. Toxic responses of the kidney. In: Klassen CD, editor. Casarett and Doull's toxicology: The basic science of poisons. New York, NY: McGraw-Hill. pp 417-442.
7. Green CR, Ham KN, Tange JD. 1969. Kidney lesions induced in rats by p-aminophenol. British Medical Journal 1:162-164.
8. Guengerich FP, Shimada T. 1993. Human cytochrome P450 enzymes and chemical carcinogenesis. In: Jeffrey EH, editor. Human drug metabolism: from molecular biology to man. Boca Raton, FL: CRC Press. pp 5-12.
9. Hinson JA. 1983. Reactive metabolites of phenacetin and acetaminophen: A review. Environmental Health Perspectives 49:71-79.
10. McLaughlin JK, Lipworth L, Wong-Ho C, Blot WJ. 1998. Analgesic use and chronic renal failure: A critical review of the epidemiologic literature. Kidney International 54:679-686.
11. Nelson SD. 1982. Metabolic activation and drug toxicity. Journal of Medical Chemistry 25:753-765.
12. Nicholls AW, Caddick S, Wilson ID, Farrant RD, Lindon JC, Nicholson JK. 1995. High resolution NMR spectroscopic studies on the metabolism and futile deacetylation of 4-hydroxyacetanilide (paracetamol) in the rat. Biochemical Pharmacology 49:1155-1164.
13. Nicholls AW, Farrant RD, Shockcor JP, Unger SE, Wilson ID, Lindon JC, Nicholson JK. 1997b. NMR and HPLC-NMR spectroscopic studies of futile deacetylation in paracetamol metabolites in rat and man. Journal of Pharmaceutical and Biomedical Analysis 15:901-910.
14. Nicholls AW, Lindon JC, Caddick S, Farrant RD, Wilson ID, Nicholson JK. 1997a. NMR spectroscopic studies on the metabolism and futile deacetylation of phenacetin in the rat. Xenobiotica 27:1175-1186.
15. Raaflaub J, Dubach UC. 1975. On the pharmacokinetics of phenacetin in man. European Journal of Clinical Pharmacology 8:261-265.
16. Sandler DP, Smith JC, Weinberg CR, Buckalew MD Jr, Dennis VW, Blythe WB, Burgess WP. 1989. Analgesic use and chronic renal disease. New England Journal of Medicine 320:1238-1243.
17. Smith PK. 1958. Acetophenetidin: A critical bibliographic review. New York, NY: Interscience.
18. Spühler O, Zollinger HU. 1953. Die chronisch- interstitiellenephritis. Zeitschrift für Klinische Medizin 151:1-50.
19. Thomas SHL. 1993. Paracetamol (acetaminophen) poisoning. Pharmacology and Therapeutics 60:91-120.