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N-hydroxyphenacetin, a new urinary metabolite of phenacetin in the rat

Citation

McLean, S and Davies, NW and Watson, H and Favretto, WA and Bignall, JC, N-hydroxyphenacetin, a new urinary metabolite of phenacetin in the rat, Drug Metabolism and Disposition, 9, (3) pp. 255-260. ISSN 0090-9556 (1981) [Refereed Article]

Abstract

N-Hydroxyphenacetin has been found in the urine of rats dosed with phenacetin, extending previous reports that phenacetin is N-hydroxylated by liver microsomes in vitro. After an oral dose of phenacetin (500 mg/kg) urine was collected for 24 hr, conjugates hydrolyzed with extract of Helix pomatia, and the metabolites extracted with dichloromethane and treated with diazomethane. Methylation of N-hydroxyphenacetin produced a stable derivative, N-methoxyphenacetin, which was separated from most other metabolites by thin layer chromatography. Identification of N-methoxyphenacetin was by combined gas chromatography-mass spectrometry and comparison with the synthetic reference compound. Quantification by gas chromatography with flame-ionization detection showed that 0.023% of the dose of phenacetin was recovered from urine as N-hydroxyphenacetin. It is probable that this value considerably underestimates the extent of phenacetin N-hydroxylation in vivo, inasmuch as N-hydroxyphenacetin is known to be rapidly degraded in biological systems.

Item Details

Item Type:Refereed Article
Research Division:Medical and Health Sciences
Research Group:Medical Biochemistry and Metabolomics
Research Field:Medical Biochemistry and Metabolomics not elsewhere classified
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Medical and Health Sciences
Author:McLean, S (Professor Stuart McLean)
Author:Davies, NW (Associate Professor Noel Davies)
ID Code:102207
Year Published:1981
Web of Science® Times Cited:12
Deposited By:Central Science Laboratory
Deposited On:2015-08-04
Last Modified:2015-08-04
Downloads:0

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