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Chemical Compound Review:

CCRIS 339 N-(4-ethoxyphenyl)-N-hydroxy- ethanamide

Synonyms: NSC-229647, AC1L1HNK, LS-13108, NSC229647, AKOS006272871, ...

Camus, A.M. et al., Hayward, N.K. et al., Fischbach, T. et al., Glowinski, I.B. et al., Wirth, P.J. et al., et al.

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Disease relevance of CCRIS 339

Mechanism of N-hydroxyacetylarylamine mutagenicity in the Salmonella test system: metabolic activation of N-hydroxyphenacetin by liver and kidney fractions from rat, mouse, hamster, and man [1].
Subchronic toxicity of N-hydroxyphenacetin was tested in two experiments on male and female Sprague Dawley rats after IP or SC injection of 50 or 100 mg (0.26 or 0.51 mmol)/kg [2].
The effects of N-hydroxyphenacetin on DNA function and structure were investigated to elucidate the involvement of phenacetin in analgesic nephropathy and transitional cell carcinoma [3].

High impact information on CCRIS 339

Derivatives of both N-hydroxy-2-acetylaminofluorene (N-OH-AAF) and N-hydroxyphenacetin (N-OH-P) were tested for their ability to cause DNA damage in Reuber (H4-II-E) cells using the alkaline elution technique [4].
Its known or putative metabolites were synthesized; of these, N-hydroxyphenacetin and N-acetoxyphenacetin were found to be mutagenic in liquid and plate assays, both requiring activation by liver fractions from Aroclor-treated hamsters [5].
N-Hydroxyphenacetin was activated to a mutagen in the Salmonella-Ames test by rabbit liver acyltransferase, rat liver cytosol, and rat liver microsomes [6].
Methylation of N-hydroxyphenacetin produced a stable derivative, N-methoxyphenacetin, which was separated from most other metabolites by thin layer chromatography [7].
Metabolism of phenacetin and N-hydroxyphenacetin in isolated rat hepatocytes [8].

Biological context of CCRIS 339

No single-strand breaks were detectable in DNA after N-hydroxyphenacetin treatment and no appreciable effect on cell viability was observed at concentrations up to 5 mM [3].

Anatomical context of CCRIS 339

The N-hydroxyphenacetin can be further metabolized by the microsomes, and the reaction is inhibited by phenacetin [9].
N-Hydroxyphenacetin incubated with rat erythrocytes formed ferrihaemoglobin; the relationship between ferrihaemoglobin, phenacetin and 4-nitrosophenetole concn indicated that N-hydroxyphenacetin was oxidized by oxyhaemoglobin to acetyl 4-ethoxyphenyl nitroxide, which yielded phenacetin and 4-nitrosophenetole spontaneously [10].

Analytical, diagnostic and therapeutic context of CCRIS 339

After treatment with deconjugating enzymes, N-hydroxyphenacetin was isolated from hamster urine by high-performance liquid chromatography and identified by mass spectral analysis [5].
Mass spectrometric determination of N-hydroxyphenacetin in urine using multiple metastable peak monitoring following thin-layer chromatography [11].

References

Mechanism of N-hydroxyacetylarylamine mutagenicity in the Salmonella test system: metabolic activation of N-hydroxyphenacetin by liver and kidney fractions from rat, mouse, hamster, and man. Wirth, P.J., Dybing, E., von Bahr, C., Thorgeirsson, S.S. Mol. Pharmacol. (1980) [Pubmed]
N-Hydroxy-N-arylacetamides. I. Toxicity of certain polycyclic and monocyclic N-hydroxy-N-arylacetamides in rats. Fischbach, T., Hertle, H., Kiese, M., Lenk, W., Sterzl, H., Meister, P. Arch. Toxicol. (1984) [Pubmed]
Inhibition of DNA, RNA and protein synthesis and chromatin alteration by N-hydroxyphenacetin. Hayward, N.K., Lavin, M.F. Xenobiotica (1987) [Pubmed]
Metabolic activation and genotoxicity of N-hydroxy-2-acetylaminofluorene and N-hydroxyphenacetin derivatives in Reuber (H4-II-E) hepatoma cells. Glowinski, I.B., Sanderson, N.D., Hayashi, S., Thorgeirsson, S.S. Cancer Res. (1984) [Pubmed]
Species-specific activation of phenacetin into bacterial mutagens by hamster liver enzymes and identification of N-hydroxyphenacetin O-glucuronide as a promutagen in the urine. Camus, A.M., Friesen, M., Croisy, A., Bartsch, H. Cancer Res. (1982) [Pubmed]
Activation of N-hydroxyphenacetin to mutagenic and nucleic acid-binding metabolites by acyltransfer, deacylation, and sulfate conjugation. Vaught, J.B., McGarvey, P.B., Lee, M.S., Garner, C.D., Wang, C.Y., Linsmaier-Bednar, E.M., King, C.M. Cancer Res. (1981) [Pubmed]
N-hydroxyphenacetin, a new urinary metabolite of phenacetin in the rat. McLean, S., Davies, N.W., Watson, H., Favretto, W.A., Bignall, J.C. Drug Metab. Dispos. (1981) [Pubmed]
Metabolism of phenacetin and N-hydroxyphenacetin in isolated rat hepatocytes. McLean, S. Naunyn Schmiedebergs Arch. Pharmacol. (1978) [Pubmed]
N-Hydroxylation of phenacetin by hamster liver microsomes. Hinson, J.A., Mitchell, J.R. Drug Metab. Dispos. (1976) [Pubmed]
The metabolism of N-hydroxyphenacetin in vitro and in vivo. Fischbach, T., Lenk, W. Xenobiotica (1985) [Pubmed]
Mass spectrometric determination of N-hydroxyphenacetin in urine using multiple metastable peak monitoring following thin-layer chromatography. Davies, N.W., Veronese, M.E., McLean, S. J. Chromatogr. (1984) [Pubmed]

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