2-Hydroxyacetophenetidine, a New Metabolite of Acetophenetidine

Klutch, A.; Harfenist, M.; Ah, Conney

doi:10.1021/jm00319a017

Cited by 35 publications

(6 citation statements)

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“…ldentification 0/ 3MT -4HA as a metabolite 0/ phenacetin. The chromatographie procedure used to isolate and identify 2-hydroxyphenacetin from dog urine 8 indicated the presence of an unidentified metabolite. Crystals of this metab-olite were isolated as described in the section on methods.…”

Section: Resultsmentioning

confidence: 99%

“…chloroform, and chromatography on an alumlnum oxide column as described earlier. 8 One fraction from the column contained large amounts of 2-hydroxyphenacetin when examined by thin-Iayer chromatography, and this metabolite was recrystallized in aqueous-ethanol. 8 The aqueous-ethanol filtrate obtained from recrystallization of the 2-hydroxyphenacetin was then evaporated, and the resulting residue was recrystallized from ethyl acetate-cyclohexane.…”

Section: Methodsmentioning

confidence: 99%

“…Thin-Iayer plates were prepared from aluminum oxide gel filtration by means of techniques previously described. 8 The dried urine extracts were dissolved in 50 JLI of chloroform be fore application to the thin-Iayerplate. The solvent systems used are described in Table I.…”

Section: Methodsmentioning

confidence: 99%

“…During studies on the metabolism of phenacetin (4-ethoxyacetanilide), a metabolite was isolated from the urine of dogs, and this compound was identified as 2-hydroxyphenacetin. 8 During the isolation procedure, chromatographie data indicated a second previously unidentified metabolite. Areport describing the identification of this metabolite by comparison to synthetic standards has recently appeared.…”

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confidence: 99%

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Formation of a thiomethyl metabolite of phenacetin and acetaminophen in dogs and man

Klutch

Levin

Chang

et al. 1978

Clin Pharma and Therapeutics

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Conjugates of 3-methylthio-4-hydroxyactanilide were found in the urine of dogs and humans treated with phenacetin (4-ethoxyacetanilide) or acetaminophen (4-hydroxyacetanilide). About 1% to 3% of the administered dose was excreted as this thiomethyl metabolite after administration of phenacetin or acetaminophen to dogs. An average of 0.39% of the dose was excreted in the urine as 3-methylthio-4-hydroxyacetanilide conjugates after administration of phenacetin to several subjects, and an average of 0.66% of the dose was excreted as this metabolite in the urine after administration of acetaminophen to humans. The possibility that the thiomethyl metabolite is derived from a mercapturic acid conjugate or an N-hydroxy derivative of phenacetin or acetaminophen is discussed.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Formation of a thiomethyl metabolite of phenacetin and acetaminophen in dogs and man

Klutch

Levin

Chang

et al. 1978

Clin Pharma and Therapeutics

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“…The metabolism ofthe drug has been the subject ofmany studies since the isolation (Morner, 1889) of potassium 4-acetamidophenyl sulphate from the urine of patients treated with phenacetin. Since then, other metabolites of phenacetin in urine that have been described are the glucosiduronate of 4-acetamidophenol together with 4-phenetidine, 2-hydroxyphenetidine and 2-hydroxyphenacetin, either in the free state or as their conjugates with sulphuric acid or glucosiduronic acid (Hinsberg & Treupel, 1894;Smith & Williams, 1949;Brodie & Axelrod, 1949;Klutch, Harfenist & Conney, 1965;Buch et al 1967;Dubach & Raaflaub, 1969;Shahidi & Hemaidan, 1969).…”

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confidence: 99%

Some new aspects of the metabolism of phenacetin in the rat

Nery

1971

Biochemical Journal

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1. Four new metabolites of phenacetin in the urine of the rat are described; these are (i) N-acetyl-S-ethylcysteine, (ii) quinol, (iii) acetamide and (iv) probably N-acetyl-S-2-(4-ethoxyacetanilido)cysteine S-oxide. 2. Metabolites (i), (iii) and (iv) were characterized and estimated by g.l.c., by t.l.c., by paper chromatography, by chemical reactions or by radioactive techniques after administration to rats of [ethyl-(14)C]phenacetin and [acetyl-(3)H]phenacetin; metabolite (ii), which was excreted mainly as conjugates of sulphuric acid and glucosiduronic acid, was measured by paper chromatography and characteristic colour reactions after enzymic and chemical hydrolysis of the conjugates. 3. Small amounts of azoxy-4-[ethyl-(14)C]ethoxybenzene and an unknown metabolite were also found in the urine of rats after administration of [ethyl-(14)C]phenacetin. 4. The likely mechanisms and some biological implications of these metabolic reactions are discussed.

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