Metabolism of 3-(Hydroxymethyl)-8-methoxychromone in the Rat: II. Classification and Identification of Urinary Drug Metabolites

Malcolm C. Crew Departments of Drug Metabolism and Analytical Physical Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey, 07950, USA

Myriam D. Melgar Departments of Drug Metabolism and Analytical Physical Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey, 07950, USA

Susan George Departments of Drug Metabolism and Analytical Physical Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey, 07950, USA

R. Clive Greenough Departments of Drug Metabolism and Analytical Physical Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey, 07950, USA

Joseph M. Szpiech Departments of Drug Metabolism and Analytical Physical Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey, 07950, USA

Frederick J. Di Carlo Departments of Drug Metabolism and Analytical Physical Chemistry, Warner-Lambert Research Institute, Morris Plains, New Jersey, 07950, USA

Abstract

1. Five metabolites were isolated from the urine of dogs dosed with 3-(hydroxymethyl)-8-methoxy[4-¹⁴C]chromone. These were identified as 8-methoxychromone, 2-hydroxy-3-methoxyacetophenone, 3-(hydroxymethyl)-8-hydroxychromone, 8-hydroxychromone and 2,3-dihydroxyacetophenone.

2. These compounds were also present in the urine of rats treated with labelled drug, together with unchanged drug and two intermediate metabolites, 3-carboxy-8-methoxychromone and 3-(carboxymethyl)-8-hydroxychromone.

3. In addition to the unconjugated labelled compounds, glucuronides and sulphates were identified.

4. Quantitative data were obtained for all of the 20 labelled compounds in rat urine.

5. A scheme is presented for the biotransformation of 3-(hydroxymethyl)-8-methoxychromone in rats and dogs, and a mechanism for scission of the γ-pyrone ring is suggested.

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Metabolism of 3-(Hydroxymethyl)-8-methoxychromone in the Rat: II. Classification and Identification of Urinary Drug Metabolites

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Metabolism of 3-(Hydroxymethyl)-8-methoxychromone in the Rat: II. Classification and Identification of Urinary Drug Metabolites

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