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Human Urinary Metabolites of 3-(2',4',5'-triethoxybenzoyl)propionic Acid, a New Biliary Smooth Muscle Relaxant With Choleretic Activity

Human Urinary Metabolites of 3-(2',4',5'-triethoxybenzoyl)propionic Acid, a New Biliary Smooth Muscle Relaxant With Choleretic Activity

T Kobayashi, Y Kanai, S Tanayama

Xenobiotica. 1978 Dec;8(12):737-43.

PMID: 726517

Abstract:

Biotransformation of 3-(2',4',5'-triethoxybenzoyl)propionic acid (tri-, ethoxybenzoylpropionate) was studied in man using isotopic cluster technique. From the 24 h urine of a male volunteer given an equimolar mixture of non-labelled and pentadeuterium-labelled triethoxybenzoylpropionate (1 mg/kg) orally, the parent drug, 3-(2',5'-diethoxy-4'-hydroxybenzoyl)propionic acid (4'-phenol) and 3-(2',4'-diethoxy-5'-hydroxybenzoyl)propionic acid (5'-phenol) were isolated and identified by g.l.c.-mass spectrometry. 2. Urinary components were also quantified by mass chromatography: the parent drug (67.4% of dose) and 4'- and 5'-phenols in a mixture (20.3%). More than 80% of urinary triethoxybenzoylpropionate was present as its glucuronic acid ester, as evidenced by using beta-glucuronidase and saccharo-1,4-lactone, a specific inhibitor of the enzyme. Almost all of 4'- and 5'-phenols appeared as conjugates with glucuronic acid and/or sulphuric acid. These findings indicated that in man triethoxybenzoylpropionate was largely conjugated with glucuronic acid and in part underwent deethylation followed by conjugation for elimination mainly in urine.

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