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Abstract

Isolation and characterization of metaproterenol-3-O-sulfate: a conjugate of metaproterenol in human urine.

T R MacGregor, L Nastasi, P R Farina and J J Keirns
Drug Metabolism and Disposition November 1983, 11 (6) 568-573;
T R MacGregor
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L Nastasi
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P R Farina
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J J Keirns
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Abstract

Metaproterenol (1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol) is primarily converted in humans to metaproterenol-3-O-sulfate following oral administration. Ion exchange column chromatography with a gradient of ammonium acetate buffer permitted the isolation of the ammonium salt of metaproterenol-3-O-sulfate from human urine. Treatment of aliquots of the column eluate with purified sulfatase and subsequent HPLC/fluorescence analysis confirmed the presence of metaproterenol. Comparison of the column eluate with a metaproterenol standard by 250-MHz proton-NMR revealed a pattern consistent with monosubstitution of the resorcinol ring. Negative and positive ion fast atom bombardment/mass spectrometry showed the metabolite to have a (M-H)- m/z of 290 and a (M + H)+ m/z ion of 292. These three methods support the structural assignment of metaproterenol-3-O-sulfate. Enzymatic hydrolysis of urine specimens from 29 different subjects with purified beta-glucuronidase as well as beta-glucuronidase-sulfatase mixtures yielded no significant increase in metaproterenol beyond purified sulfatase-treated urine, thus ruling out the presence of a glucuronide of metaproterenol. Approximately 40% of an oral 20-mg dose, given as either a tablet or a solution, was recovered in the urine as metaproterenol-3-O-sulfate. Approximately 5% of the dose was recovered in the unconjugated form. The majority of the dose was excreted over the first 12 hr with a biological half-life of 5-6 hr followed by a slower excretion phase with a half-life of 20 hr.

 

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Drug Metabolism and Disposition
Vol. 11, Issue 6
1 Nov 1983
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Abstract

Isolation and characterization of metaproterenol-3-O-sulfate: a conjugate of metaproterenol in human urine.

T R MacGregor, L Nastasi, P R Farina and J J Keirns
Drug Metabolism and Disposition November 1, 1983, 11 (6) 568-573;

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Abstract

Isolation and characterization of metaproterenol-3-O-sulfate: a conjugate of metaproterenol in human urine.

T R MacGregor, L Nastasi, P R Farina and J J Keirns
Drug Metabolism and Disposition November 1, 1983, 11 (6) 568-573;
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