| Characterization and quantification of metabolites of racemic ketoprofen excreted in urine following oral administration to man by 1H-NMR spectroscopy, directly coupled HPLC-MS and HPLC-NMR, and circular dichroism. | |
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MedLine Citation:
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PMID: 15801549 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The identity of the human metabolites of ketoprofen (2-(3-benzoylphenyl)-propanoic acid) excreted via urine was investigated after a single oral dose of the racemic drug. Drug metabolites were concentrated and partially purified from urine using solid-phase extraction chromatography before separation and identification by directly coupled HPLC-MS and HPLC-NMR. The metabolites identified were the ester glucuronides of the parent drug and its phase I metabolites, 2-[3-(3-hydroxybenzoyl)phenyl]-propanoic acid, 2-[3-(4-hydroxybenzoyl)phenyl]-propanoic acid and 2-[3-(hydroxy(phenyl)methyl)phenyl]-propanoic acid, the latter formed by reduction of the ketone group of ketoprofen. In addition, two novel minor metabolites were identified as the ether glucuronides of 2-[3-(3-hydroxybenzoyl)phenyl]-propanoic acid and 2-[3-(4-hydroxybenzoyl)phenyl]-propanoic acid. These conjugates were all observed as diastereoisomeric pairs of unequal proportions. Purification of these metabolites by preparative chromatography allowed stereochemistry assignments. Metabolites were quantified by 1H-NMR spectroscopy after spectral simplification achieved by hydrolysis of the conjugates. |
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Authors:
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E Skordi; I D Wilson; J C Lindon; J K Nicholson |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Xenobiotica; the fate of foreign compounds in biological systems Volume: 34 ISSN: 0049-8254 ISO Abbreviation: Xenobiotica Publication Date: 2004 Nov-Dec |
Date Detail:
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Created Date: 2005-04-01 Completed Date: 2005-07-19 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 1306665 Medline TA: Xenobiotica Country: England |
Other Details:
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Languages: eng Pagination: 1075-89 Citation Subset: IM |
Affiliation:
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Biological Chemistry, Sir Alexander Fleming Building, Imperial College London, South Kensington, London SW7 2AZ, UK. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Administration, Oral Adult Chromatography, High Pressure Liquid Circular Dichroism Female Glucuronides / urine* Humans Ketoprofen / administration & dosage*, urine* Magnetic Resonance Spectroscopy Mass Spectrometry Protons |
| Chemical | |
Reg. No./Substance:
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0/Glucuronides; 0/Protons; 22071-15-4/Ketoprofen |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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