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Identification of new oxycodone metabolites in human urine by capillary electrophoresis–multiple-stage ion-trap mass spectrometry

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Title: Identification of new oxycodone metabolites in human urine by capillary electrophoresis–multiple-stage ion-trap mass spectrometry
Authors: Baldacci, A.1, Caslavska, J.1, Wey, A.B.1, Thormann, W. wolfgang.thormann@ikp.unibe.ch
Source: Journal of Chromatography A. Oct2004, Vol. 1051 Issue 1/2, p273-282. 10p.
Subjects: Oxycodone, Codeine derivatives, Capillary electrophoresis, Zone electrophoresis
Abstract: Capillary electrophoresis–electrospray ionization multiple-stage ion-trap mass spectrometry (CE–MSn) and computer simulation of fragmentation are demonstrated to be effective tools to detect and identify phase I and phase II metabolites of oxycodone (OCOD) in human urine. OCOD is a strong analgesic used for the management of moderate to severe mainly postoperative or cancer-related pain whose metabolism in man is largely unknown. Using an aqueous pH 9 ammonium acetate buffer and CE–MSn (n ≤ 5), OCOD and its phase I metabolites produced by O-demethylation, N-demethylation, 6-ketoreduction and N-oxidation (such as oxymorphone, noroxycodone, noroxymorphone, 6-oxycodol, nor-6-oxycodol, oxycodone-N-oxide and 6-oxycodol-N-oxide) and phase II conjugates with glucuronic acid of several of these compounds could be detected in alkaline solid-phase extracts of a patient urine that was collected during a pharmacotherapy episode with daily ingestion of 240–320mg of OCOD chloride. The data for three known OCOD metabolites for which the standards had to be synthesized in-house, 6-oxycodol, nor-6-oxycodol and oxycodone-N-oxide, were employed to identify two new metabolites, the N-oxidized derivative of 6-oxycodol and an O-glucuronide of this compound. CE–MSn and computer simulation of fragmentation also led to the identification of the N-glucuronide of noroxymorphone, another novel OCOD metabolite for which no standard compound or mass spectra library data were available. [Copyright &y& Elsevier]
Copyright of Journal of Chromatography A is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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DbLabel: Engineering Source
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  Data: Identification of new oxycodone metabolites in human urine by capillary electrophoresis–multiple-stage ion-trap mass spectrometry
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  Data: <searchLink fieldCode="AR" term="%22Baldacci%2C+A%2E%22">Baldacci, A.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Caslavska%2C+J%2E%22">Caslavska, J.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Wey%2C+A%2EB%2E%22">Wey, A.B.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Thormann%2C+W%2E%22">Thormann, W.</searchLink><i> wolfgang.thormann@ikp.unibe.ch</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Chromatography+A%22">Journal of Chromatography A</searchLink>. Oct2004, Vol. 1051 Issue 1/2, p273-282. 10p.
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  Data: <searchLink fieldCode="DE" term="%22Oxycodone%22">Oxycodone</searchLink><br /><searchLink fieldCode="DE" term="%22Codeine+derivatives%22">Codeine derivatives</searchLink><br /><searchLink fieldCode="DE" term="%22Capillary+electrophoresis%22">Capillary electrophoresis</searchLink><br /><searchLink fieldCode="DE" term="%22Zone+electrophoresis%22">Zone electrophoresis</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Capillary electrophoresis–electrospray ionization multiple-stage ion-trap mass spectrometry (CE–MSn) and computer simulation of fragmentation are demonstrated to be effective tools to detect and identify phase I and phase II metabolites of oxycodone (OCOD) in human urine. OCOD is a strong analgesic used for the management of moderate to severe mainly postoperative or cancer-related pain whose metabolism in man is largely unknown. Using an aqueous pH 9 ammonium acetate buffer and CE–MSn (n ≤ 5), OCOD and its phase I metabolites produced by O-demethylation, N-demethylation, 6-ketoreduction and N-oxidation (such as oxymorphone, noroxycodone, noroxymorphone, 6-oxycodol, nor-6-oxycodol, oxycodone-N-oxide and 6-oxycodol-N-oxide) and phase II conjugates with glucuronic acid of several of these compounds could be detected in alkaline solid-phase extracts of a patient urine that was collected during a pharmacotherapy episode with daily ingestion of 240–320mg of OCOD chloride. The data for three known OCOD metabolites for which the standards had to be synthesized in-house, 6-oxycodol, nor-6-oxycodol and oxycodone-N-oxide, were employed to identify two new metabolites, the N-oxidized derivative of 6-oxycodol and an O-glucuronide of this compound. CE–MSn and computer simulation of fragmentation also led to the identification of the N-glucuronide of noroxymorphone, another novel OCOD metabolite for which no standard compound or mass spectra library data were available. [Copyright &y& Elsevier]
– Name: AbstractSuppliedCopyright
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  Data: <i>Copyright of Journal of Chromatography A is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.chroma.2004.07.039
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        Text: English
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        Type: general
      – SubjectFull: Codeine derivatives
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      – SubjectFull: Capillary electrophoresis
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              Text: Oct2004
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