Stereoselective high-performance liquid chromatographic assay of (+/-) -delmopinol in plasma using solid-phase extraction, a chiral derivatizing agent and electrochemical detection

Egginger, G.; Blaschke, E.; Lindner, W.; Olsson, A.M.

Journal of Chromatography A 666(1-2): 275-282


ISSN/ISBN: 0021-9673
PMID: 8205235
DOI: 10.1016/0021-9673(94)80389-7
Accession: 033492427

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An enantioselective HPLC bioanalytical method for (±)-delmopinol was established in order to elucidate the pharmacokinetic behaviour of this chiral drug. ( ± )-Delmopinol and ( ± )-M1652, a structurally related compound used as internal standard, were extracted from plasma by a solid-phase extraction procedure using CN cartridges. The enantiomers were derivatized with a chiral derivatizing agent (R,R)-O,O-di-p-toluoyl tartaric acid anhydride yielding diastereomeric derivatives which were separated on a reversed-phase column with acetonitrile-0.1 M ammonium acetate buffer (65:35, v/v) pH 5.7 as mobile phase. The resolution values of the diastereomeric derivatives of ( )- and ( + )-M1652 and of the derivatives of ( )- and ( + )-delmopinol were 1.03 and 1.46, respectively. The limit of quantitation was approximately 3 pmol (1 ng)/enantiomer per 0.5 ml plasma using electrochemical detection ( + 0.75 V versus Pd/PdO reference electrode). The effectiveness of the derivatization was > 98% and the total recovery of ( ± )-delmopinol and of ( ± )-M1652 from plasma or serum was found to be approximately 50%. The assay was applied to enantioselective pharmacokinetic investigations in humans, rats and dogs but showing here only one concentration time curve of the ( + )- and ( )-delmopinol in a human subject after administering ( ± )-delmopinol in form of an aqueous mouth wash solution for 60 s.