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Urinary metabolites of 2‐ethyl‐2‐methylsuccinimide (ethosuximide) studied by combined gas chromatography mass spectrometry
Author(s) -
Pettersen Jon Elling
Publication year - 1978
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200051102
Subject(s) - ethosuximide , chemistry , metabolite , stereospecificity , hydroxylation , chromatography , mass spectrometry , urine , gas chromatography , gas chromatography–mass spectrometry , yield (engineering) , enzyme , organic chemistry , biochemistry , anticonvulsant , catalysis , neuroscience , epilepsy , biology , materials science , metallurgy
Abstract Metabolites of 2‐ethyl‐2‐methylsuccinimide (ethosuximide) have been studied by combined gas chromatography mass spectrometry in a urine sample from a patient treated for petit mal epilepsy with ethosuximide. A new metabolite, 2‐carboxymethyl‐2‐methylsuccimide, was identified in the urine. It is presumably formed by ωl‐hydroxylation of the ethyl sidechain of the drug followed by a further oxidation of the primary alcohol to a carboxyl group. A previously identified metabolite, 2‐ethyl‐3‐hydroxy‐2‐methylsuccinimide, was shown in the present study to yield two gas chromatographic peaks (as the N ‐methylated compound), indicating the existence of a diastereoisomeric pair. Thus, the enzyme responsible for the ring hydroxylation is probably not stereospecific, or alternatively two enzymes with different stereospecificity may exist.

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