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Der Abbau des Insektizides GS 13005 in der Ratte. Strukturaufklärung der wichtigsten Metabolite [1]
Author(s) -
Esser H. O.,
Mücke W.,
Alt K. O.
Publication year - 1968
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19680510313
Subject(s) - chemistry , metabolite , urine , hydrolysis , derivative (finance) , stereochemistry , metabolism , medicinal chemistry , biochemistry , economics , financial economics
The structures of the essential metabolites which are excreted by the rat after oral application of GS 13005 (O,O‐dimethyl‐S‐[(2‐methoxy‐1,3,4‐thiadiazole‐5(4 H )‐one‐4‐yl)‐methyl] dithiophosphate) have been elucidated. The product of final oxidation, CO 2 , was found to be the main metabolite (up to 36% of the dose applied). Among the degradation products excreted in the urine (up to 45% of the dose applied) the two most important were isolated. They are 4‐methylsulfinylmethyl and 4‐methylsulfonylmethyl derivatives respectively of the intact 2‐methoxy‐1,3,4‐thiadiazole‐5‐one heterocycle (metabolites III and II, in amounts of 20–25% and 5–7% of the dose applied, respectively). These metabolites originate by methylation and subsequent oxidation from the mercaptomethyl derivative liberated after hydrolysis of the PS bond of the dithiophosphoric acid ester.