Document Detail

Metabolism of N-[4-chloro-2-fluoro-5-[(1-methyl-2- propynl)oxy]phenyl]-3,4,5,6-tetrahydrophthalimide (S-23121) in the rat: I. Identification of a new, sulphonic acid type of conjugate.
MedLine Citation:
PMID:  8212735     Owner:  NLM     Status:  MEDLINE    
1. Several metabolites of 14C-labelled N-[4-chloro-2-fluoro-5-[(1-methyl- 2-propynyl)oxy]phenyl]-3,4,5,6-tetra-hydrophthalimide (S-23121) were identified. 2. The major urinary metabolites were found to be 4-chloro-2-fluoro-5-hydroxyaniline, its sulphate and glucuronide by t.l.c. cochromatography with authentic standards. 3. The major faecal metabolites in addition to the parent compound were six sulphonic acid conjugates having a sulphonic acid group incorporated into the double bond of the 3,4,5,6-tetrahydrophthalimide moiety. These sulphonic acid conjugates have never been reported previously for this type of compound. 4. To confirm the mechanism of biosynthesis of the sulphonic acid conjugates, sodium sulphate, cysteine and glutathione labelled with 35S were administered to the male rat together with unlabelled S-23121. The same faecal metabolites as those detected in faeces of the rat dosed with 14C-labelled S-23121 were similarly found after dosing with any of the 35S-labelled chemicals. Their biosynthesis was most pronounced with 35S-labelled sodium sulphate, implying that the sulphonic acid is incorporated into the double bond after reduction of sulphate to sulphite.
H Yoshino; H Matsunaga; H Kaneko; A Yoshitake; I Nakatsuka; H Yamada
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Xenobiotica; the fate of foreign compounds in biological systems     Volume:  23     ISSN:  0049-8254     ISO Abbreviation:  Xenobiotica     Publication Date:  1993 Jun 
Date Detail:
Created Date:  1993-10-28     Completed Date:  1993-10-28     Revised Date:  2013-01-24    
Medline Journal Info:
Nlm Unique ID:  1306665     Medline TA:  Xenobiotica     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  609-19     Citation Subset:  IM    
Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd., Osaka, Japan.
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MeSH Terms
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Cysteine / metabolism
Glucuronates / urine
Glutathione / metabolism
Herbicides / metabolism*,  urine
Phthalimides / metabolism*,  urine
Rats, Sprague-Dawley
Sulfates / metabolism,  urine
Sulfonic Acids / metabolism
Sulfur Radioisotopes
Reg. No./Substance:
0/Glucuronates; 0/Herbicides; 0/Phthalimides; 0/Sulfates; 0/Sulfonic Acids; 0/Sulfur Radioisotopes; 0YPR65R21J/sodium sulfate; 52-90-4/Cysteine; 70-18-8/Glutathione; 84478-52-4/S 23121

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