| 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. | |
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MedLine Citation:
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PMID: 8212735 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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H Yoshino; H Matsunaga; H Kaneko; A Yoshitake; I Nakatsuka; H Yamada |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Xenobiotica; the fate of foreign compounds in biological systems Volume: 23 ISSN: 0049-8254 ISO Abbreviation: Xenobiotica Publication Date: 1993 Jun |
Date Detail:
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Created Date: 1993-10-28 Completed Date: 1993-10-28 Revised Date: 2013-01-24 |
Medline Journal Info:
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Nlm Unique ID: 1306665 Medline TA: Xenobiotica Country: ENGLAND |
Other Details:
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Languages: eng Pagination: 609-19 Citation Subset: IM |
Affiliation:
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Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd., Osaka, Japan. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Chromatography, High Pressure Liquid Chromatography, Thin Layer Cysteine / metabolism Feces Female Glucuronates / urine Glutathione / metabolism Herbicides / metabolism*, urine Male Phthalimides / metabolism*, urine Rats Rats, Sprague-Dawley Sulfates / metabolism, urine Sulfonic Acids / metabolism Sulfur Radioisotopes |
| Chemical | |
Reg. No./Substance:
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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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