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.

  title={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.},
  author={H. Yoshino and H. Matsunaga and H. Kaneko and A. Yoshitake and I. Nakatsuka and H. Yamada},
  journal={Xenobiotica; the fate of foreign compounds in biological systems},
  volume={23 6},
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… Expand
Metabolism of N-[4-chloro-2-fluoro-5-[(1-methyl-2-propynyl)oxy]phenyl]-3,4,5,6- tetrahydrophthalimide (S-23121) in the rat. II. Absorption, disposition, excretion and biotransformation.
The radiocarbon was almost completely eliminated from the rat within 7 days after administration for both dose groups and sulphonic acid conjugates were not detected in urine, blood, kidney or liver. Expand
Metabolism of tetramethrin isomers in rat. I. Identification of a sulphonic acid type of conjugate and reduced metabolites.
The major biotransformation reactions of trans-tetramethrin in rats are: cleavage of the ester linkage, hydroxylation of the cyclo hexene or cyclohexane ring of the 3,4,5,6-Tetrahydrophthalimide moiety, oxidation at the methyl group of the isobutenyl moiety and reduction at the 1,2-double bond. Expand
Identification of two new types of S-linked conjugates of Etoc in rat.
Two major metabolites of 14C-labelled (4S,1R)-trans-Etoc were purified using a combination of chromatographic techniques and identified by spectroanalysis, establishing new types of S-linked conjugates (sulphonic acid and mercapturic acid types). Expand
Metabolism of tetramethrin isomers in rat: II. Identification and quantitation of metabolites.
The radiocarbon was almost completely eliminated from rat within 7 days after administration in all groups and sulphonate derivatives in the faeces, and in the urine, alcohols, dicarboxylic acid and reduced metabolites derived from the 3,4,5,6-tetrahydrophthalimide moiety were found. Expand
Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites.
(R)-(+)-Menthofuran is a metabolite of (R)-(+)-pulegone, the chief constituent of pennyroyal oil. Menthofuran has been shown to account for a significant percentage of pulegone toxicity throughExpand
Metabolism, Pharmacokinetics, and Excretion of a Cholesteryl Ester Transfer Protein Inhibitor, Torcetrapib, in Rats, Monkeys, and Mice: Characterization of Unusual and Novel Metabolites by High-Resolution Liquid Chromatography-Tandem Mass Spectrometry and 1H Nuclear Magnetic Resonance
Torcetrapib was not detected in the urine and/or bile across species, suggesting that it is primarily cleared by metabolism in these species, and a mechanism for the formation of an unusual metabolite M28 has been proposed. Expand
Xenobiotic C-sulfonate derivatives; metabolites or metabonates?
  • S. Mitchell
  • Chemistry, Medicine
  • Xenobiotica; the fate of foreign compounds in biological systems
  • 2018
The potential mechanisms of formation of these C-sulfonates are discussed, both biological and chemical; the potential role of the gut microbiome raised and hopefully by highlighting this curiosity further fruitful investigation will be stimulated. Expand
Metabolism and disposition of juglone in male F344 rats
The metabolism and disposition of 14C-labelled juglone in male F344 rats following oral, intravenous and dermal administration were studied and high concentrations of jugl one-derived radioactivity were found in kidney for all three dosing routes. Expand
Identification of a rare sulfonic acid metabolite of andrographolide in rats.
The metabolites of andrographolide in rats after single oral doses of 120 mg/kg were investigated and the main metabolite was 14-deoxy-12(R)-sulfo androg grapholide, a rare metabolic reaction that may be the main metabolic pathway in rats. Expand
Four new andrographolide metabolites in rats
Four new sulfonate metabolites of andrographolide, 14-deoxy-12(R)-sulfo andrographolide (Metabolite 1), 14-deoxy-12(S)-sulfo andrographolide (Metabolite 2), 14-deoxy-12(R)-sulfo-9(S)-andrographolideExpand


Identification of metabolites from salts of pyridine-2-thiol-1-oxide following intravenous and dermal adminstration to swine.
Chromatographic evidence indicated that the major metabolites were 2,2′-pyridyldisulfide and 2-(pyridyl-N-oxide) sulfonic acid. Expand
(E)-1-(2,4-Dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol (S-3308L) の (R) および (S) 異性体のラットにおける代謝
(R)-および (S)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol (以下 (R)-Eおよび (S)-Eと略す) のベンゼン環またはトリアゾール環14C標識体を5および125mg/kgの割合で雌雄ラットに経口投与し, 体内動態を調べた. 糞および尿への14C排泄,Expand
Age-related changes in metabolism of diethofencarb: relationship between metabolism in rat and hepatic drug-metabolizing enzyme activities.
Results show that age-related differences in the ratios of urinary metabolites of DFC resulted to some extent from changes in the hepatic drug-metabolizing enzyme activities. Expand
Substrate specificity for formation of cholesterol ester conjugates from fenvalerate analogues and for granuloma formation.
Cholesterol ester formation in vitro from these fenvalerate analogues was well correlated with granuloma formation observed when the analogues were given to mice at 3000 ppm for a month. Expand
The Metabolism of Sulfate
Sulfate is utilized by living systems to form sulfate esters of polysaccharides, phenols, steroids, and other organic compounds through a series of activation and transfer reactions which will be discussed sub­ sequently. Expand
Two‐dimensional spectroscopy. Application to nuclear magnetic resonance
The possibilities for the extension of spectroscopy to two dimensions are discussed. Applications to nuclear magnetic resonance are described. The basic theory of two‐dimensional spectroscopy isExpand