title: Metabolism of N-[(R)-1-(2,4-dichlorophenyl)ethyl]-2-cyano-3,3-dimethylbutanamide (Delaus, S-2900) and its isomer, N-[(S)-1-(2,4-dichlorophenyl)ethyl]-2-cyano-3,3-dimethylbutanamide (S-2900S), in rats. 1. Identification of metabolites in feces and urine.
abstract: Rats were orally dosed with a 1:1 diastereomixture of N-[(R)-1-(2,4-dichlorophenyl)ethyl]-2-cyano-3,3-dimethylbutanamide (Delaus, S-2900) and N-[(S)-1-(2,4-dichlorophenyl)ethyl]-2-cyano-3,3-dimethylbutanamide (S-2900S), both labeled with 14C, at 200 mg/kg/day for 5 consecutive days, and 16 metabolites in urine and feces were purified by a combination of several chromatographic techniques. The chemical structures of all isolated metabolites were identified by spectroanalyses (NMR and MS). Several of them were unique decyanated and/or cyclic compounds (lactone, imide, cyclic amide, cyclic imino ether forms). Major biotransformation reactions of the mixture of S-2900 and S-2900S in rats are proposed on the basis of the metabolites identified in this study.
authors.affiliation: Environmental Health Science Laboratory, Sumitomo Chemical Company, Ltd., 1-98, 3-Chome, Kasugade-Naka, Konohana-Ku, Osaka 554-8558, Japan. tomigahara@sc.sumitomo-chem.co.jp
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Tomigahara
authors.forename: Naohiko
authors.initials: N
authors.lastname: Isobe
authors.forename: Hideo
authors.initials: H
authors.lastname: Kaneko
authors.forename: Iwao
authors.initials: I
authors.lastname: Nakatsuka
mesh_terms: D000818:Animals; D002073:Butanes / Q000032:analysis / Q000378:metabolism* / Q000652:urine; D002250:Carbon Radioisotopes; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005243:Feces / Q000737:chemistry*; D005260:Female; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D015394:Molecular Structure; D009570:Nitriles / Q000032:analysis / Q000378:metabolism* / Q000652:urine; D051381:Rats; D017207:Rats, Sprague-Dawley
chemical_list: D002073:Butanes; D002250:Carbon Radioisotopes; C512249:N-((R)-1-(2,4-dichlorophenyl)ethyl)-2-cyano-3,3-dimethylbutanamide; D009570:Nitriles