Metabolism of p-chlorophenyl N-methylcarbamate in the chicken

Abstract

Leghorn hens were given a single oral dose of either p-chlorophenyl-14C(U) A-methylcarbamate (ring label) or p-chlorophenyl jV-methylcarbamate 14C (carbonyl label). When the carbonyl-labeled compound was administered, 69.5 % of the carbon-14 was expired during the 48-hr collection period, whereas no expiratory carbon-14 was detected when the ring-labeled compound was given. Total carbon-14 excreted in the urine accounted for 95% of the activity given as the ring-labeled compound and 14% of the activity given as the carbonyllabeled compound; the feces was a minor route of excretion in both cases (less than 2%). Carbon-14 remaining in the hens 48 hr after dosing accounted for 0.7 and 7.5% of the activity given as the ringlabeled and carbonyl-labeled compounds, respectively. Eggs collected for 8 days after dosing contained 0.27% of the carbon-14 given as a single oral dose of the ring-labeled compound. Urinary metabolites were identified as p-chlorophenyl sulfate (I), p-chlorophenyl glucuronide (II), and p-chlorophenol (III). The feces contained I, II, III, and trace amounts of the parent compound. p-Chlorophenyl-14C(U) Ar-Methylcarhamate p-Chlorophenyl A'-Methylcarbamate-14C % dose/g

Metabolism of p-chlorophenyl N-methylcarbamate in the rat and goat

“…Therefore, knowledge of the metabolic fate of this compound in animals is essential. The metabolism of this compound in the chicken has been reported previously (Paulson and Zehr, 1971). This study was initiated to determine the metabolic fate of p-chlorophenyl /V-methylcarbamate in the rat and goat.…”

“…The p-chlorophenyl /V-methylcarbamate, p-chlorophenyl-14C(U) /V-methylcarbamate, and p-chlorophenyl /V-methylcarbamate-14C were supplied by PPG Industries, Inc. The radioactive chemicals were shown to be greater than 99% pure, as previously described (Paulson and Zehr, 1971). The sources of other chemicals and supplies were as follows: H235S04, New England Nuclear Corp.; 4-chlorocatechol, Pfaltz and Bauer, Inc.; dicyclohexylcarbodiimide, Eastman Organic Chemicals; dimethylformamide (DMF), Fisher Scientific Co.; Bio-Gel P-2 (100-200 mesh) and Cellex-GE, Bio-Rad Laboratories; polyethylene glycol (average molecular weight, 380-420), Matheson Coleman and Bell.…”

“…The sources of other chemicals and supplies were as follows: H235S04, New England Nuclear Corp.; 4-chlorocatechol, Pfaltz and Bauer, Inc.; dicyclohexylcarbodiimide, Eastman Organic Chemicals; dimethylformamide (DMF), Fisher Scientific Co.; Bio-Gel P-2 (100-200 mesh) and Cellex-GE, Bio-Rad Laboratories; polyethylene glycol (average molecular weight, 380-420), Matheson Coleman and Bell. The sources of other chemicals and supplies were as previously described (Paulson and Zehr, 1971).…”

“…Synthesis and Characterization of Chemicals. Potassium p-chlorophenyl sulfate, p-chlorophenyl glucuronide, p-chlorophenol-14C(U), and p-chlorophenyl-14C(U)-2-cyclopentyl acetate were synthesized as previously described (Paulson and Zehr, 1971). The method of Sullivan et al (1967) synthesize p-chlorophenyl /V-acetyl /V-methylcarbamate an 4-chloro-l ,2-diacetoxybenzene.…”

“…The urine, collected from 0 to 6 hr after dosing, was extracted three times with an equal volume of diethyl ether. The ether-soluble metabolite was derivatized with 2-cyclopentylacetyl chloride, purified, and characterized as previously described (Paulson and Zehr, 1971). After ether extraction, the radio-labeled metabolites in the aqueous phase were separated and purified by a series of column chromatographic procedures outlined in Figure 3.…”