Metabolism of o-, m- and p-fluoro-, bromo- and -iodo-nitrobenzenes in the rabbit.

doi:10.1042/BJ0680561B

Paper

Metabolism of o-, m- and p-fluoro-, bromo- and -iodo-nitrobenzenes in the rabbit.

Published Apr 1, 1958 · H. G. Bray, S. James, W. Thorpe

The Biochemical journal

Q1 SJR score

15

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0

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Abstract

In a study of the metabolism of the 19 members of the chloromononitrobenzene series (for summary and references see Table 4 of Bray, James & Thorpe, 1957 b) it was observed that in the rabbit several compounds were converted into mercapturic acids by replacement of a relatively labile chlorine atom. The formation of mercapturic acid by acetylcysteyldebromination of4-bromo-3:5-dichloronitrobenzene (Betts, Bray, James & Thorpe, 1957) and of 2-bromo-4-chloro-, 2-bromo-5-chloroand 4-bromo-3-chloro-nitrobenzene (Bray, James & Thorpe, 1957 a) has also been noted. It was therefore of interest to examine the metabolic fate of some other halogenonitrobenzenes with particular reference to the formation of mercapturic acids. For this purpose the monohalogenonitrobenzenes were chosen since they were more readily available than polyhalogenonitrobenzenes. Some preliminary experimnents have been reported by Bray & James (1957). Betts et al. (1957) found that in the rabbit 2:4:5and 2:4:6-trichloronitrobenzene yielded metabolites in which a chlorine atom was replaced by an hydroxyl group. The present investigation has revealed further examples of hydroxyldehalogenation.

Study Snapshot

In the rabbit, o-, m-, and p-fluoro-, bromo-, and -iodo-nitrobenzenes undergo hydroxyldehalogenation, resulting in mercapturic acids.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Metabolism of o-, m- and p-fluoro-, bromo- and -iodo-nitrobenzenes in the rabbit.

References

Citations

In vitro metabolism of 5-fluoro-2-glutathionyl-nitrobenzene by kidney proximal tubular cells studied by 19F-NMR.

The absence of mercapturic acid formation in LLCPK 1 cells and cultured renal proximal tubular cells is due to a decline in N-acetyltransferase activity and possibly deficient cellular uptake of cysteine conjugate.

Thioethers as urinary metabolites of thiophene and monobromothiophenes.

Thioethers are more abundant in urine than thiophene in rats, with S-substituted N-acetyl-L-cysteines not being significant metabolites.

Drug-protein conjugates--X. The role of protein conjugation in the disposition of dinitrofluorobenzene.

Dinitrofluorobenzene is rapidly metabolized in rats, with significant protein binding and metabolite elimination in bile and urine.

Biotransformation, transport and toxicity studies in rat renal proximal tubular cells

In vitro models of renal toxicity should consider the role of functional transport systems, as current models often overlook this aspect.

Different metabolic pathways of 2,5-difluoronitrobenzene and 2,5-difluoroaminobenzene compared to molecular orbital substrate characteristics.

The metabolic pathways of 2,5-difluoronitrobenzene and 2,5-difluoroaminobenzene differ based on their chemical characteristics, with cytochrome P450 hydroxylation for aminobenzene and glutathione conjugation for nitrobenzene.

Glutathione and mercapturic acid conjugations in the metabolism of 2,4-dinitrobromobenzene.

GSH conjugate is the major metabolic pathway in the detoxification of 2,4-dinitrobromobenzene, with mercapturic acid being the major radioactive metabolite in urine.

Mercapturic Acid Conjugation

Mercapturic acids are excreted from bromobenzene and chlorobenzene as unstable complexes of acetylcysteine, with iodobenzene, 1:2-dichlorobenzene, and 1:3; dichlorobenzene also