Formation of pentachlorophenol as the major product of microsomal oxidation of hexachlorobenzene.
On incubation of [14C]-hexachlorobenzene with microsomes from livers of rats induced with hexachlorobenzene, the major product (80-90%) was pentachlorophenol. The only other detectable metabolite, tetrachlorohydroquinone (4-15%), was presumably formed from pentachlorophenol. A considerable amount of radioactivity (5-10% of the amount of extracted metabolites) was covalently bound to protein. Microsomes derived from male hexachlorobenzene--induced rats gave by far the highest conversion (approx. 1% of substrate). Microsomes from female hexachlorobenzene--induced rats were 3 times less efficient. Microsomes from untreated and 3-methyl-cholanthrene--treated animals gave less than 5% of the amount of pentachlorophenol formed by microsomes from hexachlorobenzene--induced male rats, while phenobarbital and aroclor 1254-induction resulted in formation of 51% and 34% respectively.
D000818:Animals; D001140:Aroclors / Q000494:pharmacology; D002722:Chlorobenzenes / Q000378:metabolism*; D020111:Chlorodiphenyl (54% Chlorine); D002733:Chlorophenols / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D005260:Female; D006581:Hexachlorobenzene / Q000378:metabolism*; D008297:Male; D008748:Methylcholanthrene / Q000494:pharmacology; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism*; D009249:NADP / Q000378:metabolism; D010416:Pentachlorophenol / Q000378:metabolism*; D010634:Phenobarbital / Q000494:pharmacology; D011506:Proteins / Q000378:metabolism; D051381:Rats; D011919:Rats, Inbred Strains; D012737:Sex Factors
D001140:Aroclors; D002722:Chlorobenzenes; D002733:Chlorophenols; D011506:Proteins; D020111:Chlorodiphenyl (54% Chlorine); D006581:Hexachlorobenzene; D009249:NADP; D008748:Methylcholanthrene; D010416:Pentachlorophenol; D010634:Phenobarbital