Epoxidation of the lindane metabolite, beta-PCCH, by human- and rat-liver microsomes. 1984

J F Fitzloff, and J C Pan

Human- and rat-liver microsomes convert the lindane metabolite, beta-PCCH (beta-1,3,4,5,6-pentachlorocyclohex-1-ene (3,4,6/5-PCCH] to the metabolites: 1,2,4-TCB (1,2,4-trichlorobenzene), 1,2,3,4-TTCB (1,2,3,4-tetrachlorobenzene), 2,4,5-TCP (2,4,5-trichlorophenol), 3,4,5/6-PCCOL (1,2,4,5,6-pentachlorocyclohex-1-en-3-ol) and beta-PCCH oxide (1,2,3,4,5-pentachloro-7-oxabicyclo[4.1.0]heptane) or (3,4,6/5-PCCH oxide). The identity of the beta-PCCH oxide is confirmed by column chromatography and g.l.c.-mass spectrometry, in comparison to characterized synthetic material. The stability of the beta-PCCH oxide is indicated by its resistance to hydrolysis by microsomal epoxide hydrolase (EC. 3.3.2.3), or various aqueous acid conditions. It shows no mutagenicity using S. typhimurium strain TM677. However, in levels above 0.05 mg/ml it was lethal to the test cells. It is not a substrate for and is only a weak inhibitor of epoxide hydrolase. A stable halogenated hydrocarbon epoxide metabolite is described. Its toxicological role, if any, remains unaccounted for.

UI MeSH Term Description Entries
D008297 Male Males
D008862 Microsomes, Liver Closed vesicles of fragmented endoplasmic reticulum created when liver cells or tissue are disrupted by homogenization. They may be smooth or rough. Liver Microsomes,Liver Microsome,Microsome, Liver
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009152 Mutagenicity Tests Tests of chemical substances and physical agents for mutagenic potential. They include microbial, insect, mammalian cell, and whole animal tests. Genetic Toxicity Tests,Genotoxicity Tests,Mutagen Screening,Tests, Genetic Toxicity,Toxicity Tests, Genetic,Genetic Toxicity Test,Genotoxicity Test,Mutagen Screenings,Mutagenicity Test,Screening, Mutagen,Screenings, Mutagen,Test, Genotoxicity,Tests, Genotoxicity,Toxicity Test, Genetic
D011919 Rats, Inbred Strains Genetically identical individuals developed from brother and sister matings which have been carried out for twenty or more generations or by parent x offspring matings carried out with certain restrictions. This also includes animals with a long history of closed colony breeding. August Rats,Inbred Rat Strains,Inbred Strain of Rat,Inbred Strain of Rats,Inbred Strains of Rats,Rat, Inbred Strain,August Rat,Inbred Rat Strain,Inbred Strain Rat,Inbred Strain Rats,Inbred Strains Rat,Inbred Strains Rats,Rat Inbred Strain,Rat Inbred Strains,Rat Strain, Inbred,Rat Strains, Inbred,Rat, August,Rat, Inbred Strains,Rats Inbred Strain,Rats Inbred Strains,Rats, August,Rats, Inbred Strain,Strain Rat, Inbred,Strain Rats, Inbred,Strain, Inbred Rat,Strains, Inbred Rat
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D004355 Drug Stability The chemical and physical integrity of a pharmaceutical product. Drug Shelf Life,Drugs Shelf Lives,Shelf Life, Drugs,Drug Stabilities,Drugs Shelf Life,Drugs Shelf Live,Life, Drugs Shelf,Shelf Life, Drug,Shelf Live, Drugs,Shelf Lives, Drugs
D004852 Epoxy Compounds Organic compounds that include a cyclic ether with three ring atoms in their structure. They are commonly used as precursors for POLYMERS such as EPOXY RESINS. Epoxide,Epoxides,Epoxy Compound,Oxiranes,Compound, Epoxy,Compounds, Epoxy
D004988 Ethers, Cyclic Compounds of the general formula R-O-R arranged in a ring or crown formation. Cyclic Ether,Cyclic Ethers,Ether, Cyclic
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man

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