Metabolism of chlorodiphenyl ethers and Irgasan DP 300.
1. In the rat chlorodiphenyl ethers are metabolized via two routes. The predominant reaction is aromatic hydroxylation; scission of the ether bond is a minor metabolic process. 2. In all cases, primary hydroxylation takes place ortho and meta to the ether bond. Ortho-hydroxylation leads to the formation of 'predioxins' in cases where the parent compounds contain a chlorine atom in one of the ortho positions in the second ring. 3. 5-Chloro-2-(2,4--dichlorophenoxy)phenol (Irgasan DP 300), a compound that meets the structural requirements of a predioxin, did not yield chlorodibenzo-p-dioxins or hydroxylated derivatives thereof. 4. Irgasan DP 300 is excreted unchanged in faeces and urine (partly conjugated) but is also hydroxylated to five different monohydroxy metabolites which were found in urine; three of these were also present in faeces. As a result of scission of the ether bond 2,4-dichlorophenol occurred in urine and faeces, and 4-chlorocatechol in urine. 5. Neither in the case of Irgasan DP 300, nor in that of chlorodiphenyl ethers with an ortho chlorine atom, could metabolic cyclization to chlorodibenzofurans or their hydroxylated derivatives be detected.
D000273:Adipose Tissue / Q000378:metabolism; D000818:Animals; D001572:Benzofurans / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D002713:Chlorine / Q000378:metabolism; D005243:Feces / Q000378:metabolism; D006900:Hydroxylation; D008099:Liver / Q000378:metabolism; D010647:Phenyl Ethers / Q000378:metabolism*; D000072317:Polychlorinated Dibenzodioxins / Q000031:analogs & derivatives / Q000378:metabolism; D051381:Rats; D014260:Triclosan / Q000378:metabolism*
D001572:Benzofurans; D010647:Phenyl Ethers; D000072317:Polychlorinated Dibenzodioxins; D014260:Triclosan; D002713:Chlorine