Formation of benzophenone and alpha, alpha-diarylacetophenone metabolites of the antiestrogen nitromiphene (CI628) in the presence of rat cecal contents.
Incubation of the nonsteroidal antiestrogen nitromiphene (CI628) with rat cecal content suspension under aerobic or anaerobic conditions resulted in extensive biotransformation, yielding three metabolites, as determined by thin-layer chromatography. These metabolites were not recovered from incubation mixtures containing previously frozen suspension, and recoveries were decreased (that of nitromiphene was increased) when incubations were carried out in the presence of 2mM EDTA. Spectral and chromatographic comparison of two of the purified metabolites resulted in their structural characterization, as p-[beta(N-pyrrolidinyl)ethoxy]p'-methoxybenzophenone, and a similarly substituted alpha, alpha-diphenyl-acetophenone. These metabolites are, in turn, due formally to ethylenic bond cleavage and nitro group reduction/hydrolysis of nitromiphene.
D000332:Aerobiosis; D000693:Anaerobiosis; D000818:Animals; D001419:Bacteria / Q000378:metabolism; D001711:Biotransformation; D002432:Cecum / Q000382:microbiology*; D004492:Edetic Acid / Q000494:pharmacology; D008297:Male; D009594:Nitromifene / Q000031:analogs & derivatives / Q000378:metabolism*; D011759:Pyrrolidines / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains
D011759:Pyrrolidines; C039220:4-(beta(N-pyrrolidinyl)ethoxy)-4'-methoxybenzophenone; D009594:Nitromifene; C039835:2-(4-methoxyphenyl)-4'-(2-(1-pyrrolidinyl)ethoxy)deoxybenzoin; D004492:Edetic Acid