title: [The biotransformation of STS 267 [16 alpha-azido-3-methoxyestra-1,3,5(10)-triene-17-one]. Epimerization of a 16 alpha-azido group--a new metabolic reaction in the rat liver].
abstract: STS 267 [1; 16 alpha-azido-3-methoxy-estra-1,3,5(10)-trien-17-one] was found to have lipid shifting and fertility inhibitory effects in rats. In preclinical studies the metabolic fate of 1 was investigated in the rat. Demethylation in 3-position, reduction of the 17-carbonyl to the 17 beta-hydroxyl group, and for the first time the epimerization of the 16 alpha-azido to the 16 beta-azido group were established following perfusion of STS 267 in the isolated rat liver. From the perfusion medium 16 alpha-azido-estra-1,3,5(10)-trien-3-ol-17-one (2), 16 alpha-azido-estra-1,3,5(10)-trien-3,17 beta-diol (3), 16 beta-azido-3-methoxy-estra-1,3,5(10)-trien-3,17 beta-diol (4) and 16 beta-azido-estra-1,3,5(10)-trien-3,17 beta-diol (5) as the main metabolite were isolated by TLC and identified by comparison with authentic samples. The extent of the hepatic extraction of 1 in the rat liver was significant lower compared with mestranol.
authors.affiliation: Akademie der Wissenschaften der DDR, Zentralinstitut für Mikrobiologie und experimentelle Therapie, Jena.
authors.forename: W
authors.initials: W
authors.lastname: Schumann
mesh_terms: D000818:Animals; D001386:Azides / Q000378:metabolism*; D001711:Biotransformation; D003270:Contraceptive Agents / Q000378:metabolism*; D004970:Estrone / Q000031:analogs & derivatives*; D006894:Hydroxyestrones / Q000378:metabolism*; D000960:Hypolipidemic Agents / Q000378:metabolism*; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism*; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D013237:Stereoisomerism
chemical_list: D001386:Azides; D003270:Contraceptive Agents; D006894:Hydroxyestrones; D000960:Hypolipidemic Agents; D004970:Estrone; C057241:STS 267
vernacular_title: Zur Biotransformation von STS 267 [16 alpha-Azido-3-methoxyestra-1,3,5(10)-trien-17on]. Epimerisierung einer 16 alpha-Azidogruppe--eine neue Stoffwechselreaktion in der Rattenleber.