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Query: UMLS:C0338671 (Steroids)
 9,479 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

The biliary metabolites of tritiated-6,7-estriol were identified following the administration of the estrogen to rats. Glucosiduronate conjugate fraction constituted approximately 70% of the excreted metabolites. The primary metabolite found in this conjugate fraction was 3,17beta-dihydroxy-2-methoxy-1,3,5(10)-estratrien-16-one. There were also significant amounts of 3,17beta-dihydroxy-1,3,5,(10-estratrien-16-one and 2,3,17beta-trihydroxy-1,3,5(10)-estratrien-16-one. Smaller amounts of 1,3,5(10)-estratriene-2,3,16alpha,17beta-terol and 2-methoxy-1,3,5(10)-estratriene-3,16alpha,17beta-triol were also present. The administration of 17alpha-ethinyl estradiol reduced the rate of excretion of radioactivity and the proportion of 16-oxo-17-beta-ol metabolites in the glucosiduronate fraction.
Steroids 1976 May
PMID:Biliary metabolites of estriol in the rat. 94 Nov 79

By condensing 3 alpha,21-dihydroxy-5 beta-pregnan-20-one, or its appropriate monoacetate, with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucuronate in the Koenigs-Knorr reaction beta-D-glucosiduronates 10, 4, and 7 were obtained as polyacetate methyl esters. Alkaline hydrolysis of these substances cleaved the ester groups and gave the corresponding steroidal glucosiduronic acids 12, 6 and 8. Upon treatment with diazomethane, these acids produced the equivalent methyl esters. The C-3, the C-21 and the C-3,21 glucosiduronates of 3 alpha,21-dihydroxy-5 beta-pregnan-11,20-dione were prepared by previously reported methods and converted into the corresponding C-20 semicarbazones (14, 20 and 26). With C-20 stabilized by the semicarbazone group against reduction, it was possible to reduce the 11-oxo function in these substances to an 11 beta-hydroxyl group; after removal of the semi-carbazone moiety from these products at pH 2.0, glucosiduronic acids 18, 22 and 28 were obtained. The mass spectra of a representative group of the mono- and diglucosiduronic acids and esters were determined by utilizing fast atom bombardment and monitoring ions in both positive and negative modes of operation.
Steroids 1983 Oct
PMID:Synthesis of mono- and diglucosiduronates of metabolites of deoxycorticosterone and corticosterone and analysis by a new mass spectrometric technique. 667 43

On treatment with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucuronate and silver carbonate, tetrahydrocortisone 21-acetate gave the corresponding 3-glucosiduronate triacetyl methyl ester. This product was converted into the 20-semicarbazone which, by treatment with alkali to hydrolyze the ester functions and acid to hydrolyze the semicarbazone moiety, gave tetrahydrocortisone 3-glucosiduronic acid. The acid was converted into the crystalline barium salt and into the methyl ester. An analogous series of reactions was carried out on tetrahydrocortexolone 21-acetate. Treatment of the 20-semicarbazone of tetrahydrocortisone 3-glucosiduronic acid with potassium borohydride reduced the 11-oxo function to an 11 beta hydroxyl group; acid-catalyzed removal of the semicarbazone group produced tetrahydrocortisol 3-glucosiduronic acid which also was obtained as the barium salt and the methyl ester.
Steroids 1982 Jul
PMID:C-3 glucosiduronates of metabolites of adrenal steroids. 715 44