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Journal of Pharmacology And Experimental Therapeutics, Vol. 167, Issue 2, 207-216, 1969
Copyright © 1969 by American Society for Pharmacology and Experimental Therapeutics

METABOLISM OF ANTIFERTILITY STEROIDS I. NORETHYNODREL

KEITH H. PALMER 1, FRANCES T. ROSS 1, L. SUE RHODES 1, BILLY BAGGETT 1, and MONROE E. WALL 1

1 Chemistry and Life Sciences Laboratory, Research Triangle Institute, Research Triangle Park, North Carolina

The in vivo and in vitro metabolism of norethynodrel has been studied in detail, and the configuration and conformation of the major metabolites were established. In both the in vivo and in vitro studies, initial concentration of the ethynyl steroidal fractions was facilely obtained by use of silver nitrate-silica gel columns, further purification being effected by alumina chromatography. Only traces of unchanged norethynodrel were found. The major ethynyl steroidal metabolites from in vitro liver homogenate studies were isolated in pure form and were found to be identical to the product obtained by sodium borohydride reduction of norethynodrel. By means of proton nuclear magnetic resonance spectra and mass spectra studies, the configurations of the metabolites were unequivocally established as 17agr-ethynyl-3agr, 17beta-dihydroxy-Dgr5(10)-estrene and 17agr-ethynyl-3beta, 17beta-dihydroxy-Dgr5(10)-estrene. The conformation of the 3agr-hydroxyl group was shown to be equatorial and that of the 3beta-epimer to be axial.

Submitted on October 17, 1968
Accepted on February 5, 1969




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Copyright © 1969 by the American Society for Pharmacology and Experimental Therapeutics.