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Exp Clin Endocrinol Diabetes 1983; 81(2): 168-174
DOI: 10.1055/s-0029-1210222
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© J. A. Barth Verlag in Georg Thieme Verlag KG Stuttgart · New York

Studies on Biotransformation of STS 557

K. Schubert, G. Hobe, G. Kaufmann, G. Schumann, K. Weherberger, C. Hörhold
  • Academy of Sciences of the GDR, Research Centre of Molecular Biology and Medicine, Central Institute of Microbiology and Experimental Therapy (Director: Prof. Dr. U. Taubeneck), Jena/GDR
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Publication History

1982

Publication Date:
17 July 2009 (online)

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Summary

Transformation of STS 557 (17α-cyanomethyl-17β-hydroxy-estra-4, 9-dien-3-one) by female rat liver microsomes demonstrates a lower transformation rate in comparison with the analogous compound without 9-double bond: 17α-cyanomethyl-19-nortestosterone, and the basic substance: 19-nortestosterone. 17α-Cyanomethyl-estra-1, 3,5(10), 9(11)-tetraene-3, 17β-diol, 17α-cyanomethyl-11β, 17β-dihydroxy-estra-4, 9-dien-3-one, and tentatively 17α-cyanomethyl-6α, 17βdthydroxy-estra-4, 9-then- 3-one were identified as metabolites.

Microbial model investigations with species known to hydrogenate the 4.double bond in 4-en- 3-oxo steroids stereospecifically to 5αH- or 5αH-metabolites indicate 5β-hydrogenation to be prevented in STS 557 by the 9-double bond, whereas 5β-hydrogenation is not affected.

Isolation and characterization of metabolites from beagle dog and rat urine following administration of 3H-STS 557 revealed the following pathways of biotransformation: Hydroxylation in different positions of the steroid molecule, aromatization of ring A, hydrogenation of a double bond, simultaneous hydroxylation and hydrogenation, and alteration of the 17α-side chain with loss of nitrogen.

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