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Crystallographic Characterization of Trilostane and Derivatives
Author(s) -
Jopp Melanie,
Becker Jonathan,
Lerch Markus,
Miska Andreas,
Hausmann Heike,
Neiger Reto,
Schindler Siegfried
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601976
Subject(s) - metabolite , chemistry , steroid , aldosterone , medicine , endocrinology , stereochemistry , biochemistry , hormone
Trilostane, 2 α ‐cyano‐4 α ,5 α ‐epoxy‐17 β ‐hydroxyandrostan‐3‐one, as a synthetic steroid analogue, competitively inhibits the synthesis of several steroids, including cortisol and aldosterone. In veterinary medicine, trilostane has been used successfully to treat hypercortisolism. Trilostane is metabolized by the liver, producing the major metabolite ketotrilostane, 2 α ‐cyano‐4 α ,5 α ‐epoxyandrostane‐3,17‐dione, which is excreted by the liver. The parent compound and the major metabolite undergo metabolic interconversion. Pyridinium chlorochromate oxidation gave the α,β ‐unsaturated cyanoketone, which was hydrogenated to yield ketotrilostane. For the first time, all steroids were structurally characterized by X‐ray crystallography. Furthermore, a new derivative of trilostane could be synthesized and was structurally characterized.