SOME CORRELATIONS BETWEEN CHEMICAL STRUCTURE AND MAXIMAL EOSINOPENIA IN ADRENALECTOMIZED AND HYPOPHYSECTOMIZED MICE

¹ Departments of Medicine at the Harvard Medical School and the Peter Bent Brigham Hospital, Boston, Massachusetts, and the Department of Physiology of the University of Minnesota, Minneapolis 14, Minn.

1. A comparison of the first two sections with the third section in table 1 reveals that the chemical characteristics common to all the steroids which bring about maximal eosinopenia can be summarized as follows: (a) They contain 21 carbon atoms in the molecule; (b) They have a side chain of a primary hydroxyl group vicinal to a carbonyl oxygen group (primary alpha-ketol grouping); (c) They are unsaturated at C₄; (d) They are either four or five oxygen compounds; (e) They all have oxygen at C₃; (f) They all have oxygen at C₁₁.

2. Maximal eosinopenic activity depends upon the position rather than upon the total number of oxygens in the molecule. All the steroids found to bring about maximal eosinopenia are 11-oxycompounds. None of the 11-desoxycompounds examined induced maximal eosinopenia.

3. (a) Oxygen at C₁₇, in the absence of oxygen at C₁₁, does not render a steroid maximally eosinopenic, even when it increases the total number of oxygen atoms in the molecule to four or five. (b) In the presence of oxygen at C₁₁, additional oxygen at C₁₇ enhances (that is prolongs) activity.

4. The alcoholic as well as the ketonic oxygen at C₁₁ in the corticoid molecule is compatible with maximal eosinopenic activity.

5. The relationship between chemical structure and maximal eosinopenic activity (as defined in this paper) is similar to the generally accepted relationship between chemical structure and glycogenic activity of corticoids as tested in adrenalectomized mice. The essential requisite for both these effects is the oxygen substitution of the corticoid molecule at C₁₁. Both these effects are enhanced by oxygen substitution at C₁₇, in the presence of oxygen at C₁₁.

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