Mineralocorticoids

Mineralocorticoids play a major role in regulating the balance of electrolytes and water, especially in the kidneys, where they facilitate reabsorption of sodium ions and water from urine.

The main endogenic mineralocorticoid is aldosterone, which is not used in clinical medicine, however. Deoxycorticosterone is widely used.

Unlike glucocorticoids, mineralocorticoids have an insignificant effect on carbohydrate volume. They do not exhibit any anti-inflammatory or anti-allergy properties. They are used for chronic adrenal insufficiency, as well as for raising tonicity and work capacity of muscles.

The correlation between chemical structure and action of mineralocorticoids is extremely complex; however, a number of partial conclusions can be synthesized.

In particular, it should be noted that since 11-deoxycorticosterone does not exhibit glu-cocorticoid activity; yet, it is a powerful mineralocorticoid and has only two potentially reactive substituents capable of reacting with a receptor, and the interaction should occur by way of a C3-keto and/or a C17/i-CO-CH2OH groups. The necessity of either a simultaneous presence of acidic functions at C11 and C18, or the necessity of simultaneous absence of acidic functions at C11 and C17 in the structure of the pregnane system is also apparent.

Fluorination at C9a-position increases the mineralocorticoid activity of both C11-hydroxy (hydrocortisone) and C11-deoxy (deoxycorticosterone) compounds.

Aldosterone: Aldosterone, 11/i,21-dihydroxypregn-4-en-2,18,20-trione (27.2.4), is synthesized from 21-0-acetylcorticosterone, which when reacted with nitrosyl chloride in pyridine gives the nitrite 27.2.1. When photochemically irradiated, this compound is transformed to the oxime 27.2.2, which is hydrolyzed by nitrous acid and forms the semiacetal 27.2.3, which is an acetate of the desired aldosterone. Alkaline hydrolysis of the acetyl group of this compound leads to the desired aldosterone (27.2.4) [33].

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