Deoxycorticosterone

Cortisol-Cortisone Conversion. Under normal conditions, this equilibrium slightly favors the oxidized compound. Similarly, the conversion of corticosterone to 11-deoxycorticosterone is also mediated by the liP-hydroxysteroid dehydrogenase enzyme system and requites NAD(P) /NAD(P)H. This conversion is especially important both in the protection of the human fetus from excessive glucocorticoid exposure, and in the protection of distal nephron mineral ocorticoid receptors from glucocorticoid exposure (14). The impairment of this conversion is thought to result in hypertension associated with renal insufficiency (15). 

DOC Deoxycorticosterone TEBG Testosterone-estrogen-binding globulin... 

All these steroids disappear from the brain in animals after removal of the adrenals or gonads (ovary and testis). This also applies to tetrahydrodeoxycorticosterone for although it is formed by reduction of deoxycorticosterone within the brain, its synthesis depends on that steroid coming from the blood. 

The zona glomerulosa is responsible for the production of the mineralocorticoids aldosterone, deoxycorticosterone, and 18-hydroxy-deoxycorticosterone. Aldosterone promotes renal sodium retention and excretion of potassium. Its synthesis and release are regulated by renin in response to decreased vascular volume and renal perfusion. Adrenal aldosterone production is regulated by the renin-angiotensin-aldosterone system. 

Of several related steroids in the defensive secretion of dytiscid beetles, deoxycorticosterone was most effective. It deterred simfish from feeding in 94% of the tests. Other steroids (pregnolones) that differed only by lacking a keto group at one carbon atom were either intermediate or not active at all (Gerhart etal., 1991). 

Drugs belonging to this class are glucocorticoids (hydrocortisone, 11-dehydrocorti-costerone, corticosterone), mineralocorticoids (aldeosterone, 11-deoxycorticosterone, ll-deoxy-17-oxycorticosterone), and sex hormons (androsterone, androstendion, estrone, progesterone). 

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

In particular, it should be noted that since 11-deoxycorticosterone does not exhibit glucocorticoid 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 Cj-keto and/or a Ci7j3-C0-CH20H groups. The necessity of either a simultaneous presence of acidic functions at Cu and or the necessity of simultaneous absence of acidic functions at and C17 in the structure of the pregnane system is also apparent. 

Fluorination at Cja-position increases the mineralocorticoid activity of both Cji-hydroxy (hydrocortisone) and C -deoxy (deoxycorticosterone) compounds. 

For a number of reasons, aldosterone is practically never used as a therapeutic agent for correcting electrolytic irregularities in adrenal insufficiency, for which deoxycorticosterone and fludrocortisone are more frequently used. 

Deoxycorticosterone Desoxycorticosterone, 21-hydroxypregn-4-en-3,20-dione acetate (27.2.6), is synthesized in a number of ways, the easiest of which being iodination of progesterone at C21 in the methyl group, and subsequent reaction of the resulting iodo-derivative 27.2.5 with potassium acetate, which leads to formation of the desired desoxycorticosterone in the form of the acetate (27.2.6) [34]. 

The first behavioral observations related to these steroids date back to Se-lye, who over 50 years ago reported that progesterone and deoxycorticosterone... 

Wittig-Horner reaction (see p. 241). Photolysis of the nitrite of the 21-chloro-20-hydroxy-compound (194) gave the 18-oximino-compound (195) which on Jones oxidation was converted into the chlorolactone (196). Hypoiodite reaction of the 21-chloro-20-hydroxy-compound (194) also gives the chloro-lactone (196) which with modification gives 18-hydroxy-11-deoxycorticosterone (see also ref. 198). 

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