Progesterone 17a-hydroxy

J2. Jailer, J. W., Gold, J. J., Vande Wiele, R., and Lieberman, S. 17a-Hydroxy-progesterone and 21-desoxyhydrocortisone their metabolism and possible role in congenital adrenal virilism. J. Clin. Invest. 34, 1639-1646 (1955). 

The precipitate was washed carefully with water and was then dissolved in 10 ml of methanol and 1.5 ml of methylene chloride. The solution was concentrated to 10 ml, diluted with 0.5 ml of 10% sodium hydroxide, boiled for one minute and cooled. The product, which crystallized on cooling, was recrystallized to give flakes of 6a-methyl-17a-hydroxy-progesterone 17-acetate, having a MP 205° to 209°C, according to U.S. Patent 3,147,290. 

Studies in which adrenal glands were perfused with steroids of known structure have established that 21-hydroxypregnenolone and deoxycorticosterone could serve as corticosterone precursors. 21-Deoxycortisol and lljS-hydroxyprogesterone are converted to cortisone and corticosterone, in contrast to 17a-hydroxy-progesterone, which can be converted only to cortisol. On the basis of such studies, a number of alternative pathways for glucocorticoid steroidogenesis have been described. The conversion of progesterone to corticoid hormone is shown in Fig. 8-12. 

Plasma Progesterone and 17a-Hydroxy-progesterone Gas Chromatographic Determination... 

Androstenedione is the most important precursor hormone of androgens in females. Plasma levels are often increased in hirsute women. Next to 17a-hydroxy-progesterone, it is an important diagnostic parameter of 21-hydroxylase deficiency in plasma and amniotic fluid [52], A decreased ratio between testosterone and androstenedione is indicative of 17P-hydroxysteroid dehydrogenase deficiency. The first mass-spectrometrically determined concentrations of plasma an-... 

In the biosynthetic steps from progesterone to the adrenal cortical hormones are the very important 21-, lljS-, and 18-hydroxylations. The major pathway of synthesis is illustrated in Fig. 18. The properties of the enzyme, 17a-hydroxylase, which catalyzes the initial step in the formation of cortisol, have been described in a previous section, IV.B, of this manuscript. 21-Hydroxylation of progesterone or 17a-hydroxy-progesterone precedes 1 lj8-hydroxylation resulting in the eventual formation of the glucocorticoids, corticosterone, and cortisol respectively. The further conversion of corticosterone by 18-hydroxylation and sub-... 

Preparation of Ba-Methyi-17-Hydroxy progesterone 17-Acetate 1 g of 6a-methyl-17a-hy-droxyprogesterone was dissolved in a mixture of 10 ml of acetic acid and 2 ml of acetic anhydride by heating. After solution was effected the mixture was cooled to 15°C, and 0.3 g of p-toluenesulfonic acid was added. After allowing the mixture to stand for a period of 2 /a hours at room temperature, the pink solution was poured into ice water to give an amorphous solid which was recovered by filtration. 

Figure 42-5. Pathways of testosterone biosynthesis. The pathway on the left side of the figure is called the or dehydroepiandrosterone pathway the pathway on the right side is called the A" or progesterone pathway. The asterisk indicates that the 17a-hydroxy-lase and 17,20-lyase activities reside in a single protein, P450cl7.

Mass Spectra.—A computer analysis of mass spectra of progesterone and twenty-nine of its stereoisomers and alkylated derivatives has established the main fragmentation pathways and their dependence on configurations, particularly at C-10 and C-17, and on the substitution pattern. Mass spectra of 17a-acetoxy-, Ha-hydroxy-, and 17a-methoxy-progesterones are dominated by fragmentations J. Dillon and K. Nakanishi, J. Amer. Chem. Soc., 1975,97, 5409, 5417. 

A series of pregnane-17-thiol derivatives (e.g. 16a-OH-17a-SH, 16/8-OH-17a-SH, and 16/8-OH-17/8-SH derivatives of progesterone, and some of their esters) has been prepared for biological evaluation. 3a,6a-Dihydroxy-5a-pregn-9(ll) en-20-one, isolated from starfish, has been synthesized from 1 la-hydroxy-progesterone. 5-Bromo-6/8 -fluoro-3/8,16a, 17a -trihydroxy-5a -pregnan-20-one... 

HI. Hagen, A. A., and Eik-Nes, K. B., Testosterone biosynthesis in the canine in vivo following infusion of 17a-hydroxy (4t- [Pg.207]

Among the many naturally occurring processes leading to molecular modifications of progesterone and its precursor, pregnenolone, is the formation of the 17a-hydroxy derivative. Although 17a-hydroxyprogesterone... 

Several structural modifications of progesterone have resulted in desirable oral activity. One is the addition of a 17a-hydroxy function (usually esterified) a A6dehydro feature is another. Megestrol acetate incorporates both successfully. 

Melengestrol. 17a -Hydroxy 6 methyl-16-methyl-enepregna-4,6-diene-3,20-dione 6-methyl-16-methylene -17a -hydroxy-A4-progesterone. mol wt 354.47. C... 

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