19-Hydroxy-4-androsterone-3,17-dione

Fig. 6.12. Gradient CEC separation of derivatized neutral steroids. (Reprinted with permission [38], Copyright 2000 Elsevier). Conditions Column 35 cm (active length 25 cm) x 100 pm i.d., mobile phase gradient of acetonitrile-water-240 mmol/L phosphate buffer pH 3 from 35 60 5 to 65 30 50 in 15 min 600 V/cm injection 100 V/cm for 10 s. Peaks labeling reagent 1, progesterone 2, 11 P-hydroxyandrosterone 3, dehydroisoandrosterone and equiline 4, estrone 5, androsterone 6, 19-hydroxy-4-androsterone-3,17-dione 7, 5-a-androstan-17-one 8.

This enzyme [EC 1.1.1.50], also referred to as hydroxy-prostaglandin dehydrogenase, catalyzes the reaction of androsterone with NAD(P)+ to produce 5a-androstane-3,17-dione and NAD(P)H. Other 3a-hydroxysteroids can act as substrates as well as 9-, 11- and 15-hydroxy-prostaglandins. The stereochemistry is B-specific with respect to the pyridine coenzymes. 

Androsterone 11 p-Hydroxyandrosterone 5-(3-Androstan-17-one 19-Hydroxy-4-androstene-3,17-dione... 

The metabolism of 17)3-hydroxy-l-methyl-A -androstene-3-one is markedly different from that of testosterone. In addition to the large amount of unchanged compound, small amounts of l-methyl-A -andro-stene-3,17-dione and la-methyl-androstane-3,17-dione also are excreted in the urine, but the 1-methylated androsterone or etiocholane derivatives are not found [275]. 

The metabolism of DHEA was studied by means of human prostate homogenates [80], as well as human and rat liver microsomal fractions [81-82]. Using human prostate homogenates, androst-5-ene-3P,17P-diol (major component), androst-4-ene-3,17-dione, testosterone, 5a-dihydrotestosterone, androsterone, and 7a-hydroxy-DHEA were identified as metabolites of DHEA [80]. By means of liver microsomal fractions, 16a-hydroxy-DHEA, 7a-hydroxy-DHEA, and 7-oxo-DHEA were identified by Fitzpatrick et al. [81], while in total 19 DHEA metabolites were reported by Marwah et al. [82]. Some of these metabohtes were characterized for the first time. (Quantitative analysis of 5a-androstane-3p,17P-diol in plasma was recently reported by Reddy et al. [83]. 

Names synonyms ANDROSTERONE cis>androsterone 3ai-hydroxy-17-androstanone androstane-3a>ol> 7 one. FtUOXYMESTERONE 9a fluoro 11 hydroxy 17 methyltesiostcrone 9s>fluoro l I/U7/ >dihydroxy l7a methyi 4-androsten 3 one. ALDOSTERONE electrocorttn 18 oxocorticosterone 18 formyM l/ .2l dthydroxy-4> pregnene>3.20 dione. 

Amongst other less successful applications, however, are the oxidations of some steroidal systems such as testosterone, which afforded A -androsterone-3,17-dione in only 34% yield and 1 la-hydroxypro-gesterone, in which the equatorial hydroxy group was oxidized to afford a poor yield of 11-oxoproges-terone(13%). ... 

Names synonyms ANDROSTERONE cis ndrosterone 3 4iydrox]r-17-andro ianone androstane>3fl ol-17 methyltesiosterone 9a>Auoro l IA l7/ 4ibydroxy 17c methyl>4-androsten 3 e. ALDOSTERONE electrocortin 18 oxoconicosierone 18 formyM 1 A 2l dthydroxy-4> pregnene>3.20-dione. 

The systematic and common names and abbreviations of the steroids used throughout this text are indicated in Table I. Using this nomenclature, the steroid ester-sulfates and steroid glucuronides are followed by the suffix yl thus, androsterone sulfate is called 17-oxo-5a-androstan-3a-yl-sulfate, and corticosterone-21-glucuronide is ll/3-hydroxy-4-pregnetie-3,20-dion-21 -y l-j8-D-gIucopyranosiduronatc. 

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