Androsterone 11-hydroxy

Ketoetiocholanolone 11/3-Hydroxy androsterone 1 l/S-Hydroxyetiocholanolone 0.4-2.0) 0.2-1.0> 0.1-0.5j Cortisol, 11/3-hydroxy-androstenedione... 

OH-AN 11-Hydroxy-androsterone Cortisol, 11-hydroxy-andro-stenedione... 

Sa-Reductase DeSciency. In genetically male infants, ambiguous genitalia at birth and pubertal virilization are the clinical symptoms in inherited 5a-reductase deficiency. In urine, extremely low excretion of 5a-THF in young infants, and additional low excretion of androsterone and lip-hydroxy-androsterone in older children indicate Sa-reductase deficiency [34],... 

Adrenocortical Tumors. Virilization, hypercortisolism, feminization, abdominal pain, palpable abdominal tumor, or combinations of these features are clinical symptoms of adrenocortical tumors. Both types of adrenocortical tumors (carcinoma and adenoma) can produce a wide variety of steroid hormones. This is a consequence of multiple enzyme deficiencies in tumor tissues. The tumor cells are capable of synthesizing large amounts of steroid hormone precursors independent of ACTFI stimulation. Excessively high amounts of DHEA and other 3p hydroxy-5-ene steroids characterize the urinary steroid profile in children with adrenocortical carcinoma, but similar profiles can also be produced by adrenal adenomas. Elevated lip hydroxy-androsterone excretion alone or combined with high excretion of cortisol metabolites or 3p hydroxy-5-ene steroids are characteristic of the urinary steroid profile for adrenocortical adenomas [36,37]. 

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. 

Hydroxy-17a-methyl-3-androsterone [521-11-9] M 304.5 , m 192-193 . Crystd from ethyl acetate. 

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

Nucleophilic substitution of toluene- -sulphonates (tosy-lates) and other sulphonic esters of secondary steroidal alcohols has received much attention, both in studies of reaction mechanisms, and also as a route for the conversion of alcohols into their epimers. One of the most important practical objectives has been the synthesis of 3a-hydroxy-5a-steroids, which include androsterone and a wide variety of metabolites of the steroid hormones, Tosylates of equatorial 3jS-alcohols (15) give 3a-alcohols or their derivatives (16) in acceptable... 

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]. 

Force-field calculations have given the atomic co-ordinates for 3a-hydroxy-5a-androstan-17-one ( androsterone ) with about the same accuracy as X-ray measurements, the errors being no greater than 0.1 A. The value of this method lies partly in its speed (10 minutes of IBM 360 computer time) and partly in the fact that no crystal is required. Variations of energy with conformation can also be computed. The authors stress the likely dangers in using Dreiding models, which may differ markedly in shape from actual molecules because they fail to simulate torsional and van der Waals effects. 

Ingenious application of remote oxidation has opened the way to a novel and potentially useful degradation of 5a-cholestan-3a-ol to 3a-hydroxy-5a-androstan-17-one ( androsterone ). The radical relay process, whereby photolysis of an iodoaryl ester with iodobenzene dichloride introduces a chlorine atom or unsaturation into the steroid nucleus, has been adapted by use of the 3a-(4 -iodobiphenyl-3-carboxylate) (301). The size of this ester grouping allows the iodine atom to come... 

Hydroxy-steroid dehydrogenases co-immobilized on Sepharose 4B with NADH FMN oxidoreductase and luciferase provide light-emission assays for picomole levels of androsterone or testosterone.145... 

The level of DHA in cord blood is very high and the lack of significant quantities of the compound in infant urine may be explained by 16a-hydroxylation being the dominant metabolic pathway (see Section 8 for the excretion of 16a-hydroxy-A steroids). In adults DHA is the principal precursor of androsterone and etiocholanolone, and they are its main metabolites (R11,V1). 

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

In an attempt to overcome the above-mentioned problems, acrylates bearing pendant androsterone with 6-hydroxy acid (Fig. 133), 3 - (3 - a cry loy loxy a n -drosterone, was polymerized with a radical initiator in THF to 80-90% yield [ 385 ]. The polymer was oxidized with CH3C02H/H202 to form 6-lactone in 95% yield. The lactone ring was hydrolyzed in THF with 0.2 N aqueous NaOH in 85-90% yield. The final polymer contained 25 mol% unreacted lactone, had a good transparency of 0.21/pm at 193 nm, and a much better shelf life than the y-hydroxy acid system. 13C NMR of the polymer treated with methanesulfonic acid in THF and IR studies of the resist film after exposure indicated that the... 

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%). ... 

P-Hydroxy-17a-methyl-3-androsterone (Mestanolone) [521-11-9] M 304.5 , m 192-193 . Dissolve mestanolone in Et20, wash it with N NaOH, H2O, dry it (Na2S04), evaporate and reciystallise it from EtOAc. The semicarbazone has in 235-236° (from EtOH). [Ruzicka et al. Helv Chim Acta 18 1487 7955.]... 

A mixture of androsterone, molecular sieve (4A, Linde), and n-butylamine kept 3 weeks at room temp, under Ng N-(3a-hydroxy-5a-androstan-17-ylidene)-n-butylamine. Y 78. F. e. s. R. Bonnett and T. R. Emerson, Soc. 1965, 4508. 

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