2- Oxosteroids

Oxosteroids (17-ketosteroids) [1, 2] e.g. dihydroxyandrosterone, androsterone, aetiocholanolone, 11-oxoandrosterone... 

Oxosteroids produce blue-black chromatogram zones on colorless to pale yellow backgrounds. 

Oxides of nitrogen vapor la 86 11 -Oxoanderosterone lb 78 11 -Oxolanostenyl acetate la 62 Oxomemazine lb 354 17-Oxosteroids lb 78,79 Oxprenolol la 299 lb 268 Oxycodeinone lb 280 Oxydemeton methyl lb 164,165 Oxyhemoglobin, dipole moment la 97 Oxymorphone lb 280 Oxypertin lb 354 Oxytetracycline lb 271... 

Betamethasone is well absorbed after oral administration to be extensively bound to plasma proteins in humans, dogs, cows, and rats. Its metabolism does not differ of the other corticosteroids, involving oxidation of the 11 -hydroxyl group to ketone, reduction of the ketone group at the position C-20 to give the corresponding alcohol, and hydroxylation at the C-6 position and loss of the C-17 side chain to give 17-oxosteroids. 

ZIMMERMANN REACTION. The reaction that occurs between methylene ketones and aromatic polynitro compounds in the presence of alkali. When applied to 17-oxosleroids, the colored compounds formed can be used for the quantitative determination of 17-oxosteroids. 

This interconversion is catalaysed by 17)3-hydroxysteroid dehydrogenase (17/3-HSD), an enzyme generally found in the ER of numerous tissues such as adrenal, liver, testis, ovary and kidney. Like many of the enzymes described above, there appear to be different forms [52,87]. For example, rat adrenal cytosol and ER contain separate 17/3-HSDs, with NADH as the preferred cofactor. The rat testicular enzyme, however, prefers NADPH. Guinea-pig liver also contains two 17j3-HSDs, one solubilized from cytosol, the other associated with the ER [88], These enzymes exhibit different activities towards C19 steroids, the cytosolic one preferring 5/3-reduced 17-oxosteroids and the microsomal counterpart being involved with 5a-reduced steroids, such as 5a-DHT. In this case, the product of the reaction would be 5a-an-drostane-3,17-dione. 

Oxidative photolysis of the acetyllQrdrazones of 17-oxosteroids gives the lactam together with its 13-a isomer (H. Suginome and T. Uchida, J. chem. Soc. Perkin I, 1980, 1356). 

K5. Kellie, A. E., and Smith, E. Characterization of 17-oxosteroids by derivatives formed in the Zimmerman reaction. Nature 178, 323 (1956). 

Thomas, B. S., and Walton, D. R. M., Chloromethyldimethylsilyl ethers in the routine assay of urinary ll-deoxy-17-oxosteroids by gas-liquid chromatography. J. Endocrinol. 41, 203-211 (1968). 

In the case of a 17-oxosteroid, 3-methoxy-14a-melhylestra-l,3.5(10)-trien-17-one. reduction with sodium/2-propanol provided the 17-alcohols in 84 6 ratio (/ /a)19. MMX calculations19 suggest a ratio of 85 15 (/ / ) at equilibrium. Thus, the single electron transfer reduction provided the more stable cyclopentanol. 

Qualitative and Quantitative Analysis of Urinary 17-Oxosteroids and 20-Hydroxy-21-deoxysteroids by Gas-Liquid Cgromatography and Mass Spectroscopy... 

Gas Chromatography Method to Determine 17-Hydroxycorticosteroids, Pregnanes and 17-Oxosteroids in Urine Ergeb. Exp. Med, 20(Fortschr. Chrom- 1425. 

Analysis of 17-Oxosteroids by Gas-Liquid Chromatography After Purification of the Urine Extract by Girard Reagent T... 

An Improved Method for the Simultaneous Determination of Individual 17-Oxosteroids and of Pregnanediol in Urine by Gas-Liquid Chromatography J. Clin. Chem. Clin. Biochem. 15(4) 225-231 (1977) CA 87 18343v... 

The Indirect Analysis of 17-Oxosteroid Glucosiduronates and Sulfates in Human Urine... 

An Improved Gas-Liquid Chromatographic Method for Simultaneous Estimation of Pregnanediol, Pregnanetriol and the Seven Major 17-Oxosteroids Aust. J. Med. Technol. 10(3) 117-121 (1979) CA 93 64993d... 

One of the end products of androgen metabolism. It is excreted in the urine and can be measured as part of the 17-oxosteroid group of compounds. 

These are a group of C-19 steroids which influence the male secondary sex characteristics. They are made by the testes, adrenals and to a lesser extent by the ovaries. The testes secrete testosterone while the main adrenal androgens are dehydro-epiandrosterone and androstenedione. Urinary 17-oxosteroid estimations give an indication of androgen production. 

The increased production of androgens and cortisol precursors results in raised urinary 17-oxosteroids and 17-oxogenic steroids. 

Oxosteroid excretion can be raised in adrenocortical carcinomas when androgens can be secreted in addition to corticosteroids. 

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