115-Hydroxy testosterone

Other new but conventional radioimmunoassays have involved oestra-l,3,5(10)-triene-3,15a,16a,17/S-tetrol ( oestetrol ), as its 6-(0-carboxy-methyloximino)-derivative, the 16-carboxymethyloximino-derivative of androst-5-ene-3/S,17 8-diol, the 15-hemisuccinate of 15a-hydroxy-testosterone, some oestriol monoglucoside derivatives, the 6-carboxy-methyloximino- and 3-hemisuccinate derivatives of the synthetic oestrogen 17a-ethynyloestradiol, the 3-carboxymethyloximes of the contraceptive steroids norethindrone and norgestrel , and the pituitary gonadotropin inhibitor, the isoxazole derivative Danazol (25), which was effectively bound by an antiserum for the corresponding 17-carboxymethyloxime (26)7°... 

Canick, J.A. and K.J. Ryan (1976). Cytochrome P-450 and the aromatization of 16-alpha-hydroxy-testosterone and androstenedione by human placental microsomes. Mol. Cell Endocrinol 6, 105-115. 

A solution of testosterone (54 10 g) in 300 ml methanol is cooled to 0° and treated successively with 60 ml of cold 30 % hydrogen peroxide and 20 ml of cold aqueous 10% sodium hydroxide. The reaction mixture is stored for 48 hr at 0° and then poured into ice water. The resultant oil is extracted with methylene dichloride (or ether) and the extract is dried (MgS04). Removal of the solvent affords the crude product, a mixture of 4a,5a- and 4, 5 -isomers, which is purified by chromatography. A sample of pure 17j5-hydroxy-4/3,5 -oxidoandrostan-3-one, mp 157-158°, crystallizes after trituration of the crude product with ether. 

The properties of chlorine azide resemble those of bromine azide. Pon-sold has taken advantage of the stronger carbon-chlorine bond, i.e., the resistance to elimination, in the chloro azide adducts and thus synthesized several steroidal aziridines. 5a-Chloro-6 -azidocholestan-3 -ol (101) can be converted into 5, 6 -iminocholestan-3l -ol (102) in almost quantitative yield with lithium aluminum hydride. It is noteworthy that this aziridine cannot be synthesized by the more general mesyloxyazide route. Addition of chlorine azide to testosterone followed by acetylation gives both a cis- and a trans-2iddMct from which 4/S-chloro-17/S-hydroxy-5a-azidoandrostan-3-one acetate (104) is obtained by fractional crystallization. In this case, sodium borohydride is used for the stereoselective reduction of the 3-ketone... 

Irradiations of Testosterone Acetate (114), —In t-Butanol. 1.25 g of (114) in 250 ml t-butanol is irradiated for 32 hr at 30° under nitrogen with a Hanau Q81 high-pressure mercury lamp placed in a central water-cooled Pyrex immersion well with acetone filter. The solvent is evaporated in vacuo and the residue chromatographed on 125 g silica gel with benzene-ethyl acetate (4 1) to yield 0.29 g 17 -hydroxy-la,5 -cyclo-10a-androstan-2-one acetate [(118) 23%] mp 164-165°, after crystallization from acetone-hexane [a]i3 37 (CHCI3) 0.14 g cyclopentanone (120) (11%) mp 106-107° [aJo 38° (CHCI3) and 0.58 g starting material [(114) 46%]. Ratio (118) (120) - 2 1. 

Testosterone acetate, 312, 320, 322, 343 lOa-Testosterone acetate, 320 5a,6/3,17a,21-Tetrabromo-3/3-hydroxy-pregnan-20-one acetate, 160 3,ll/3,17a,21 -tetrahy droxy- 19-norpregna-l,3,5(10)-trien-20-one 11,21-diacetate 3-methyl ether, 224... 

Cyclopentyl- 3-(N-piperidyl)ethyl ketone Cycrimlne HCI /3-Cyclopentyl propionic acid Testosterone 17/3-cypionate Cyclopentyl (tt-thienyl) hydroxy acetic acid Penthienate bromide Cyclopropanecarboxylic acid chloride Prazepam... 

Hydroxy-5-oxo-3,5-seco-4-norandrostane-3-carboxylic acid has been prepared by ozonolysis of testosterone2-4 or of testosterone acetate, followed by alkaline hydrolysis,5 and by the oxidation of testosterone acetate with ruthenium tetroxide.9... 

C24H30O5) see lloprost 17P-benzoyloxy-3p-hydroxy-5-androstene (C2ijH3403 1175-12-8) see Mesterolone Testosterone 2-[l-(benzoyloxymethyl)cyclopropyl]acetonitrile (C13H13NO2 142148-12-7) see Montelukast sodium... 

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.

Horinouchi M, T Hayashi, H Koshino, T Kurita, T Kudo (2005) Identification of 9,17-dioxo-l,2,3,4,10,11, 19-hexanorandrostan-5-oic acid, 4-hydroxy-2-oxohexanoic acid, and 2-hydroxyhexa-2,4-dienoic acid and related enzymes involved in testosterone degradation in Comamonas testosteroni TA441. Appl Environ Microbiol 71 5275-5281. 

A somewhat related sequence leads to trilostane (111), a compound that inhibits the adrenal gland more specifically the agent blocks some of the metabolic responses elicited by the adrenal hormone ACTH in experimental animals. Reaction of the hydroxy-methylene derivative 108, obtained from testosterone, with hydroxylamine gives the corresponding isoxazole (109). Oxidation of the C-4,5 double bond by means... 

The structures of the drugs used as a small test set for the model are listed in Table 17.1. Loperamide and asimadoline are P-gp substrates terfenadine and ebastine are compounds that are rapidly metabolized alprazolam, dobazam, di-and mono-hydroxy-L66858 [11] are benzodiazepines testosterone and corticosterone are hormones and cefadroxyl, cefaclor, cephalotin and cefmetazole are cephalosporins [12]. Finally, peptides 1 to 10 are peptidomimetic drugs [13]. 

A second example can be found in the metabolism of the male sex steroid hormone testosterone. In addition to 7a -hydroxy- and 6a-hydroxytestosterone, CYP2A1 was also found to form A6-testosterone (136) (Fig. 4.69). Using selectively deuterated analogs (136), A6-testosterone was established as being formed in competition with 6o -hydroxytestosterone after initial hydrogen atom abstraction from C6 to form the common radical intermediate. Little, if any, A6-testosterone was found to be formed in competition with la-hydroxytestosterone after initial hydrogen abstraction from Cl. 

Hydroxy ketones and hydroxy-a,/3-unsaturated ketones in the steroids such as estrone and testosterone, respectively, can be reduced to diols biochemically. Estrone acetate gave 68% yield of a-estradiol on incubation with baker s yeast at room temperature after five days [909]. Testosterone was reduced by bacteria to the saturated hydroxy ketones, etiocholan-17-ol-3-one and androstan-17-ol-3-one, and further to the diols, ep/-etiocholane-3,17-diol and the epimeric isoandrostane-3,17-diol, both in low yields [329]. 

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