• Journal of the Korean Chemical Society
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• v.19 no.3
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• pp.174-178
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• 1975

The intermediate, 17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(Ⅸ) required for the synthesis of 4-(${\beta}$-guanidinoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(V) was obtained through a reaction of 17${\alpha}$-methyl-3,5-seco-4-norandrostan-17${\beta}$-ol-5-on-3-oic acid(VI) with ammonium hydroxide followed by two reductions(platinum dioxide with hydrogen and lithium aluminium hydride). Condensation of Ⅸ with chloroacetonitrile under anhydrous condition, followed by reduction of the nitrile with lithium aluminium hydride gave 4-(${\beta}$-aminoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(XI). The reaction of XI with 2-methyl-2-thiopseudourea or 3,5-dimethylpyrazole-1-carboxamidine, or cyanamide provided the title compound, V. Relaxation of the nictitating membrane, in the absence of mydriasis, is considered to be evidence of adrenergic neurone blockade. Thus the test compound(V) resembles that of the classical adrenergic neurone blocking agents.

• Archives of Pharmacal Research
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• v.14 no.3
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• pp.261-265
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• 1991

In a microbial cell-free extract system, side chain cleavage on various sterols and steroids was tested. The cell-free extracts of Mycobacterium sp. NRRL B-3805 showed the side chain cleavage activity on lithocholic acid to form 5$\beta$-androstan-3.17-dione. The properties of the activity were examined.

• Analytical Science and Technology
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• v.12 no.3
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• pp.190-195
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• 1999

The metabolism of testosterone ($17{\beta}$-hydroxy-androst-4-en-3-one) was confirmed in horse after a single intramuscular administration of testosterone cypionate (750 mg). Solvent extracts of urine obtained with enzymatic hydrolysis and methanolysis were analyzed by GC/MS after oxime t-butyldimethylsilyl (oxime-TBDMS) derivatization. The structures of four urinary metabolite after testosterone administration in horse were determined based on EI mass spectra and $5{\alpha}$-androstane-$3{\beta}$, $17{\alpha}$-diol and $5{\alpha}$-androstane-$3{\beta}$-ol-17-one as major was confirmed with authentic standard. Also the concentrations of $5{\alpha}$-androstane-$3{\beta}$, $17{\alpha}$-diol, $5{\alpha}$-androstane-$3{\beta}$, $17{\beta}$-diol, dehydroepiandrosterone (DHEA), $5{\alpha}$-androstane-$3{\beta}$-ol-17-one and testosterone were determined in the urine of normal subjects and the urine after administration. The recovery and detection limit in the most drugs were 86.3~94.7% and 1~3 ppb, respectively. Correlation coefficients for calibration were in the range of 0.984~0.999. Excretion profile of testosterone presents the rapid and large increasement up to maximum values at days 5 after administration and the slow regression. The relative ratios of testosterone, its metabolites over DHEA were determined for indication of testosterone administration in horse doping.

• Bulletin of the Korean Chemical Society
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• v.30 no.10
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• pp.2398-2402
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• 2009

Ten steroidal compounds as impurities in canrenone were isolated from the enriched mother liquor by using various chromatographic methods. Their structures were elucidated by spectrometric analysis, among which three new compounds were characterized as 3-(3-oxo-7$\alpha$-(ethoxycarbonyl)methyl-17$\beta$-hydroxy-4-androsten-17$\alpha$-yl) propionic acid $\gamma$-lactone (1), 3-(3-oxo-7$\alpha$-ethoxy-17$\beta$-hydroxy-4-androsten-17$\alpha$-yl) propionic acid $\gamma$-lactone (2) and 3-(3-oxo- 5$\beta$-propionic acid-$\gamma$-lactone-6$\beta$,17$\beta$-hydroxy-4-androstan-17$\alpha$-yl) propionic acid $\gamma$-lactone (3).

• YAKHAK HOEJI
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• v.51 no.6
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• pp.495-499
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• 2007

Seven epoxy- and hydroxyandrostane derivatives ($DH-1{\sim}DH-7$) and nine epoxy- and hydroxycholestane derivatives ($CH-1{\sim}CH-9$) with unsaturation in ring A and ring B were synthesized from DHEA and cholesterol, respectively. The antinociceptive effects of all synthesized compounds were measured by hot plate method. Most of androstane derivatives except $1{\alpha},2{\alpha}$-epoxy-4,6-androstadiene-3,17-dione (DH-3), and CH-6, CH-7 and CH-9 exhibited antinociceptive effect. 1,4-Androstadiene-$3{\beta},17{\beta}$-diol (DH-5, 100 mg/kg, $35.8{\pm}7.39$), $6{\alpha},7{\alpha}$-epoxy-1,4-androstadiene-3,17-dione (DH-4, 100 mg/kg, $32.6{\pm}5.50$) and $5{\alpha},6{\alpha}$-epoxy-17-oxo-androstan-$3{\beta}$-ol (DH-1, 100 mg/kg, $32.5{\pm}2.98$) were more effective than morphine (10 mg/kg, $30.6{\pm}0.5$). The analgesic effects of androstane derivatives on acetic acid writhing in mice were lower than aspirin. The androstane derivatives were less effective than ibuprofen at inhibiting effects on the carrageenin induced paw oedema. 4,6-Cholestadien-$3{\beta}$-ol (CH-5), $1{\alpha},2{\alpha}$-epoxy-4,6-cholestadien-$3{\beta}$-ol (CH-7) and $7{\alpha}$-hydroxy4-cholesten-3-one (CH-9) showed the decrease of serum triglyceride and total cholesterol levels in poloxamer P-407 injected rat.