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Isolation and identification of a sulfur-containing metabolite of spironolactone from human urine. 1976

K Koch, and M Senn, and W Steingross

In the urine of normal subjects who were given an oral dose of 500 mg spironolactone (3-(3-oxo-7alpha-acetylthio-17beta-hydroxy-4-androsten-17alpha-yl)-propionic acid gamma-lactone; Aldactone) together with 100uCi H-20, 21 spironolactone, a so far unknown major metabolite has been detected by thin layer chromatography. The metabolite then could be isolated by means of counter-current-distribution. According to masspectral and magnetic resonance data, the metabolite has been assigned the structure of 3-(3-oxo-7alpha-methyl sulfonyl-6beta, 17beta-dihydroxy-4-androsten-17alpha-yl)-propionic acid gamma-lactone. By oxidation of the corresponding methylsulfinyl compound - another already known metabolite of spironolactone - with m-chloroperbenzoic acid, a compound has been isolated which proved to be identical with the new metabolite according to TLC, MS and NMR.

UI MeSH Term Description Entries
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D003377 Countercurrent Distribution A method of separation of two or more substances by repeated distribution between two immiscible liquid phases that move past each other in opposite directions. It is a form of liquid-liquid chromatography. (Stedman, 25th ed) Chromatography, Countercurrent,Countercurrent Chromatography,Distribution, Countercurrent
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013058 Mass Spectrometry An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers. Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass
D013148 Spironolactone A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827) Spirolactone,Aldactone,Aldactone A,Aquareduct,Duraspiron,Espironolactona Alter,Espironolactona Mundogen,Flumach,Frumikal,Jenaspiron,Novo-Spiroton,Practon,SC-9420,Spiractin,Spiro L.U.T.,Spiro Von Ct,Spirobeta,Spirogamma,Spirolang,Spirono-Isis,Spironone,Spirospare,Veroshpiron,Verospiron,Verospirone,Ct, Spiro Von,Novo Spiroton,NovoSpiroton,SC 9420,SC9420,Spirono Isis,Von Ct, Spiro
D013450 Sulfones Sulfone

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