Microbial Transformation of Mesterolone

Choudhary, M. Iqbal; Sultan, Sadia; Jalil, Saima; Anjum, Shazia; Rahman, Azhar Abdul; Fun, Hoong‐Kun; Atta-ur-Rahman, _

doi:10.1002/cbdv.200590019

Cited by 30 publications

(10 citation statements)

References 15 publications

(3 reference statements)

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“…Mesterolone is metabolized 12–14 h after ingestion and excreted primarily through urine (approximately 77% of the metabolites) and feces (approximately 13%) . Ahmad et al .…”

Section: Introductionmentioning

confidence: 99%

New potential biomarkers for mesterolone misuse in human urine by liquid chromatography quadrupole time-of-flight mass spectrometry

Fernández-Álvarez

Yang

et al. 2015

J. Mass Spectrom.

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In this paper, mesterolone metabolic profiles were investigated carefully. Mesterolone was administered to one healthy male volunteer. Urinary extracts were analyzed by liquid chromatography quadruple time-of-flight mass spectrometry (LC-QTOFMS) for the first time. Liquid-liquid extraction was applied to processing urine samples, and dilute-shoot analyses of intact metabolites were also presented. In LC-QTOFMS analysis, chromatographic peaks for potential metabolites were hunt down by using the theoretical [M-H](-) as target ions in full scan experiment, and their actual deprotonated ions were analyzed in targeted MS/MS mode. Ten metabolites including seven new sulfate and three glucuronide conjugates were found for mesterolone. Because of no useful fragment ion for structural elucidation, gas chromatography-mass spectrometry instrumentation was employed to obtain structural details of the trimethylsilylated phase I metabolite released after solvolysis. Thus, their potential structures were proposed particularly by a combined MS approach. All the metabolites were also evaluated in terms of how long they could be detected, and S1 (1α-methyl-5α-androst-3-one-17β-sulfate) together with S2 (1α-methyl-5α-androst-17-one-3β-sulfate) was detected up to 9 days after oral administration, which could be the new potential biomarkers for mesterolone misuse.

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“…Mesterolone is metabolized 12–14 h after ingestion and excreted primarily through urine (approximately 77% of the metabolites) and feces (approximately 13%) . Ahmad et al .…”

Section: Introductionmentioning

confidence: 99%

New potential biomarkers for mesterolone misuse in human urine by liquid chromatography quadrupole time-of-flight mass spectrometry

Fernández-Álvarez

Yang

et al. 2015

J. Mass Spectrom.

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“…[18][19][20] The comparison of the 1 H-NMR spectra (Table 1) (Table 1) of 3 with the physalin H (1) indicated the disappearance of the signal for the hydroxysubstituted C-6 methine proton (d 3.82). The deoxygenation of C-6 was further supported by the appearance of a methylene carbon signal at d 42.2 in the 13 C-NMR spectrum ( Table 2).…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of Physalin H and Leishmanicidal Activity of Its Transformed Products

Choudhary

Yousuf

Samreen

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The biotransformation of mesterolone (1α-methyl-17β-hydroxy-5α-androst-3one, 149), a synthetic androgenic steroid, was performed using different fungi as described by Choudhary et al [85]. From the biotransformation of 149 using C. aphidicola, the compounds 1α-methyl-5α-androst-3,17-dione (150), 1α-methyl-5αandrost-3,17-diol (151), and 1α-methyl-15α-hydroxy-5α-androst-3,17-dione (152) were obtained.…”

Section: Microbiological Transformations Of Steroidsmentioning

confidence: 99%

Biotransformation of Steroids Using Different Microorganisms

Cano-Flores¹,

Gómez²,

Ramos³

2020

Chemistry and Biological Activity of Steroids

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The introduction of a hydroxyl group "biohydroxylation" in the steroid skeleton is an important step in the synthesis of new steroids used physiologically as hormones and active drugs. There are currently about 300 known steroid drugs whose production constitutes the second category within the pharmaceutical market after antibiotics. Several biotransformations at industrial scale have been applied in the production of steroid hormones and drugs, which have functionalized different types of raw materials by means of chemo-, regio-, and stereoselective reactions (hydroxylation, Baeyer-Villiger oxidation, oxidation reactions, reduction of group carbonyl, isomerization, and Michael additions, condensation reactions, among others). In Green Chemistry, biotransformations are an important chemical methodology toward more sustainable industrial processes.

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Microbial Transformation of Mesterolone

Cited by 30 publications

References 15 publications

New potential biomarkers for mesterolone misuse in human urine by liquid chromatography quadrupole time-of-flight mass spectrometry

New potential biomarkers for mesterolone misuse in human urine by liquid chromatography quadrupole time-of-flight mass spectrometry

Biotransformation of Physalin H and Leishmanicidal Activity of Its Transformed Products

Biotransformation of Steroids Using Different Microorganisms

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