Studies on anabolic steroids—12. Epimerization and degradation of anabolic 17β-sulfate-17α-methyl steroids in human: Qualitative and quantitative GC/MS analysis

Bi, Honggang; Massé, Robert

doi:10.1016/0960-0760(92)90267-m

Cited by 37 publications

(40 citation statements)

References 19 publications

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“…[27] After the synthesis procedure, only one sulfate metabolite per each compound was detected by LC-MS/MS analysis. [23,24] For 4β-hydroxy-stanozolol sulfate (4STAN-S) only one chromatographic peak at the retention time of the parent compound (RT: 4.92 min) was detected after degradation of the sulfate ( Figure S1). However, the re-injection of the same vials after 24 h demonstrated the degradation of these products.…”

Section: Resultsmentioning

confidence: 99%

“…Thereafter, two glucuronide metabolites resistant to hydrolysis, epi-stanozolol-1'N-glucuronide (eSTAN-N-G) (Figure 1, 9) and stanozolol-1'N-glucuronide (STAN-N-G) (Figure 1, 10), were directly detected and eSTAN-N-G enabled the determination of drug abuse for up to 28 days after oral administration. [23,24] The aim of the present study was to identify metabolites of STAN conjugated with sulfate using LC-MS/MS analysis. [22] Up to now, studies have focused in glucuronoconjugated metabolites obtained using both, hydrolysis with β-glucuronidase enzymes and direct detection.…”

Section: Introductionmentioning

confidence: 99%

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Detection of stanozolol O‐ and N‐sulfate metabolites and their evaluation as additional markers in doping control

Balcells

Matabosch

Ventura

2016

Drug Testing and Analysis

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Stanozolol (STAN) is one of the most frequently detected anabolic androgenic steroids in sports drug testing. STAN misuse is commonly detected by monitoring metabolites excreted conjugated with glucuronic acid after enzymatic hydrolysis or using direct detection by liquid chromatography-tandem mass spectrometry (LC-MS/MS). It is well known that some of the previously described metabolites are the result of the formation of sulfate conjugates in C17, which are converted to their 17-epimers in urine. Therefore, sulfation is an important phase II metabolic pathway of STAN that has not been comprehensively studied. The aim of this work was to evaluate the sulfate fraction of STAN metabolism by LC-MS/MS to establish potential long-term metabolites valuable for doping control purposes. STAN was administered to six healthy male volunteers involving oral or intramuscular administration and urine samples were collected up to 31 days after administration. Sulfation of the phase I metabolites commercially available as standards was performed in order to obtain MS data useful to develop analytical strategies (neutral loss scan, precursor ion scan and selected reaction monitoring acquisitions modes) to detect potential sulfate metabolites. Eleven sulfate metabolites (M-I to M-XI) were detected and characterized by LC-MS/MS. This paper provides valuable data on the ionization and fragmentation of O-sulfates and N-sulfates. For STAN, results showed that sulfates do not improve the retrospectivity of the detection compared to the previously described long-term metabolite (epistanozolol-N-glucuronide). However, sulfate metabolites could be additional markers for the detection of STAN misuse. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Detection of stanozolol O‐ and N‐sulfate metabolites and their evaluation as additional markers in doping control

Balcells

Matabosch

Ventura

2016

Drug Testing and Analysis

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“…Reduction of C-3 keto group and hydroxylation at C-6 position are also proposed. M7 concerns steroids with heteroatom at steroidal structure (as in oxandrolone molecule [20,21]) which directs metabolism to C-/D-rings leading to the 17-epimerized, 16-hydroxylated and dehydration products.…”

Section: Proposed Metabolism Scheme For Steroids With 5˛-androstan-3-mentioning

confidence: 99%

Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine

Fragkaki

Angelis

Tsantili‐Kakoulidou

et al. 2009

The Journal of Steroid Biochemistry and Molecular Biology

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“…[8] Based on the common ionization and collision-induced dissociation (CID) behaviour of steroid glucuronides, [16] a series of open detection methods based on neutral loss (NL) and precursor ion (PI) scan have been proposed to detect them by LC-MS/MS. [2,3,5,6,12,[18][19][20][21][22][23][24] The most important metabolites are glucuronoconjugates that have been studied using β-glucuronidase hydrolysis. [11,12,17] Metandienone (MTD) is one of the most frequently detected AAS, and its metabolism has been widely studied.…”

Section: Introductionmentioning

confidence: 99%

LC‐MS/MS detection of unaltered glucuronoconjugated metabolites of metandienone

Esquivel

Pozo

Garrostas

et al. 2016

Drug Testing and Analysis

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The aim of this study was to evaluate the direct detection of glucuronoconjugated metabolites of metandienone (MTD) and their detection times. Metabolites resistant to enzymatic hydrolysis were also evaluated. Based on the common mass spectrometric behaviour of steroid glucuronides, three liquid chromatography-tandem mass spectrometry (LC-MS/MS) strategies were applied for the detection of unpredicted and predicted metabolites: precursor ion scan (PI), neutral loss scan (NL), and theoretical selected reaction monitoring (SRM) methods. Samples from four excretion studies of MTD were analyzed for both the detection of metabolites and the establishment of their detection times. Using PI and NL methods, seven metabolites were observed in post-administration samples. SRM methods allowed for the detection of 13 glucuronide metabolites. The detection times, measured by analysis with an SRM method, were between 1 and 22 days. The metabolite detected for the longest time was 18-nor-17β-hydroxymethyl-17α-methyl-5β-androsta-1,4,13-triene-3-one-17-glucuronide. One metabolite was resistant to hydrolysis with β-glucuronidase; however it was only detected in urine up to four days after administration. The three glucuronide metabolites with the highest retrospectivity were identified by chemical synthesis or mass spectrometric data, and although they were previously reported, this is the first time that analytical data of the intact phase II metabolites are presented for some of them. The LC-MS/MS strategies applied have demonstrated to be useful for detecting glucuronoconjugated metabolites of MTD, including glucuronides resistant to enzymatic hydrolysis which cannot be detected by conventional approaches. Copyright © 2016 John Wiley & Sons, Ltd.

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Studies on anabolic steroids—12. Epimerization and degradation of anabolic 17β-sulfate-17α-methyl steroids in human: Qualitative and quantitative GC/MS analysis

Cited by 37 publications

References 19 publications

Detection of stanozolol O‐ and N‐sulfate metabolites and their evaluation as additional markers in doping control

Detection of stanozolol O‐ and N‐sulfate metabolites and their evaluation as additional markers in doping control

Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine

LC‐MS/MS detection of unaltered glucuronoconjugated metabolites of metandienone

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