Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes

Gauthier, Jean-Paul; Goudreault, Danielle; Poirier, Donald; Ayotte, Christiane

doi:10.1016/j.steroids.2008.11.002

Cited by 27 publications

(54 citation statements)

References 32 publications

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“…In the chimeric mice a closely related spectrum as those previously described [29] was found for metabolites S1a-b (MW 550), so a tentative structure of x-hydroxy-superdrol was proposed ( Fig. 4 and Table 2).…”

Section: Superdrol -Methasteronesupporting

confidence: 65%

“…In vitro hydroxylations at the C12 or C16 position of superdrol (methasterone) itself were already described [29]. In the chimeric mice a closely related spectrum as those previously described [29] was found for metabolites S1a-b (MW 550), so a tentative structure of x-hydroxy-superdrol was proposed ( Fig.…”

Section: Superdrol -Methasteronementioning

confidence: 55%

“…The only reported metabolite in vivo, namely the 3-keto-reduced metabolite of methasterone: 2␣,17␣-dimethylandrostanediol (DM-AD, MW 464) was not detected in the mouse urine. However, one of the compounds mentioned in the in vitro cultures of Gauthier et al [29] could be detected in the chimeric mouse urine, namely S2 (Fig. 4).…”

Section: Superdrol -Methasteronementioning

confidence: 89%

“…4 and Table 2). The position of the hydroxyl-group is unknown, however when comparing with the metabolites detected by Gauthier et al it is clear that it is not at the C16 position (because lack of m/z 218/231) and not at C12 position (lack of m/z 170), but rather on the B or C ring [29,30]. The structures/metabolites proposed are based on molecular weight and GC-MS fragmentation pattern only.…”

Section: Superdrol -Methasteronementioning

confidence: 96%

“…Results of the superdrol (methasterone) post-administration chimeric mouse urine: GC-MS chromatograms with the corresponding mass spectra. Legend: 17a-methyltestosterone (ISTD, internal standard), and several metabolites with tentative structure and name: 2 isomers of x-hydroxy-superdrol (S1a-b), confirmed [29] 2,16-dihydroxy-2a,17a-dimethyl-5a-androstane-3a,17b-diol (S2) with chemical structure presentation, 3 isomers of trihydroxy-superdrol (S3a-b-c) and x,16-dihydroxysuperdrol metabolite (S4). …”

Section: Superdrol -Methasteronementioning

confidence: 99%

See 4 more Smart Citations

Metabolic studies with promagnon, methylclostebol and methasterone in the uPA+/+-SCID chimeric mice

Lootens

Meuleman

Leroux‐Roels

et al. 2011

The Journal of Steroid Biochemistry and Molecular Biology

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Section: Superdrol -Methasteronesupporting

confidence: 65%

Section: Superdrol -Methasteronementioning

confidence: 55%

Section: Superdrol -Methasteronementioning

confidence: 89%

Section: Superdrol -Methasteronementioning

confidence: 96%

Section: Superdrol -Methasteronementioning

confidence: 99%

See 3 more Smart Citations

Metabolic studies with promagnon, methylclostebol and methasterone in the uPA+/+-SCID chimeric mice

Lootens

Meuleman

Leroux‐Roels

et al. 2011

The Journal of Steroid Biochemistry and Molecular Biology

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Metabolism of methylstenbolone studied with human liver microsomes and the uPA^+/+‐SCID chimeric mouse model

Geldof

Lootens

Polet

et al. 2014

Biomedical Chromatography

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Anti-doping laboratories need to be aware of evolutions on the steroid market and elucidate steroid metabolism to identify markers of misuse. Owing to ethical considerations, in vivo and in vitro models are preferred to human excretion for nonpharmaceutical grade substances. In this study the chimeric mouse model and human liver microsomes (HLM) were used to elucidate the phase I metabolism of a new steroid product containing, according to the label, methylstenbolone. Analysis revealed the presence of both methylstenbolone and methasterone, a structurally closely related steroid. Via HPLC fraction collection, methylstenbolone was isolated and studied with both models. Using HLM, 10 mono-hydroxylated derivatives (U1-U10) and a still unidentified derivative of methylstenbolone (U13) were detected. In chimeric mouse urine only di-hydroxylated metabolites (U11-U12) were identified. Although closely related, neither methasterone nor its metabolites were detected after administration of isolated methylstenbolone. Administration of the steroid product resulted mainly in the detection of methasterone metabolites, which were similar to those already described in the literature. Methylstenbolone metabolites previously described were not detected. A GC-MS/MS multiple reaction monitoring method was developed to detect methylstenbolone misuse. In one out of three samples, previously tested positive for methasterone, methylstenbolone and U13 were additionally detected, indicating the applicability of the method.

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In vitro and in vivo metabolism studies of dimethazine

Geldof

Tudela

Lootens

et al. 2016

Biomedical Chromatography

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The use of anabolic steroids is prohibited in sports. Effective control is done by monitoring their metabolites in urine samples collected from athletes. Ethical objections however restrict the use of designer steroids in human administration studies. To overcome these problems alternative in vitro and in vivo models were developed to identify metabolites and to assure a fast response by anti-doping laboratories to evolutions on the steroid market. In this study human liver microsomes and an uPA(+/+) -SCID chimeric mouse model were used to elucidate the metabolism of a steroid product called 'Xtreme DMZ'. This product contains the designer steroid dimethazine (DMZ), which consists of two methasterone molecules linked by an azine group. In the performed stability study, degradation from dimethazine to methasterone was observed. By a combination of LC-High Resolution Mass Spectrometry (HRMS) and GC-MS(/MS) analysis methasterone and six other dimethazine metabolites (M1-M6), which are all methasterone metabolites, could be detected besides the parent compound in both models. The phase II metabolism of dimethazine was also investigated in the mouse urine samples. Only metabolites M1 and M2 were exclusively detected in the glucuro-conjugated fraction; all other compounds were also found in the free fraction. For effective control of DMZ misuse in doping control samples, screening for methasterone and methasterone metabolites should be sufficient. Copyright © 2016 John Wiley& Sons, Ltd.

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Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes

Cited by 27 publications

References 32 publications

Metabolic studies with promagnon, methylclostebol and methasterone in the uPA+/+-SCID chimeric mice

Metabolic studies with promagnon, methylclostebol and methasterone in the uPA+/+-SCID chimeric mice

Metabolism of methylstenbolone studied with human liver microsomes and the uPA^+/+‐SCID chimeric mouse model

In vitro and in vivo metabolism studies of dimethazine

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Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes

Cited by 27 publications

References 32 publications

Metabolic studies with promagnon, methylclostebol and methasterone in the uPA+/+-SCID chimeric mice

Metabolic studies with promagnon, methylclostebol and methasterone in the uPA+/+-SCID chimeric mice

Metabolism of methylstenbolone studied with human liver microsomes and the uPA+/+‐SCID chimeric mouse model

In vitro and in vivo metabolism studies of dimethazine

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Product

Resources

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Metabolism of methylstenbolone studied with human liver microsomes and the uPA^+/+‐SCID chimeric mouse model