Méthoxyisoflavone et dépistage du cannabis dans les urines : mise en évidence d’une réaction croisée peu connue

Lecompte, Yannick; Perrin, M.; Daude, Bernard; Arpino, Patrick

doi:10.1051/ata/2012002

Cited by 4 publications

(2 citation statements)

References 11 publications

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“…Human studies did not show significant modification of some key parameters usually considered in the assessment of anabolic properties (among them, body weight, body mass index, blood cortisol level, and isokinetic peak force) and for this reason the anabolic and ergogenic properties of methoxyisoflavone have not been further explored . Furthermore, focus on methoxyisoflavone in forensic toxicological analysis has been limited to the fact that its metabolites can cross‐react with the antibodies used for the screening of synthetic cannabinoids, causing false‐positive results in urinary immunoassay …”

Section: Introductionmentioning

confidence: 99%

“…15,16 Furthermore, focus on methoxyisoflavone in forensic toxicological analysis has been limited to the fact that its metabolites can cross-react with the antibodies used for the screening of synthetic cannabinoids, causing falsepositive results in urinary immunoassay. 17 The use of ipriflavone is indicated in the treatment of osteoporosis in postmenopausal women 18 due to its normalizing effects on calcitonin levels. Ipriflavone and its most abundant metabolite, 7-hydroxy-isoflavone, can also inhibit CYP1A2 and CYP2C9, leading to an increase in plasma levels of some drugs, including theophylline and tolbutamide.…”

Section: Introductionmentioning

confidence: 99%

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Synthetic isoflavones and doping: A novel class of aromatase inhibitors?

Iannone

Botrè

Cardillo

et al. 2018

Drug Testing and Analysis

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Anectodical information suggests that flavonoids may be widely used among athletes for their multiple biochemical and pharmacological effects. We have evaluated in vitro the effects of two synthetic isoflavones, methoxyisoflavone and ipriflavone, on the catalytic activity of human aromatase (CYP19), the enzyme catalyzing the conversion of androgens (ie, testosterone or androstenedione) to estrogens (ie, estradiol and estrone). The potential inhibitory effect was evaluated by measuring the rate of aromatization of testosterone, monitored by gas chromatography-mass spectrometry (GC-MS), both in the presence and in the absence of methoxyisoflavone or ipriflavone, comparing their effects with those of synthetic aromatase inhibitors (formestane, anastrozole, and aminoglutethimide) presently included in the list of prohibited substances and methods, and of natural flavonoids (chrysin, quercetin, and daidzein), that are known inhibitors of CYP19. The preliminary results of our in vitro study show that methoxyisoflavone and ipriflavone act as competitive inhibitors of aromatase, the degree of inhibition measured in vitro being of the same order of magnitude of that of the aromatase inhibitors commonly used in anti-estrogenic therapies. Our preliminary in vitro results indicate that, in principle, a sufficiently large intake of isoflavones could alter the kinetics of the dynamic equilibria between androgens and estrogens, suggesting their monitoring in doping control routine analysis.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthetic isoflavones and doping: A novel class of aromatase inhibitors?

Iannone

Botrè

Cardillo

et al. 2018

Drug Testing and Analysis

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An investigation on the metabolic pathways of synthetic isoflavones by gas chromatography coupled to high accuracy mass spectrometry

Iannone

Botrè

Parenti

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale:Isoflavones are a group of flavonoids that may be of interest in sport doping because they can be used by athletes in the recovery periods after the administration of anabolic steroids, with the aim of increasing the natural production of luteinizing hormone (LH) and, consequently, the biosynthesis of endogenous androgens. Methods:The in vivo metabolism of methoxyisoflavone (5-methyl-7methoxyisoflavone) and ipriflavone (7-isopropoxyisoflavone), respectively present in a dietary supplement and in a pharmaceutical preparation, was investigated. The study was carried out by the analysis of urinary samples collected from male Caucasian subjects before, during and after the oral administration of methoxyisoflavone or ipriflavone. After enzymatic hydrolysis and liquid-liquid extraction, all urinary samples were analyzed by gas chromatography/quadrupole time-of-flight (qTOF MS system/qTOF) electron ionization mass spectrometry (EI-MS).Results: Eight metabolites of methoxyisoflavone and six metabolites of ipriflavone were isolated. The corresponding accurate mass spectra are specific for isoflavone structures and revealed also a retro-Diels-Alder fragmentation. Conclusions:When excreted in large amounts, the urinary metabolites of methoxyisoflavone and ipriflavone can be traced to potential confounding factors in doping analysis. As methoxyisoflavone and ipriflavone have been shown to inhibit the enzyme aromatase, thus interfering with the normal metabolic pathways of testosterone, the detection of their intake, by screening for the presence of their main metabolites in urine, might be helpful in routine doping control analysis.

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