Investigations on the in vivo metabolism of 5α-androst-2-en-17-one

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Investigations on the in vivo metabolism of 5α-androst-2-en-17-one. / Piper, Thomas; Fusshöller, Gregor; Schänzer, Wilhelm et al.

in: Rapid communications in mass spectrometry : RCM, Jahrgang 36, Nr. 17, 2022, S. e9343.

Publikationen: Beitrag in FachzeitschriftZeitschriftenaufsätzeForschungBegutachtung

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@article{31a35f592c8c4a7ab5df7a77981007a8,
title = "Investigations on the in vivo metabolism of 5α-androst-2-en-17-one",
abstract = "Rationale The anabolic steroid 5α-androst-2-en-17-one (2EN) is sold as a prohormone and has been investigated regarding its potential as a steroidal aromatase inhibitor. The administration of 2EN was detected in a doping control sample in 2015, and investigations into its metabolism allowed for the identification and characterization of three urinary metabolites. Unfortunately, the utility of the main metabolite 2?,3α-dihydroxy-5α-androstan-17-one for doping control purposes was hampered under routine doping control conditions due to chromatographic issues, thus warranting further studies on the metabolism of the prohibited substance. Methods The metabolism of 2EN was reinvestigated after oral administration of twofold-deuterated 2EN employing hydrogen isotope ratio mass spectrometry (IRMS) in combination with high-accuracy/high-resolution mass spectrometry. After a single dose of 50?mg of doubly labeled 2EN, urine samples were collected for 9 days. All samples were processed using routine doping control methods for IRMS analysis, and all detected metabolites were further characterized by mass spectrometry-based investigations. Results More than 15 different metabolites still containing the deuterium label were detected after administration. The presence of steroids exhibiting a 5?-configuration was unexpected as the administered 2EN features a 5α-configured pharmacophore. Further investigations corroborated a significant impact of the administered 2EN on etiocholanolone and 5?-androstanediol. Seven metabolites of 2EN not present as endogenous compounds were identified as potential candidates for routine doping controls and could be detected for up to 9 days after administration. Conclusions The new metabolites identified in this study enable the detection of the misuse of 2EN for up to 9 days. The conversion of a 5α-steroid to urinary metabolites with 5?-configuration has not been reported so far and should be further investigated.",
author = "Thomas Piper and Gregor Fussh{\"o}ller and Wilhelm Sch{\"a}nzer and Mario Thevis",
note = "https://doi.org/10.1002/rcm.9343",
year = "2022",
doi = "10.1002/rcm.9343",
language = "English",
volume = "36",
pages = "e9343",
journal = "Rapid communications in mass spectrometry : RCM",
issn = "0951-4198",
publisher = "John Wiley and Sons Ltd",
number = "17",

}

RIS

TY - JOUR

T1 - Investigations on the in vivo metabolism of 5α-androst-2-en-17-one

AU - Piper, Thomas

AU - Fusshöller, Gregor

AU - Schänzer, Wilhelm

AU - Thevis, Mario

N1 - https://doi.org/10.1002/rcm.9343

PY - 2022

Y1 - 2022

N2 - Rationale The anabolic steroid 5α-androst-2-en-17-one (2EN) is sold as a prohormone and has been investigated regarding its potential as a steroidal aromatase inhibitor. The administration of 2EN was detected in a doping control sample in 2015, and investigations into its metabolism allowed for the identification and characterization of three urinary metabolites. Unfortunately, the utility of the main metabolite 2?,3α-dihydroxy-5α-androstan-17-one for doping control purposes was hampered under routine doping control conditions due to chromatographic issues, thus warranting further studies on the metabolism of the prohibited substance. Methods The metabolism of 2EN was reinvestigated after oral administration of twofold-deuterated 2EN employing hydrogen isotope ratio mass spectrometry (IRMS) in combination with high-accuracy/high-resolution mass spectrometry. After a single dose of 50?mg of doubly labeled 2EN, urine samples were collected for 9 days. All samples were processed using routine doping control methods for IRMS analysis, and all detected metabolites were further characterized by mass spectrometry-based investigations. Results More than 15 different metabolites still containing the deuterium label were detected after administration. The presence of steroids exhibiting a 5?-configuration was unexpected as the administered 2EN features a 5α-configured pharmacophore. Further investigations corroborated a significant impact of the administered 2EN on etiocholanolone and 5?-androstanediol. Seven metabolites of 2EN not present as endogenous compounds were identified as potential candidates for routine doping controls and could be detected for up to 9 days after administration. Conclusions The new metabolites identified in this study enable the detection of the misuse of 2EN for up to 9 days. The conversion of a 5α-steroid to urinary metabolites with 5?-configuration has not been reported so far and should be further investigated.

AB - Rationale The anabolic steroid 5α-androst-2-en-17-one (2EN) is sold as a prohormone and has been investigated regarding its potential as a steroidal aromatase inhibitor. The administration of 2EN was detected in a doping control sample in 2015, and investigations into its metabolism allowed for the identification and characterization of three urinary metabolites. Unfortunately, the utility of the main metabolite 2?,3α-dihydroxy-5α-androstan-17-one for doping control purposes was hampered under routine doping control conditions due to chromatographic issues, thus warranting further studies on the metabolism of the prohibited substance. Methods The metabolism of 2EN was reinvestigated after oral administration of twofold-deuterated 2EN employing hydrogen isotope ratio mass spectrometry (IRMS) in combination with high-accuracy/high-resolution mass spectrometry. After a single dose of 50?mg of doubly labeled 2EN, urine samples were collected for 9 days. All samples were processed using routine doping control methods for IRMS analysis, and all detected metabolites were further characterized by mass spectrometry-based investigations. Results More than 15 different metabolites still containing the deuterium label were detected after administration. The presence of steroids exhibiting a 5?-configuration was unexpected as the administered 2EN features a 5α-configured pharmacophore. Further investigations corroborated a significant impact of the administered 2EN on etiocholanolone and 5?-androstanediol. Seven metabolites of 2EN not present as endogenous compounds were identified as potential candidates for routine doping controls and could be detected for up to 9 days after administration. Conclusions The new metabolites identified in this study enable the detection of the misuse of 2EN for up to 9 days. The conversion of a 5α-steroid to urinary metabolites with 5?-configuration has not been reported so far and should be further investigated.

U2 - 10.1002/rcm.9343

DO - 10.1002/rcm.9343

M3 - Journal articles

VL - 36

SP - e9343

JO - Rapid communications in mass spectrometry : RCM

JF - Rapid communications in mass spectrometry : RCM

SN - 0951-4198

IS - 17

ER -

ID: 6753538