The synthesis of 4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrosta-4,13-diene-3α-ol – Proposed long term metabolite (M4) of oralturinabol

Shostko, Dmitri Yu.; Liubina, Aliaksandra I.; Kozyrkov, Yu.Yu.; Беляев, С. А.

doi:10.1016/j.steroids.2020.108601

Cited by 7 publications

(6 citation statements)

References 27 publications

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“…37 An extension of Kratena's work, Shostko et al (2020) also synthesized D-ring-modified long-term metabolites of oral turinabol (4-chloro-17β-(hydroxymethyl)-17α-methyl-18-norandrosta-4,13-diene-3α-ol) 235 starting from DHEA 1 (Scheme 32). 39 Similarly, in 2017, Hurski and co-workers reported the Pdcatalyzed D-ring modified long-term metabolites of C−H acetoxylation of 17 β-methylated androgenic anabolic steroids (AAS) metandienone 248 (17β-Hydroxymethyl-17α-methyl-18-norandrost-13-ene) (Scheme 33). 40 The Pd-catalyzed C−H acetoxylation of the 17β-methyl group was employed to invert the configuration at a quaternary stereocenter of the epimeric synthetic intermediate.…”

Section: Arylidene Dehydroepiandrosterone Derivativesmentioning

confidence: 99%

Synthesis and Pharmacological Properties of Modified A- and D-Ring in Dehydroepiandrosterone (DHEA): A Review

Ali,

Motaleb,

Alam

et al. 2024

ACS Omega

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Dehydroepiandrosterone (3β-hydroxyandrost-5-en-17-one) (DHEA) is a naturally occurring steroid hormone primarily produced in the zona reticularis of the human adrenal glands. It serves as a crucial precursor for sex hormones, such as testosterone, estradiol, and androstenedione. Recent findings indicate that DHEA serves as the primary source of sex steroids in women during both pre-and postmenopausal stages. Additionally, a decline in DHEA levels with age is linked to various hormone-deficiency symptoms. Despite the wide array of biological activities that make DHEA a valuable polycyclic natural steroid, particularly for pharmaceutical and cosmetic applications, reports suggest that oral DHEA has limited clinical effect. Thus, Aand D-ring modified DHEA are synthesized and their biological activities are carried out by different research groups and enhanced biological activity reported in the literature. Here, in this review, we have tried to cover all of the synthetic routes and biological studies of modified A-and D-ring DHEA from 2015 to mid-2022.

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Section: Arylidene Dehydroepiandrosterone Derivativesmentioning

confidence: 99%

Synthesis and Pharmacological Properties of Modified A- and D-Ring in Dehydroepiandrosterone (DHEA): A Review

Ali,

Motaleb,

Alam

et al. 2024

ACS Omega

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“…Several studies have been published related to the identification of long-term metabolites of prohibited substances, in vivo and in vitro metabolism and synthesis of reference materials. The production of long-term metabolite reference material of oxymetholone [149] and long-term metabolite of oral-turinabol [150] has been achieved. Martinez-Brito et al evaluated the in vivo and in vitro metabolism of the MT related to hydroxylated metabolites using gas chromatography-time-of-flight (GC-Q/TOF) and GC-MS/MS [151].…”

Section: Expanding the Window Detection Of Exogenous Aas For Itp And ...mentioning

confidence: 99%

Olympic Anti-Doping Laboratory: The Analytical Technological Road From 2016 Rio De Janeiro to 2021 Tokyo

et al. 2021

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The summer Olympic Games is the major mega sports event since the first modern era Olympiad, held in Athens, Greece in 1896. International Olympic Committee (IOC) has the responsibility of the organization of the summer and winter Games ensuring the broadcast in all corners of earth. The World Anti-Doping Agency (WADA) is the responsible organization of the fight against doping in sports. IOC and WADA support the event's country WADA Accredited Laboratory to incorporate the maximum of the new analytical technologies to become applicable during the event's antidoping testing. The current study reviewed the last 5 years progresses of the antidoping system with emphasis on the laboratory field.

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“…A critical factor of anti‐doping analysis is the efficiency of ITPs in reliable and specific detection of indicators for the use of a prohibited substance. Hence, a considerable number of studies conducted during the past 12 months focused on the identification of new diagnostic (long‐term) metabolites, synthesis of reference material, 56,57 and implementation into routine doping controls, with four recent projects investigating 17α‐methyl steroids. For instance, Göschl et al reported on the rapid and facile detection and confirmation of stanozolol‐ N ‐glucuronides in human urine by means of urine dilution followed by online‐SPE and LC‐HRMS/MS analysis 58 .…”

Section: Anabolic Agentsmentioning

confidence: 99%

Annual banned‐substance review: Analytical approaches in human sports drug testing 2019/2020

Thevis

Kuuranne

Geyer

2020

Drug Testing and Analysis

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Analytical chemistry-based research in sports drug testing has been a dynamic endeavor for several decades, with technology-driven innovations continuously contributing to significant improvements in various regards including analytical sensitivity, comprehensiveness of target analytes, differentiation of natural/ endogenous substances from structurally identical but synthetically derived compounds, assessment of alternative matrices for doping control purposes, and so forth. The resulting breadth of tools being investigated and developed by anti-doping researchers has allowed to substantially improve anti-doping programs and data interpretation in general. Additionally, these outcomes have been an extremely valuable pledge for routine doping controls during the unprecedented global health crisis that severely affected established sports drug testing strategies. In this edition of the annual banned-substance review, literature on recent developments in antidoping published between October 2019 and September 2020 is summarized and discussed, particularly focusing on human doping controls and potential applications of new testing strategies to substances and methods of doping specified the World Anti-Doping Agency's 2020 Prohibited List.

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The synthesis of 4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrosta-4,13-diene-3α-ol – Proposed long term metabolite (M4) of oralturinabol

Cited by 7 publications

References 27 publications

Synthesis and Pharmacological Properties of Modified A- and D-Ring in Dehydroepiandrosterone (DHEA): A Review

Synthesis and Pharmacological Properties of Modified A- and D-Ring in Dehydroepiandrosterone (DHEA): A Review

Olympic Anti-Doping Laboratory: The Analytical Technological Road From 2016 Rio De Janeiro to 2021 Tokyo

Annual banned‐substance review: Analytical approaches in human sports drug testing 2019/2020

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