Synthetic Androgens as Designer Supplements

Joseph, Jan Felix; Parr, Maria Kristina

doi:10.2174/1570159x13666141210224756

Cited by 48 publications

(51 citation statements)

References 124 publications

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“…Due to the lack of clinical studies, little is known about the pharmacological effects of these designer steroids. Use of other banned anabolic‐androgenic steroids are known to cause long‐term health effects . Regulatory agencies are increasingly tasked with detecting and identifying these designer steroids in products.…”

Section: Introductionmentioning

confidence: 99%

Identification of the designer steroid Androsta‐3,5‐diene‐7,17‐dione in a dietary supplement

Lorenz

Toomey

Lanzarotta

et al. 2019

Drug Testing and Analysis

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A liquid chromatography‐mass spectrometry (LC–MS) screen for known anabolic‐androgenic steroids in a dietary supplement product marketed for “performance enhancement” detected an unknown compound having steroid‐like spectral characteristics. The compound was isolated using high performance liquid chromatography with ultraviolet detection (HPLC–UV) coupled with an analytical scale fraction collector. After the compound was isolated, it was then characterized using gas chromatography with simultaneous Fourier Transform infrared detection and mass spectrometry (GC–FT–IR–MS), liquid chromatography–high resolution accurate mass–mass spectrometry (LC–HRAM–MS) and nuclear magnetic resonance (NMR). The steroid had an accurate mass of m/z 285.1847 (error−0.57 ppm) for the protonated species [M + H]+, corresponding to a molecular formula of C19H24O2. Based on the GC–FT–IR–MS data, NMR data, and accurate mass, the compound was identified as androsta‐3,5‐diene‐7,17‐dione. Although this is not the first reported identification of this designer steroid in a dietary supplement, the data provided adds information for identification of this compound not previously reported. This compound was subsequently detected in another dietary supplement product, which contained three additional active ingredients.

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Section: Introductionmentioning

confidence: 99%

Identification of the designer steroid Androsta‐3,5‐diene‐7,17‐dione in a dietary supplement

Lorenz

Toomey

Lanzarotta

et al. 2019

Drug Testing and Analysis

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show abstract

“…It is very powerful, prohormone, does not retain water in the body, and has a strong anabolic and androgenic ratio of 300:1 (Joseph and Parr, 2015). 6 β -Chloro-androst-4-en-17 β-ol-3-one (22) is an epimer of hexadrone, and has milder properties than hexadrone.…”

Section: Chlorinated Steroidsmentioning

confidence: 99%

Halogenated (F, Cl, Br, I) Anabolic Steroids and their Biological Activities

Kilimnik¹,

Gloriozova²,

Dembitsky³

2017

Int. J. Curr. Res. Biosci. Plant Biol.

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A b s t r a c t A r t i c l e I n f oThe present review describes the biological activities of synthetic anabolic halogenated (F, Cl, Br and I) steroids. About sixty biologically active halogenated steroids have shown confirmed anti-inflammatory, estrogenic, anabolic, gynecological disorders, anti-arthritic, antineoplastic, and other activities. The structures and reported and predicted activities of halogenated steroids are available. With the computer programme PASS and based on structure-activity relationships (SAR), some additional activities are also predicted, which point towards new possible applications of these lipids. This review emphasizes the role of halogenated steroids as an important source and potential leads for drug discovery and they are of great interest to chemists, physicians, biologists, pharmacologists and the pharmaceutical industry.

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“…Alternatively, in vitro technologies based on cultured liver cells or liver extracts provide methods that mitigate many of the ethical concerns regarding human or animal health and safety . These issues are of particular relevance in the case of synthetic or so‐called designer steroids since they are often brought to market in a clandestine fashion, and the majority of these compounds do not have available data regarding their purity, safety, or efficacy . Given this, in vitro experiments would offer a safer approach to identifying metabolite markers.…”

Section: Introductionmentioning

confidence: 99%

Replacing PAPS: In vitro phase II sulfation of steroids with the liver S9 fraction employing ATP and sodium sulfate

Weththasinghe

Waller

Fam

et al. 2017

Drug Testing and Analysis

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In vitro technologies provide the capacity to study drug metabolism where in vivo studies are precluded due to ethical or financial constraints. The metabolites generated by in vitro studies can assist anti-doping laboratories to develop protocols for the detection of novel substances that would otherwise evade routine screening efforts. In addition, professional bodies such as the Association of Official Racing Chemists (AORC) currently permit the use of in-vitro-derived reference materials for confirmation purposes providing additional impetus for the development of cost effective in vitro metabolism platforms. In this work, alternative conditions for in vitro phase II sulfation using human, equine or canine liver S9 fraction were developed, with adenosine triphosphate (ATP) and sodium sulfate in place of the expensive and unstable co-factor 3'-phosphoadenosine-5'-phosphosulfate (PAPS), and employed for the generation of six representative steroidal sulfates. Using these conditions, the equine in vitro phase II metabolism of the synthetic or so-called designer steroid furazadrol ([1',2']isoxazolo[4',5':2,3]-5α-androstan-17β-ol) was investigated, with ATP and Na SO providing comparable metabolism to reactions using PAPS. The major in vitro metabolites of furazadrol matched those observed in a previously reported equine in vivo study. Finally, the equine in vitro phase II metabolism of the synthetic steroid superdrol (methasterone, 17β-hydroxy-2α,17α-dimethyl-5α-androstan-3-one) was performed as a prediction of the in vivo metabolic profile.

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Synthetic Androgens as Designer Supplements

Cited by 48 publications

References 124 publications

Identification of the designer steroid Androsta‐3,5‐diene‐7,17‐dione in a dietary supplement

Identification of the designer steroid Androsta‐3,5‐diene‐7,17‐dione in a dietary supplement

Halogenated (F, Cl, Br, I) Anabolic Steroids and their Biological Activities

Replacing PAPS: In vitro phase II sulfation of steroids with the liver S9 fraction employing ATP and sodium sulfate

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