Communications. Steroidal[2,3-d]isoxazoles

Clinton, R King; Manson, A. J.; Stonner, F. W.; Christiansen, Robert G.; Beyler, A. L.; Potts, Graeme B. S.; Arnold, Aaron

doi:10.1021/jo01060a059

Cited by 40 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Mixtures of F and IF were first identified in Orastan-A (Gaspari Nutrition) predominately as the tetrahydropyranyl ether [16] and more recently in Furazadrol (Axis Labs) [17], with incorrect labelling of the contents in both cases. Both F and IF have been reported to exert anabolic activity in the older steroid literature that was dependent on the mode of administration [18] [19] and more recently in both yeast and human HuH7 androgen bioassays [17], with the former isomer reported to display greater activity [18] [19]. Related isoxazole containing steroids, including the structurally similar danazol, are banned in competition by the World Anti-Doping Agency (WADA) and the International Federation of Horseracing Authorities (IFHA) [20] [21].…”

Section: Introductionmentioning

confidence: 99%

In vivo and in vitro metabolism of the designer anabolic steroid furazadrol in thoroughbred racehorses

Waller

Cawley

Suann

et al. 2016

Journal of Pharmaceutical and Biomedical Analysis

View full text Add to dashboard Cite

Furazadrol ([1',2']isoxazolo[4',5':2,3]-5α-androstan-17β-ol) is a designer anabolic androgenic steroid that is readily available via the internet. It contains an isoxazole fused to the steroid A-ring which offers metabolic stability and noteworthy anabolic activity raising concerns over the potential for abuse of this compound in equine sports. The metabolism of furazadrol was studied by in vivo and in vitro methods for the first time. Urinary furazadrol 17-sulfate and furazadrol 17-glucuronide metabolites were detected in vivo after a controlled administration and compared with synthetically-derived reference materials in order to confirm their identities. They were quantified to establish the excretion profile and a suitable limit of detection. Minor metabolites were also detected, including epifurazadrol, hydroxylated furazadrol, and hydroxylated and oxidised furazadrol, present as the sulfate and glucuronide conjugates. Phase II metabolites were subjected to enzymatic hydrolysis by Escherichia coli β-glucuronidase and Pseudomonas aeruginosa arylsulfatase to further confirm the identity of the corresponding phase I metabolites. The metabolism profile was compared to the products obtained from an in vitro phase I metabolism study, with all but two of the minor in vivo phase I metabolites observed in the in vitro system. These investigations identify the key urinary metabolites of furazadrol following oral administration, which can be incorporated into anti-doping screening and confirmation procedures.

show abstract

Section: Introductionmentioning

confidence: 99%

In vivo and in vitro metabolism of the designer anabolic steroid furazadrol in thoroughbred racehorses

Waller

Cawley

Suann

et al. 2016

Journal of Pharmaceutical and Biomedical Analysis

View full text Add to dashboard Cite

show abstract

“…(10) J. A. Edwards, P. G. Holton, J. C. Orr, E. Necoechea, A. de la Roz, E. Segovia, R. Urquiza, and A. Bowers, ibid., 6,174 (1963).…”

mentioning

confidence: 99%

Steroids. CCXXI.¹ Syntheses of Some Steroid Dienes

Berkoz¹,

Cross²,

Adame³

et al. 1963

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…In both cases, these supplements had incorrect labelling of the content information . Furazadrol has been reported to exert anabolic activity in the older literature, and in more recent yeast and human HuH7 androgen bioassays …”

Section: Furazadrol ([1'2’]isoxazolo[4’5’:23]‐5α‐androstan‐17β‐ol)mentioning

confidence: 87%

“…Since the first synthesis of testosterone over 80 years ago, there has been substantial work aiming to produce steroid compounds with differing and useful biological properties. During the so‐called golden age of steroid research during the 1950 and 1960s, numerous potent analogues of testosterone were synthesized, some of which were published whilst others were patented. Most of these compounds, however, were only briefly tested for their anabolic activity and were never subsequently evaluated through clinical testing or approved for sale.…”

Section: Designer Anabolic Steroidsmentioning

confidence: 99%

A review of designer anabolic steroids in equine sports

Waller

McLeod

2016

Drug Testing and Analysis

View full text Add to dashboard Cite

In recent years, the potential for anabolic steroid abuse in equine sports has increased due to the growing availability of designer steroids. These compounds are readily accessible online in 'dietary' or 'nutritional' supplements and contain steroidal compounds which have never been tested or approved as veterinary agents. They typically have unusual structures or substitution and as a result may pass undetected through current anti-doping screening protocols, making them a significant concern for the integrity of the industry. Despite considerable focus in human sports, until recently there has been limited investigation into these compounds in equine systems. To effectively respond to the threat of designer steroids, a detailed understanding of their metabolism is needed to identify markers and metabolites arising from their misuse. A summary of the literature detailing the metabolism of these compounds in equine systems is presented with an aim to identify metabolites suitable for incorporation into screening protocols by anti-doping laboratories. The future of equine anti-doping research is likely to be guided by the incorporation of alternate testing matrices into routine screening, the improvement of in vitro technologies that can mimic in vivo equine metabolism, and the improvement of instrumentation or analytical methods that allow for the development of untargeted screening, and metabolomics approaches for use in anti-doping screening protocols.

show abstract

Communications. Steroidal[2,3-d]isoxazoles

Cited by 40 publications

References 0 publications

In vivo and in vitro metabolism of the designer anabolic steroid furazadrol in thoroughbred racehorses

In vivo and in vitro metabolism of the designer anabolic steroid furazadrol in thoroughbred racehorses

Steroids. CCXXI.¹ Syntheses of Some Steroid Dienes

A review of designer anabolic steroids in equine sports

Contact Info

Product

Resources

About

Communications. Steroidal[2,3-d]isoxazoles

Cited by 40 publications

References 0 publications

In vivo and in vitro metabolism of the designer anabolic steroid furazadrol in thoroughbred racehorses

In vivo and in vitro metabolism of the designer anabolic steroid furazadrol in thoroughbred racehorses

Steroids. CCXXI.1 Syntheses of Some Steroid Dienes

A review of designer anabolic steroids in equine sports

Contact Info

Product

Resources

About

Steroids. CCXXI.¹ Syntheses of Some Steroid Dienes