title: Easy stereoselective synthesis of 5α-estrane-3β,17α-diol, the major metabolite of nandrolone in the horse.
abstract: 5α-Estrane-3β,17α-diol is the major metabolite of nandrolone in horse urine. The presence of 5α-estrane-3β,17α-diol in female and gelding urines is prohibited by Racing Rules and its natural presence in male urine led regulation authorities to establish a concentration threshold of 45 ng/mL. This paper describes a rapid, simple and stereoselective synthesis of 5α-estrane-3β,17α-diol, providing horseracing laboratories with an essential reference material for their antidoping performance.
authors.affiliation: Laboratoire des Courses Hippiques, 15 rue de Paradis, 91370 Verrières le Buisson, France. f.balssa@lchfrance.fr
authors.forename: Frédéric
authors.initials: F
authors.lastname: Balssa
authors.forename: Michael
authors.initials: M
authors.lastname: Fischer
authors.forename: Yves
authors.initials: Y
authors.lastname: Bonnaire
mesh_terms: D000818:Animals; D004300:Doping in Sports / Q000517:prevention & control; D006736:Horses; D009277:Nandrolone / Q000378:metabolism*; D009641:Norethynodrel / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D015203:Reproducibility of Results; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C003578:17-ethynyl-5-estrane-3,17-diol; D009277:Nandrolone; D009641:Norethynodrel