19-Noretiocholanolone
IUPAC 名称
(1R,2S,5R,7R,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one
描述
19-noretiocholanolone (19-NE) is one of the two main indicators used to prove the illegal use of nandrolone by humans. Recent studies showed that 19-NE can be endogenously produced in some individuals. The mediated cases observed over the last years generated some questions about the appropriateness of the official International Olympic Committee cutoff level, which is 2 ng/mL of 19-NA in male urine samples. In 1997, in France, quite a few sportsmen had concentrations of nandrolone metabolites very close to the IOC cut off limit (2ng/ml). At that time, a debate took place about the capability of the human male body to produce by itself these metabolites without any intake of nandrolone or related compounds. The International Football Federation (FIFA) was very concerned with this problem, especially because the World Cup was about to start in France. Concentrations of 19- noretiocholanolone after a game are generally higher than those before games. Recent studies demonstrated the endogenous production of these compounds in man at concentrations very close to the threshold of the International Olympic Committee (IOC), i.e. 2 ng/ml. Because the possibility of reaching or exceeding this fateful limit is difficult to exclude, a complementary biochemical parameter is necessary for the differentiation of endogenous 19-NE production from residues resulting from nandrolone consumption. (PMID: 11888015, 11755174) [HMDB]
异构
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12[H]
InChI标识符
InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h11-16,19H,2-10H2,1H3/t11-,12-,13+,14-,15-,16+,18+/m1/s1
键
UOUIARGWRPHDBX-DHMVHTBWSA-N