[2,2,4,4-²H4]-19-noretiocholanolone | 361432-50-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [2,2,4,4-²H4]-19-noretiocholanolone
• 英文别名: d4-19-Noretiocholanolone；(3R,5R,8R,9R,10S,13S,14S)-2,2,4,4-tetradeuterio-3-hydroxy-13-methyl-3,5,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 361432-50-0
• 化学式: C₁₈H₂₈O₂
• 分子量: 280.387
• InChiKey: UOUIARGWRPHDBX-GWMFAPGHSA-N

反应信息

• 作为反应物：
  描述：

  [2,2,4,4-²H4]-19-noretiocholanolone 、 三甲基乙炔基硅 在 N-甲基-N-(三甲基硅烷基)三氟乙酰胺 、 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 [2,2,4,4-²H4]-5β-estran-17α-ethynyl-3α,17β-diol
  参考文献：
  名称：

  Doping in sport: 3. Metabolic conversion of oral norethisterone to urinary 19-norandrosterone

  摘要：

  The detection of 19 norandrosterone (19-NA) in a competitor's urine sample is taken as prima facie evidence of administration of nandrolone or other 19-norsteroid but a potential problem is that administration of norethisterone, a progestogen used for menstrual disorders and for hormonal contraception, also results in the excretion of 19-NA that can exceed the laboratory reporting threshold of 2 ng/mL The contribution of norethisterone to urinary 19-NA with and without 19-norandrostenedione. a known norethisterone tablet impurity, requires evaluation. Preparations containing, either <2 ng or 1 mu g 19-norandrostenedione impurity per 5mg of norethisterone, administered to female volunteers (n=10) in doses comparable to those used for menstrual disorders (5mg three times daily for 10 days), resulted in maximal 19-NA concentrations of 51 and 63 ng/mL, respectively. The maximal concentration of 19-NA, 2h post-administration of a single 1 mu g dose of 19-norandrostenedione, was 2.4 ng/mL These results prove unequivocally that norethisterone is metabolized to 19-NA and that there is only a minor contribution from the impurity 19-norandrostenedione. Administration to women (n=30) of a single contraceptive tablet containing norethisterone (I mg) with one of the highest proportions of the impurity 19-norandrostenedione (similar to 0.5 mu g, 0.05%, w/w) resulted in a urinary 19-NA concentration of 9.1 ng/mL, with a maximum concentration ratio of 19-NA to the norethisterone metabolite 3 alpha,5 beta-tetra hydronorethisterone of 0.36. We provide data that should remove the need for time-consuming follow-up investigations to consider whether doping with 19-norandrogens has occurred. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.11.008