19-Nor-5-androstenediol (BioDeep_00000027901)

   

human metabolite Endogenous


代谢物信息卡片


(1S,2R,5S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol

化学式: C18H28O2 (276.2089188)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC12CCC3C4CCC(CC4=CCC3C1CCC2O)O
InChI: 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/h2,12-17,19-20H,3-10H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1

描述信息

19-Nor-5-androstenediol is an androgen steroid that has been found to be part of nutritional supplements that are commercialized as nandrolone-free. Some reports regarding nandrolone-positive cases have been related to intake of some of these supplements. Nandrolone is the most frequently abused substance in doping control because it does not convert to estrogens and does not have and androgenic side effects. For this reason, one the major metabolites of nandrolone, 19-norandrosterone (19-NA) have been used as determinants for doping of nandrolone. However, there are situations where the occurrence of nandrolone metabolites is a phenomenon not necessarily associated with doping: a) in human ovarian follicular fluid is a possible intermediate in the multistep enzymatic conversion of androgen to estrogen, b) during the course of pregnancy, 19-NA increases in urine, c) human chorionic gonadotropin (hCG) also stimulates 19-NA excretion in urine, d) exercise has been shown to affect the urinary excretion of nandrolone metabolites such as 19-NA, e) 19-NA is a minor metabolite of oral contraceptives such as norethisterone. Furthermore, 19-NA is the main urinary metabolite of 19-Nor-5-androstenediol. Nevertheless, the prevalence of nandrolone abuse is evident; internationally, 212 cases were found in 1995 and 232 cases were found in 1996. From 1998 to 2001, nandrolone-positive findings reported by the IOC-accredited laboratories ranged from 0.17\\% to 0.65\\%. (PMID: 15902981) [HMDB]
19-Nor-5-androstenediol is an androgen steroid that has been found to be part of nutritional supplements that are commercialized as nandrolone-free. Some reports regarding nandrolone-positive cases have been related to intake of some of these supplements. Nandrolone is the most frequently abused substance in doping control because it does not convert to estrogens and does not have and androgenic side effects. For this reason, one the major metabolites of nandrolone, 19-norandrosterone (19-NA) have been used as determinants for doping of nandrolone. However, there are situations where the occurrence of nandrolone metabolites is a phenomenon not necessarily associated with doping: a) in human ovarian follicular fluid is a possible intermediate in the multistep enzymatic conversion of androgen to estrogen, b) during the course of pregnancy, 19-NA increases in urine, c) human chorionic gonadotropin (hCG) also stimulates 19-NA excretion in urine, d) exercise has been shown to affect the urinary excretion of nandrolone metabolites such as 19-NA, e) 19-NA is a minor metabolite of oral contraceptives such as norethisterone. Furthermore, 19-NA is the main urinary metabolite of 19-Nor-5-androstenediol. Nevertheless, the prevalence of nandrolone abuse is evident; internationally, 212 cases were found in 1995 and 232 cases were found in 1996. From 1998 to 2001, nandrolone-positive findings reported by the IOC-accredited laboratories ranged from 0.17\\% to 0.65\\%. (PMID: 15902981).

同义名列表

6 个代谢物同义名

(1S,2R,5S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol; 19-Nor-5-androstene-3b,17b-diol; (3b,17b)-Estr-5-ene-3,17-diol; 19-Nor-5-androstenediol; Estr-5-ene-3b,17b-diol; D5-Estrene-3b,17b-diol



数据库引用编号

8 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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WikiPathways(0)

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INOH(0)

PlantCyc(0)

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1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Wei Liu, Lan Zhang, Liangbiao Fan, Zian Lin, Yimin Cai, Zhenyi Wei, Guonan Chen. An improved hollow fiber solvent-stir bar microextraction for the preconcentration of anabolic steroids in biological matrix with determination by gas chromatography-mass spectrometry. Journal of chromatography. A. 2012 Apr; 1233(?):1-7. doi: 10.1016/j.chroma.2012.01.064. [PMID: 22386059]
  • Xavier de la Torre, Cristiana Colamonici, Davide Curcio, Francesco Molaioni, Marta Pizzardi, Francesco Botrè. A simplified procedure for GC/C/IRMS analysis of underivatized 19-norandrosterone in urine following HPLC purification. Steroids. 2011 Apr; 76(5):471-7. doi: 10.1016/j.steroids.2011.01.001. [PMID: 21236283]
  • Y L Tseng, C-Y Sun, F-H Kuo. Detection and quantification of glucuro- and sulfoconjugated metabolites in human urine following oral administration of xenobiotic 19-norsteroids. Steroids. 2006 Sep; 71(9):817-27. doi: 10.1016/j.steroids.2006.05.012. [PMID: 16814335]
  • Yvonne Schrader, Mario Thevis, Wilhelm Schänzer. Quantitative determination of metabolic products of 19-norandrostenediol in human plasma using gas chromatography/mass spectrometry. Drug metabolism and disposition: the biological fate of chemicals. 2006 Aug; 34(8):1328-35. doi: 10.1124/dmd.106.010165. [PMID: 16714373]
  • Ying Lung Tseng, Fan-Hsin Kuo, Kuo-Hu Sun. Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids. Journal of analytical toxicology. 2005 Mar; 29(2):124-34. doi: 10.1093/jat/29.2.124. [PMID: 15902981]
  • Craig E Broeder. Oral andro-related prohormone supplementation: do the potential risks outweigh the benefits?. Canadian journal of applied physiology = Revue canadienne de physiologie appliquee. 2003 Feb; 28(1):102-16. doi: 10.1139/h03-009. [PMID: 12671199]
  • L Dehennin, Y Bonnaire, P Plou. Human nutritional supplements in the horse: comparative effects of 19-norandrostenedione and 19-norandrostenediol on the 19-norsteroid profile and consequences for doping control. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2002 Jan; 766(2):257-63. doi: 10.1016/s0378-4347(01)00506-0. [PMID: 11824814]
  • G Pépin, F Vayssette, Y Gaillard. [Urinary nandrolone metabolites in antidoping control]. Annales pharmaceutiques francaises. 2001 Sep; 59(5):345-9. doi: . [PMID: 11787429]