Nandrolone decanoate (BioDeep_00000002085)

 

Secondary id: BioDeep_00001867905

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl decanoate

化学式: C28H44O3 (428.3290274)
中文名称: 癸酸诺龙
谱图信息: 最多检出来源 Homo sapiens(blood) 4.17%

分子结构信息

SMILES: CCCCCCCCCC(=O)OC1CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C
InChI: InChI=1S/C28H44O3/c1-3-4-5-6-7-8-9-10-27(30)31-26-16-15-25-24-13-11-20-19-21(29)12-14-22(20)23(24)17-18-28(25,26)2/h19,22-26H,3-18H2,1-2H3/t22-,23+,24+,25-,26-,28-/m0/s1

描述信息

Nandrolone decanoate is only found in individuals that have used or taken this drug. It is a C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedule III drug in the U.S. Nandrolone is an androgen receptor agonist. The drug bound to the receptor complexes which allows it to enter the nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D050071 - Bone Density Conservation Agents

同义名列表

13 个代谢物同义名

(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl decanoate; 19-Nor-4-androstene-17 beta-ol-3-one 17-decanoate; 17 beta-Hydroxyestr-4-en-3-one 17-decanoate; 19-Nortestosterone decanoate; Norandrostenolone decanoate; Nortestosterone decanoate; Nandrolone decanoic acid; Nandrolone decanoate; Deca-Durabolin; Decadurobolin; Decadurabolin; Retabolyl; Retabolil



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

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

  • Sofia Zelleroth, Erik Nylander, Ellinor Kjellgren, Alfhild Grönbladh, Mathias Hallberg. Nandrolone decanoate and testosterone undecanoate differently affect stress hormones, neurotransmitter systems, and general activity in the male rat. Behavioural brain research. 2022 08; 432(?):113971. doi: 10.1016/j.bbr.2022.113971. [PMID: 35738337]
  • Renan Pozzi, Leandro Fernandes, Vanessa Cavalcante da Silva, Vânia D'Almeida. Nandrolone decanoate and resistance exercise affect body composition and energy metabolism. Steroids. 2021 10; 174(?):108899. doi: 10.1016/j.steroids.2021.108899. [PMID: 34358557]
  • Vinícius Augusto Simão, Luiz Antonio Lupi Júnior, Gabriel Adan Araujo Leite, Isabel Cristina Cherici Camargo, Luiz Gustavo de Almeida Chuffa. Nandrolone decanoate causes uterine injury by changing hormone levels and sex steroid receptors in a dose- and time-dependent manner. Reproductive toxicology (Elmsford, N.Y.). 2021 06; 102(?):98-108. doi: 10.1016/j.reprotox.2021.05.002. [PMID: 33984419]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Fernando A C Seara, Pedro P Pereira-Junior, Claudio Silva-Almeida, Raoni C Dos-Santos, Raquel N Souza, César R M Costa, Ainá E Domingos, Raiana A Q Barbosa, Ana P Ferraz, André A N Machado, Vânia M Ceccato, Christina M Takiya, Cristiano G Ponte, Luis C Reis, Emerson L Olivares, Jose H M Nascimento. Anabolic steroid excess promotes hydroelectrolytic and autonomic imbalance in adult male rats: Is it enough to alter blood pressure?. Steroids. 2020 11; 163(?):108711. doi: 10.1016/j.steroids.2020.108711. [PMID: 32739291]
  • Jasmina Sretenovic, Vladimir Zivkovic, Ivan Srejovic, Vladimir Ajdzanovic, Natasa Ristic, Miroljub Trifunovic, Suzana Pantovic, Slavoljub Jovic, Vladimir Jakovljevic, Sergey Bolevich, Zoran Milosavljevic, Verica Milosevic. Immunohistomorphometric and Hormonal Analysis of the Pituitary Gonadotropic Cells After Application of the Nandrolone Decanoate and Swimming Training in Adult Male Rats. Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada. 2020 08; 26(4):699-707. doi: 10.1017/s143192762000166x. [PMID: 32519626]
  • Aida Kahal, Rachida Allem, Touria Zahzeh, Saida Oulmane, Zahra Tafroukhte. Abuse of androgenic anabolic drugs with "Cycling" induces hepatic steatosis in adult male mice. Steroids. 2020 03; 155(?):108574. doi: 10.1016/j.steroids.2019.108574. [PMID: 31901422]
  • Eman Taha Mohammed, Abeer M Radi, Lotfi Aleya, Mohamed M Abdel-Daim. Cynara scolymus leaves extract alleviates nandrolone decanoate-induced alterations in testicular function and sperm quality in albino rats. Environmental science and pollution research international. 2020 Feb; 27(5):5009-5017. doi: 10.1007/s11356-019-07302-4. [PMID: 31845274]
  • Ewelyne Miranda de Lima, Karla de Oliveira Dos Santos Cassaro, Cristiane Lyrio da Silva, Mirian de Almeida Silva, Mikaella Polonine Poltronieri, Andrews Marques do Nascimento, Tadeu Uggere de Andrade, Nazaré Souza Bissoli, Girlandia Alexandre Brasil. Eight weeks of treatment with nandrolone decanoate in female rats promotes disruption in the redox homeostasis and impaired renal function. Life sciences. 2020 Feb; 242(?):117227. doi: 10.1016/j.lfs.2019.117227. [PMID: 31881226]
  • David Balgoma, Sofia Zelleroth, Alfhild Grönbladh, Mathias Hallberg, Curt Pettersson, Mikael Hedeland. Anabolic androgenic steroids exert a selective remodeling of the plasma lipidome that mirrors the decrease of the de novo lipogenesis in the liver. Metabolomics : Official journal of the Metabolomic Society. 2020 01; 16(1):12. doi: 10.1007/s11306-019-1632-0. [PMID: 31925559]
  • Neveen A Salem, Hanan S Alnahdi. The impact of nandrolone decanoate abuse on experimental animal model: Hormonal and biochemical assessment. Steroids. 2020 01; 153(?):108526. doi: 10.1016/j.steroids.2019.108526. [PMID: 31669061]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • A E Rosca, Camelia Sorina Stancu, Corin Badiu, Bogdan Ovidiu Popescu, Radu Mirica, Constantin Căruntu, Serban Gologan, Suzana Elena Voiculescu, Ana-Maria Zagrean. Lipid Profile Changes Induced by Chronic Administration of Anabolic Androgenic Steroids and Taurine in Rats. Medicina (Kaunas, Lithuania). 2019 Aug; 55(9):. doi: 10.3390/medicina55090540. [PMID: 31462007]
  • Amany Mohamed Shalaby, Dina Fouad El Shaer. Lycopene protects against renal cortical damage induced by nandrolone decanoate in adult male rats. Annals of anatomy = Anatomischer Anzeiger : official organ of the Anatomische Gesellschaft. 2019 Jul; 224(?):142-152. doi: 10.1016/j.aanat.2019.05.003. [PMID: 31108192]
  • Amer A Almaiman, Sulaiman H Almaiman, Elsayed I Elagamy, Osama Al Wutayd, Mohammed Almarzuqi, Rayyan Alzunaidi, Sami Alhatlani, Eltayeb E Eid. Side effects of anabolic steroids used by athletes at Unaizah Gyms, Saudi Arabia: a pilot study. The Journal of sports medicine and physical fitness. 2019 Mar; 59(3):489-495. doi: 10.23736/s0022-4707.18.08366-4. [PMID: 29687691]
  • Fatemeh Zarei, Farshad Moradpour, Ahmad Ali Moazedi, Ali Pourmotabbed, Mozhgan Veisi. Nandrolone administration abolishes hippocampal fEPSP-PS potentiation and passive avoidance learning of adolescent male rats. Canadian journal of physiology and pharmacology. 2019 Feb; 97(2):130-139. doi: 10.1139/cjpp-2018-0293. [PMID: 30562047]
  • Umut H Kantarci, Zekine Punduk, Omer Senarslan, Alper Dirik. Evaluation of anabolic steroid induced renal damage with sonography in bodybuilders. The Journal of sports medicine and physical fitness. 2018 Nov; 58(11):1681-1687. doi: 10.23736/s0022-4707.17.06763-9. [PMID: 29148625]
  • Aida Kahal, Rachida Allem. Reversible effects of anabolic steroid abuse on cyto-architectures of the heart, kidneys and testis in adult male mice. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Oct; 106(?):917-922. doi: 10.1016/j.biopha.2018.07.038. [PMID: 30119263]
  • Asghar Tofighi, Shima Ahmadi, Seyyedeh Masoumeh Seyyedi, Alireza Shirpoor, Fatemeh Kheradmand, Farzaneh Hosseini Gharalari. Nandrolone administration with or without strenuous exercise promotes overexpression of nephrin and podocin genes and induces structural and functional alterations in the kidneys of rats. Toxicology letters. 2018 Jan; 282(?):147-153. doi: 10.1016/j.toxlet.2017.10.015. [PMID: 29097219]
  • Ibtesam Saad Al-Dhuayan. Possible Protective Role of Whey Protein on the Rat's Liver Tissues Treated with Nandrolone decanoate. Pakistan journal of biological sciences : PJBS. 2018 Jan; 21(6):262-274. doi: 10.3923/pjbs.2018.262.274. [PMID: 30311477]
  • Rosario Barone, Alessandro Pitruzzella, Antonella Marino Gammazza, Francesca Rappa, Monica Salerno, Fulvio Barone, Claudia Sangiorgi, Daniela D'Amico, Nicola Locorotondo, Francesca Di Gaudio, Luigi Cipolloni, Valentina Di Felice, Stefania Schiavone, Venerando Rapisarda, Gabriele Sani, Amos Tambo, Francesco Cappello, Emanuela Turillazzi, Cristoforo Pomara. Nandrolone decanoate interferes with testosterone biosynthesis altering blood-testis barrier components. Journal of cellular and molecular medicine. 2017 08; 21(8):1636-1647. doi: 10.1111/jcmm.13092. [PMID: 28244681]
  • Josilene M Rodrigues, Vinicius P P Oliveira, Julia P Furlan, Ana Claudia Munhoz, Marcelo R S Rempel, Marcia N Brito, Nilton A Brito, Maria M D Pedrosa, Cecília E M Costa. Immediate and residual effects of low-dose nandrolone decanoate and treadmill training on adipose and reproductive tissues of male Wistar rats. Archives of physiology and biochemistry. 2017 May; 123(2):68-77. doi: 10.1080/13813455.2016.1260592. [PMID: 28019124]
  • Izabela F Caliman, Cristian S Bernabe, Antônio F de Melo, Girlândia A Brasil, Andrews M do Nascimento, Ewelyne M de Lima, Suely G Figueiredo, Tadeu U de Andrade, Nazaré S Bissoli. Long-term treatment with Nandrolone Decanoate impairs mesenteric vascular relaxation in both sedentary and exercised female rats. Steroids. 2017 04; 120(?):7-18. doi: 10.1016/j.steroids.2017.02.001. [PMID: 28192127]
  • Jovana Joksimovic, Dragica Selakovic, Milovan Matovic, Ivan Zaletel, Nela Puskas, Gvozden Rosic. The role of neuropeptide-Y in nandrolone decanoate-induced attenuation of antidepressant effect of exercise. PloS one. 2017; 12(6):e0178922. doi: 10.1371/journal.pone.0178922. [PMID: 28582442]
  • Parmita Chowdhury, Rita Mahanta. Effect of Administration of Nandrolone Decanoate upon Aldosterone Concentration and Serum Na+/K+ Levels in Albino Mice. Cardiovascular & hematological agents in medicinal chemistry. 2017; 14(3):160-166. doi: 10.2174/1871525715666161121152116. [PMID: 27875951]
  • R W Kalicharan, M R Bout, C Oussoren, H Vromans. Where does hydrolysis of nandrolone decanoate occur in the human body after release from an oil depot?. International journal of pharmaceutics. 2016 Dec; 515(1-2):721-728. doi: 10.1016/j.ijpharm.2016.10.068. [PMID: 27989828]
  • Christina Tsitsimpikou, Fotini Vasilaki, Konstantinos Tsarouhas, Persefoni Fragkiadaki, Maria Tzardi, Nikolaos Goutzourelas, Charitini Nepka, Alexandra Kalogeraki, Ioannis Heretis, Zoi Epitropaki, Dimitrios Kouretas, Aristidis M Tsatsakis. Nephrotoxicity in rabbits after long-term nandrolone decanoate administration. Toxicology letters. 2016 Sep; 259(?):21-27. doi: 10.1016/j.toxlet.2016.06.1122. [PMID: 27346656]
  • N Gårevik, A Börjesson, E Choong, L Ekström, M Lehtihet. Impact of single-dose nandrolone decanoate on gonadotropins, blood lipids and HMG CoA reductase in healthy men. Andrologia. 2016 Jun; 48(5):595-600. doi: 10.1111/and.12488. [PMID: 26370185]
  • Elzbieta Palonek, Magnus Ericsson, Nina Gårevik, Anders Rane, Mikael Lehtihet, Lena Ekström. Atypical excretion profile and GC/C/IRMS findings may last for nine months after a single dose of nandrolone decanoate. Steroids. 2016 Apr; 108(?):105-11. doi: 10.1016/j.steroids.2016.02.004. [PMID: 26853157]
  • Emanuela Turillazzi, Margherita Neri, Daniela Cerretani, Santina Cantatore, Paola Frati, Laura Moltoni, Francesco Paolo Busardò, Cristoforo Pomara, Irene Riezzo, Vittorio Fineschi. Lipid peroxidation and apoptotic response in rat brain areas induced by long-term administration of nandrolone: the mutual crosstalk between ROS and NF-kB. Journal of cellular and molecular medicine. 2016 Apr; 20(4):601-12. doi: 10.1111/jcmm.12748. [PMID: 26828721]
  • Tamara Nikolic, Vladimir Zivkovic, Maja Jevdjevic, Marko Djuric, Ivan Srejovic, Dragan Djuric, Nevena Jeremic, Dusan Djuric, Sergey Bolevich, Vladimir Jakovljevic. The effects of chronic administration of nandrolone decanoate on redox status in exercised rats. Molecular and cellular biochemistry. 2016 Jan; 411(1-2):95-105. doi: 10.1007/s11010-015-2571-3. [PMID: 26361780]
  • A E Roşca, I Stoian, C Badiu, L Gaman, B O Popescu, L Iosif, R Mirica, I C Tivig, C S Stancu, C Căruntu, S E Voiculescu, L Zăgrean. Impact of chronic administration of anabolic androgenic steroids and taurine on blood pressure in rats. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2016; 49(6):e5116. doi: 10.1590/1414-431x20165116. [PMID: 27254659]
  • Girlandia Alexandre Brasil, Ewelyne Miranda de Lima, Andrews Marques do Nascimento, Izabela Facco Caliman, Ana Raquel Santos de Medeiros, Mauro Sérgio Batista Silva, Gláucia Rodrigues de Abreu, Adelina Martha dos Reis, Tadeu Uggere de Andrade, Nazaré Souza Bissoli. Nandrolone decanoate induces cardiac and renal remodeling in female rats, without modification in physiological parameters: The role of ANP system. Life sciences. 2015 Sep; 137(?):65-73. doi: 10.1016/j.lfs.2015.07.005. [PMID: 26165753]
  • Hanaa Mahmoud Mohamed, Manal Abdul-Hamid Mohamed. Effect of different doses of nandrolone decanoate on lipid peroxidation, DNA fragmentation, sperm abnormality and histopathology of testes of male Wister rats. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie. 2015 Jan; 67(1):1-11. doi: 10.1016/j.etp.2014.09.003. [PMID: 25440442]
  • Qianchun Yang, Minawaer Abudou, Xi Sheng Xie, Taixiang Wu. Androgens for the anaemia of chronic kidney disease in adults. The Cochrane database of systematic reviews. 2014 Oct; ?(10):CD006881. doi: 10.1002/14651858.cd006881.pub2. [PMID: 25300168]
  • Irene Riezzo, Emanuela Turillazzi, Stefania Bello, Santina Cantatore, Daniela Cerretani, Marco Di Paolo, Anna Ida Fiaschi, Paola Frati, Margherita Neri, Monica Pedretti, Vittorio Fineschi. Chronic nandrolone administration promotes oxidative stress, induction of pro-inflammatory cytokine and TNF-α mediated apoptosis in the kidneys of CD1 treated mice. Toxicology and applied pharmacology. 2014 Oct; 280(1):97-106. doi: 10.1016/j.taap.2014.06.031. [PMID: 25065671]
  • Gurmeet K S Singh, Leo Turner, Reena Desai, Mark Jimenez, David J Handelsman. Pharmacokinetic-pharmacodynamic study of subcutaneous injection of depot nandrolone decanoate using dried blood spots sampling coupled with ultrapressure liquid chromatography tandem mass spectrometry assays. The Journal of clinical endocrinology and metabolism. 2014 Jul; 99(7):2592-8. doi: 10.1210/jc.2014-1243. [PMID: 24684468]
  • Serafim Tsitsilonis, Panayiotis E Chatzistergos, Chatzistergos E Panayiotis, Athanasios S Mitousoudis, Mitousoudis S Athanasios, Stavros K Kourkoulis, Kourkoulis K Stavros, Ioannis S Vlachos, Vlachos S Ioannis, George Agrogiannis, Agrogiannis George, Konstantinos Fasseas, Fasseas Konstantinos, Despina N Perrea, Perrea N Despina, Aristides B Zoubos, Zoubos B Aristides. Anabolic androgenic steroids reverse the beneficial effect of exercise on tendon biomechanics: an experimental study. Foot and ankle surgery : official journal of the European Society of Foot and Ankle Surgeons. 2014 Jun; 20(2):94-9. doi: 10.1016/j.fas.2013.12.001. [PMID: 24796826]
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  • Stephan Pinheiro Frankenfeld, Leonardo Pires de Oliveira, Daniele Leão Ignacio, Raquel Guimarães Coelho, Mariana Nigro Mattos, Andrea Claudia Freitas Ferreira, Denise Pires Carvalho, Rodrigo Soares Fortunato. Nandrolone decanoate inhibits gluconeogenesis and decreases fasting glucose in Wistar male rats. The Journal of endocrinology. 2014 Feb; 220(2):143-53. doi: 10.1530/joe-13-0259. [PMID: 24403377]
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  • Alfhild Grönbladh, Jenny Johansson, Mark M Kushnir, Jonas Bergquist, Mathias Hallberg. The impact of nandrolone decanoate and growth hormone on biosynthesis of steroids in rats. Steroids. 2013 Dec; 78(12-13):1192-9. doi: 10.1016/j.steroids.2013.08.012. [PMID: 24012727]
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