Estan (BioDeep_00000860362)

Main id: BioDeep_00000002829

 


代谢物信息卡片


(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one

化学式: C20H30O2 (302.2246)
中文名称: 17α-甲基睾甾酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C)O)C
InChI: InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1

描述信息

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03E - Androgens and female sex hormones in combination > G03EK - Androgens and female sex hormones in combination with other drugs
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03B - Androgens > G03BA - 3-oxoandrosten (4) derivatives
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D000970 - Antineoplastic Agents

同义名列表

121 个代谢物同义名

(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one; Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17.beta.)-; Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17beta)-; 17(alpha)-Methyl-delta4-androsten-17(beta)-ol-3-one; (17-beta)-17-Hydroxy-17-methylandrost-4-en-3-one; 4-Androstene-17.alpha.-methyl-17.beta.-ol-3-one; Androst-4-en-3-one, 17.beta.-hydroxy-17-methyl-; 17beta-Hydroxy-17alpha-methyl-4-androsten-3-one; (17beta)-17-hydroxy-17-methylandrost-4-en-3-one; Androst-4-en-3-one, 17-beta-hydroxy-17-methyl-; 17.alpha.-Methyl-3-oxo-4-androsten-17.beta.-ol; 17alpha-Methyl-delta-androsten-17beta-ol-3-one; 4-Androstene-17-alpha-methyl-17-beta-ol-3-one; Androst-4-en-3-one, 17beta-hydroxy-17-methyl-; 4-08-00-01010 (Beilstein Handbook Reference); 4-Androstene-17alpha-methyl-17beta-ol-3-one; 17-beta-Hydroxy-17-methylandrost-4-en-3-one; 17alpha-Methyl-4-androsten-17beta-ol-3-one; 17alpha-Methyl-3-oxo-4-androsten-17beta-ol; 17beta-hydroxy-17-methylandrost-4-en-3-one; 17-Hydroxy-17-methyl-3-keto-androstene-4; WLN: L E5 B666 OV MUTJ A E FQ F -B&AEF; Methyltestosterone [USAN:BAN:INN:JAN]; Methyltestosterone (JP15\USP\INN); Premarin with Methyltestosterone; Metiltestosterona [INN-Spanish]; Methyltestosteronum [INN-Latin]; 17.alpha.-Methyltestosterone; 17alpha-Methyltestosterone; Metiltestosterone [DCIT]; Testosterone, 17-methyl-; component of Tylosterone; component of Gynetone; 17-Methyltestosterone; 17-Methyltestosteron; METHYL TESTOSTERONE; Testoviron (tablet); component of Estan; methyltestosterone; Homandren, tablets; Androsan (tablets); Neo-Homobreol [M]; Glosso sterandryl; Androsan, tablets; Testovis (tablet); Glosso-Sterandryl; Anertan (tablets); Neo-Hombreol [M]; Anertan, tablets; EINECS 200-366-3; Testoviron (VAN); Homandren (VAN); NCGC00091009-01; NCGC00091009-03; M.T.Mucorettes; Testovis Depot; Orchisterone-M; Neo-Hombreol-M; Androsan (VAN); Oreton Methyl; Anertan (VAN); LMST02020029; Android (TN); Synandrotabs; SMR000058528; MLS000759474; 46444_RIEDEL; ZINC03814422; Testred (TN); M7252_SIGMA; BRN 2057425; 69240_FLUKA; Testhormone; 69241_FLUKA; Mastestona; NSC 139965; CCRIS 3723; Testoviron; 31745-24-1; Synandrets; Malestrone; Estratest; Andrometh; L 589.372; 1300-17-0; Androsten; Metestone; Mesterone; Homandren; HSDB 3365; Metandren; NSC139965; Oreton-M; Stenolon; NSC-9701; Oraviron; RU 24400; Oreton M; Masenone; Dumogran; Steronyl; Androsan; Dianabol; Hormale; 58-18-4; NSC9701; Metrone; Malogen; CDB 110; Nabolin; Syndren; Android; Anertan; Testora; Testred; C07198; Nu-man; D00408; U 2842; Estan; Methyltestosterone



数据库引用编号

12 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。

亚细胞结构定位 关联基因列表
Cytoplasm 6 AR, CASP3, DMRT1, ESR1, HPGDS, NR3C1
Peripheral membrane protein 3 CYP11A1, CYP11B2, ESR1
Endoplasmic reticulum membrane 4 CYP17A1, CYP19A1, HSP90B1, STAR
Mitochondrion membrane 2 CYP11A1, CYP11B2
Nucleus 8 AR, CASP3, DMRT1, ESR1, FIGLA, FOXL2, HSP90B1, NR3C1
cytosol 7 AR, CASP3, ESR1, GPT, HPGDS, HSP90B1, NR3C1
centrosome 1 NR3C1
nucleoplasm 6 AR, CASP3, ESR1, FOXL2, HPGDS, NR3C1
Cell membrane 2 ESR1, STAR
Cytoplasmic side 1 ESR1
Multi-pass membrane protein 1 CYP19A1
Synapse 1 NR3C1
glutamatergic synapse 1 CASP3
Golgi apparatus 1 ESR1
Golgi membrane 1 INS
mitochondrial inner membrane 2 CYP11A1, CYP11B2
neuronal cell body 2 CASP3, CYP17A1
smooth endoplasmic reticulum 1 HSP90B1
plasma membrane 3 AR, ESR1, STAR
Membrane 7 AR, CYP11A1, CYP11B2, CYP19A1, ESR1, HSP90B1, NR3C1
axon 1 CYP17A1
extracellular exosome 3 GPT, HSP90B1, SHBG
endoplasmic reticulum 3 CYP17A1, CYP19A1, HSP90B1
extracellular space 4 AMH, CGA, GNRH1, INS
perinuclear region of cytoplasm 1 HSP90B1
mitochondrion 4 CYP11A1, CYP11B2, NR3C1, STAR
protein-containing complex 4 AR, ESR1, HSP90B1, NR3C1
intracellular membrane-bounded organelle 1 HPGDS
Microsome membrane 2 CYP17A1, CYP19A1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 STAR
Secreted 4 AMH, CGA, INS, SHBG
extracellular region 6 AMH, CGA, GNRH1, HSP90B1, INS, SHBG
mitochondrial matrix 3 CYP11A1, NR3C1, STAR
transcription regulator complex 2 ESR1, FIGLA
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 NR3C1
midbody 1 HSP90B1
Mitochondrion inner membrane 2 CYP11A1, CYP11B2
Cytoplasm, cytoskeleton, spindle 1 NR3C1
focal adhesion 1 HSP90B1
spindle 1 NR3C1
mitochondrial intermembrane space 1 STAR
collagen-containing extracellular matrix 1 HSP90B1
nuclear speck 2 AR, NR3C1
chromatin 6 AR, DMRT1, ESR1, FIGLA, FOXL2, NR3C1
Chromosome 1 NR3C1
Flemming body 1 FOXL2
endosome lumen 1 INS
female germ cell nucleus 1 DMRT1
Nucleus, nucleoplasm 1 NR3C1
Melanosome 1 HSP90B1
euchromatin 1 ESR1
sperm plasma membrane 1 HSP90B1
secretory granule lumen 1 INS
Golgi lumen 2 CGA, INS
endoplasmic reticulum lumen 2 HSP90B1, INS
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Sarcoplasmic reticulum lumen 1 HSP90B1
[Isoform 1]: Nucleus 1 ESR1
death-inducing signaling complex 1 CASP3
[Isoform Alpha]: Cytoplasm 1 NR3C1
endocytic vesicle lumen 1 HSP90B1
follicle-stimulating hormone complex 1 CGA
pituitary gonadotropin complex 1 CGA
[Isoform Beta]: Nucleus 1 NR3C1
[Isoform Alpha-B]: Nucleus 1 NR3C1
endoplasmic reticulum chaperone complex 1 HSP90B1


文献列表

  • Wenhui Yao, Rongpin Tao, Yue Xu, Zhe-Sheng Chen, Xuansheng Ding, Lisheng Wan. AR/RKIP pathway mediates the inhibitory effects of icariin on renal fibrosis and endothelial-to-mesenchymal transition in type 2 diabetic nephropathy. Journal of ethnopharmacology. 2024 Feb; 320(?):117414. doi: 10.1016/j.jep.2023.117414. [PMID: 37977422]
  • Shaozhen Liu, Junliang Zhou, Qiong Yang, Yue Chen, Qing Liu, Weiwei Wang, Jing Song, Xianzong Wang, Yu Liu. Comparative Analysis of miRNA-mRNA Regulation in the Testes of Gobiocypris rarus following 17α-Methyltestosterone Exposure. International journal of molecular sciences. 2023 Feb; 24(4):. doi: 10.3390/ijms24044239. [PMID: 36835651]
  • Min He, Siyuan Guo, Yan Yin, Chi Zhang, Xianan Zhang. A novel sterol glycosyltransferase catalyses steroidal sapogenin 3-O glucosylation from Paris polyphylla var. yunnanensis. Molecular biology reports. 2022 Dec; ?(?):. doi: 10.1007/s11033-022-08199-y. [PMID: 36562935]
  • Ivana R Sequeira, Jonathan S T Woodhead, Alex Chan, Randall F D'Souza, Junxiang Wan, Kieren G Hollingsworth, Lindsay D Plank, Pinchas Cohen, Sally D Poppitt, Troy L Merry. Plasma mitochondrial derived peptides MOTS-c and SHLP2 positively associate with android and liver fat in people without diabetes. Biochimica et biophysica acta. General subjects. 2021 11; 1865(11):129991. doi: 10.1016/j.bbagen.2021.129991. [PMID: 34419510]
  • Chun-Yang Guo, Peng-Wei Tseng, Jiang-Shiou Hwang, Guan-Chung Wu, Ching-Fong Chang. Potential role of DNA methylation of cyp19a1a promoter during sex change in protogynous orange-spotted grouper, Epinephelus coioides. General and comparative endocrinology. 2021 09; 311(?):113840. doi: 10.1016/j.ygcen.2021.113840. [PMID: 34216589]
  • 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]
  • Steffen Loke, Lingyu Liu, Maxi Wenzel, Heike Scheffler, Michele Iannone, Xavier de la Torre, Nils Schlörer, Francesco Botrè, Annekathrin Martina Keiler, Matthias Bureik, Maria Kristina Parr. New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites. Molecules (Basel, Switzerland). 2021 Mar; 26(5):. doi: 10.3390/molecules26051354. [PMID: 33802606]
  • Sajwan-Khatri Mamta, Chenichery Sudhakumari, Hirohiko Kagawa, Aparna Dutta-Gupta, Balasubramanian Senthilkumaran. Controlled release of sex steroids through osmotic pump alters brain GnRH1 and catecholaminergic system dimorphically in the catfish, Clarias gariepinus. Brain research bulletin. 2020 11; 164(?):325-333. doi: 10.1016/j.brainresbull.2020.08.022. [PMID: 32860867]
  • Dayamin Martinez-Brito, Michele Iannone, Maria Antonietta Tatangelo, Francesco Molaioni, Xavier de la Torre, Francesco Botrè. A further insight into methyltestosterone metabolism: New evidences from in vitro and in vivo experiments. Rapid communications in mass spectrometry : RCM. 2020 Oct; 34(19):e8870. doi: 10.1002/rcm.8870. [PMID: 32570291]
  • Lihui Meng, Haiyang Yu, Feifei Ni, Jingjing Niu, Xiumei Liu, Xubo Wang. Roles of two cyp11 genes in sex hormone biosynthesis in Japanese flounder (Paralichthys olivaceus). Molecular reproduction and development. 2020 01; 87(1):53-65. doi: 10.1002/mrd.23301. [PMID: 31746503]
  • 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]
  • Minwei Huang, Qing Wang, Jiaxing Chen, Huimin Chen, Ling Xiao, Mi Zhao, Haifa Zhang, Shuisheng Li, Yun Liu, Yong Zhang, Haoran Lin. The co-administration of estradiol/17α-methyltestosterone leads to male fate in the protogynous orange-spotted grouper, Epinephelus coioides. Biology of reproduction. 2019 03; 100(3):745-756. doi: 10.1093/biolre/ioy211. [PMID: 30418499]
  • Xiao-Jian Lai, Zhong-Qin Li, Yang-Jie Xie, Shi-Xi Chen, Yi-Lei Wang. Androstenedione and 17α-methyltestosterone induce early ovary development of Anguilla japonica. Theriogenology. 2018 Oct; 120(?):16-24. doi: 10.1016/j.theriogenology.2018.07.009. [PMID: 30081244]
  • Gabriel Passini, Fabio Carneiro Sterzelecki, Cristina Vaz Avelar de Carvalho, Manecas Francisco Baloi, Virginia Naide, Vinicius Ronzani Cerqueira. 17α-Methyltestosterone implants accelerate spermatogenesis in common snook, Centropomus undecimalis, during first sexual maturation. Theriogenology. 2018 Jan; 106(?):134-140. doi: 10.1016/j.theriogenology.2017.10.015. [PMID: 29059600]
  • Christopher M Murray, Mark Merchant, Michael Easter, Sergio Padilla, Davinia B Garrigós, Mahmood Sasa Marin, Craig Guyer. Detection of a synthetic sex steroid in the American crocodile (Crocodylus acutus): Evidence for a novel environmental androgen. Chemosphere. 2017 Aug; 180(?):125-129. doi: 10.1016/j.chemosphere.2017.04.020. [PMID: 28399454]
  • Haitham G Abo-Al-Ela, Abeer F El-Nahas, Shawky Mahmoud, Essam M Ibrahim. Vitamin C Modulates the Immunotoxic Effect of 17α-Methyltestosterone in Nile Tilapia. Biochemistry. 2017 04; 56(14):2042-2050. doi: 10.1021/acs.biochem.6b01284. [PMID: 28322549]
  • Qiaomu Hu, Yan Meng, Haifeng Tian, Y U Zhang, Hanbing Xiao. Sexually Dimorphic Expression of Foxl2 and Ftz-F1 in Chinese Giant Salamander Andrias Davidianus. Journal of experimental zoology. Part B, Molecular and developmental evolution. 2016 09; 326(6):363-374. doi: 10.1002/jez.b.22693. [PMID: 27527384]
  • Qing-Ping Xie, Xue He, Yi-Ning Sui, Li-Li Chen, Li-Na Sun, De-Shou Wang. Haploinsufficiency of SF-1 Causes Female to Male Sex Reversal in Nile Tilapia, Oreochromis niloticus. Endocrinology. 2016 06; 157(6):2500-14. doi: 10.1210/en.2015-2049. [PMID: 27046435]
  • Lili Chen, Xiaolong Jiang, Haiwei Feng, Hongjuan Shi, Lina Sun, Wenjing Tao, Qingping Xi, Deshou Wang. Simultaneous exposure to estrogen and androgen resulted in feminization and endocrine disruption. The Journal of endocrinology. 2016 Mar; 228(3):205-18. doi: 10.1530/joe-15-0432. [PMID: 26759274]
  • Qiaomu Hu, Hanbing Xiao, HaiFeng Tian, Yan Meng. Characterization and expression of cyp19a gene in the Chinese giant salamander Andrias davidianus. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2016 Feb; 192(?):21-9. doi: 10.1016/j.cbpb.2015.11.005. [PMID: 26593771]
  • Qiaomu Hu, Yan Meng, Haifeng Tian, Songlin Chen, Hanbing Xiao. Cloning, expression of, and evidence of positive selection for, the prolactin receptor gene in Chinese giant salamander (Andrias davidianus). Journal of experimental zoology. Part B, Molecular and developmental evolution. 2015 Dec; 324(8):707-19. doi: 10.1002/jez.b.22659. [PMID: 26526303]
  • Sushant Kumar Verma, Abdul Alim. Ultimobranchial gland respond in a different way in male and female fresh water teleost Mastacembelus armatus (Lacepede) during reproductive cycle. Animal reproduction science. 2015 May; 156(?):111-7. doi: 10.1016/j.anireprosci.2015.03.007. [PMID: 25818521]
  • Robert Rutherford, Andrea Lister, L Mark Hewitt, Deborah MacLatchy. Effects of model aromatizable (17α-methyltestosterone) and non-aromatizable (5α-dihydrotestosterone) androgens on the adult mummichog (Fundulus heteroclitus) in a short-term reproductive endocrine bioassay. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2015 Apr; 170(?):8-18. doi: 10.1016/j.cbpc.2015.01.004. [PMID: 25634815]
  • Zhang-Yan Zhou, Fei Li, Shao-Ping Cheng, Hui Huang, Bi-Wen Peng, Jing Wang, Chang-Mao Liu, Cheng Xing, Ya-Ling Sun, Najeeb Bsoul, Hui Pan, Cun-Jian Yi, Rong-Hua Liu, Guang-Jun Zhong. Short hairpin ribonucleic acid constructs targeting insulin-like growth factor binding protein-3 rehabilitated decreased testosterone concentrations in diabetic rats. Medical science monitor : international medical journal of experimental and clinical research. 2015 Jan; 21(?):94-9. doi: 10.12659/msm.891382. [PMID: 25582342]
  • Guan-Chung Wu, Wei-Guan Tey, Hau-Wen Li, Ching-Fong Chang. Sexual Fate Reprogramming in the Steroid-Induced Bi-Directional Sex Change in the Protogynous Orange-Spotted Grouper, Epinephelus coioides. PloS one. 2015; 10(12):e0145438. doi: 10.1371/journal.pone.0145438. [PMID: 26714271]
  • C Schweizer Grundisch, N Baume, M Saugy. Degradation of methyltestosterone in urine samples. Drug testing and analysis. 2014 Nov; 6(11-12):1170-3. doi: 10.1002/dta.1761. [PMID: 25516451]
  • Anbazhagan Rajakumar, Balasubramanian Senthilkumaran. Expression analysis of cyp11a1 during gonadal development, recrudescence and after hCG induction and sex steroid analog treatment in the catfish, Clarias batrachus. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2014 Oct; 176(?):42-7. doi: 10.1016/j.cbpb.2014.07.007. [PMID: 25107325]
  • Anthony Sébillot, Pauliina Damdimopoulou, Yukiko Ogino, Petra Spirhanzlova, Shinichi Miyagawa, David Du Pasquier, Nora Mouatassim, Taisen Iguchi, Gregory F Lemkine, Barbara A Demeneix, Andrew J Tindall. Rapid fluorescent detection of (anti)androgens with spiggin-gfp medaka. Environmental science & technology. 2014 Sep; 48(18):10919-28. doi: 10.1021/es5030977. [PMID: 25171099]
  • Qisheng Zhong, Yufei Hu, Gongke Li. A novel protocol for molecularly imprinted polymer filaments online coupled to GC-MS for the determination of androgenic steroids in urine. Journal of separation science. 2013 Dec; 36(24):3903-10. doi: 10.1002/jssc.201300874. [PMID: 24151099]
  • Laura Hintikka, Markus Haapala, Tiia Kuuranne, Antti Leinonen, Risto Kostiainen. Analysis of anabolic steroids in urine by gas chromatography-microchip atmospheric pressure photoionization-mass spectrometry with chlorobenzene as dopant. Journal of chromatography. A. 2013 Oct; 1312(?):111-7. doi: 10.1016/j.chroma.2013.08.098. [PMID: 24041507]
  • Chang-Beom Park, Kiyoshi Soyano, Solomon Kiros, Tomokazu Kitamura, Mizuhiko Minamiyama, Yutaka Suzuki. Transient effects of methyltestosterone injection on different reproductive parameters of the hermaphrodite fish Kryptolebias marmoratus. Ecotoxicology (London, England). 2013 Sep; 22(7):1145-54. doi: 10.1007/s10646-013-1101-x. [PMID: 23839512]
  • Céline Ferre, Sara Belluco, Helen Tinwell, Rémi Bars, Mohamed Benahmed, David Rouquie, Frédéric Schorsch. Comparison of early morphological and molecular changes induced by 17-alpha-methyltestosterone and estradiol benzoate in the rat ovary. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie. 2013 May; 65(4):397-407. doi: 10.1016/j.etp.2011.12.004. [PMID: 22405603]
  • C Gómez, O J Pozo, J Marcos, J Segura, R Ventura. Alternative long-term markers for the detection of methyltestosterone misuse. Steroids. 2013 Jan; 78(1):44-52. doi: 10.1016/j.steroids.2012.10.008. [PMID: 23127819]
  • Barbara Wozniak, Iwona Matraszek-Zuchowska, Jan Zmudzki. LC-MS/MS fast analysis of androgenic steroids in urine. Analytical and bioanalytical chemistry. 2012 Jul; 403(10):2965-72. doi: 10.1007/s00216-012-5859-0. [PMID: 22392373]
  • Natacha S Hogan, Melanie J Gallant, Michael R van den Heuvel. Exposure to the pesticide linuron affects androgen-dependent gene expression in the three-spined stickleback (Gasterosteus aculeatus). Environmental toxicology and chemistry. 2012 Jun; 31(6):1391-5. doi: 10.1002/etc.1815. [PMID: 22514014]
  • Miguel A Delgadillo, Lorena Garrostas, Oscar J Pozo, Rosa Ventura, Benjamín Velasco, Jordi Segura, Josep Marcos. Sensitive and robust method for anabolic agents in human urine by gas chromatography-triple quadrupole mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 May; 897(?):85-9. doi: 10.1016/j.jchromb.2012.03.037. [PMID: 22516531]
  • 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]
  • Erik Hoffmann, Anders Walstad, Johnny Karlsson, Per-Erik Olsson, Bertil Borg. Androgen receptor-beta mRNA levels in different tissues in breeding and post-breeding male and female sticklebacks, Gasterosteus aculeatus. Reproductive biology and endocrinology : RB&E. 2012 Mar; 10(?):23. doi: 10.1186/1477-7827-10-23. [PMID: 22455382]
  • K S Schmidt, R Hackenberg, C S Stachel, P Gowik. Endogenous and synthetic steroids in bovine urine--preparation of in-house reference material, stability studies and results of a proficiency test. Analytica chimica acta. 2012 Mar; 717(?):85-91. doi: 10.1016/j.aca.2011.12.038. [PMID: 22304819]
  • Prasanth N Surampudi, Christina Wang, Ronald Swerdloff. Hypogonadism in the aging male diagnosis, potential benefits, and risks of testosterone replacement therapy. International journal of endocrinology. 2012; 2012(?):625434. doi: 10.1155/2012/625434. [PMID: 22505891]
  • Christiaan J Malherbe, Dalene De Beer, Elizabeth Joubert. Development of on-line high performance liquid chromatography (HPLC)-biochemical detection methods as tools in the identification of bioactives. International journal of molecular sciences. 2012; 13(3):3101-3133. doi: 10.3390/ijms13033101. [PMID: 22489144]
  • Maria K Parr, Christina Blatt, Oliver Zierau, Cornelius Hess, Michael Gütschow, Gregor Fusshöller, Georg Opfermann, Wilhelm Schänzer, Patrick Diel. Endocrine characterization of the designer steroid methyl-1-testosterone: investigations on tissue-specific anabolic-androgenic potency, side effects, and metabolism. Endocrinology. 2011 Dec; 152(12):4718-28. doi: 10.1210/en.2011-1164. [PMID: 21990312]
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