Methyltestosterone (BioDeep_00000002829)

Secondary id: BioDeep_00000405902, BioDeep_00000860362

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

化学式: C20H30O2 (302.224568)
中文名称: 17α-甲基睾甾酮, 甲睾酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.62%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@](C)(O)CC[C@@]4([H])[C@]3([H])CCC2=CC(=O)C1
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

描述信息

A synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedule III drug in the US.
CONFIDENCE standard compound; INTERNAL_ID 1072; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9426; ORIGINAL_PRECURSOR_SCAN_NO 9425
CONFIDENCE standard compound; INTERNAL_ID 1072; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9487; ORIGINAL_PRECURSOR_SCAN_NO 9483
CONFIDENCE standard compound; INTERNAL_ID 1072; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9433; ORIGINAL_PRECURSOR_SCAN_NO 9431
CONFIDENCE standard compound; INTERNAL_ID 1072; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9476; ORIGINAL_PRECURSOR_SCAN_NO 9475
CONFIDENCE standard compound; INTERNAL_ID 1072; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9423; ORIGINAL_PRECURSOR_SCAN_NO 9422
CONFIDENCE standard compound; INTERNAL_ID 1072; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9541; ORIGINAL_PRECURSOR_SCAN_NO 9538
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
CONFIDENCE standard compound; INTERNAL_ID 2816
D000970 - Antineoplastic Agents

同义名列表

69 个代谢物同义名

数据库引用编号

31 个数据库交叉引用编号

ChEBI: CHEBI:125362
ChEBI: CHEBI:27436
KEGG: C07198
KEGGdrug: D00408
PubChem: 6010
PubChem: 4160
HMDB: HMDB0015655
Metlin: METLIN41848
DrugBank: DB06710
ChEMBL: CHEMBL1395
Wikipedia: Methyltestosterone
LipidMAPS: LMST02020029
MeSH: Methyltestosterone
chemspider: 5788
CAS: 58-18-4
MoNA: AU281605
MoNA: LU107204
MoNA: AU281601
MoNA: LU107201
MoNA: LU107202
MoNA: AU281604
MoNA: LU107206
MoNA: AU281606
MoNA: LU107205
MoNA: AU281602
MoNA: LU107203
MoNA: AU281603
PMhub: MS000006318
PubChem: 9407
3DMET: B02108
NIKKAJI: J1.385D

分类词条

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

9606 - Homo sapiens: -

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

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]
Neerja Puri. A study of pathogenesis of acanthosis nigricans and its clinical implications. Indian journal of dermatology. 2011 Nov; 56(6):678-83. doi: 10.4103/0019-5154.91828. [PMID: 22345770]
Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma. BMC cancer. 2011 Aug; 11(?):342. doi: 10.1186/1471-2407-11-342. [PMID: 21824401]
Yasuto Kido, Pär Matsson, Kathleen M Giacomini. Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. Journal of medicinal chemistry. 2011 Jul; 54(13):4548-58. doi: 10.1021/jm2001629. [PMID: 21599003]
Xuesong Hu, Xiaochun Liu, Haifa Zhang, Yong Zhang, Shuisheng Li, Qing Sang, Qian Wang, Wenna Luo, Qizhi Liu, Danqi Lu, Zining Meng, Haoran Lin. Expression profiles of gonadotropins and their receptors during 17α-methyltestosterone implantation-induced sex change in the orange-spotted grouper (Epinephelus coioides). Molecular reproduction and development. 2011 Jun; 78(6):376-90. doi: 10.1002/mrd.21319. [PMID: 21567650]
Anne S Mortensen, Robert J Letcher, Maria V Cangialosi, Shaogang Chu, Augustine Arukwe. Tissue bioaccumulation patterns, xenobiotic biotransformation and steroid hormone levels in Atlantic salmon (Salmo salar) fed a diet containing perfluoroactane sulfonic or perfluorooctane carboxylic acids. Chemosphere. 2011 May; 83(8):1035-44. doi: 10.1016/j.chemosphere.2011.01.067. [PMID: 21354591]
Michael J Hemmer, Kimberly A Salinas, Peggy S Harris. Application of protein expression profiling to screen chemicals for androgenic activity. Aquatic toxicology (Amsterdam, Netherlands). 2011 May; 103(1-2):71-8. doi: 10.1016/j.aquatox.2011.02.008. [PMID: 21392497]
Greg A Rosenfeld, Albert Chang, Michael Poulin, Peter Kwan, Eric Yoshida. Cholestatic jaundice, acute kidney injury and acute pancreatitis secondary to the recreational use of methandrostenolone: a case report. Journal of medical case reports. 2011 Apr; 5(?):138. doi: 10.1186/1752-1947-5-138. [PMID: 21470406]
Sylvi Wolf, Patrick Diel, Maria Kristina Parr, Felicitas Rataj, Willhelm Schänzer, Günter Vollmer, Oliver Zierau. Long-term detection of methyltestosterone (ab-) use by a yeast transactivation system. Archives of toxicology. 2011 Apr; 85(4):285-92. doi: 10.1007/s00204-010-0590-0. [PMID: 20924560]
Maria K Parr, Gregor Fusshöller, Nils Schlörer, Georg Opfermann, Hans Geyer, Grigory Rodchenkov, Wilhelm Schänzer. Detection of Δ6-methyltestosterone in a 'dietary supplement' and GC-MS/MS investigations on its urinary metabolism. Toxicology letters. 2011 Mar; 201(2):101-4. doi: 10.1016/j.toxlet.2010.11.018. [PMID: 21134425]
E Espinosa, A Josa, L Gil, N González. Sex steroid levels in XY males and sex-reversed XX males, of rainbow trout (Oncorhynchus mykiss), during the reproductive cycle. Reproduction in domestic animals = Zuchthygiene. 2011 Feb; 46(1):8-14. doi: 10.1111/j.1439-0531.2009.01512.x. [PMID: 19663812]
Lucyna Konieczna, Alina Plenis, Ilona Olędzka, Piotr Kowalski, Tomasz Bączek. Optimization of LC method for the determination of testosterone and epitestosterone in urine samples in view of biomedical studies and anti-doping research studies. Talanta. 2011 Jan; 83(3):804-14. doi: 10.1016/j.talanta.2010.10.044. [PMID: 21147323]
Yuanyang Zhang, Fangyang He, Yuping Wan, Meng Meng, Jing Xu, Jian Yi, Yabin Wang, Caiwei Feng, Shanliang Wang, Rimo Xi. Generation of anti-trenbolone monoclonal antibody and establishment of an indirect competitive enzyme-linked immunosorbent assay for detection of trenbolone in animal tissues, feed and urine. Talanta. 2011 Jan; 83(3):732-7. doi: 10.1016/j.talanta.2010.10.020. [PMID: 21147313]
George Kaklamanos, Georgios A Theodoridis, Themistoklis Dabalis, Ioannis Papadoyannis. Determination of anabolic steroids in bovine serum by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Jan; 879(2):225-9. doi: 10.1016/j.jchromb.2010.11.029. [PMID: 21167798]
Henriette Farkas, Lilian Varga. Ecallantide is a novel treatment for attacks of hereditary angioedema due to C1 inhibitor deficiency. Clinical, cosmetic and investigational dermatology. 2011; 4(?):61-8. doi: 10.2147/ccid.s10322. [PMID: 21760740]
Jun Kitano, Yui Kawagishi, Seiichi Mori, Catherine L Peichel, Takashi Makino, Masakado Kawata, Makoto Kusakabe. Divergence in sex steroid hormone signaling between sympatric species of Japanese threespine stickleback. PloS one. 2011; 6(12):e29253. doi: 10.1371/journal.pone.0029253. [PMID: 22216225]
Lijun Qiu, Wei Liu, Min Huang, Lan Zhang. Preparation and application of solid-phase microextraction fiber based on molecularly imprinted polymer for determination of anabolic steroids in complicated samples. Journal of chromatography. A. 2010 Nov; 1217(48):7461-70. doi: 10.1016/j.chroma.2010.08.056. [PMID: 20965510]
Horst Fr Schröder, Wilhelm Gebhardt, Mario Thevis. Anabolic, doping, and lifestyle drugs, and selected metabolites in wastewater--detection, quantification, and behaviour monitored by high-resolution MS and MS(n) before and after sewage treatment. Analytical and bioanalytical chemistry. 2010 Oct; 398(3):1207-29. doi: 10.1007/s00216-010-3958-3. [PMID: 20652555]
Keita Saito, Katsuharu Yagi, Atsushi Ishizaki, Hiroyuki Kataoka. Determination of anabolic steroids in human urine by automated in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2010 Sep; 52(5):727-33. doi: 10.1016/j.jpba.2010.02.027. [PMID: 20236787]
Sheri Ann Hild, Barbara J Attardi, Sailaja Koduri, Bruce A Till, Jerry R Reel. Effects of synthetic androgens on liver function using the rabbit as a model. Journal of andrology. 2010 Sep; 31(5):472-81. doi: 10.2164/jandrol.109.009365. [PMID: 20378929]
Min-ting Wang, Yun Jin, Yun-xia Yang, Chun-yan Zhao, Hong-yun Yang, Xue-fan Xu, Xuan Qin, Zhao-dan Wang, Zhi-rong Zhang, Yan-lin Jian, Yuan Huang. In vivo biodistribution, anti-inflammatory, and hepatoprotective effects of liver targeting dexamethasone acetate loaded nanostructured lipid carrier system. International journal of nanomedicine. 2010 Aug; 5(?):487-97. doi: 10.2147/ijn.s10393. [PMID: 20957171]
Bernadette Tse Sum Bui, Franck Merlier, Karsten Haupt. Toward the use of a molecularly imprinted polymer in doping analysis: selective preconcentration and analysis of testosterone and epitestosterone in human urine. Analytical chemistry. 2010 Jun; 82(11):4420-7. doi: 10.1021/ac100128c. [PMID: 20438053]
E Albertsson, D G J Larsson, L Förlin. Induction of hepatic carbonyl reductase/20beta-hydroxysteroid dehydrogenase mRNA in rainbow trout downstream from sewage treatment works--possible roles of aryl hydrocarbon receptor agonists and oxidative stress. Aquatic toxicology (Amsterdam, Netherlands). 2010 May; 97(3):243-9. doi: 10.1016/j.aquatox.2009.11.007. [PMID: 20004983]
Linda L Ahonen, Markus Haapala, Ville Saarela, Sami Franssila, Tapio Kotiaho, Risto Kostiainen. Feasibility of capillary liquid chromatography/microchip atmospheric pressure photoionization mass spectrometry in analyzing anabolic steroids in urine samples. Rapid communications in mass spectrometry : RCM. 2010 Apr; 24(7):958-64. doi: 10.1002/rcm.4468. [PMID: 20209666]
Lijun Qiu, Liangmin Shangguan, Wei Liu, Guonan Chen, Lan Zhang. [Component analysis of a new anabolic androgenic steroid and its monitoring research in human urine]. Se pu = Chinese journal of chromatography. 2010 Jan; 28(1):49-53. doi: 10.3724/sp.j.1123.2010.00049. [PMID: 20458920]
Chiaki Kondo, Yohsuke Minowa, Takeki Uehara, Yasushi Okuno, Noriyuki Nakatsu, Atsushi Ono, Toshiyuki Maruyama, Ikuo Kato, Jyoji Yamate, Hiroshi Yamada, Yasuo Ohno, Tetsuro Urushidani. Identification of genomic biomarkers for concurrent diagnosis of drug-induced renal tubular injury using a large-scale toxicogenomics database. Toxicology. 2009 Nov; 265(1-2):15-26. doi: 10.1016/j.tox.2009.09.003. [PMID: 19761811]
Quanlin Wang, Aizhi Zhang, Liren Chen. [Study on simultaneous determination method for banded synthesis hormones residues in egg products]. Wei sheng yan jiu = Journal of hygiene research. 2009 Nov; 38(6):740-6. doi: . [PMID: 20047238]
Oscar J Pozo, Peter Van Eenoo, Koen Deventer, Leen Lootens, Wim Van Thuyne, Maria K Parr, Wilhelm Schänzer, Juan V Sancho, Felix Hernández, Philip Meuleman, Geert Leroux-Roels, Frans T Delbeke. Detection and characterization of a new metabolite of 17alpha-methyltestosterone. Drug metabolism and disposition: the biological fate of chemicals. 2009 Nov; 37(11):2153-62. doi: 10.1124/dmd.109.028373. [PMID: 19704028]
Shang-Wei Li, Zhang-Fu Long, Juan Du, Shi-Gui Liu, Jian-Jun Wen. Analysis of differential expression and characterization of PIN in the gonads during sex reversal in the red-spotted grouper. Molecular and cellular endocrinology. 2009 Oct; 309(1-2):32-8. doi: 10.1016/j.mce.2009.04.015. [PMID: 19422880]
Yueying Liu, Ziqing Lin, Sichun Zhang, Chengdui Yang, Xinrong Zhang. Rapid screening of active ingredients in drugs by mass spectrometry with low-temperature plasma probe. Analytical and bioanalytical chemistry. 2009 Oct; 395(3):591-9. doi: 10.1007/s00216-009-2947-x. [PMID: 19641907]
Zhuomin Zhang, Hongbin Duan, Lan Zhang, Xi Chen, Wei Liu, Guonan Chen. Direct determination of anabolic steroids in pig urine by a new SPME-GC-MS method. Talanta. 2009 May; 78(3):1083-9. doi: 10.1016/j.talanta.2009.01.022. [PMID: 19269476]
Håkan Berg, Nikolai Scherbak, Harri Liimatta, Erik Hoffmann, Johnny Karlsson, Per-Erik Olsson. Characterization of antibodies for quantitative determination of spiggin protein levels in male and female three-spined stickleback (Gasterosteus aculeatus). Reproductive biology and endocrinology : RB&E. 2009 May; 7(?):46. doi: 10.1186/1477-7827-7-46. [PMID: 19442269]
Carina Björkblom, Eva Högfors, Lotta Salste, Eija Bergelin, Per-Erik Olsson, Ioanna Katsiadaki, Tom Wiklund. Estrogenic and androgenic effects of municipal wastewater effluent on reproductive endpoint biomarkers in three-spined stickleback (Gasterosteus aculeatus). Environmental toxicology and chemistry. 2009 May; 28(5):1063-71. doi: 10.1897/08-337.1. [PMID: 19161248]
A I Silva, H M G Pereira, A Casilli, F C Conceição, F R Aquino Neto. Analytical challenges in doping control: Comprehensive two-dimensional gas chromatography with time of flight mass spectrometry, a promising option. Journal of chromatography. A. 2009 Apr; 1216(14):2913-22. doi: 10.1016/j.chroma.2008.10.042. [PMID: 19013575]
Toine F H Bovee, Gerrit Bor, Henri H Heskamp, Johan J P Lasaroms, Marieke B Sanders, Michel W F Nielen. Validation and application of a yeast bioassay for screening androgenic activity in calf urine and feed. Analytica chimica acta. 2009 Apr; 637(1-2):225-34. doi: 10.1016/j.aca.2008.06.047. [PMID: 19286034]
S T B Biddle, A O'Donnell, E Houghton, C Creaser. Metabolism of methyltestosterone in the greyhound. Rapid communications in mass spectrometry : RCM. 2009 Mar; 23(5):713-21. doi: 10.1002/rcm.3929. [PMID: 19199316]
Lan Zhang, Jinfeng Chen, Yu He, Yuwu Chi, Guonan Chen. A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids. Talanta. 2009 Jan; 77(3):1002-8. doi: 10.1016/j.talanta.2008.07.060. [PMID: 19064082]
Limin He, Xianhui Huang, Binghu Fang, Shixin Huang, Ying Cao, Jianxin Chen, Zhenling Zeng, Zhangliu Chen. [Determination of eleven steroid hormones in animal muscle tissues and eggs using ultra-performance liquid chromatography-tandem mass spectrometry]. Se pu = Chinese journal of chromatography. 2008 Nov; 26(6):714-9. doi: . [PMID: 19253550]
P Magnisali, M Dracopoulou, M Mataragas, A Dacou-Voutetakis, P Moutsatsou. Routine method for the simultaneous quantification of 17alpha-hydroxyprogesterone, testosterone, dehydroepiandrosterone, androstenedione, cortisol, and pregnenolone in human serum of neonates using gas chromatography-mass spectrometry. Journal of chromatography. A. 2008 Oct; 1206(2):166-77. doi: 10.1016/j.chroma.2008.07.057. [PMID: 18760785]
M Valentim-Zabott, L Vargas, R P R Ribeiro, R Piau, M B A Torres, M Rönnau, J C Souza. Effects of a homeopathic complex in Nile tilapia (Oreochromis niloticus L.) on performance, sexual proportion and histology. Homeopathy : the journal of the Faculty of Homeopathy. 2008 Oct; 97(4):190-5. doi: 10.1016/j.homp.2008.08.007. [PMID: 19371567]
Jianxiong Yang, Yali Wang, Yu Bao, Juan Guo. The total flavones from Semen cuscutae reverse the reduction of testosterone level and the expression of androgen receptor gene in kidney-yang deficient mice. Journal of ethnopharmacology. 2008 Sep; 119(1):166-71. doi: 10.1016/j.jep.2008.06.027. [PMID: 18640256]
Masayuki Yamada, Sugako Aramaki, Masahiko Kurosawa, Isao Kijima-Suda, Koichi Saito, Hiroyuki Nakazawa. Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2008 Sep; 24(9):1199-204. doi: 10.2116/analsci.24.1199. [PMID: 18781036]
Xiao-Hua Qi, Li-Wei Zhang, Xin-Xiang Zhang. Simultaneous determination of nandrolone, testosterone, and methyltestosterone by multi-immunoaffinity column and capillary electrophoresis. Electrophoresis. 2008 Aug; 29(16):3398-405. doi: 10.1002/elps.200700673. [PMID: 18702063]
Laura Hintikka, Tiia Kuuranne, Antti Leinonen, Mario Thevis, Wilhelm Schänzer, John Halket, David Cowan, Joachim Grosse, Peter Hemmersbach, Michel W F Nielen, Risto Kostiainen. Liquid chromatographic-mass spectrometric analysis of glucuronide-conjugated anabolic steroid metabolites: method validation and interlaboratory comparison. Journal of mass spectrometry : JMS. 2008 Jul; 43(7):965-73. doi: 10.1002/jms.1434. [PMID: 18563858]
Masayuki Yamada, Sugako Aramaki, Masahiko Kurosawa, Koichi Saito, Hiroyuki Nakazawa. Detection of urinary metabolites common to structurally related 17alpha-alkyl anabolic steroids in horses and application to doping tests in racehorses: methandienone, methandriol, and oxymetholone. Journal of analytical toxicology. 2008 Jun; 32(5):387-91. doi: 10.1093/jat/32.5.387. [PMID: 18544225]
Laura Hintikka, Tiia Kuuranne, Olli Aitio, Mario Thevis, Wilhelm Schänzer, Risto Kostiainen. Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites. Steroids. 2008 Mar; 73(3):257-65. doi: 10.1016/j.steroids.2007.10.008. [PMID: 18082235]
Mengye Wang, Ping Xiang, Hui Yan, Baohua Shen, Min Shen. [Determination of endogenous steroids in urine by liquid chromatography-tandem mass spectromretry]. Se pu = Chinese journal of chromatography. 2008 Jan; 26(1):10-4. doi: NULL. [PMID: 18438017]
Chong-Eon Lee, Jung-Suk Kang, Kyu-Il Kim. Effects of gender, gonadectomy and sex hormones on growth and plasma cholesterol level in rats. Annals of nutrition & metabolism. 2008; 53(1):1-5. doi: 10.1159/000152867. [PMID: 18772583]
Maria K Parr, Rymantas Kazlauskas, Nils Schlörer, Georg Opfermann, Thomas Piper, Gabriele Schulze, Wilhelm Schänzer. 6alpha-Methylandrostenedione: gas chromatographic mass spectrometric detection in doping control. Rapid communications in mass spectrometry : RCM. 2008; 22(3):321-9. doi: 10.1002/rcm.3367. [PMID: 18181236]
W Sanchez, C Goin, F Brion, P E Olsson, A Goksøyr, J M Porcher. A new ELISA for the three-spined stickleback (Gasterosteus aculeatus L.) spiggin, using antibodies against synthetic peptide. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2008 Jan; 147(1):129-37. doi: 10.1016/j.cbpc.2007.08.007. [PMID: 17921071]
Lotta K Amundsen, Heli Sirén. Determination of association constants between steroid compounds and albumins by partial-filling ACE. Electrophoresis. 2007 Oct; 28(20):3737-44. doi: 10.1002/elps.200700271. [PMID: 17893945]
Masayuki Yamada, Sugako Aramaki, Toshimasa Okayasu, Tomoo Hosoe, Masahiko Kurosawa, Isao Kijima-Suda, Koichi Saito, Hiroyuki Nakazawa. Identification and quantification of metabolites common to 17alpha-methyltestosterone and mestanolone in horse urine. Journal of pharmaceutical and biomedical analysis. 2007 Sep; 45(1):125-133. doi: 10.1016/j.jpba.2007.06.020. [PMID: 17709226]
Gemma Janer, Juan Carlos Navarro, Cinta Porte. Exposure to TBT increases accumulation of lipids and alters fatty acid homeostasis in the ramshorn snail Marisa cornuarietis. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2007 Sep; 146(3):368-74. doi: 10.1016/j.cbpc.2007.04.009. [PMID: 17544855]
Willem G E J Schoonen, Cathelijne P A M Kloks, Jan-Peter H T M Ploemen, Martin J Smit, Pieter Zandberg, G Jean Horbach, Jan-Remt Mellema, Carol Thijssen-Vanzuylen, Albert C Tas, Joop H J van Nesselrooij, Jack T W E Vogels. Uniform procedure of (1)H NMR analysis of rat urine and toxicometabonomics Part II: comparison of NMR profiles for classification of hepatotoxicity. Toxicological sciences : an official journal of the Society of Toxicology. 2007 Jul; 98(1):286-97. doi: 10.1093/toxsci/kfm077. [PMID: 17420222]
Weimin Zhang, Yong Zhang, Lihong Zhang, Huihong Zhao, Xin Li, He Huang, Haoran Lin. The mRNA expression of P450 aromatase, gonadotropin beta-subunits and FTZ-F1 in the orange-spotted grouper (Epinephelus Coioides) during 17alpha-methyltestosterone-induced precocious sex change. Molecular reproduction and development. 2007 Jun; 74(6):665-73. doi: 10.1002/mrd.20642. [PMID: 17075797]
Andrew R McKinney, Craig J Suann, Allen M Stenhouse. A stereochemical examination of the equine metabolism of 17alpha-methyltestosterone. Analytica chimica acta. 2007 Jan; 581(2):377-87. doi: 10.1016/j.aca.2006.08.025. [PMID: 17386466]
Aksam A Yassin, Mohamed Haffejee. Testosterone depot injection in male hypogonadism: a critical appraisal. Clinical interventions in aging. 2007; 2(4):577-90. doi: NULL. [PMID: 18225458]
Shyh-Jye Lee, Chi-Ching Ju, Shian-Ling Chu, Ming-Shan Chien, Tun-Hao Chan, Wen-Liang Liao. Molecular cloning, expression and phylogenetic analyses of parvalbumin in tilapia, Oreochromis mossambicus. Journal of experimental zoology. Part A, Ecological genetics and physiology. 2007 Jan; 307(1):51-61. doi: 10.1002/jez.a.345. [PMID: 17094115]