Gestrinone (BioDeep_00000026912)

   

human metabolite blood metabolite


代谢物信息卡片


(10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one

化学式: C21H24O2 (308.17762039999997)
中文名称: 孕三烯酮
谱图信息: 最多检出来源 Homo sapiens(blood) 83.57%

分子结构信息

SMILES: C#CC1(O)CCC2C3CCC4=CC(=O)CCC4=C3C=CC21CC
InChI: InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1

描述信息

Gestrinone was developed in the early 1970s and was tested clinically as a weekly oral contraceptive in European and North American countries. ]. Without significant advantages over other oral contraceptives and with its high price, gestrinone was no longer used after the Stage II clinical trial. However, from 1982 aroused widespread interest due to substantial therapeutic effects in treating endometriosis. Under different endocrine conditions, gestrinone possesses estrogenic, progestational, androgenic, antiestrogenic and antiprogesterone actions. Starting from gestrinone, chemists can synthesize tetrahydrogestrinone (THG) in one reaction step. THG is a real designer steroid; designer steroids (chemically modified steroids) pose a threat to the integrity of the sport community. These compounds have recently been detected in urine specimens from athletes, resulting in temporary or permanent suspension from amateur and/or professional competition. (PMID: 15934041, 17707720) [HMDB]
Gestrinone was developed in the early 1970s and was tested clinically as a weekly oral contraceptive in European and North American countries. ]. Without significant advantages over other oral contraceptives and with its high price, gestrinone was no longer used after the Stage II clinical trial. However, from 1982 aroused widespread interest due to substantial therapeutic effects in treating endometriosis. Under different endocrine conditions, gestrinone possesses estrogenic, progestational, androgenic, antiestrogenic and antiprogesterone actions. Starting from gestrinone, chemists can synthesize tetrahydrogestrinone (THG) in one reaction step. THG is a real designer steroid; designer steroids (chemically modified steroids) pose a threat to the integrity of the sport community. These compounds have recently been detected in urine specimens from athletes, resulting in temporary or permanent suspension from amateur and/or professional competition. (PMID: 15934041, 17707720).
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03X - Other sex hormones and modulators of the genital system > G03XA - Antigonadotropins and similar agents
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D011372 - Progestins
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents

同义名列表

15 个代谢物同义名

(10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one; (17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one; 13-Ethyl-17-hydroxy-18,19-dinor-17a-pregna-4,9,11-trien-20-yn-3-one; 13-Ethyl-17a-ethynyl-17b-hydroxygona-4,9,11-trien-3-one; R-2323a-46745RU-2323gestrinone; Florizel brand OF gestrinone; Aventis brand OF gestrinone; Hoechst brand OF gestrinone; Ethylnorgestrienone; Gestrigone; Dimetriose; Gestrinone; Gestrinona; Tridomose; Nemestran



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。



文献列表

  • Chih-Chen Chen, Chun-Yen Huang, Li-Yen Shiu, Ya-Chun Yu, Jui-Chi Lai, Chi-Chang Chang, Chi-Feng Fu, S Joseph Huang. Combinatory effects of current regimens and Guizhi Fuling Wan on the development of endometriosis. Taiwanese journal of obstetrics & gynecology. 2022 Jan; 61(1):70-74. doi: 10.1016/j.tjog.2021.11.013. [PMID: 35181049]
  • 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]
  • Henglian Liu, Xianli Sun, Yan Zhao, Min Xia, Caixia Wang. Anti-angiogenesis effect and mechanism study of Huangzhi Neiyi capsule in a rat endometriosis model. The Journal of international medical research. 2020 Jan; 48(1):300060519899767. doi: 10.1177/0300060519899767. [PMID: 31965879]
  • 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]
  • Xiao-Hong Zhou, Wen-Jun Fu, Bao-di Wang, Qiu-Xian Fu. [Effect of Tripterygium wilfordii glycosides combined with gestrinone on endometriosis and serum cytokine expression]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Sep; 41(18):3478-3482. doi: 10.4268/cjcmm20161826. [PMID: 28925135]
  • Andrew Flower, Jian Ping Liu, George Lewith, Paul Little, Qing Li. Chinese herbal medicine for endometriosis. The Cochrane database of systematic reviews. 2012 May; ?(5):CD006568. doi: 10.1002/14651858.cd006568.pub3. [PMID: 22592712]
  • F J Sanza, M Holgado, F J Ortega, R Casquel, D López-Romero, M J Bañuls, M F Laguna, C A Barrios, R Puchades, A Maquieira. Bio-Photonic Sensing Cells over transparent substrates for anti-gestrinone antibodies biosensing. Biosensors & bioelectronics. 2011 Aug; 26(12):4842-7. doi: 10.1016/j.bios.2011.06.010. [PMID: 21733669]
  • Eva M Brun, Alejandro Hernández-Albors, Rosa Ventura, Rosa Puchades, Angel Maquieira. Enzyme-linked immunosorbent assays for the synthetic steroid gestrinone. Talanta. 2010 Sep; 82(4):1581-7. doi: 10.1016/j.talanta.2010.07.067. [PMID: 20801376]
  • Monica Mazzarino, Xavier de la Torre, Francesco Botrè, Nicola Gray, David Cowan. A rapid screening LC-MS/MS method based on conventional HPLC pumps for the analysis of low molecular weight xenobiotics: application to doping control analysis. Drug testing and analysis. 2010 Jul; 2(7):311-22. doi: 10.1002/dta.148. [PMID: 20818799]
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  • Shangchun Wu, Jing Dong, Jie Cong, Cuiping Wang, Helena VonHertzen, Emily M Godfrey. Gestrinone compared with mifepristone for emergency contraception: a randomized controlled trial. Obstetrics and gynecology. 2010 Apr; 115(4):740-744. doi: 10.1097/aog.0b013e3181d43ae4. [PMID: 20308833]
  • Qing Wang, Hong Zhao, Qing Xiang, Hai Ju, Shu-min Han, Ling-yan Wang, Bo Xu. Effect of Yikun Neiyi Wan on the expression of aromatase P450, COX-2, and ER related receptor in endometrial cells in vitro from patients with endometriosis. Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan. 2009 Dec; 29(4):296-300. doi: 10.1016/s0254-6272(09)60088-1. [PMID: 20112494]
  • Ruud J B Peters, Marcel C van Engelen, Manja E Touber, Costas Georgakopoulus, Michel W F Nielen. Searching for in silico predicted metabolites and designer modifications of (cortico)steroids in urine by high-resolution liquid chromatography/time-of-flight mass spectrometry. Rapid communications in mass spectrometry : RCM. 2009 Aug; 23(15):2329-37. doi: 10.1002/rcm.4153. [PMID: 19575408]
  • Andrew Flower, Jian Ping Liu, Sisi Chen, George Lewith, Paul Little. Chinese herbal medicine for endometriosis. The Cochrane database of systematic reviews. 2009 Jul; ?(3):CD006568. doi: 10.1002/14651858.cd006568.pub2. [PMID: 19588398]
  • M Machnik, M Gerlach, M Kietzmann, F Niedorf, M Thevis, I Schenk, S Guddat, M Düe, W Schänzer. Detection and pharmacokinetics of tetrahydrogestrinone in horses. Journal of veterinary pharmacology and therapeutics. 2009 Apr; 32(2):197-202. doi: 10.1111/j.1365-2885.2008.01021.x. [PMID: 19290951]
  • I Madhusudhana Reddy, Alka Beotra, S Jain, S Ahi. A simple and rapid ESI-LC-MS/MS method for simultaneous screening of doping agents in urine samples. Indian journal of pharmacology. 2009 Apr; 41(2):80-6. doi: 10.4103/0253-7613.51347. [PMID: 20336223]
  • Oliver Zierau, Sylvi Lehmann, Günter Vollmer, Willhelm Schänzer, Patrick Diel. Detection of anabolic steroid abuse using a yeast transactivation system. Steroids. 2008 Oct; 73(11):1143-7. doi: 10.1016/j.steroids.2008.04.015. [PMID: 18550137]
  • Yang Qin, Xin Liu, Zhanliang Wang, Moutian Wu. [Determination of three anabolic steroids by liquid chromatography-mass spectrometry]. Se pu = Chinese journal of chromatography. 2008 Jul; 26(4):465-8. doi: . [PMID: 18959243]
  • Nola H Yu, Emmie N M Ho, Francis P W Tang, Terence S M Wan, April S Y Wong. Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2008 May; 1189(1-2):426-34. doi: 10.1016/j.chroma.2007.11.022. [PMID: 18054785]
  • L McRobb, D J Handelsman, R Kazlauskas, S Wilkinson, M D McLeod, A K Heather. Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay. The Journal of steroid biochemistry and molecular biology. 2008 May; 110(1-2):39-47. doi: 10.1016/j.jsbmb.2007.10.008. [PMID: 18395441]
  • Tiia Kuuranne, Kati-Henna Pystynen, Mario Thevis, Antii Leinonen, Wilhelm Schänzer, Risto Kostiainen. Screening of in vitro synthesised metabolites of 4,9,11-trien-3-one steroids by liquid chromatography mass spectrometry. European journal of mass spectrometry (Chichester, England). 2008; 14(3):181-9. doi: 10.1255/ejms.923. [PMID: 18708698]
  • Xuefeng Gao, Erruo Wu, Guian Chen. Mechanism of emergency contraception with gestrinone: a preliminary investigation. Contraception. 2007 Sep; 76(3):221-7. doi: 10.1016/j.contraception.2007.05.089. [PMID: 17707720]
  • Marlice Aparecida Sípoli Marques, Henrique Marcelo Gualberto Pereira, Monica Costa Padilha, Francisco Radler de Aquino Neto. Analysis of synthetic 19-norsteroids trenbolone, tetrahydrogestrinone and gestrinone by gas chromatography-mass spectrometry. Journal of chromatography. A. 2007 May; 1150(1-2):215-25. doi: 10.1016/j.chroma.2006.08.032. [PMID: 16963059]
  • J-Pablo Salvador, Francisco Sanchez-Baeza, M-Pilar Marco. Preparation of antibodies for the designer steroid tetrahydrogestrinone and development of an enzyme-linked immunosorbent assay for human urine analysis. Analytical chemistry. 2007 May; 79(10):3734-40. doi: 10.1021/ac061757x. [PMID: 17441677]
  • M E Touber, M C van Engelen, C Georgakopoulus, J A van Rhijn, M W F Nielen. Multi-detection of corticosteroids in sports doping and veterinary control using high-resolution liquid chromatography/time-of-flight mass spectrometry. Analytica chimica acta. 2007 Mar; 586(1-2):137-46. doi: 10.1016/j.aca.2006.09.058. [PMID: 17386705]
  • Dong-xia Yang, Wen-guang Ma, Fan Qu, Bao-zhang Ma. Comparative study on the efficacy of Yiweining and Gestrinone for post-operational treatment of stage III endometriosis. Chinese journal of integrative medicine. 2006 Sep; 12(3):218-20. doi: 10.1007/bf02836527. [PMID: 17005086]
  • M-H Spyridaki, P Kiousi, A Vonaparti, P Valavani, V Zonaras, M Zahariou, E Sianos, G Tsoupras, C Georgakopoulos. Doping control analysis in human urine by liquid chromatography-electrospray ionization ion trap mass spectrometry for the Olympic Games Athens 2004: determination of corticosteroids and quantification of ephedrines, salbutamol and morphine. Analytica chimica acta. 2006 Jul; 573-574(?):242-9. doi: 10.1016/j.aca.2006.04.042. [PMID: 17723530]
  • Michel W F Nielen, Toine F H Bovee, Marcel C van Engelen, Paula Rutgers, Astrid R M Hamers, J Hans A van Rhijn, L Ron A P Hoogenboom. Urine testing for designer steroids by liquid chromatography with androgen bioassay detection and electrospray quadrupole time-of-flight mass spectrometry identification. Analytical chemistry. 2006 Jan; 78(2):424-31. doi: 10.1021/ac051317q. [PMID: 16408923]
  • Monica Mazzarino, Francesco Botrè. A fast liquid chromatographic/mass spectrometric screening method for the simultaneous detection of synthetic glucocorticoids, some stimulants, anti-oestrogen drugs and synthetic anabolic steroids. Rapid communications in mass spectrometry : RCM. 2006; 20(22):3465-76. doi: 10.1002/rcm.2729. [PMID: 17066372]
  • Mario Thevis, Hans Geyer, Ute Mareck, Wilhelm Schänzer. Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry. Journal of mass spectrometry : JMS. 2005 Jul; 40(7):955-62. doi: 10.1002/jms.873. [PMID: 15934041]
  • Britt E Erickson. Detecting doping. Analytical chemistry. 2005 Jun; 77(11):211 A. doi: 10.1021/ac053395j. [PMID: 15957228]
  • Jean-François Lévesque, Erin Templeton, Laird Trimble, Carl Berthelette, Nathalie Chauret. Discovery, biosynthesis, and structure elucidation of metabolites of a doping agent and a direct analogue, tetrahydrogestrinone and gestrinone, using human hepatocytes. Analytical chemistry. 2005 May; 77(10):3164-72. doi: 10.1021/ac050150y. [PMID: 15889905]
  • Nola H Yu, Emmie N M Ho, David K K Leung, Terence S M Wan. Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2005 Apr; 37(5):1031-8. doi: 10.1016/j.jpba.2004.08.041. [PMID: 15862683]
  • Ping Zheng, Yu-fang Zhang, Jian-dong Wang. [Effect of gestrinone on the lipid metabolic parameters and bone mineral density in patients with endometriosis]. Zhonghua fu chan ke za zhi. 2005 Mar; 40(3):175-7. doi: NULL. [PMID: 15840312]
  • Fernand Labrie, Van Luu-The, Ezequiel Calvo, Céline Martel, Julie Cloutier, Sylvain Gauthier, Pascal Belleau, Jean Morissette, Marie-Hélène Lévesque, Claude Labrie. Tetrahydrogestrinone induces a genomic signature typical of a potent anabolic steroid. The Journal of endocrinology. 2005 Feb; 184(2):427-33. doi: 10.1677/joe.1.05997. [PMID: 15684350]
  • Zoë J Foster, Jeffrey A Housner. Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport. Current sports medicine reports. 2004 Aug; 3(4):234-41. doi: 10.1249/00149619-200408000-00011. [PMID: 15231229]
  • Steven Ashley. Doping by design. Scientific American. 2004 Feb; 290(2):22-3. doi: 10.1038/scientificamerican0204-22. [PMID: 14743721]
  • Don H Catlin, Michael H Sekera, Brian D Ahrens, Borislav Starcevic, Yu-Chen Chang, Caroline K Hatton. Tetrahydrogestrinone: discovery, synthesis, and detection in urine. Rapid communications in mass spectrometry : RCM. 2004; 18(12):1245-049. doi: 10.1002/rcm.1495. [PMID: 15174177]
  • Jonathan Knight. Drugs in sport: no dope. Nature. 2003 Nov; 426(6963):114-5. doi: 10.1038/426114a. [PMID: 14614473]
  • Jonathan Knight. Drugs bust reveals athletes' secret steroid. Nature. 2003 Oct; 425(6960):752. doi: 10.1038/425752a. [PMID: 14574369]
  • Q Wang, Z Wu, Y Wang, G Luo, E Wu, X Gao. Determination of gestrinone in human serum by liquid chromatography--electrospray tandem mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications. 2000 Sep; 746(2):151-9. doi: 10.1016/s0378-4347(00)00302-9. [PMID: 11076067]
  • Y Kim, Y Lee, M Kim, Y H Yim, W Lee. Determination and excretion study of gestrinone in human urine by high performance liquid chromatography and gas chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM. 2000; 14(14):1293-300. doi: 10.1002/1097-0231(20000730)14:14<1293::aid-rcm28>3.0.co;2-0. [PMID: 10918383]
  • Y Kim, Y Lee, M Kim, Y H Yim, W Lee. Determination of the metabolites of gestrinone in human urine by high performance liquid chromatography, liquid chromatography/mass spectrometry and gas chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM. 2000; 14(18):1717-26. doi: 10.1002/1097-0231(20000930)14:18<1717::aid-rcm65>3.0.co;2-2. [PMID: 10962496]
  • M Y Dawood, C W Obasiolu, J Ramos, F S Khan-Dawood. Clinical, endocrine, and metabolic effects of two doses of gestrinone in treatment of pelvic endometriosis. American journal of obstetrics and gynecology. 1997 Feb; 176(2):387-94. doi: 10.1016/s0002-9378(97)70504-0. [PMID: 9065187]
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