Bicalutamide (BioDeep_00000001531)

 

Secondary id: BioDeep_00000397768

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


4-Cyano-3-(4-fluorophenylsulfonyl)-2-hydroxy-2-methyl-3-(trifluoromethyl)propionanilide

化学式: C18H14F4N2O4S (430.06103720000004)
中文名称: 毕卡鲁胺
谱图信息: 最多检出来源 Homo sapiens(blood) 25%

分子结构信息

SMILES: CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
InChI: InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)

描述信息

Bicalutamide is only found in individuals that have used or taken this drug. It is an oral non-steroidal anti-androgen for prostate cancer. It binds to the androgen receptor.Bicalutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin which stimulate the growth of normal and malignant prostatic tissue.
L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02B - Hormone antagonists and related agents > L02BB - Anti-androgens
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D000726 - Androgen Antagonists
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C146993 - Androgen Receptor Inhibitor
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
D000970 - Antineoplastic Agents
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS

同义名列表

7 个代谢物同义名

4-Cyano-3-(4-fluorophenylsulfonyl)-2-hydroxy-2-methyl-3-(trifluoromethyl)propionanilide; AstraZeneca brand OF bicalutamide; Zeneca brand OF bicalutamide; Astra brand OF bicalutamide; Bicalutamide; Casodex; Cosudex



数据库引用编号

18 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

  • Akira Yokomizo, Masaki Shiota, Futoshi Morokuma, Masatoshi Eto, Hideyasu Matsuyama, Hiroaki Matsumoto, Toshiyuki Kamoto, Naoki Terada, Kazuya Kawahara, Hideki Enokida, Shuichi Tatarano, Naohiro Fujimoto, Katsuyoshi Higasijima, Hideki Sakai, Tomoaki Hakariya, Tsukasa Igawa, Shigetaka Suekane, Tomomi Kamba, Yutaka Sugiyama, Junji Kishimoto, Seiji Naito. GnRH antagonist monotherapy versus a GnRH agonist plus bicalutamide for advanced hormone-sensitive prostate cancer; KYUCOG-1401. International journal of urology : official journal of the Japanese Urological Association. 2023 Dec; ?(?):. doi: 10.1111/iju.15371. [PMID: 38148124]
  • Berlise Yengwa Bakam, Judith Christiane Ngo Pambe, Timothy Grey, Sebastian Maxeiner, Jochen Rutz, Dieudonne Njamen, Roman A Blaheta, Stéphane Zingue. Cucumis sativus (Cucurbitaceae) seed oil prevents benzo(a)pyrene-induced prostate cancer in vitro and in vivo. Environmental toxicology. 2023 Jun; ?(?):. doi: 10.1002/tox.23830. [PMID: 37310102]
  • Lei Tian, Yanfei Peng, Kuo Yang, Jiasong Cao, Xiaoling Du, Zhixian Liang, Jiandang Shi, Ju Zhang. The ERα-NRF2 signalling axis promotes bicalutamide resistance in prostate cancer. Cell communication and signaling : CCS. 2022 11; 20(1):178. doi: 10.1186/s12964-022-00979-0. [PMID: 36376959]
  • Alicia L Garcia-Costa, Teresa I A Gouveia, M Fernando R Pereira, Adrián M T Silva, Luís M Madeira, Arminda Alves, Mónica S F Santos. Intensification strategies for cytostatics degradation by ozone-based processes in aqueous phase. Journal of hazardous materials. 2022 10; 440(?):129743. doi: 10.1016/j.jhazmat.2022.129743. [PMID: 35963086]
  • Mohammadreza Mahdavijalal, Homayon Ahmad Panahi, Ali Niazi, Atefeh Tamaddon. Preparation of responsive nano-adsorbent to near-infrared laser based on tungsten disulfide for bicalutamide extraction in human biological fluids. Journal of pharmaceutical and biomedical analysis. 2022 Jun; 215(?):114759. doi: 10.1016/j.jpba.2022.114759. [PMID: 35430410]
  • Chiung-Chi Peng, Chang-Rong Chen, Chang-Yu Chen, Kuan-Chou Chen, Robert Y Peng. Bicalutamide may enhance kidney injury in diabetes by concomitantly damaging energy production from OXPHOS and glycolysis. Chemico-biological interactions. 2022 Apr; 356(?):109858. doi: 10.1016/j.cbi.2022.109858. [PMID: 35151640]
  • Karin Welén, Ebba Rosendal, Magnus Gisslén, Annasara Lenman, Eva Freyhult, Osvaldo Fonseca-Rodríguez, Daniel Bremell, Johan Stranne, Åse Östholm Balkhed, Katarina Niward, Johanna Repo, David Robinsson, Anna J Henningsson, Johan Styrke, Martin Angelin, Elisabeth Lindquist, Annika Allard, Miriam Becker, Stina Rudolfsson, Robert Buckland, Camilla Thellenberg Carlsson, Anders Bjartell, Anna C Nilsson, Clas Ahlm, Anne-Marie Fors Connolly, Anna K Överby, Andreas Josefsson. A Phase 2 Trial of the Effect of Antiandrogen Therapy on COVID-19 Outcome: No Evidence of Benefit, Supported by Epidemiology and In Vitro Data. European urology. 2022 03; 81(3):285-293. doi: 10.1016/j.eururo.2021.12.013. [PMID: 34980495]
  • Mohammadreza Mahdavijalal, Homayon Ahmad Panahi, Ali Niazi, Atefeh Tamaddon. Near-infrared light responsive dendrimers facilitate the extraction of bicalutamide from human plasma and urine. Biotechnology journal. 2021 Dec; 16(12):e2100299. doi: 10.1002/biot.202100299. [PMID: 34519173]
  • Valerie Carpenter, Tareq Saleh, So Min Lee, Graeme Murray, Jason Reed, Andrew Souers, Anthony C Faber, Hisashi Harada, David A Gewirtz. Androgen-deprivation induced senescence in prostate cancer cells is permissive for the development of castration-resistance but susceptible to senolytic therapy. Biochemical pharmacology. 2021 11; 193(?):114765. doi: 10.1016/j.bcp.2021.114765. [PMID: 34536356]
  • Amer Jamalpoor, Charlotte Agh van Gelder, Fjodor A Yousef Yengej, Esther A Zaal, Sante P Berlingerio, Koenraad R Veys, Carla Pou Casellas, Koen Voskuil, Khaled Essa, Carola Me Ammerlaan, Laura Rita Rega, Reini En van der Welle, Marc R Lilien, Maarten B Rookmaaker, Hans Clevers, Judith Klumperman, Elena Levtchenko, Celia R Berkers, Marianne C Verhaar, Maarten Altelaar, Rosalinde Masereeuw, Manoe J Janssen. Cysteamine-bicalutamide combination therapy corrects proximal tubule phenotype in cystinosis. EMBO molecular medicine. 2021 07; 13(7):e13067. doi: 10.15252/emmm.202013067. [PMID: 34165243]
  • 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]
  • Henrique J Cardoso, Marília I Figueira, Cátia V Vaz, Tiago M A Carvalho, Luís A Brás, Patrícia A Madureira, Paulo J Oliveira, Vilma A Sardão, Sílvia Socorro. Glutaminolysis is a metabolic route essential for survival and growth of prostate cancer cells and a target of 5α-dihydrotestosterone regulation. Cellular oncology (Dordrecht). 2021 Apr; 44(2):385-403. doi: 10.1007/s13402-020-00575-9. [PMID: 33464483]
  • Hongwen Cao, Dan Wang, Renjie Gao, Lei Chen, Yigeng Feng. Down regulation of U2AF1 promotes ARV7 splicing and prostate cancer progression. Biochemical and biophysical research communications. 2021 02; 541(?):56-62. doi: 10.1016/j.bbrc.2020.12.111. [PMID: 33477033]
  • Yoko Koh, Atsunari Kawashima, Takeshi Ujike, Akira Nagahara, Kazutoshi Fujita, Hiroshi Kiuchi, Ryoichi Imamura, Yasushi Miyagawa, Norio Nonomura, Motohide Uemura. Failure to achieve castrate level of serum testosterone during luteinizing hormone-releasing hormone agonist therapy in a patient with prostate cancer. Anti-cancer drugs. 2020 11; 31(10):1099-1102. doi: 10.1097/cad.0000000000000986. [PMID: 32804697]
  • Yu Seob Shin, Dong Sup Lee. Re: Impact of androgen deprivation therapy on volume reduction and lower urinary tract symptoms in patients with prostate cancer. Lower urinary tract symptoms. 2020 09; 12(3):293-294. doi: 10.1111/luts.12310. [PMID: 32924313]
  • Heike Lorenz, Andreas Seidel-Morgenstern. Separation Processes to Provide Pure Enantiomers and Plant Ingredients. Annual review of chemical and biomolecular engineering. 2020 06; 11(?):469-502. doi: 10.1146/annurev-chembioeng-100419-103732. [PMID: 32197049]
  • Claudia Kesch, Veronika Schmitt, Samir Bidnur, Marisa Thi, Eliana Beraldi, Igor Moskalev, Virginia Yago, Mary Bowden, Hans Adomat, Ladan Fazil, John K Jackson, Martin E Gleave. A polymeric paste-drug formulation for intratumoral treatment of prostate cancer. Prostate cancer and prostatic diseases. 2020 06; 23(2):324-332. doi: 10.1038/s41391-019-0190-x. [PMID: 31767941]
  • Gorkem Turkkan, Caner Dogan, Burak Tek. Bicalutamide-associated hallucinations in a metastatic prostate cancer patient: A case report. Journal of oncology pharmacy practice : official publication of the International Society of Oncology Pharmacy Practitioners. 2020 Jun; 26(4):1029-1031. doi: 10.1177/1078155219886918. [PMID: 31707924]
  • Harutake Sawazaki, Daiji Araki, Yosuke Kitamura, Kota Yagi. Metabolic changes with degarelix vs leuprolide plus bicalutamide in patients with prostate cancer: a randomized clinical study. World journal of urology. 2020 Jun; 38(6):1465-1471. doi: 10.1007/s00345-019-02937-x. [PMID: 31482294]
  • Kuan-Chou Chen, Chang-Rong Chen, Chang-Yu Chen, Kai-Yi Tzou, Chiung-Chi Peng, Robert Y Peng. Bicalutamide Elicits Renal Damage by Causing Mitochondrial Dysfunction via ROS Damage and Upregulation of HIF-1. International journal of molecular sciences. 2020 May; 21(9):. doi: 10.3390/ijms21093400. [PMID: 32403414]
  • 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]
  • P Suvarov, J-W Lee, A Vande Wouwer, A Seidel-Morgenstern, A Kienle. Online estimation of optimal operating conditions for simulated moving bed chromatographic processes. Journal of chromatography. A. 2019 Sep; 1602(?):266-272. doi: 10.1016/j.chroma.2019.05.042. [PMID: 31164228]
  • Darren J Bryk, Kenneth W Angermeier, Eric A Klein. A Case of Metastatic Prostate Cancer to the Urethra That Resolved After Androgen Deprivation Therapy. Urology. 2019 Jul; 129(?):e4-e5. doi: 10.1016/j.urology.2019.03.022. [PMID: 30935936]
  • Ved Bhushan Arya, Justin H Davies. Idiopathic gonadotropin-independent precocious puberty - is regular surveillance required?. Journal of pediatric endocrinology & metabolism : JPEM. 2019 Apr; 32(4):403-407. doi: 10.1515/jpem-2018-0419. [PMID: 30849047]
  • Chiung Chi Peng, Chang-Yu Chen, Chang-Rong Chen, Chang-Jui Chen, Kun-Hung Shen, Kuan-Chou Chen, Robert Y Peng. Renal Damaging Effect Elicited by Bicalutamide Therapy Uncovered Multiple Action Mechanisms As Evidenced by the Cell Model. Scientific reports. 2019 03; 9(1):3392. doi: 10.1038/s41598-019-39533-3. [PMID: 30833616]
  • M van Nuland, N Venekamp, N de Vries, K A M de Jong, H Rosing, J H Beijnen. Development and validation of an UPLC-MS/MS method for the therapeutic drug monitoring of oral anti-hormonal drugs in oncology. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Feb; 1106-1107(?):26-34. doi: 10.1016/j.jchromb.2019.01.001. [PMID: 30639947]
  • Adam Bohr, Thais Leite Nascimento, Necati Harmankaya, Johan Juhl Weisser, Yingya Wang, Holger Grohganz, Thomas Rades, Korbinian Löbmann. Efflux Inhibitor Bicalutamide Increases Oral Bioavailability of the Poorly Soluble Efflux Substrate Docetaxel in Co-Amorphous Anti-Cancer Combination Therapy. Molecules (Basel, Switzerland). 2019 Jan; 24(2):. doi: 10.3390/molecules24020266. [PMID: 30642009]
  • Changwen Zhang, Penghao Li, Yingwu Wen, Guowei Feng, Yu Liu, Yangyi Zhang, Yong Xu, Zhihong Zhang. The promotion on cell growth of androgen-dependent prostate cancer by antimony via mimicking androgen activity. Toxicology letters. 2018 May; 288(?):136-142. doi: 10.1016/j.toxlet.2018.02.021. [PMID: 29462692]
  • Chang Hee Kim, Kwang Teack Kim, Jin Kyu Oh, Kyung Jin Chung, Tae Beom Kim, Han Jung, Sang Jin Yoon, Khae Hawn Kim. The Association of A Number of Risk Factors With Depression in Patients With Prostate Cancer Undergoing Androgen Deprivation Therapy. Urology journal. 2018 05; 15(3):104-108. doi: 10.22037/uj.v0i0.4138. [PMID: 29388185]
  • Akihiro Yano, Makoto Kagawa, Hideki Takeshita, Yohei Okada, Makoto Morozumi, Satoru Kawakami. Baseline low serum dehydroepiandrosterone sulfate can predict poor responsiveness to hormone therapy in patients with hormone-naïve prostate cancer with skeletal metastases. International journal of urology : official journal of the Japanese Urological Association. 2017 12; 24(12):861-862. doi: 10.1111/iju.13445. [PMID: 28895205]
  • Bertrand Tombal, Erik B Cornel, Raj Persad, Anny Stari, Francisco Gómez Veiga, Claude Schulman. Clinical Outcomes and Testosterone Levels Following Continuous Androgen Deprivation in Patients with Relapsing or Locally Advanced Prostate Cancer: A Post Hoc Analysis of the ICELAND Study. The Journal of urology. 2017 11; 198(5):1054-1060. doi: 10.1016/j.juro.2017.05.072. [PMID: 28552710]
  • Yang Zhang, Bo-Han Lei, Qing Zou, Qing-Yi Zhu, Zi-Jie Lu, Yue Wang. [Clinical efficacy of integrated traditional Chinese and Western medicine for castration-resistant prostate cancer]. Zhonghua nan ke xue = National journal of andrology. 2017 Oct; 23(10):922-927. doi: NULL. [PMID: 29727544]
  • Congbin Yang, Peiwen Di, JinPing Fu, Hui Xiong, Qiufang Jing, Guobin Ren, Yun Tang, Wenyun Zheng, Guixia Liu, Fuzheng Ren. Improving the physicochemical properties of bicalutamide by complex formation with bovine serum albumin. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2017 Aug; 106(?):381-392. doi: 10.1016/j.ejps.2017.05.059. [PMID: 28571783]
  • Dante Rojas, Gaud Dervilly-Pinel, Nora Cesbron, Mylène Penot, Alexandre Sydor, Stéphanie Prévost, Bruno Le Bizec. Selective androgen receptor modulators: comparative excretion study of bicalutamide in bovine urine and faeces. Drug testing and analysis. 2017 Jul; 9(7):1017-1025. doi: 10.1002/dta.2113. [PMID: 27726308]
  • Kyu-Pyo Kim, Robert A Parise, Julianne L Holleran, Lionel D Lewis, Leonard Appleman, Nielka van Erp, Michael J Morris, Jan H Beumer. Simultaneous quantitation of abiraterone, enzalutamide, N-desmethyl enzalutamide, and bicalutamide in human plasma by LC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2017 May; 138(?):197-205. doi: 10.1016/j.jpba.2017.02.018. [PMID: 28219796]
  • J Morote, L Regis, A Celma, J Planas. Measurement of serum testosterone during androgenic suppression in patients with prostate cancer: A systematic review. Actas urologicas espanolas. 2016 Oct; 40(8):477-84. doi: 10.1016/j.acuro.2016.01.006. [PMID: 26899928]
  • Huiyan Wang, Lixia Zhang, Ying Fu, Fang Fang, Yong Jiang, Yuan Dong, Wenhe Zhu. CSL regulates AKT to mediate androgen independence in prostate cancer progression. The Prostate. 2016 Feb; 76(2):140-50. doi: 10.1002/pros.23104. [PMID: 26437743]
  • Nada Lallous, Stanislav V Volik, Shannon Awrey, Eric Leblanc, Ronnie Tse, Josef Murillo, Kriti Singh, Arun A Azad, Alexander W Wyatt, Stephane LeBihan, Kim N Chi, Martin E Gleave, Paul S Rennie, Colin C Collins, Artem Cherkasov. Functional analysis of androgen receptor mutations that confer anti-androgen resistance identified in circulating cell-free DNA from prostate cancer patients. Genome biology. 2016 Jan; 17(?):10. doi: 10.1186/s13059-015-0864-1. [PMID: 26813233]
  • Natalia Mast, Joseph B Lin, Irina A Pikuleva. Marketed Drugs Can Inhibit Cytochrome P450 27A1, a Potential New Target for Breast Cancer Adjuvant Therapy. Molecular pharmacology. 2015 Sep; 88(3):428-36. doi: 10.1124/mol.115.099598. [PMID: 26082378]
  • Masahiro Nozawa, Isao Hara, Hideyasu Matsuyama, Masayuki Iki, Kazuhiro Nagao, Tsukasa Nishioka, Takahiro Komura, Atsunobu Esa, Shigeya Uejima, Masaaki Imanishi, Yasunari Uekado, Takatoshi Ogawa, Hiroshi Kajikawa, Hirotsugu Uemura. Significance of baseline bone markers on disease progression and survival in hormone-sensitive prostate cancer with bone metastasis. World journal of urology. 2015 Sep; 33(9):1263-8. doi: 10.1007/s00345-014-1431-1. [PMID: 25354720]
  • Sho Uehara, Takeshi Yuasa, Yasuhisa Fujii, Akihiro Yano, Shinya Yamamoto, Hitoshi Masuda, Iwao Fukui, Junji Yonese. Prior administration of a non-steroidal anti-androgen failed to prevent the flare-up caused by a luteinizing hormone-releasing hormone agonist in a patient with metastatic prostate cancer. BMC research notes. 2015 Aug; 8(?):335. doi: 10.1186/s13104-015-1297-3. [PMID: 26242866]
  • Jing Li, SongTao Xiang, QiouHong Zhang, JingJing Wu, Qing Tang, JianFu Zhou, LiJun Yang, ZhiQiang Chen, Swei Sunny Hann. Combination of curcumin and bicalutamide enhanced the growth inhibition of androgen-independent prostate cancer cells through SAPK/JNK and MEK/ERK1/2-mediated targeting NF-κB/p65 and MUC1-C. Journal of experimental & clinical cancer research : CR. 2015 May; 34(?):46. doi: 10.1186/s13046-015-0168-z. [PMID: 25971429]
  • Evan Y Yu, Hongli Li, Celestia S Higano, Neeraj Agarwal, Sumanta K Pal, Ajjai Alva, Elisabeth I Heath, Elaine T Lam, Shilpa Gupta, Michael B Lilly, Yoshio Inoue, Kim N Chi, Nicholas J Vogelzang, David I Quinn, Heather H Cheng, Stephen R Plymate, Maha Hussain, Catherine M Tangen, Ian M Thompson. SWOG S0925: A Randomized Phase II Study of Androgen Deprivation Combined With Cixutumumab Versus Androgen Deprivation Alone in Patients With New Metastatic Hormone-Sensitive Prostate Cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2015 May; 33(14):1601-8. doi: 10.1200/jco.2014.59.4127. [PMID: 25847934]
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