Zosuquidar (BioDeep_00000781960)

   


代谢物信息卡片


(2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol

化学式: C32H31F2N3O2 (527.238421)
中文名称: (6R,7R)-7-[[2-[2-(氨基甲基)苯基]乙酰]氨基]-3-[[1-(羧甲基)四唑-5-基]硫甲基]-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CN(CCN1CC(COC2=CC=CC3=C2C=CC=N3)O)C4C5=CC=CC=C5C6C(C6(F)F)C7=CC=CC=C47
InChI: InChI=1S/C32H31F2N3O2/c33-32(34)29-22-7-1-3-9-24(22)31(25-10-4-2-8-23(25)30(29)32)37-17-15-36(16-18-37)19-21(38)20-39-28-13-5-12-27-26(28)11-6-14-35-27/h1-14,21,29-31,38H,15-20H2

描述信息

C1744 - Multidrug Resistance Modulator

同义名列表

2 个代谢物同义名

Zosuquidar; (2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol



数据库引用编号

8 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)

0 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

  • Yoko Nagaya, Kazuhide Katayama, Hiroyuki Kusuhara, Yoshitane Nozaki. Impact of P-Glycoprotein-Mediated Active Efflux on Drug Distribution into Lumbar Cerebrospinal Fluid in Nonhuman Primates. Drug metabolism and disposition: the biological fate of chemicals. 2020 11; 48(11):1183-1190. doi: 10.1124/dmd.120.000099. [PMID: 32862147]
  • Dong Ye, Anna Harder, Zhizhou Fang, Manuel Weinheimer, Loic Laplanche, Mario Mezler. Characterization and Validation of Canine P-Glycoprotein-Deficient MDCK II Cell Lines for Efflux Substrate Screening. Pharmaceutical research. 2020 Sep; 37(10):194. doi: 10.1007/s11095-020-02895-9. [PMID: 32918191]
  • Ming Yang, Lin Cheng, Qing Dai, Bo Yang, Qian Yuan, MingJie Yu, Wei Feng, Fengjun Sun, Peiyuan Xia. A Novel Cryptococcal Meningitis Therapy: The Combination of Amphotericin B and Posaconazole Promotes the Distribution of Amphotericin B in the Brain Tissue. BioMed research international. 2020; 2020(?):8878158. doi: 10.1155/2020/8878158. [PMID: 33313322]
  • Ashutosh K Dash, Debaraj Mukherjee, Abhijeet Dhulap, Saqlain Haider, Deepak Kumar. Green chemistry appended synthesis, metabolic stability and pharmacokinetic assessment of medicinally important chromene dihydropyrimidinones. Bioorganic & medicinal chemistry letters. 2019 12; 29(24):126750. doi: 10.1016/j.bmcl.2019.126750. [PMID: 31699608]
  • Asmita Magotra, Abhishek Gour, Deepak K Sharma, Ashutosh K Dash, Gurdarshan Singh, Debaraj Mukherjee, Utpal Nandi. Pharmacokinetic evaluation of medicinally important synthetic N,N' diindolylmethane glucoside: Improved synthesis and metabolic stability. Bioorganic & medicinal chemistry letters. 2019 04; 29(8):1007-1011. doi: 10.1016/j.bmcl.2019.02.010. [PMID: 30777609]
  • Amer Alam, Julia Kowal, Eugenia Broude, Igor Roninson, Kaspar P Locher. Structural insight into substrate and inhibitor discrimination by human P-glycoprotein. Science (New York, N.Y.). 2019 02; 363(6428):753-756. doi: 10.1126/science.aav7102. [PMID: 30765569]
  • Amer Alam, Raphael Küng, Julia Kowal, Robert A McLeod, Nina Tremp, Eugenia V Broude, Igor B Roninson, Henning Stahlberg, Kaspar P Locher. Structure of a zosuquidar and UIC2-bound human-mouse chimeric ABCB1. Proceedings of the National Academy of Sciences of the United States of America. 2018 02; 115(9):E1973-E1982. doi: 10.1073/pnas.1717044115. [PMID: 29440498]
  • Houfu Liu, Liang Huang, Yi Li, Tingting Fu, Xueying Sun, Yan-Yan Zhang, Ruina Gao, Qingfang Chen, Wandong Zhang, Jasminder Sahi, Scott Summerfield, Kelly Dong. Correlation between Membrane Protein Expression Levels and Transcellular Transport Activity for Breast Cancer Resistance Protein. Drug metabolism and disposition: the biological fate of chemicals. 2017 05; 45(5):449-456. doi: 10.1124/dmd.116.074245. [PMID: 28209803]
  • Fei Liu, Xiaoqing Wang, Zheng Li, Jin Li, Xiaomei Zhuang, Zhenqing Zhang. P-Glycoprotein (ABCB1) limits the brain distribution of YQA-14, a novel dopamine D3 receptor antagonist. Chemical & pharmaceutical bulletin. 2015; 63(7):512-8. doi: 10.1248/cpb.c15-00089. [PMID: 26133067]
  • Mikiko Tsukimoto, Rikiya Ohashi, Nao Torimoto, Yoko Togo, Takashi Suzuki, Toshio Maeda, Yoshiyuki Kagawa. Effects of the inhibition of intestinal P-glycoprotein on aliskiren pharmacokinetics in cynomolgus monkeys. Biopharmaceutics & drug disposition. 2015 Jan; 36(1):15-33. doi: 10.1002/bdd.1920. [PMID: 25264342]
  • Serena Marchetti, Dick Pluim, Jos H Beijnen, Roberto Mazzanti, Olaf van Tellingen, Jan H M Schellens. "Effect of the drug transporters ABCB1, ABCC2, and ABCG2 on the disposition and brain accumulation of the taxane analog BMS-275,183". Investigational new drugs. 2014 Dec; 32(6):1083-95. doi: 10.1007/s10637-014-0143-0. [PMID: 25078948]
  • Holger Fuchs, Wataru Kishimoto, Dietmar Gansser, Paul Tanswell, Naoki Ishiguro. Brain penetration of WEB 2086 (Apafant) and dantrolene in Mdr1a (P-glycoprotein) and Bcrp knockout rats. Drug metabolism and disposition: the biological fate of chemicals. 2014 Oct; 42(10):1761-5. doi: 10.1124/dmd.114.058545. [PMID: 25053619]
  • Yoshiki Matsuda, Yoshihiro Konno, Takashi Hashimoto, Mika Nagai, Takayuki Taguchi, Masahiro Satsukawa, Shinji Yamashita. In vivo assessment of the impact of efflux transporter on oral drug absorption using portal vein-cannulated rats. Drug metabolism and disposition: the biological fate of chemicals. 2013 Aug; 41(8):1514-21. doi: 10.1124/dmd.113.051680. [PMID: 23686319]
  • Xiaofeng Bao, Shuiyu Lu, Jeih-San Liow, Cheryl L Morse, Kacey B Anderson, Sami S Zoghbi, Robert B Innis, Victor W Pike. [¹¹C]Rhodamine-123: synthesis and biodistribution in rodents. Nuclear medicine and biology. 2012 Nov; 39(8):1128-36. doi: 10.1016/j.nucmedbio.2012.06.013. [PMID: 22898316]
  • Mukul Minocha, Varun Khurana, Bin Qin, Dhananjay Pal, Ashim K Mitra. Enhanced brain accumulation of pazopanib by modulating P-gp and Bcrp1 mediated efflux with canertinib or erlotinib. International journal of pharmaceutics. 2012 Oct; 436(1-2):127-34. doi: 10.1016/j.ijpharm.2012.05.038. [PMID: 22688250]
  • Rajendar K Mittapalli, Shruthi Vaidhyanathan, Ramola Sane, William F Elmquist. Impact of P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2) on the brain distribution of a novel BRAF inhibitor: vemurafenib (PLX4032). The Journal of pharmacology and experimental therapeutics. 2012 Jul; 342(1):33-40. doi: 10.1124/jpet.112.192195. [PMID: 22454535]
  • Jinfeng Hou, Feng Qu, Caisheng Wu, Qiang Ren, Jinlan Zhang. Quantitative determination and pharmacokinetic study of the novel anti-Parkinson's disease candidate drug FLZ in rat brain by high performance liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2012 Jul; 66(?):232-9. doi: 10.1016/j.jpba.2012.03.001. [PMID: 22472186]
  • Ishrat Jabeen, Karin Pleban, Uwe Rinner, Peter Chiba, Gerhard F Ecker. Structure-activity relationships, ligand efficiency, and lipophilic efficiency profiles of benzophenone-type inhibitors of the multidrug transporter P-glycoprotein. Journal of medicinal chemistry. 2012 Apr; 55(7):3261-73. doi: 10.1021/jm201705f. [PMID: 22452412]
  • Holger Fuchs, Frank Runge, Heinz-Dieter Held. Excretion of the dipeptidyl peptidase-4 inhibitor linagliptin in rats is primarily by biliary excretion and P-gp-mediated efflux. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2012 Apr; 45(5):533-8. doi: 10.1016/j.ejps.2011.11.018. [PMID: 22198311]
  • Wendy A Teft, Sara E Mansell, Richard B Kim. Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1). Drug metabolism and disposition: the biological fate of chemicals. 2011 Mar; 39(3):558-62. doi: 10.1124/dmd.110.036160. [PMID: 21148080]
  • Ying Chen, Sagar Agarwal, Naveed M Shaik, Cliff Chen, Zheng Yang, William F Elmquist. P-glycoprotein and breast cancer resistance protein influence brain distribution of dasatinib. The Journal of pharmacology and experimental therapeutics. 2009 Sep; 330(3):956-63. doi: 10.1124/jpet.109.154781. [PMID: 19491323]
  • Jeffrey E Lancet, Maria R Baer, George E Duran, Alan F List, Robert Fielding, John F Marcelletti, Pratik S Multani, Branimir I Sikic. A phase I trial of continuous infusion of the multidrug resistance inhibitor zosuquidar with daunorubicin and cytarabine in acute myeloid leukemia. Leukemia research. 2009 Aug; 33(8):1055-61. doi: 10.1016/j.leukres.2008.09.015. [PMID: 19108889]
  • Erin R Gardner, Nicola F Smith, William D Figg, Alex Sparreboom. Influence of the dual ABCB1 and ABCG2 inhibitor tariquidar on the disposition of oral imatinib in mice. Journal of experimental & clinical cancer research : CR. 2009 Jul; 28(?):99. doi: 10.1186/1756-9966-28-99. [PMID: 19591692]
  • Roos L Oostendorp, Evita van de Steeg, Cornelia M M van der Kruijssen, Jos H Beijnen, Kathryn E Kenworthy, Alfred H Schinkel, Jan H M Schellens. Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors. Drug metabolism and disposition: the biological fate of chemicals. 2009 Apr; 37(4):917-23. doi: 10.1124/dmd.108.024901. [PMID: 19139163]
  • Uwe Muenster, Birgit Grieshop, Karsten Ickenroth, Mark Jean Gnoth. Characterization of substrates and inhibitors for the in vitro assessment of Bcrp mediated drug-drug interactions. Pharmaceutical research. 2008 Oct; 25(10):2320-6. doi: 10.1007/s11095-008-9632-1. [PMID: 18523872]
  • Anne T Nies, Elke Herrmann, Manuela Brom, Dietrich Keppler. Vectorial transport of the plant alkaloid berberine by double-transfected cells expressing the human organic cation transporter 1 (OCT1, SLC22A1) and the efflux pump MDR1 P-glycoprotein (ABCB1). Naunyn-Schmiedeberg's archives of pharmacology. 2008 Feb; 376(6):449-61. doi: 10.1007/s00210-007-0219-x. [PMID: 18157518]
  • Naveed Shaik, Nagdeep Giri, Guoyu Pan, William F Elmquist. P-glycoprotein-mediated active efflux of the anti-HIV1 nucleoside abacavir limits cellular accumulation and brain distribution. Drug metabolism and disposition: the biological fate of chemicals. 2007 Nov; 35(11):2076-85. doi: 10.1124/dmd.107.017723. [PMID: 17709369]
  • Jan-Hendrik Beumer, Tessa Buckle, Mariet Ouwehand, Niels E F Franke, Luis Lopez-Lazaro, Jan H M Schellens, Jos H Beijnen, Olaf van Tellingen. Trabectedin (ET-743, Yondelis) is a substrate for P-glycoprotein, but only high expression of P-glycoprotein confers the multidrug resistance phenotype. Investigational new drugs. 2007 Feb; 25(1):1-7. doi: 10.1007/s10637-006-7773-9. [PMID: 16633714]
  • Bradley D Anderson, Melissa J May, Sherri Jordan, Lin Song, Michael J Roberts, Markos Leggas. Dependence of nelfinavir brain uptake on dose and tissue concentrations of the selective P-glycoprotein inhibitor zosuquidar in rats. Drug metabolism and disposition: the biological fate of chemicals. 2006 Apr; 34(4):653-9. doi: 10.1124/dmd.105.006536. [PMID: 16434546]
  • Paula M Fracasso, Lori J Goldstein, Dinesh P de Alwis, Janet S Rader, Matthew A Arquette, Sherry A Goodner, Lisa P Wright, Carole L Fears, Robert J Gazak, Valerie A M Andre, Michael F Burgess, Christopher A Slapak, Jan H M Schellens. Phase I study of docetaxel in combination with the P-glycoprotein inhibitor, zosuquidar, in resistant malignancies. Clinical cancer research : an official journal of the American Association for Cancer Research. 2004 Nov; 10(21):7220-8. doi: 10.1158/1078-0432.ccr-04-0452. [PMID: 15534095]
  • Heleen A Bardelmeijer, Mariët Ouwehand, Jos H Beijnen, Jan H M Schellens, Olaf van Tellingen. Efficacy of novel P-glycoprotein inhibitors to increase the oral uptake of paclitaxel in mice. Investigational new drugs. 2004 Aug; 22(3):219-29. doi: 10.1023/b:drug.0000026248.45084.21. [PMID: 15122069]
  • E Marleen Kemper, Cindy Cleypool, Willem Boogerd, Jos H Beijnen, Olaf van Tellingen. The influence of the P-glycoprotein inhibitor zosuquidar trihydrochloride (LY335979) on the brain penetration of paclitaxel in mice. Cancer chemotherapy and pharmacology. 2004 Feb; 53(2):173-8. doi: 10.1007/s00280-003-0720-y. [PMID: 14605863]
  • E M Kemper, M Ouwehand, J H Beijnen, O van Tellingen. Bioanalysis of zosuquidar trihydrochloride (LY335979) in small volumes of human and murine plasma by ion-pairing reversed-phase high-performance liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Dec; 798(1):63-8. doi: 10.1016/j.jchromb.2003.08.047. [PMID: 14630360]
  • Sophie Callies, Dinesh P de Alwis, Adrian Harris, Paul Vasey, Jos H Beijnen, Jan H Schellens, Michael Burgess, Leon Aarons. A population pharmacokinetic model for paclitaxel in the presence of a novel P-gp modulator, Zosuquidar Trihydrochloride (LY335979). British journal of clinical pharmacology. 2003 Jul; 56(1):46-56. doi: 10.1046/j.1365-2125.2003.01826.x. [PMID: 12848775]
  • Eric H Rubin, Dinesh P de Alwis, Isabelle Pouliquen, Lisa Green, Phil Marder, Yong Lin, Rita Musanti, Stephanie L Grospe, Sharon L Smith, Deborah L Toppmeyer, Judy Much, Michael Kane, Ajai Chaudhary, Christopher Jordan, Michael Burgess, Christopher A Slapak. A phase I trial of a potent P-glycoprotein inhibitor, Zosuquidar.3HCl trihydrochloride (LY335979), administered orally in combination with doxorubicin in patients with advanced malignancies. Clinical cancer research : an official journal of the American Association for Cancer Research. 2002 Dec; 8(12):3710-7. doi: NULL. [PMID: 12473580]
  • Susan F Bates, Clara Chen, Robert Robey, Min Kang, William D Figg, Tito Fojo. Reversal of multidrug resistance: lessons from clinical oncology. Novartis Foundation symposium. 2002; 243(?):83-96; discussion 96. doi: 10.1002/0470846356.ch7. [PMID: 11990784]
  • B I Florea, I C van der Sandt, S M Schrier, K Kooiman, K Deryckere, A G de Boer, H E Junginger, G Borchard. Evidence of P-glycoprotein mediated apical to basolateral transport of flunisolide in human broncho-tracheal epithelial cells (Calu-3). British journal of pharmacology. 2001 Dec; 134(7):1555-63. doi: 10.1038/sj.bjp.0704390. [PMID: 11724763]
  • E F Choo, B Leake, C Wandel, H Imamura, A J Wood, G R Wilkinson, R B Kim. Pharmacological inhibition of P-glycoprotein transport enhances the distribution of HIV-1 protease inhibitors into brain and testes. Drug metabolism and disposition: the biological fate of chemicals. 2000 Jun; 28(6):655-60. doi: NULL. [PMID: 10820137]
  • A H Dantzig, R L Shepard, K L Law, L Tabas, S Pratt, J S Gillespie, S N Binkley, M T Kuhfeld, J J Starling, S A Wrighton. Selectivity of the multidrug resistance modulator, LY335979, for P-glycoprotein and effect on cytochrome P-450 activities. The Journal of pharmacology and experimental therapeutics. 1999 Aug; 290(2):854-62. doi: NULL. [PMID: 10411602]
  • G D Luker, K R Nilsson, D F Covey, D Piwnica-Worms. Multidrug resistance (MDR1) P-glycoprotein enhances esterification of plasma membrane cholesterol. The Journal of biological chemistry. 1999 Mar; 274(11):6979-91. doi: 10.1074/jbc.274.11.6979. [PMID: 10066752]
  • W J Ehlhardt, J M Woodland, T M Baughman, M Vandenbranden, S A Wrighton, J S Kroin, B H Norman, S R Maple. Liquid chromatography/nuclear magnetic resonance spectroscopy and liquid chromatography/mass spectrometry identification of novel metabolites of the multidrug resistance modulator LY335979 in rat bile and human liver microsomal incubations. Drug metabolism and disposition: the biological fate of chemicals. 1998 Jan; 26(1):42-51. doi: NULL. [PMID: 9443851]
  • J J Starling, R L Shepard, J Cao, K L Law, B H Norman, J S Kroin, W J Ehlhardt, T M Baughman, M A Winter, M G Bell, C Shih, J Gruber, W F Elmquist, A H Dantzig. Pharmacological characterization of LY335979: a potent cyclopropyldibenzosuberane modulator of P-glycoprotein. Advances in enzyme regulation. 1997; 37(?):335-47. doi: 10.1016/s0065-2571(96)00021-0. [PMID: 9381979]
  • A H Dantzig, R L Shepard, J Cao, K L Law, W J Ehlhardt, T M Baughman, T F Bumol, J J Starling. Reversal of P-glycoprotein-mediated multidrug resistance by a potent cyclopropyldibenzosuberane modulator, LY335979. Cancer research. 1996 Sep; 56(18):4171-9. doi: . [PMID: 8797588]