Fialuridine (BioDeep_00000731941)

   


代谢物信息卡片


Fialuridine

化学式: C9H10FIN2O5 (371.9618492)
中文名称: 1-(2-脱氧-2-氟-β-D-阿拉伯呋喃基)-5-碘尿嘧啶
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)F)I
InChI: InChI=1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5+,6-,8-/m1/s1

描述信息

D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
C471 - Enzyme Inhibitor > C29575 - DNA Polymerase Inhibitor
C254 - Anti-Infective Agent > C281 - Antiviral Agent
Fialuridine is a nucleoside analog with antiviral activity[1]. Fialuridine shows anti-orthopoxvirus activity.

同义名列表

4 个代谢物同义名

Fialuridine; FIAU; DRG-0098; NSC 678514



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

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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

  • Delilah F G Hendriks, Tracey Hurrell, Julia Riede, Muriëlle van der Horst, Sarianna Tuovinen, Magnus Ingelman-Sundberg. Mechanisms of chronic fialuridine hepatotoxicity as revealed in primary human hepatocyte spheroids. Toxicological sciences : an official journal of the Society of Toxicology. 2019 Aug; ?(?):. doi: 10.1093/toxsci/kfz195. [PMID: 31505000]
  • Xiaoyan M Zhang, Halle H Zhang, Patrick McLeroth, Richard D Berkowitz, Michael A Mont, Michael G Stabin, Barry A Siegel, Abass Alavi, T Marc Barnett, Jeffrey Gelb, Chantal Petit, John Spaltro, Steve Y Cho, Martin G Pomper, James J Conklin, Chetan Bettegowda, Saurabh Saha. [(124)I]FIAU: Human dosimetry and infection imaging in patients with suspected prosthetic joint infection. Nuclear medicine and biology. 2016 May; 43(5):273-9. doi: 10.1016/j.nucmedbio.2016.01.004. [PMID: 27150029]
  • David Tung, Gary DeCrescenzo, Dean Welsch, Peter H Cheung, Chetan Bettegowda, Saurabh Saha. Evaluation of 1-(2-deoxy-2-fluoro-1-D-arabinofuranosyl)-5-iodouracil (FIAU) as an ex vivo bacterial detection agent. World journal of microbiology & biotechnology. 2014 Nov; 30(11):3003-10. doi: 10.1007/s11274-014-1709-x. [PMID: 25085723]
  • Dan Xu, Toshi Nishimura, Sachiko Nishimura, Haili Zhang, Ming Zheng, Ying-Ying Guo, Marylin Masek, Sara A Michie, Jeffrey Glenn, Gary Peltz. Fialuridine induces acute liver failure in chimeric TK-NOG mice: a model for detecting hepatic drug toxicity prior to human testing. PLoS medicine. 2014 Apr; 11(4):e1001628. doi: 10.1371/journal.pmed.1001628. [PMID: 24736310]
  • Frida Gustafsson, Alison J Foster, Sunil Sarda, Matthew H Bridgland-Taylor, J Gerry Kenna. A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. Toxicological sciences : an official journal of the Society of Toxicology. 2014 Jan; 137(1):189-211. doi: 10.1093/toxsci/kft223. [PMID: 24085192]
  • Laia Tolosa, Sandra Pinto, M Teresa Donato, Agustín Lahoz, José V Castell, J Enrique O'Connor, M José Gómez-Lechón. Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs. Toxicological sciences : an official journal of the Society of Toxicology. 2012 May; 127(1):187-98. doi: 10.1093/toxsci/kfs083. [PMID: 22331495]
  • Sarah Dawson, Simone Stahl, Nikki Paul, Jane Barber, J Gerald Kenna. In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jan; 40(1):130-8. doi: 10.1124/dmd.111.040758. [PMID: 21965623]
  • Joo Ho Tai, Binh Nguyen, R Glenn Wells, Michael S Kovacs, Rebecca McGirr, Frank S Prato, Timothy G Morgan, Savita Dhanvantari. Imaging of gene expression in live pancreatic islet cell lines using dual-isotope SPECT. Journal of nuclear medicine : official publication, Society of Nuclear Medicine. 2008 Jan; 49(1):94-102. doi: 10.2967/jnumed.107.043430. [PMID: 18077534]
  • Sridhar Nimmagadda, Thomas J Mangner, Kirk A Douglas, Otto Muzik, Anthony F Shields. Biodistribution, PET, and radiation dosimetry estimates of HSV-tk gene expression imaging agent 1-(2'-Deoxy-2'-18F-Fluoro-beta-D-arabinofuranosyl)-5-iodouracil in normal dogs. Journal of nuclear medicine : official publication, Society of Nuclear Medicine. 2007 Apr; 48(4):655-60. doi: 10.2967/jnumed.106.036830. [PMID: 17401105]
  • Eun-Woo Lee, Yurong Lai, Huixia Zhang, Jashvant D Unadkat. Identification of the mitochondrial targeting signal of the human equilibrative nucleoside transporter 1 (hENT1): implications for interspecies differences in mitochondrial toxicity of fialuridine. The Journal of biological chemistry. 2006 Jun; 281(24):16700-6. doi: 10.1074/jbc.m513825200. [PMID: 16595656]
  • Yurong Lai, Chung-Ming Tse, Jashvant D Unadkat. Mitochondrial expression of the human equilibrative nucleoside transporter 1 (hENT1) results in enhanced mitochondrial toxicity of antiviral drugs. The Journal of biological chemistry. 2004 Feb; 279(6):4490-7. doi: 10.1074/jbc.m307938200. [PMID: 14607828]
  • Donald F Smee, Robert W Sidwell. Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides. Nucleosides, nucleotides & nucleic acids. 2004; 23(1-2):375-83. doi: 10.1081/ncn-120028334. [PMID: 15043161]
  • Juri Gelovani Tjuvajev, Mikhail Doubrovin, Timothy Akhurst, Shangde Cai, Julius Balatoni, Mian M Alauddin, Ronald Finn, William Bornmann, Howard Thaler, Peter S Conti, Ronald G Blasberg. Comparison of radiolabeled nucleoside probes (FIAU, FHBG, and FHPG) for PET imaging of HSV1-tk gene expression. Journal of nuclear medicine : official publication, Society of Nuclear Medicine. 2002 Aug; 43(8):1072-83. doi: NULL. [PMID: 12163634]
  • J Tjuvajev, R Blasberg, X Luo, L M Zheng, I King, D Bermudes. Salmonella-based tumor-targeted cancer therapy: tumor amplified protein expression therapy (TAPET) for diagnostic imaging. Journal of controlled release : official journal of the Controlled Release Society. 2001 Jul; 74(1-3):313-5. doi: 10.1016/s0168-3659(01)00340-6. [PMID: 11489512]
  • A Jacobs, I Bräunlich, R Graf, M Lercher, T Sakaki, J Voges, V Hesselmann, W Brandau, K Wienhard, W D Heiss. Quantitative kinetics of [124I]FIAU in cat and man. Journal of nuclear medicine : official publication, Society of Nuclear Medicine. 2001 Mar; 42(3):467-75. doi: NULL. [PMID: 11337525]
  • K R Zinn, T R Chaudhuri, D J Buchsbaum, J M Mountz, B E Rogers. Simultaneous evaluation of dual gene transfer to adherent cells by gamma-ray imaging. Nuclear medicine and biology. 2001 Feb; 28(2):135-44. doi: 10.1016/s0969-8051(00)00207-9. [PMID: 11295424]
  • B C Tennant, B H Baldwin, L A Graham, M A Ascenzi, W E Hornbuckle, P H Rowland, I A Tochkov, A E Yeager, H N Erb, J M Colacino, C Lopez, J A Engelhardt, R R Bowsher, F C Richardson, W Lewis, P J Cote, B E Korba, J L Gerin. Antiviral activity and toxicity of fialuridine in the woodchuck model of hepatitis B virus infection. Hepatology (Baltimore, Md.). 1998 Jul; 28(1):179-91. doi: 10.1002/hep.510280124. [PMID: 9657111]
  • G Vaidyanathan, M R Zalutsky. Preparation of 5-[131I]iodo- and 5-[211At]astato-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) uracil by a halodestannylation reaction. Nuclear medicine and biology. 1998 Jul; 25(5):487-96. doi: 10.1016/s0969-8051(98)00004-3. [PMID: 9720667]
  • C Semino-Mora, M Leon-Monzon, M C Dalakas. Mitochondrial and cellular toxicity induced by fialuridine in human muscle in vitro. Laboratory investigation; a journal of technical methods and pathology. 1997 Apr; 76(4):487-95. doi: ". [PMID: 9111511]
  • D E Kleiner, M J Gaffey, R Sallie, M Tsokos, L Nichols, R McKenzie, S E Straus, J H Hoofnagle. Histopathologic changes associated with fialuridine hepatotoxicity. Modern pathology : an official journal of the United States and Canadian Academy of Pathology, Inc. 1997 Mar; 10(3):192-9. doi: ". [PMID: 9071726]
  • W Lewis, B Griniuviene, K O Tankersley, E S Levine, R Montione, L Engelman, G de Courten-Myers, M A Ascenzi, W E Hornbuckle, J L Gerin, B C Tennant. Depletion of mitochondrial DNA, destruction of mitochondria, and accumulation of lipid droplets result from fialuridine treatment in woodchucks (Marmota monax). Laboratory investigation; a journal of technical methods and pathology. 1997 Jan; 76(1):77-87. doi: NULL. [PMID: 9010451]
  • W Lewis, E S Levine, B Griniuviene, K O Tankersley, J M Colacino, J P Sommadossi, K A Watanabe, F W Perrino. Fialuridine and its metabolites inhibit DNA polymerase gamma at sites of multiple adjacent analog incorporation, decrease mtDNA abundance, and cause mitochondrial structural defects in cultured hepatoblasts. Proceedings of the National Academy of Sciences of the United States of America. 1996 Apr; 93(8):3592-7. doi: 10.1073/pnas.93.8.3592. [PMID: 8622980]
  • L Cui, S Yoon, R F Schinazi, J P Sommadossi. Cellular and molecular events leading to mitochondrial toxicity of 1-(2-deoxy-2-fluoro-1-beta-D-arabinofuranosyl)-5-iodouracil in human liver cells. The Journal of clinical investigation. 1995 Feb; 95(2):555-63. doi: 10.1172/jci117698. [PMID: 7860738]
  • R A De Man, R A Heijtink, H G Niesters, S W Schalm. New developments in antiviral therapy for chronic hepatitis B infection. Scandinavian journal of gastroenterology. Supplement. 1995; 212(?):100-4. doi: 10.3109/00365529509090307. [PMID: 8578221]
  • J P Miller, P D Mintz. Falsely low calcium measurements after high volume plasma exchange in a patient with liver failure. Transfusion science. 1994 Sep; 15(3):299-302. doi: 10.1016/0955-3886(94)90157-0. [PMID: 10161259]
  • R R Bowsher, J A Compton, J A Kirkwood, G D Place, C D Jones, T E Mabry, D L Hyslop, B L Hatcher, K A DeSante. Sensitive and specific radioimmunoassay for fialuridine: initial assessment of pharmacokinetics after single oral doses to healthy volunteers. Antimicrobial agents and chemotherapy. 1994 Sep; 38(9):2134-42. doi: 10.1128/aac.38.9.2134. [PMID: 7811032]
  • J M Pawlotsky, C Andre, J M Metreau, M Beaugrand, E S Zafrani, D Dhumeaux. Multiple nuclear dots antinuclear antibodies are not specific for primary biliary cirrhosis. Hepatology (Baltimore, Md.). 1992 Jul; 16(1):127-31. doi: 10.1002/hep.1840160121. [PMID: 1319948]
  • B E Korba, J L Gerin. Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication. Antiviral research. 1992 Jul; 19(1):55-70. doi: 10.1016/0166-3542(92)90056-b. [PMID: 1444322]
  • D R Tovell, H P Yacyshyn, H K Misra, E E Knaus, L I Wiebe, J Samuel, M J Gill, D L Tyrrell. Effect of acyclovir on the uptake of 131I-labelled 1-(2'fluoro-2'-deoxy-beta-D-arabinofuranosyl)-5-iodouracil in herpes infected cells. Journal of medical virology. 1987 Jun; 22(2):183-8. doi: 10.1002/jmv.1890220210. [PMID: 3039053]
  • K F Soike, C Cantrell, P J Gerone. Activity of 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-iodouracil against simian varicella virus infections in African green monkeys. Antimicrobial agents and chemotherapy. 1986 Jan; 29(1):20-5. doi: 10.1128/aac.29.1.20. [PMID: 3729332]