Desacetyl-nitazoxanide (BioDeep_00000027027)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


2-hydroxy-N-(5-nitro-1,3-thiazol-2-yl)benzamide

化学式: C10H7N3O4S (265.0157262)
中文名称: 替唑尼特
谱图信息: 最多检出来源 Homo sapiens(blood) 11.11%

分子结构信息

SMILES: C1=CC=C(C(=C1)C(=O)NC2=NC=C(S2)[N+](=O)[O-])O
InChI: InChI=1S/C10H7N3O4S/c14-7-4-2-1-3-6(7)9(15)12-10-11-5-8(18-10)13(16)17/h1-5,14H,(H,11,12,15)

描述信息

Desacetyl-nitazoxanide is a metabolite of lamivudine. Lamivudine (2,3-dideoxy-3-thiacytidine, commonly called 3TC) is a potent nucleoside analog reverse transcriptase inhibitor (nRTI). It is marketed by GlaxoSmithKline with the brand names Zeffix, Heptovir, Epivir, and Epivir-HBV. Lamivudine has been used for treatment of chronic hepatitis B at a lower dose than for treatment of HIV. It improves the seroconversion of e-antigen positive hepatitis B and also improves histology staging of the liver. (Wikipedia)
D000890 - Anti-Infective Agents

同义名列表

3 个代谢物同义名

2-hydroxy-N-(5-nitro-1,3-thiazol-2-yl)benzamide; Desacetyl-nitazoxanide; Tizoxanide



数据库引用编号

7 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

  • Xi He, Wenjun Hu, Fanhua Meng, Xingzhou Li. Design, Synthesis, and Pharmacokinetic Evaluation of O-Carbamoyl Tizoxanide Prodrugs. Medicinal chemistry (Shariqah (United Arab Emirates)). 2022; 18(1):140-150. doi: 10.2174/1573406416666201120102905. [PMID: 33222677]
  • El Hadji Diawara, Arnaud François, Andrew V Stachulski, Romy Razakandrainibe, Damien Costa, Loïc Favennec, Jean-François Rossignol, Gilles Gargala. Systemic efficacy on Cryptosporidium parvum infection of aminoxanide (RM-5061), a new amino-acid ester thiazolide prodrug of tizoxanide. Parasitology. 2021 07; 148(8):975-984. doi: 10.1017/s0031182021000524. [PMID: 33775260]
  • K A Yamamoto, K Blackburn, E Migowski, M B Goshe, D T Brown, D F Ferreira, M R Soares. Quantitative proteomic analysis of the tizoxanide effect in vero cells. Scientific reports. 2020 09; 10(1):14733. doi: 10.1038/s41598-020-71634-2. [PMID: 32895447]
  • Danielle Tilmanis, Paulina Koszalka, Ian G Barr, Jean-Francois Rossignol, Edin Mifsud, Aeron C Hurt. Host-targeted nitazoxanide has a high barrier to resistance but does not reduce the emergence or proliferation of oseltamivir-resistant influenza viruses in vitro or in vivo when used in combination with oseltamivir. Antiviral research. 2020 08; 180(?):104851. doi: 10.1016/j.antiviral.2020.104851. [PMID: 32544408]
  • Sixun Guo, Fang Li, Bin Wang, Yilei Zhao, Xiaoxiong Wang, Hua Wei, Kaijiang Yu, Xin Hai. Analysis of tizoxanide, active metabolite of nitazoxanide, in rat brain tissue and plasma by UHPLC-MS/MS. Biomedical chromatography : BMC. 2020 Feb; 34(2):e4716. doi: 10.1002/bmc.4716. [PMID: 31633824]
  • Sara Piacentini, Simone La Frazia, Anna Riccio, Jens Z Pedersen, Alessandra Topai, Orazio Nicolotti, Jean-Francois Rossignol, M Gabriella Santoro. Nitazoxanide inhibits paramyxovirus replication by targeting the Fusion protein folding: role of glycoprotein-specific thiol oxidoreductase ERp57. Scientific reports. 2018 Jul; 8(1):10425. doi: 10.1038/s41598-018-28172-9. [PMID: 29992955]
  • Danielle Tilmanis, Carel van Baalen, Ding Yuan Oh, Jean-Francois Rossignol, Aeron C Hurt. The susceptibility of circulating human influenza viruses to tizoxanide, the active metabolite of nitazoxanide. Antiviral research. 2017 Nov; 147(?):142-148. doi: 10.1016/j.antiviral.2017.10.002. [PMID: 28986103]
  • Anuradha Gupta, Sachin L Tulsankar, Rabi S Bhatta, Amit Misra. Pharmacokinetics, Metabolism, and Partial Biodistribution of 'Pincer Therapeutic' Nitazoxanide in Mice following Pulmonary Delivery of Inhalable Particles. Molecular pharmaceutics. 2017 04; 14(4):1204-1211. doi: 10.1021/acs.molpharmaceut.6b01089. [PMID: 28263078]
  • Jinqiu Liu, Fanhua Meng, Zhaofeng Li, Lin Yu, Shuangqing Peng, Jifen Guo, Haiyan Xu. Simultaneous quantification of tizoxanide and tizoxanide glucuronide in mouse plasma by liquid chromatography-tandem mass spectrometry. Biomedical chromatography : BMC. 2016 Nov; 30(11):1744-1749. doi: 10.1002/bmc.3748. [PMID: 27105783]
  • Elizabeth P Harausz, Keith A Chervenak, Caryn E Good, Michael R Jacobs, Robert S Wallis, Manuel Sanchez-Felix, W Henry Boom. Activity of nitazoxanide and tizoxanide against Mycobacterium tuberculosis in vitro and in whole blood culture. Tuberculosis (Edinburgh, Scotland). 2016 05; 98(?):92-6. doi: 10.1016/j.tube.2016.03.002. [PMID: 27156623]
  • Ghada M Hadad, Randa A Abdel Salam, Samy Emara. Validated and optimized high-performance liquid chromatographic determination of tizoxanide, the main active metabolite of nitazoxanide in human urine, plasma and breast milk. Journal of chromatographic science. 2012 Jul; 50(6):509-15. doi: 10.1093/chromsci/bms041. [PMID: 22525879]
  • Gabriel Marcelín-Jiménez, Leticia Contreras-Zavala, Martha Maggi-Castellanos, Alionka P Angeles-Moreno, Alberto García-González. Development of a method by UPLC-MS/MS for the quantification of tizoxanide in human plasma and its pharmacokinetic application. Bioanalysis. 2012 May; 4(8):909-17. doi: 10.4155/bio.12.41. [PMID: 22533565]
  • Wosen Aman, Shaymaa Mousa, Gamal Shiha, Shaker A Mousa. Current status and future directions in the management of chronic hepatitis C. Virology journal. 2012 Mar; 9(?):57. doi: 10.1186/1743-422x-9-57. [PMID: 22385500]
  • Karen K Y Lam, Xingji Zheng, Roberto Forestieri, Aruna D Balgi, Matt Nodwell, Sarah Vollett, Hilary J Anderson, Raymond J Andersen, Yossef Av-Gay, Michel Roberge. Nitazoxanide stimulates autophagy and inhibits mTORC1 signaling and intracellular proliferation of Mycobacterium tuberculosis. PLoS pathogens. 2012; 8(5):e1002691. doi: 10.1371/journal.ppat.1002691. [PMID: 22589723]
  • Z Zhao, F Xue, L Zhang, K Zhang, C Fei, W Zheng, X Wang, M Wang, Z Zhao, X Meng. The pharmacokinetics of nitazoxanide active metabolite (tizoxanide) in goats and its protein binding ability in vitro. Journal of veterinary pharmacology and therapeutics. 2010 Apr; 33(2):147-53. doi: 10.1111/j.1365-2885.2009.01119.x. [PMID: 20444039]
  • Ashik Hayat, Ahmad Mitwalli. Hepatitis C and kidney disease. Hepatitis research and treatment. 2010; 2010(?):534327. doi: 10.1155/2010/534327. [PMID: 21188196]
  • Sara M Erickson, Kerstin Fischer, Gary J Weil, Bruce M Christensen, Peter U Fischer. Distribution of Brugia malayi larvae and DNA in vector and non-vector mosquitoes: implications for molecular diagnostics. Parasites & vectors. 2009 Nov; 2(1):56. doi: 10.1186/1756-3305-2-56. [PMID: 19922607]
  • Jean François Rossignol, Simone La Frazia, Lucia Chiappa, Alessandra Ciucci, M Gabriella Santoro. Thiazolides, a new class of anti-influenza molecules targeting viral hemagglutinin at the post-translational level. The Journal of biological chemistry. 2009 Oct; 284(43):29798-808. doi: 10.1074/jbc.m109.029470. [PMID: 19638339]
  • M I Ruiz-Olmedo, J L Gallegos-Perez, K G Calderon-Gonzalez, J Franco-Perez, H Jung-Cook. Sensitive high performance liquid chromatographic assay for nitazoxanide metabolite in plasma. Die Pharmazie. 2009 Jul; 64(7):419-22. doi: NULL. [PMID: 19694176]
  • M Schnyder, L Kohler, A Hemphill, P Deplazes. Prophylactic and therapeutic efficacy of nitazoxanide against Cryptosporidium parvum in experimentally challenged neonatal calves. Veterinary parasitology. 2009 Mar; 160(1-2):149-54. doi: 10.1016/j.vetpar.2008.10.094. [PMID: 19062195]
  • Zhanzhong Zhao, Lifang Zhang, Feiqun Xue, Xiaoyang Wang, Wenli Zheng, Tao Zhang, Chenzhong Fei, Keyu Zhang, Minqi Qiu, Ruixiang Xin, Fengkun Yang. Liquid chromatography-tandem mass spectrometry analysis of nitazoxanide and its major metabolites in goat. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Nov; 875(2):427-36. doi: 10.1016/j.jchromb.2008.09.017. [PMID: 18849204]
  • Brent E Korba, Abigail B Montero, Kristine Farrar, Karen Gaye, Sampa Mukerjee, Marc S Ayers, Jean-François Rossignol. Nitazoxanide, tizoxanide and other thiazolides are potent inhibitors of hepatitis B virus and hepatitis C virus replication. Antiviral research. 2008 Jan; 77(1):56-63. doi: 10.1016/j.antiviral.2007.08.005. [PMID: 17888524]
  • Francisca Palomares-Alonso, Juan Carlos Piliado, Guadalupe Palencia, Alma Ortiz-Plata, Helgi Jung-Cook. Efficacy of nitazoxanide, tizoxanide and tizoxanide/albendazole sulphoxide combination against Taenia crassiceps cysts. The Journal of antimicrobial chemotherapy. 2007 Feb; 59(2):212-8. doi: 10.1093/jac/dkl463. [PMID: 17114175]
  • Sangita Agarwal, W D Sam Solomon, K Veeran Gowda, P Senthamil Selvan, Debotri Ghosh, Amlan Kanti Sarkar, Tapas Kumar Chattaraj, Tapan Kumar Pal. Bioequivalence study of a fixed dose combination of nitazoxanide and ofloxacin in Indian healthy volunteers. Arzneimittel-Forschung. 2007; 57(10):679-83. doi: 10.1055/s-0031-1296667. [PMID: 18074762]
  • A Stockis, A M Allemon, S De Bruyn, C Gengler. Nitazoxanide pharmacokinetics and tolerability in man using single ascending oral doses. International journal of clinical pharmacology and therapeutics. 2002 May; 40(5):213-20. doi: 10.5414/cpp40213. [PMID: 12051573]
  • A Stockis, S De Bruyn, C Gengler, D Rosillon. Nitazoxanide pharmacokinetics and tolerability in man during 7 days dosing with 0.5 g and 1 g b.i.d. International journal of clinical pharmacology and therapeutics. 2002 May; 40(5):221-7. doi: 10.5414/cpp40221. [PMID: 12051574]
  • E S Didier, J A Maddry, C D Kwong, L C Green, K F Snowden, J A Shadduck. Screening of compounds for antimicrosporidial activity in vitro. Folia parasitologica. 1998; 45(2):129-39. doi: . [PMID: 9684323]