(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile (BioDeep_00000015508)

   


代谢物信息卡片


(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

化学式: C12H13N5O4 (291.0967)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=C2C(=NC=NN2C(=C1)C3(C(C(C(O3)CO)O)O)C#N)N
InChI: InChI=1S/C12H13N5O4/c13-4-12(10(20)9(19)7(3-18)21-12)8-2-1-6-11(14)15-5-16-17(6)8/h1-2,5,7,9-10,18-20H,3H2,(H2,14,15,16)/t7-,9-,10-,12+/m1/s1

描述信息

COVID info from DrugBank, PDB, Protein Data Bank, clinicaltrial, clinicaltrials, clinical trial, clinical trials
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS

同义名列表

1 个代谢物同义名

(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile



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。

亚细胞结构定位 关联基因列表


文献列表

  • Ling Yang, I-Hsin Lin, Lie-Chwen Lin, Jeffrey W Dalley, Tung-Hu Tsai. Biotransformation and transplacental transfer of the anti-viral remdesivir and predominant metabolite, GS-441524 in pregnant rats. EBioMedicine. 2022 Jul; 81(?):104095. doi: 10.1016/j.ebiom.2022.104095. [PMID: 35671622]
  • Jared Pitts, Darius Babusis, Meghan S Vermillion, Raju Subramanian, Kim Barrett, Diane Lye, Bin Ma, Xiaofeng Zhao, Nicholas Riola, Xuping Xie, Adriana Kajon, Xianghan Lu, Roy Bannister, Pei-Yong Shi, Maria Toteva, Danielle P Porter, Bill J Smith, Tomas Cihlar, Richard Mackman, John P Bilello. Intravenous delivery of GS-441524 is efficacious in the African green monkey model of SARS-CoV-2 infection. Antiviral research. 2022 07; 203(?):105329. doi: 10.1016/j.antiviral.2022.105329. [PMID: 35525335]
  • E Leegwater, D J A R Moes, L B E Bosma, T H Ottens, I M van der Meer, C van Nieuwkoop, E B Wilms. Population Pharmacokinetics of Remdesivir and GS-441524 in Hospitalized COVID-19 Patients. Antimicrobial agents and chemotherapy. 2022 06; 66(6):e0025422. doi: 10.1128/aac.00254-22. [PMID: 35647646]
  • Jared Pitts, Jiani Li, Jason K Perry, Venice Du Pont, Nicholas Riola, Lauren Rodriguez, Xianghan Lu, Chaitanya Kurhade, Xuping Xie, Gregory Camus, Savrina Manhas, Ross Martin, Pei-Yong Shi, Tomas Cihlar, Danielle P Porter, Hongmei Mo, Evguenia Maiorova, John P Bilello. Remdesivir and GS-441524 Retain Antiviral Activity against Delta, Omicron, and Other Emergent SARS-CoV-2 Variants. Antimicrobial agents and chemotherapy. 2022 06; 66(6):e0022222. doi: 10.1128/aac.00222-22. [PMID: 35532238]
  • Marina L Meli, Andrea M Spiri, Katharina Zwicklbauer, Daniela Krentz, Sandra Felten, Michèle Bergmann, Roswitha Dorsch, Kaspar Matiasek, Martin Alberer, Laura Kolberg, Ulrich von Both, Katrin Hartmann, Regina Hofmann-Lehmann. Fecal Feline Coronavirus RNA Shedding and Spike Gene Mutations in Cats with Feline Infectious Peritonitis Treated with GS-441524. Viruses. 2022 05; 14(5):. doi: 10.3390/v14051069. [PMID: 35632813]
  • Henrik Berg Rasmussen, Ragnar Thomsen, Peter Riis Hansen. Nucleoside analog GS-441524: pharmacokinetics in different species, safety, and potential effectiveness against Covid-19. Pharmacology research & perspectives. 2022 04; 10(2):e00945. doi: 10.1002/prp2.945. [PMID: 35396928]
  • Carla Obradors, Benjamin Mitschke, Miles H Aukland, Markus Leutzsch, Oleg Grossmann, Sebastian Brunen, Sebastian A Schwengers, Benjamin List. Direct and Catalytic C-Glycosylation of Arenes: Expeditious Synthesis of the Remdesivir Nucleoside. Angewandte Chemie (International ed. in English). 2022 03; 61(11):e202114619. doi: 10.1002/anie.202114619. [PMID: 34856043]
  • Pyoeng Gyun Choe, Sae Im Jeong, Chang Kyung Kang, Liju Yang, SeungHwan Lee, Joo-Youn Cho, Seung Seok Han, Dong Ki Kim, Sang Min Lee, Wan Beom Park, Myoung-Don Oh, Nam Joong Kim. Exploration for the effect of renal function and renal replacement therapy on pharmacokinetics of remdesivir and GS-441524 in patients with COVID-19: A limited case series. Clinical and translational science. 2022 03; 15(3):732-740. doi: 10.1111/cts.13194. [PMID: 34761554]
  • Yingjun Li, Liu Cao, Ge Li, Feng Cong, Yunfeng Li, Jing Sun, Yinzhu Luo, Guijiang Chen, Guanguan Li, Ping Wang, Fan Xing, Yanxi Ji, Jincun Zhao, Yu Zhang, Deyin Guo, Xumu Zhang. Remdesivir Metabolite GS-441524 Effectively Inhibits SARS-CoV-2 Infection in Mouse Models. Journal of medicinal chemistry. 2022 02; 65(4):2785-2793. doi: 10.1021/acs.jmedchem.0c01929. [PMID: 33523654]
  • Laura Vangeel, Winston Chiu, Steven De Jonghe, Piet Maes, Bram Slechten, Joren Raymenants, Emmanuel André, Pieter Leyssen, Johan Neyts, Dirk Jochmans. Remdesivir, Molnupiravir and Nirmatrelvir remain active against SARS-CoV-2 Omicron and other variants of concern. Antiviral research. 2022 02; 198(?):105252. doi: 10.1016/j.antiviral.2022.105252. [PMID: 35085683]
  • Andrea Defant, Federico Dosi, Nicole Innocenti, Ines Mancini. Synthesis of Nucleoside-like Molecules from a Pyrolysis Product of Cellulose and Their Computational Prediction as Potential SARS-CoV-2 RNA-Dependent RNA Polymerase Inhibitors. International journal of molecular sciences. 2022 Jan; 23(1):. doi: 10.3390/ijms23010518. [PMID: 35008944]
  • Asami Sukeishi, Kotaro Itohara, Atsushi Yonezawa, Yuki Sato, Katsuyuki Matsumura, Yoshiki Katada, Takayuki Nakagawa, Satoshi Hamada, Naoya Tanabe, Eishi Imoto, Shinichi Kai, Toyohiro Hirai, Motoko Yanagita, Shigeru Ohtsuru, Tomohiro Terada, Isao Ito. Population pharmacokinetic modeling of GS-441524, the active metabolite of remdesivir, in Japanese COVID-19 patients with renal dysfunction. CPT: pharmacometrics & systems pharmacology. 2022 01; 11(1):94-103. doi: 10.1002/psp4.12736. [PMID: 34793625]
  • Michael K Lo, Punya Shrivastava-Ranjan, Payel Chatterjee, Mike Flint, James R Beadle, Nadejda Valiaeva, Joyce Murphy, Robert T Schooley, Karl Y Hostetler, Joel M Montgomery, Christina F Spiropoulou. Broad-Spectrum In Vitro Antiviral Activity of ODBG-P-RVn: An Orally-Available, Lipid-Modified Monophosphate Prodrug of Remdesivir Parent Nucleoside (GS-441524). Microbiology spectrum. 2021 12; 9(3):e0153721. doi: 10.1128/spectrum.01537-21. [PMID: 34817209]
  • Robert M Cox, Josef D Wolf, Carolin M Lieber, Julien Sourimant, Michelle J Lin, Darius Babusis, Venice DuPont, Julie Chan, Kim T Barrett, Diane Lye, Rao Kalla, Kwon Chun, Richard L Mackman, Chengjin Ye, Tomas Cihlar, Luis Martinez-Sobrido, Alexander L Greninger, John P Bilello, Richard K Plemper. Oral prodrug of remdesivir parent GS-441524 is efficacious against SARS-CoV-2 in ferrets. Nature communications. 2021 11; 12(1):6415. doi: 10.1038/s41467-021-26760-4. [PMID: 34741049]
  • Gang Wang, Guangli Hu, Rui Liang, Jiale Shi, Xiuxiu Qiu, Yiling Yang, Zhe Jiao, Yixi Chen, Zhou Shen, Mengxia Li, Yuejun Shi, Junfu Mao, Guiqing Peng. Establishment of Full-Length cDNA Clones and an Efficient Oral Infection Model for Feline Coronavirus in Cats. Journal of virology. 2021 10; 95(21):e0074521. doi: 10.1128/jvi.00745-21. [PMID: 34406859]
  • Robert T Schooley, Aaron F Carlin, James R Beadle, Nadejda Valiaeva, Xing-Quan Zhang, Alex E Clark, Rachel E McMillan, Sandra L Leibel, Rachael N McVicar, Jialei Xie, Aaron F Garretson, Victoria I Smith, Joyce Murphy, Karl Y Hostetler. Rethinking Remdesivir: Synthesis, Antiviral Activity, and Pharmacokinetics of Oral Lipid Prodrugs. Antimicrobial agents and chemotherapy. 2021 09; 65(10):e0115521. doi: 10.1128/aac.01155-21. [PMID: 34310217]
  • Daibao Wei, Tianwen Hu, Yumin Zhang, Wei Zheng, Haitao Xue, Jingshan Shen, Yuanchao Xie, Haji A Aisa. Potency and pharmacokinetics of GS-441524 derivatives against SARS-CoV-2. Bioorganic & medicinal chemistry. 2021 09; 46(?):116364. doi: 10.1016/j.bmc.2021.116364. [PMID: 34450570]
  • Ping Du, Guoyong Wang, Song Yang, Pengfei Li, Lihong Liu. Quantitative HPLC-MS/MS determination of Nuc, the active metabolite of remdesivir, and its pharmacokinetics in rat. Analytical and bioanalytical chemistry. 2021 Sep; 413(23):5811-5820. doi: 10.1007/s00216-021-03561-8. [PMID: 34302183]
  • Julius J Schmidt, Stefanie M Bode-Böger, Jens Martens-Lobenhoffer, Marius M Hoeper, Jan T Kielstein. Pharmacokinetics of Remdesivir and GS-441524 during PIRRT and Seraph 100 Therapy. Clinical journal of the American Society of Nephrology : CJASN. 2021 08; 16(8):1256-1257. doi: 10.2215/cjn.17601120. [PMID: 34301737]
  • Henrik Berg Rasmussen, Gesche Jürgens, Ragnar Thomsen, Olivier Taboureau, Kornelius Zeth, Poul Erik Hansen, Peter Riis Hansen. Cellular Uptake and Intracellular Phosphorylation of GS-441524: Implications for Its Effectiveness against COVID-19. Viruses. 2021 07; 13(7):. doi: 10.3390/v13071369. [PMID: 34372575]
  • Saverio Paltrinieri, Alessia Giordano, Angelica Stranieri, Stefania Lauzi. Feline infectious peritonitis (FIP) and coronavirus disease 19 (COVID-19): Are they similar?. Transboundary and emerging diseases. 2021 Jul; 68(4):1786-1799. doi: 10.1111/tbed.13856. [PMID: 32985113]
  • Ellen Van Damme, Sandra De Meyer, Denisa Bojkova, Sandra Ciesek, Jindrich Cinatl, Steven De Jonghe, Dirk Jochmans, Pieter Leyssen, Christophe Buyck, Johan Neyts, Marnix Van Loock. In vitro activity of itraconazole against SARS-CoV-2. Journal of medical virology. 2021 Jul; 93(7):4454-4460. doi: 10.1002/jmv.26917. [PMID: 33666253]
  • Andrew Reckers, Alan H B Wu, Chui Mei Ong, Monica Gandhi, John Metcalfe, Roy Gerona. A combined assay for quantifying remdesivir and its metabolite, along with dexamethasone, in serum. The Journal of antimicrobial chemotherapy. 2021 06; 76(7):1865-1873. doi: 10.1093/jac/dkab094. [PMID: 33864090]
  • Rita Humeniuk, Anita Mathias, Brian J Kirby, Justin D Lutz, Huyen Cao, Anu Osinusi, Darius Babusis, Danielle Porter, Xuelian Wei, John Ling, Y Sunila Reddy, Polina German. Pharmacokinetic, Pharmacodynamic, and Drug-Interaction Profile of Remdesivir, a SARS-CoV-2 Replication Inhibitor. Clinical pharmacokinetics. 2021 05; 60(5):569-583. doi: 10.1007/s40262-021-00984-5. [PMID: 33782830]
  • Paul Biever, Dawid L Staudacher, Michaela J Sommer, Hannah Triebel, Merja A Neukamm, Christoph Bode, Alexander Supady, Achim Lother. Hemoadsorption eliminates remdesivir from the circulation: Implications for the treatment of COVID-19. Pharmacology research & perspectives. 2021 04; 9(2):e00743. doi: 10.1002/prp2.743. [PMID: 33710753]
  • Katharina Habler, Mathias Brügel, Daniel Teupser, Uwe Liebchen, Christina Scharf, Ulf Schönermarck, Michael Vogeser, Michael Paal. Simultaneous quantification of seven repurposed COVID-19 drugs remdesivir (plus metabolite GS-441524), chloroquine, hydroxychloroquine, lopinavir, ritonavir, favipiravir and azithromycin by a two-dimensional isotope dilution LC-MS/MS method in human serum. Journal of pharmaceutical and biomedical analysis. 2021 Mar; 196(?):113935. doi: 10.1016/j.jpba.2021.113935. [PMID: 33548872]
  • Deqing Xiao, Kah Hiing John Ling, Thomas Tarnowski, Rita Humeniuk, Polina German, Anita Mathias, Jasper Chu, Yuan-Shek Chen, Eric van Ingen. Validation of LC-MS/MS methods for determination of remdesivir and its metabolites GS-441524 and GS-704277 in acidified human plasma and their application in COVID-19 related clinical studies. Analytical biochemistry. 2021 03; 617(?):114118. doi: 10.1016/j.ab.2021.114118. [PMID: 33508271]
  • Tomas Friman, Alexey Chernobrovkin, Daniel Martinez Molina, Laurence Arnold. CETSA MS Profiling for a Comparative Assessment of FDA-Approved Antivirals Repurposed for COVID-19 Therapy Identifies TRIP13 as a Remdesivir Off-Target. SLAS discovery : advancing life sciences R & D. 2021 03; 26(3):336-344. doi: 10.1177/2472555220973597. [PMID: 33208020]
  • Matthew R Davis, Christine U Pham, Jeffrey J Cies. Remdesivir and GS-441524 plasma concentrations in patients with end-stage renal disease on haemodialysis. The Journal of antimicrobial chemotherapy. 2021 02; 76(3):822-825. doi: 10.1093/jac/dkaa472. [PMID: 33152758]
  • Toshihiro Sato, Masamitsu Maekawa, Nariyasu Mano, Takaaki Abe, Hiroaki Yamaguchi. Role of OATP4C1 in Renal Handling of Remdesivir and its Nucleoside Analog GS-441524: The First Approved Drug for Patients with COVID-19. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2021; 24(?):227-236. doi: 10.18433/jpps31813. [PMID: 34048668]
  • Subrata Deb, Anthony Allen Reeves. Simulation of Remdesivir Pharmacokinetics and Its Drug Interactions. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2021; 24(?):277-291. doi: 10.18433/jpps32011. [PMID: 34107241]
  • Minh Patrick Lê, Christine Le Beller, Quentin Le Hingrat, Pierre Jaquet, Paul-Henri Wicky, Vincent Bunel, Laurent Massias, Benoit Visseaux, Jonathan Messika, Diane Descamps, Hervé Mal, Jean-François Timsit, Gilles Peytavin. Reply to Yan and Muller, 'Captisol and GS-704277, but Not GS-441524, Are Credible Mediators of Remdesivir's Nephrotoxicity'. Antimicrobial agents and chemotherapy. 2020 11; 64(12):. doi: 10.1128/aac.01937-20. [PMID: 32988815]
  • Victoria C Yan, Florian L Muller. Captisol and GS-704277, but Not GS-441524, Are Credible Mediators of Remdesivir's Nephrotoxicity. Antimicrobial agents and chemotherapy. 2020 11; 64(12):. doi: 10.1128/aac.01920-20. [PMID: 32988821]
  • Minh Patrick Lê, Quentin Le Hingrat, Pierre Jaquet, Paul-Henri Wicky, Vincent Bunel, Laurent Massias, Benoit Visseaux, Jonathan Messika, Diane Descamps, Hervé Mal, Jean-François Timsit, Gilles Peytavin. Removal of Remdesivir's Metabolite GS-441524 by Hemodialysis in a Double Lung Transplant Recipient with COVID-19. Antimicrobial agents and chemotherapy. 2020 10; 64(11):. doi: 10.1128/aac.01521-20. [PMID: 32868327]
  • Jean-Claude Alvarez, Pierre Moine, Isabelle Etting, Djillali Annane, Islam Amine Larabi. Quantification of plasma remdesivir and its metabolite GS-441524 using liquid chromatography coupled to tandem mass spectrometry. Application to a Covid-19 treated patient. Clinical chemistry and laboratory medicine. 2020 08; 58(9):1461-1468. doi: 10.1515/cclm-2020-0612. [PMID: 32573468]