Oseltamivir (BioDeep_00000002213)

 

Secondary id: BioDeep_00000398255

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid

化学式: C16H28N2O4 (312.20489680000003)
中文名称: 奥司他韦
谱图信息: 最多检出来源 Homo sapiens(blood) 2.53%

分子结构信息

SMILES: CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC
InChI: InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1

描述信息

Oseltamivir is only found in individuals that have used or taken this drug. It is an acetamido cyclohexene that is a structural homolog of sialic acid and inhibits neuraminidase. [PubChem]Oseltamivir is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. The proposed mechanism of action of oseltamivir is inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release.
J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AH - Neuraminidase inhibitors
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
C254 - Anti-Infective Agent > C281 - Antiviral Agent
CONFIDENCE standard compound; EAWAG_UCHEM_ID 658
CONFIDENCE standard compound; INTERNAL_ID 2068
D004791 - Enzyme Inhibitors
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS

同义名列表

12 个代谢物同义名

Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid; ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate; Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate; GS 4104;GOP-A-Flu;GS-4104;Tamiflu-Free;Tamvir; Oseltamivir phosphate; (-)-Oseltamivir; Oseltamivirum; Oseltamivir; HSDB 7433; GS-4104; Tamiflu; Agucort



数据库引用编号

37 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)

2 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

  • Adriána Čelková, Alexander Búcsi, Mária Klacsová, Tomáš Fazekaš, Juan Carlos Martínez, Daniela Uhríková. Oseltamivir phosphate interaction with model membranes. Biochimica et biophysica acta. Biomembranes. 2024 Mar; 1866(3):184273. doi: 10.1016/j.bbamem.2024.184273. [PMID: 38211646]
  • Irina Gaisina, Ping Li, Ruikun Du, Qinghua Cui, Meiyue Dong, Chengcheng Zhang, Balaji Manicassamy, Michael Caffrey, Terry Moore, Laura Cooper, Lijun Rong. An orally active entry inhibitor of influenza A viruses protects mice and synergizes with oseltamivir and baloxavir marboxil. Science advances. 2024 Feb; 10(8):eadk9004. doi: 10.1126/sciadv.adk9004. [PMID: 38394202]
  • Yuheng Huang, Xiaoxin Guo, Zhen Wang, Cong Yin, Mu Chen, Jiaming Xie, Ning Li, Zhengchao Tu, Juan Li, Jiaqing Cao, Zhengjin Jiang, Weihuan Huang, Haiyan Tian. High-resolution neuraminidase inhibition profiling of Arnebia euchroma (Royle) I.M. Johnst. based on HR-MS and target isolation: An example study of anti-infectious constituents in traditional Chinese medicine. Journal of ethnopharmacology. 2024 Jan; 319(Pt 1):117074. doi: 10.1016/j.jep.2023.117074. [PMID: 37619859]
  • Chuanfeng Liu, Ying Zhang, Ping Li, Huinan Jia, Han Ju, Jiwei Zhang, Edeildo Ferreira da Silva-Júnior, Sunanda Samanta, Parimal Kar, Bing Huang, Xinyong Liu, Peng Zhan. Development of chalcone-like derivatives and their biological and mechanistic investigations as novel influenza nuclear export inhibitors. European journal of medicinal chemistry. 2023 Sep; 261(?):115845. doi: 10.1016/j.ejmech.2023.115845. [PMID: 37804770]
  • Philip W Melchert, Qingchen Zhang, Sushobhan Mukhopadhyay, Siva Rama Raju Kanumuri, Christopher R McCurdy, John S Markowitz. An in vitro evaluation of kratom (Mitragyna speciosa) on the catalytic activity of carboxylesterase 1 (CES1). Chemico-biological interactions. 2023 Sep; ?(?):110715. doi: 10.1016/j.cbi.2023.110715. [PMID: 37716419]
  • Xinfeng Bai, Suya Xi, Guiyan Chen, Xiaoying Fan, Kaiwei Wang, Yong Li, Yang Zhao, Weizhan Wang, Yingping Tian. Multicenter, randomized controlled, open label evaluation of the efficacy and safety of arbidol hydrochloride tablets in the treatment of influenza-like cases. BMC infectious diseases. 2023 Sep; 23(1):585. doi: 10.1186/s12879-023-08570-9. [PMID: 37674112]
  • Qiang Ding, Chao Ye. Microbial engineering for shikimate biosynthesis. Enzyme and microbial technology. 2023 Aug; 170(?):110306. doi: 10.1016/j.enzmictec.2023.110306. [PMID: 37598506]
  • Li-Man Ding, Dao-Wen Yang, Hong-Chun Zhang, Xiao Ma, Zhen-Gang Yan, Sheng-Tang Zhang, Wu-Zhi Ma, Wei-Ge Li, Dong-Xing Wu, Qing-Rong Jiang. [Cost-effectiveness analysis of Chaiyin Granules in treatment of influenza]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Aug; 48(16):4529-4535. doi: 10.19540/j.cnki.cjcmm.20230323.501. [PMID: 37802879]
  • Xuran Cui, Xibao Liu, Feng Wang, Kun Lou, Junping Hong, Hequn Bai, Rongchu Chen, Yang Yang, Qingquan Liu. Determination of the synergistic anti-influenza effect of Huangqin Su tablet and Oseltamivir and investigation of mechanism of the tablet based on gut microbiota and network pharmacology. BMC complementary medicine and therapies. 2023 Feb; 23(1):36. doi: 10.1186/s12906-023-03858-4. [PMID: 36739385]
  • Zhixu Chen, Jincai Wang, Jiaming Yuan, Zhen Wang, Zhengchao Tu, Jacques Crommen, Wenhui Luo, Jialiang Guo, Tingting Zhang, Zhengjin Jiang. Rapid screening of neuraminidase inhibitors using an at-line nanofractionation platform involving parallel oseltamivir-sensitive/resistant neuraminidase bioassays. Journal of chromatography. A. 2023 Jan; 1687(?):463693. doi: 10.1016/j.chroma.2022.463693. [PMID: 36516530]
  • Na Jiang, Liqiu Quan, Yan Zhou, Yungyi Cheng, Hongmei Li, Xuanqin Chen, Rongtao Li, Dan Liu. Exploring the anti-influenza virus activity of novel triptolide derivatives targeting nucleoproteins. Bioorganic chemistry. 2022 12; 129(?):106118. doi: 10.1016/j.bioorg.2022.106118. [PMID: 36067538]
  • Yanyan Bao, Yujing Shi, Lirun Zhou, Shuangrong Gao, Rongmei Yao, Shanshan Guo, Zihan Geng, Lei Bao, Ronghua Zhao, Xiaolan Cui. MicroRNA-205-5p: A potential therapeutic target for influenza A. Journal of cellular and molecular medicine. 2022 12; 26(23):5917-5928. doi: 10.1111/jcmm.17615. [PMID: 36403222]
  • Mengjie Xiao, Fei Cao, Tao Huang, Yun-Sang Tang, Xin Zhao, Pang-Chui Shaw. Urolithin M5 from the Leaves of Canarium album (Lour.) DC. Inhibits Influenza Virus by Targeting Neuraminidase. Molecules (Basel, Switzerland). 2022 Sep; 27(17):. doi: 10.3390/molecules27175724. [PMID: 36080488]
  • Xiao-Lan Ye, Chen-Chen Tang, Hui Liu, You Hu, Tian-Nan Xiang, Yue-Juan Zheng. [Reduning Injection protects flu-infected mice by inhibiting infiltration of inflammatory cells in lung and down-regulating cytokine storm]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Sep; 47(17):4698-4706. doi: 10.19540/j.cnki.cjcmm.20220427.402. [PMID: 36164877]
  • Wei-Feng Li, Chan-Chan Hu, Ya-Li Ding, Bin Yuan. [Overview of Meta-analysis of Lianhua Qingwen preparations in treatment of viral diseases]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Aug; 47(16):4505-4516. doi: 10.19540/j.cnki.cjcmm.20220510.501. [PMID: 36046880]
  • Yu-Meng Yan, Xiao-Jing Yang, Chun-Xia Zhao, Ze-Yu Li, Guo-Zhen Zhao, Yu-Hong Guo, Bo Li, Qing-Quan Liu. [Systematic review and Meta-analysis of Lianhua Qingwen preparations combined with Oseltamivir in treatment of influenza]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Aug; 47(15):4238-4247. doi: 10.19540/j.cnki.cjcmm.20220512.501. [PMID: 36046914]
  • Vladimir V Zarubaev, Angelica V Garshinina, Alexandrina S Volobueva, Alexander V Slita, Olga I Yarovaya, Vladimir V Bykov, Klim A Leonov, Valery S Motov, Veniamin A Khazanov, Nariman F Salakhutdinov. Optimization of application schedule of camphecene, a novel anti-influenza compound, based on its pharmacokinetic characteristics. Fundamental & clinical pharmacology. 2022 Jun; 36(3):518-525. doi: 10.1111/fcp.12750. [PMID: 34984730]
  • David Calderón Guzmán, Norma Osnaya Brizuela, Maribel Ortiz Herrera, Hugo Juárez Olguín, Quetzalli Veloz Corona, Lulu Sanchez Reyes, Armando Valenzuela Peraza, Gerardo Barragán Mejía. Oseltamivir induces favorable response on oxidative damage in the brain of rats treated with Bezafibrate. The International journal of neuroscience. 2022 Jun; 132(6):574-581. doi: 10.1080/00207454.2020.1828882. [PMID: 32976735]
  • Jie Wang-Jairaj, Irene Miller, Aditya Joshi, Tharaka Jayabalan, Amanda Peppercorn, Peter Zammit-Tabona, Amanda Oliver. Zanamivir aqueous solution in severe influenza: A global Compassionate Use Program, 2009-2019. Influenza and other respiratory viruses. 2022 05; 16(3):542-551. doi: 10.1111/irv.12947. [PMID: 34939702]
  • Agustín Pijierro Amador, Alba Suárez Cordero, Pedro Sánchez Risco. Acute intermittent porphyria: is oseltamivir safe in these patients?. Clinical medicine (London, England). 2022 05; 22(3):280-281. doi: 10.7861/clinmed.2022-0100. [PMID: 35584827]
  • Gareth Iacobucci. Covid-19: Stockpiling antivirals risks repeating Tamiflu mistakes, experts warn. BMJ (Clinical research ed.). 2022 04; 377(?):o1053. doi: 10.1136/bmj.o1053. [PMID: 35477692]
  • Philip W Melchert, Yuli Qian, Qingchen Zhang, Brandon O Klee, Chengguo Xing, John S Markowitz. In vitro inhibition of carboxylesterase 1 by Kava (Piper methysticum) Kavalactones. Chemico-biological interactions. 2022 Apr; 357(?):109883. doi: 10.1016/j.cbi.2022.109883. [PMID: 35278473]
  • Qasim M Zeeshan, Shuang Qiu, Jia Gu, Abdul-Wahab Abbew, Zhengshuai Wu, Zhipeng Chen, Sai Xu, Shijian Ge. Unravelling multiple removal pathways of oseltamivir in wastewater by microalgae through experimentation and computation. Journal of hazardous materials. 2022 04; 427(?):128139. doi: 10.1016/j.jhazmat.2021.128139. [PMID: 34983009]
  • Uli Schmitz, Swami Swaminathan. Discovery and development of oseltamivir at Gilead Sciences. Antiviral therapy. 2022 04; 27(2):13596535211067598. doi: 10.1177/13596535211067598. [PMID: 35499178]
  • Basiru Aliyu, Yakubu Egigogo Raji, Hui-Yee Chee, Mui-Yun Wong, Zamberi Bin Sekawi. Systematic review and meta-analysis of the efficacy and safety of oseltamivir (Tamiflu) in the treatment of Coronavirus Disease 2019 (COVID-19). PloS one. 2022; 17(12):e0277206. doi: 10.1371/journal.pone.0277206. [PMID: 36454880]
  • Ryuichi Kambayashi, Ai Goto, Mayu Onozato, Hiroko Izumi-Nakaseko, Yoshinori Takei, Akio Matsumoto, Shinichi Kawai, Takeshi Fukushima, Atsushi Sugiyama. Simultaneous analyses of hemodynamic and electrophysiological effects of oseltamivir along with its pharmacokinetic profile using the canine paroxysmal atrial fibrillation model. Journal of pharmacological sciences. 2022 Jan; 148(1):179-186. doi: 10.1016/j.jphs.2021.11.002. [PMID: 34924124]
  • Brian I Grajeda, Atasi De Chatterjee, Carmen M Villalobos, Breanna C Pence, Cameron C Ellis, Vanessa Enriquez, Sourav Roy, Sukla Roychowdhury, Aaron K Neumann, Igor C Almeida, Steven E Patterson, Siddhartha Das. Giardial lipid rafts share virulence factors with secreted vesicles and participate in parasitic infection in mice. Frontiers in cellular and infection microbiology. 2022; 12(?):974200. doi: 10.3389/fcimb.2022.974200. [PMID: 36081774]
  • Xiaona Li, Bin Liu, Naifan Duan, Yibai Xiong, Yan Zhang, Chi Zhang, Cheng Lu, Li Li. Clinical Efficacy and Safety of Chinese Patent Medicine Combined with Oseltamivir for the Treatment of Adult Influenza: A Systematic Review and Meta-Analysis. The American journal of Chinese medicine. 2022; 50(4):1043-1061. doi: 10.1142/s0192415x22500422. [PMID: 35475973]
  • Rahajeng N Tunjungputri, Silvita Fitri Riswari, Setyo G Pramudo, Lydia Kuntjoro, Bachti Alisjahbana, Harry Galuh Nugraha, Andre van der Ven, Muhammad Hussein Gasem, Quirijn de Mast. Effect of oseltamivir phosphate versus placebo on platelet recovery and plasma leakage in adults with dengue and thrombocytopenia; a phase 2, multicenter, double-blind, randomized trial. PLoS neglected tropical diseases. 2022 Jan; 16(1):e0010051. doi: 10.1371/journal.pntd.0010051. [PMID: 34995275]
  • Gülsel Yurtdaş-Kırımlıoğlu, Kadri Güleç, Şennur Görgülü, Hülya Tuba Kıyan. Oseltamivir phosphate loaded pegylated-Eudragit nanoparticles for lung cancer therapy: Characterization, prolonged release, cytotoxicity profile, apoptosis pathways and in vivo anti-angiogenic effect by using CAM assay. Microvascular research. 2022 01; 139(?):104251. doi: 10.1016/j.mvr.2021.104251. [PMID: 34520775]
  • Xiao-Yan Liu, Gui-Yun Cao, Yi Luo, Zhao-Qing Meng, You-Bo Zhang. Anti-pandemic influenza A (H1N1) virus potential of Xilingjiedu capsule in vitro. Pakistan journal of pharmaceutical sciences. 2022 Jan; 35(1):123-128. doi: ". [PMID: 35221280]
  • Han Ju, N Arul Murugan, Lingxin Hou, Ping Li, Laura Guizzo, Ying Zhang, Chiara Bertagnin, Xiujie Kong, Dongwei Kang, Ruifang Jia, Xiuli Ma, Ruikun Du, Vasanthanathan Poongavanam, Arianna Loregian, Bing Huang, Xinyong Liu, Peng Zhan. Identification of C5-NH2 Modified Oseltamivir Derivatives as Novel Influenza Neuraminidase Inhibitors with Highly Improved Antiviral Activities and Favorable Druggability. Journal of medicinal chemistry. 2021 12; 64(24):17992-18009. doi: 10.1021/acs.jmedchem.1c01366. [PMID: 34735766]
  • Kübra Demir Önder, Ayşegül Seremet Keskin, Hande Berk, Derya Seyman, Nefise Öztoprak. Retrospective evaluation of seven different treatment protocols in hospitalized COVID-19 patients. Turkish journal of medical sciences. 2021 12; 51(6):2835-2849. doi: 10.3906/sag-2106-114. [PMID: 34418000]
  • C Joaquín Cáceres, Yanmei Hu, Stivalis Cárdenas-García, Xiangmeng Wu, Haozhou Tan, Silvia Carnaccini, L Claire Gay, Ginger Geiger, Chunlong Ma, Qing-Yu Zhang, Daniela Rajao, Daniel R Perez, Jun Wang. Rational design of a deuterium-containing M2-S31N channel blocker UAWJ280 with in vivo antiviral efficacy against both oseltamivir sensitive and -resistant influenza A viruses. Emerging microbes & infections. 2021 Dec; 10(1):1832-1848. doi: 10.1080/22221751.2021.1972769. [PMID: 34427541]
  • Nour K Younis, Rana O Zareef, Ghina Fakhri, Fadi Bitar, Ali H Eid, Mariam Arabi. COVID-19: potential therapeutics for pediatric patients. Pharmacological reports : PR. 2021 Dec; 73(6):1520-1538. doi: 10.1007/s43440-021-00316-1. [PMID: 34458951]
  • Mario Karolyi, Erich Pawelka, Hasan Kelani, Georg Christian Funk, Boris Lindner, Christoph Porpaczy, Sabine Publig, Sara Omid, Tamara Seitz, Marianna Traugott, Michael Turner, Alexander Zoufaly, Christoph Wenisch. Management of hospitalized influenza A patients during the season 2018/19 : Comparison of three medical departments and the effect on outcome and antibiotic usage. Wiener klinische Wochenschrift. 2021 Dec; 133(23-24):1310-1317. doi: 10.1007/s00508-021-01950-8. [PMID: 34613478]
  • Burcu Ucar, Tayfun Acar, Pelin Pelit Arayici, Serap Derman. A nanotechnological approach in the current therapy of COVID-19: model drug oseltamivir-phosphate loaded PLGA nanoparticles targeted with spike protein binder peptide of SARS-CoV-2. Nanotechnology. 2021 Sep; 32(48):. doi: 10.1088/1361-6528/ac1c22. [PMID: 34375967]
  • Jing Tang, Rongbao Gao, Liqi Liu, Shuxia Zhang, Jia Liu, Xiyan Li, Qiongqiong Fang, Zhaomin Feng, Cuiling Xu, Weijuan Huang, Dayan Wang. Substitution of I222L-E119V in neuraminidase from highly pathogenic avian influenza H7N9 virus exhibited synergistic resistance effect to oseltamivir in mice. Scientific reports. 2021 08; 11(1):16293. doi: 10.1038/s41598-021-95771-4. [PMID: 34381119]
  • Mengwei Li, Yuxu Wang, Jing Jin, Jie Dou, Qinglong Guo, Xue Ke, Changlin Zhou, Min Guo. Inhibitory Activity of Honeysuckle Extracts against Influenza A Virus In Vitro and In Vivo. Virologica Sinica. 2021 Jun; 36(3):490-500. doi: 10.1007/s12250-020-00302-6. [PMID: 33044658]
  • Angelita Pusparani, Joshua Henrina, Alius Cahyadi. Co-infection of COVID-19 and recurrent malaria. Journal of infection in developing countries. 2021 05; 15(5):625-629. doi: 10.3855/jidc.13793. [PMID: 34106884]
  • Olivier Bocquet, Amandine Wahart, Thomas Sarazin, Elise Vincent, Christophe Schneider, Anne Fougerat, Stéphanie Gayral, Aubéri Henry, Sébastien Blaise, Béatrice Romier-Crouzet, Camille Boulagnon, Stéphane Jaisson, Philippe Gillery, Amar Bennasroune, Hervé Sartelet, Muriel Laffargue, Laurent Martiny, Laurent Duca, Pascal Maurice. Adverse Effects of Oseltamivir Phosphate Therapy on the Liver of LDLR-/- Mice Without Any Benefit on Atherosclerosis and Thrombosis. Journal of cardiovascular pharmacology. 2021 05; 77(5):660-672. doi: 10.1097/fjc.0000000000001002. [PMID: 33760798]
  • Eda Ferahkaya. Oseltamivir-Induced Mania in a Patient With Influenza A. Clinical neuropharmacology. 2021 May; 44(3):106-107. doi: 10.1097/wnf.0000000000000446. [PMID: 33811194]
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