Zanamivir (BioDeep_00001868183)
Main id: BioDeep_00000006660
代谢物信息卡片
Zanamivir
化学式: C12H20N4O7 (332.1332)
中文名称: 扎那米韦
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=O)NC1C(C=C(OC1C(C(CO)O)O)C(=O)O)N=C(N)N
InChI: InChI=1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,8+,9+,10+/m0/s1
描述信息
J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AH - Neuraminidase inhibitors
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
C254 - Anti-Infective Agent > C281 - Antiviral Agent
D004791 - Enzyme Inhibitors
同义名列表
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:50663
- KEGG: C08095
- KEGG: C72554
- KEGGdrug: D00902
- PubChem: 60855
- DrugBank: DB00558
- ChEMBL: CHEMBL222813
- MeSH: Zanamivir
- CAS: 139110-80-8
- CAS: 551942-41-7
- PubChem: 10295
- PDB-CCD: ZMR
- NIKKAJI: J621.505J
- NIKKAJI: J680.760G
- RefMet: Zanamivir
- KNApSAcK: 50663
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
- 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] - 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] - Xun Lv, Pengfei Wang, Chenning Li, Shuihong Cheng, Yuhai Bi, Xuebing Li. Zanamivir-Cholesterol Conjugate: A Long-Acting Neuraminidase Inhibitor with Potent Efficacy against Drug-Resistant Influenza Viruses.
Journal of medicinal chemistry.
2021 12; 64(23):17403-17412. doi:
10.1021/acs.jmedchem.1c01531. [PMID: 34797984] - Xin Liu, Weichuan Luo, Boning Zhang, Yong Gu Lee, Imrul Shahriar, Madduri Srinivasarao, Philip S Low. Design of Neuraminidase-Targeted Imaging and Therapeutic Agents for the Diagnosis and Treatment of Influenza Virus Infections.
Bioconjugate chemistry.
2021 08; 32(8):1548-1553. doi:
10.1021/acs.bioconjchem.1c00255. [PMID: 34161726] - Bettina Sehnert, Juliane Mietz, Rita Rzepka, Stefanie Buchholz, Andrea Maul-Pavicic, Sandra Schaffer, Falk Nimmerjahn, Reinhard E Voll. Neuraminidase Inhibitor Zanamivir Ameliorates Collagen-Induced Arthritis.
International journal of molecular sciences.
2021 Jan; 22(3):. doi:
10.3390/ijms22031428. [PMID: 33572654] - Liqian Zhou, Juanjuan Wang, Guangyi Liu, Qingqing Lu, Ruyi Dong, Geng Tian, Jialiang Yang, Lihong Peng. Probing antiviral drugs against SARS-CoV-2 through virus-drug association prediction based on the KATZ method.
Genomics.
2020 11; 112(6):4427-4434. doi:
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Viruses.
2020 10; 12(10):. doi:
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Angewandte Chemie (International ed. in English).
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Virology journal.
2019 11; 16(1):149. doi:
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Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy.
2019 Aug; 25(8):584-588. doi:
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2019 08; 168(?):68-75. doi:
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2019 07; 16(1):87. doi:
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Journal of virology.
2019 03; 93(6):. doi:
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Nano letters.
2019 03; 19(3):1875-1882. doi:
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Journal of medicinal chemistry.
2018 11; 61(22):9976-9999. doi:
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Bioorganic & medicinal chemistry.
2018 05; 26(9):2262-2270. doi:
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Journal of clinical virology : the official publication of the Pan American Society for Clinical Virology.
2018 05; 102(?):1-6. doi:
10.1016/j.jcv.2018.02.005. [PMID: 29448067] - Almiro Tivane, Rodney Daniels, Neuza Nguenha, Loira Machalele, Afonso Nacoto, Mirela Pale, Edirsse Mateonane, Sandra Mavale, Josina Chilundo, Délcio Muteto, Judite Salência, Félix Albati, Eduardo Gudo, Tufária Mussá, John McCauley. Antigenic and genetic characterization of influenza viruses isolated in Mozambique during the 2015 season.
PloS one.
2018; 13(7):e0201248. doi:
10.1371/journal.pone.0201248. [PMID: 30048502] - Won-Suk Choi, Ju Hwan Jeong, Jin Jung Kwon, Su Jeong Ahn, Khristine Kaith S Lloren, Hyeok-Il Kwon, Hee Bok Chae, Jungwon Hwang, Myung Hee Kim, Chul-Joong Kim, Richard J Webby, Elena A Govorkova, Young Ki Choi, Yun Hee Baek, Min-Suk Song. Screening for Neuraminidase Inhibitor Resistance Markers among Avian Influenza Viruses of the N4, N5, N6, and N8 Neuraminidase Subtypes.
Journal of virology.
2018 01; 92(1):. doi:
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Antimicrobial agents and chemotherapy.
2018 01; 62(1):. doi:
10.1128/aac.01722-17. [PMID: 29061751] - Mitsuru Tsuji, Nongluk Sriwilaijaroen, Hideo Inoue, Kazuhiko Miki, Kaoru Kinoshita, Kiyotaka Koyama, Kimio Furuhata, Yasuo Suzuki, Kunio Takahashi. Synthesis and anti-influenza virus evaluation of triterpene-sialic acid conjugates.
Bioorganic & medicinal chemistry.
2018 01; 26(1):17-24. doi:
10.1016/j.bmc.2017.09.038. [PMID: 29198893] - Junhyung Cho, Hwajung Yi, Eun Young Jang, Mi-Seon Lee, Joo-Yeon Lee, Chun Kang, Chan Hee Lee, Kisoon Kim. Mycophenolic mofetil, an alternative antiviral and immunomodulator for the highly pathogenic avian influenza H5N1 virus infection.
Biochemical and biophysical research communications.
2017 12; 494(1-2):298-304. doi:
10.1016/j.bbrc.2017.10.037. [PMID: 29017920] - Stefanie Quosdorf, Anja Schuetz, Herbert Kolodziej. Different Inhibitory Potencies of Oseltamivir Carboxylate, Zanamivir, and Several Tannins on Bacterial and Viral Neuraminidases as Assessed in a Cell-Free Fluorescence-Based Enzyme Inhibition Assay.
Molecules (Basel, Switzerland).
2017 Nov; 22(11):. doi:
10.3390/molecules22111989. [PMID: 29149072] - Abraham Ochoa, Enrique Álvarez-Bohórquez, Eduardo Castillero, Luis F Olguin. Detection of Enzyme Inhibitors in Crude Natural Extracts Using Droplet-Based Microfluidics Coupled to HPLC.
Analytical chemistry.
2017 05; 89(9):4889-4896. doi:
10.1021/acs.analchem.6b04988. [PMID: 28374582] - Takashi Azuma, Mao Ishida, Kanae Hisamatsu, Ayami Yunoki, Kana Otomo, Mari Kunitou, Mai Shimizu, Kaori Hosomaru, Shiori Mikata, Yoshiki Mino. Fate of new three anti-influenza drugs and one prodrug in the water environment.
Chemosphere.
2017 Feb; 169(?):550-557. doi:
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Euro surveillance : bulletin Europeen sur les maladies transmissibles = European communicable disease bulletin.
2017 Jan; 22(3):. doi:
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Journal of virological methods.
2016 11; 237(?):192-199. doi:
10.1016/j.jviromet.2016.09.014. [PMID: 27659246] - Lifeng Fu, Yuhai Bi, Yan Wu, Shanshan Zhang, Jianxun Qi, Yan Li, Xuancheng Lu, Zhenning Zhang, Xun Lv, Jinghua Yan, George F Gao, Xuebing Li. Structure-Based Tetravalent Zanamivir with Potent Inhibitory Activity against Drug-Resistant Influenza Viruses.
Journal of medicinal chemistry.
2016 07; 59(13):6303-12. doi:
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Journal of medicinal chemistry.
2016 05; 59(10):4563-77. doi:
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Scientific reports.
2016 Apr; 6(?):24138. doi:
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Saudi medical journal.
2016 Apr; 37(4):461-5. doi:
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Drug discoveries & therapeutics.
2016 ; 10(4):201-10. doi:
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Pediatrics international : official journal of the Japan Pediatric Society.
2015 Dec; 57(6):1172-4. doi:
10.1111/ped.12712. [PMID: 26482326] - Dennis Schade, Jürke Kotthaus, Lukas Riebling, Joscha Kotthaus, Helge Müller-Fielitz, Walter Raasch, Anja Hoffmann, Michaela Schmidtke, Bernd Clement. Zanamivir Amidoxime- and N-Hydroxyguanidine-Based Prodrug Approaches to Tackle Poor Oral Bioavailability.
Journal of pharmaceutical sciences.
2015 Sep; 104(9):3208-19. doi:
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Bioorganic & medicinal chemistry letters.
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Antiviral research.
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2015 Apr; 89(8):4575-87. doi:
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Antiviral research.
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International journal of pharmaceutics.
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PloS one.
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Euro surveillance : bulletin Europeen sur les maladies transmissibles = European communicable disease bulletin.
2015; 20(45):. doi:
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Bioorganic & medicinal chemistry.
2014 Apr; 22(7):2236-43. doi:
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2014 Feb; 57(3):759-69. doi:
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Antimicrobial agents and chemotherapy.
2014; 58(4):2045-51. doi:
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PloS one.
2014; 9(9):e107966. doi:
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PloS one.
2014; 9(2):e89306. doi:
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Antiviral research.
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Antimicrobial agents and chemotherapy.
2013 Dec; 57(12):6141-6. doi:
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Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy.
2013 Oct; 19(5):891-5. doi:
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Enfermedades infecciosas y microbiologia clinica.
2013 Oct; 31(8):526.e1-526.e20. doi:
10.1016/j.eimc.2013.01.013. [PMID: 23528341] - Jennifer L McKimm-Breschkin, Janelle Williams, Susan Barrett, Kim Jachno, Mandy McDonald, Peter G Mohr, Takehiko Saito, Masato Tashiro. Reduced susceptibility to all neuraminidase inhibitors of influenza H1N1 viruses with haemagglutinin mutations and mutations in non-conserved residues of the neuraminidase.
The Journal of antimicrobial chemotherapy.
2013 Oct; 68(10):2210-21. doi:
10.1093/jac/dkt205. [PMID: 23759505] - J N Makau, K Watanabe, N Kobayashi. Anti-influenza activity of Alchemilla mollis extract: possible virucidal activity against influenza virus particles.
Drug discoveries & therapeutics.
2013 Oct; 7(5):189-95. doi:
10.5582/ddt.2013.v7.5.189. [PMID: 24270383] - H-L Yen, J L McKimm-Breschkin, K-T Choy, D D Y Wong, P P H Cheung, J Zhou, I H Ng, H Zhu, R J Webby, Y Guan, R G Webster, J S M Peiris. Resistance to neuraminidase inhibitors conferred by an R292K mutation in a human influenza virus H7N9 isolate can be masked by a mixed R/K viral population.
mBio.
2013 Jul; 4(4):. doi:
10.1128/mbio.00396-13. [PMID: 23860768] - Stephen Weller, Lori S Jones, Yu Lou, Amanda Peppercorn, Judith Ng-Cashin. Pharmacokinetics of zanamivir following intravenous administration to subjects with and without renal impairment.
Antimicrobial agents and chemotherapy.
2013 Jul; 57(7):2967-71. doi:
10.1128/aac.02330-12. [PMID: 23587959] - Y Shida, K Hara, S Nohda, T Soutome, T Hirama. The pharmacokinetic and safety profiles of zanamivir after single and repeat intravenous administration in healthy Japanese males.
Journal of clinical pharmacy and therapeutics.
2013 Jun; 38(3):236-40. doi:
10.1111/jcpt.12056. [PMID: 23489210] - Jin-Hyo Kim, Ricardo Resende, Tom Wennekes, Hong-Ming Chen, Nicole Bance, Sabrina Buchini, Andrew G Watts, Pat Pilling, Victor A Streltsov, Martin Petric, Richard Liggins, Susan Barrett, Jennifer L McKimm-Breschkin, Masahiro Niikura, Stephen G Withers. Mechanism-based covalent neuraminidase inhibitors with broad-spectrum influenza antiviral activity.
Science (New York, N.Y.).
2013 Apr; 340(6128):71-5. doi:
10.1126/science.1232552. [PMID: 23429702] - Enguang Feng, Woo-Jin Shin, Xuelian Zhu, Jian Li, Deju Ye, Jiang Wang, Mingyue Zheng, Jian-Ping Zuo, Kyoung Tai No, Xian Liu, Weiliang Zhu, Wei Tang, Baik-Lin Seong, Hualiang Jiang, Hong Liu. Structure-based design and synthesis of C-1- and C-4-modified analogs of zanamivir as neuraminidase inhibitors.
Journal of medicinal chemistry.
2013 Feb; 56(3):671-84. doi:
10.1021/jm3009713. [PMID: 23330908] - Kazutaka Yoshihara, Hitoshi Ishizuka, Yuichi Kubo. Population pharmacokinetics of laninamivir and its prodrug laninamivir octanoate in healthy subjects and in adult and pediatric patients with influenza virus infection.
Drug metabolism and pharmacokinetics.
2013; 28(5):416-26. doi:
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Nature communications.
2013; 4(?):1491. doi:
10.1038/ncomms2487. [PMID: 23422659] - Füsun Göktaş, Evelien Vanderlinden, Lieve Naesens, Nesrin Cesur, Zafer Cesur. Microwave assisted synthesis and anti-influenza virus activity of 1-adamantyl substituted N-(1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives.
Bioorganic & medicinal chemistry.
2012 Dec; 20(24):7155-9. doi:
10.1016/j.bmc.2012.09.064. [PMID: 23117173] - Chia Min Lee, Alisha K Weight, Jayanta Haldar, Ling Wang, Alexander M Klibanov, Jianzhu Chen. Polymer-attached zanamivir inhibits synergistically both early and late stages of influenza virus infection.
Proceedings of the National Academy of Sciences of the United States of America.
2012 Dec; 109(50):20385-90. doi:
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Biochemical and biophysical research communications.
2012 Dec; 429(1-2):51-6. doi:
10.1016/j.bbrc.2012.10.095. [PMID: 23131559] - Ting-Jen R Cheng, Steven Weinheimer, E Bart Tarbet, Jia-Tsrong Jan, Yih-Shyun E Cheng, Jiun-Jie Shie, Chun-Lin Chen, Chih-An Chen, Wei-Che Hsieh, Pei-Wei Huang, Wen-Hao Lin, Shi-Yun Wang, Jim-Min Fang, Oliver Yoa-Pu Hu, Chi-Huey Wong. Development of oseltamivir phosphonate congeners as anti-influenza agents.
Journal of medicinal chemistry.
2012 Oct; 55(20):8657-70. doi:
10.1021/jm3008486. [PMID: 23009169] - Jing Ge, Fengmao Liu, Eric H Holmes, Gary K Ostrander, Qing X Li. Aqueous normal phase liquid chromatography coupled with tandem time-of-flight quadrupole mass spectrometry for determination of zanamivir in human serum.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2012 Oct; 906(?):58-62. doi:
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Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy.
2012 Aug; 18(4):534-43. doi:
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European journal of medicinal chemistry.
2012 Aug; 54(?):764-70. doi:
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Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy.
2012 Aug; 18(4):529-33. doi:
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Pediatric transplantation.
2012 Aug; 16(5):E153-7. doi:
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Antimicrobial agents and chemotherapy.
2012 Jul; 56(7):3873-8. doi:
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Journal of biomedical science.
2012 Apr; 19(?):37. doi:
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PloS one.
2012; 7(6):e38214. doi:
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2012; 2012(?):820621. doi:
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PloS one.
2012; 7(8):e42419. doi:
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Mediators of inflammation.
2012; 2012(?):236345. doi:
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Natural product reports.
2012 Jan; 29(1):11-36. doi:
10.1039/c1np00053e. [PMID: 22025274] - James B Hudson. Applications of the phytomedicine Echinacea purpurea (Purple Coneflower) in infectious diseases.
Journal of biomedicine & biotechnology.
2012; 2012(?):769896. doi:
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Virology journal.
2011 Dec; 8(?):538. doi:
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Pediatrics international : official journal of the Japan Pediatric Society.
2011 Dec; 53(6):910-4. doi:
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Journal of clinical medicine research.
2011 Dec; 3(6):291-5. doi:
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Revista panamericana de salud publica = Pan American journal of public health.
2011 Dec; 30(6):634-40. doi:
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Journal of controlled release : official journal of the Controlled Release Society.
2011 Nov; 152 Suppl 1(?):e2-4. doi:
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Clinical pharmacokinetics.
2011 Nov; 50(11):689-704. doi:
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Antimicrobial agents and chemotherapy.
2011 Nov; 55(11):5178-84. doi:
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Archives of gynecology and obstetrics.
2011 Nov; 284(5):1133-5. doi:
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Phytochemical analysis : PCA.
2011 Sep; 22(5):432-41. doi:
10.1002/pca.1299. [PMID: 21495103] - Sasithon Pukrittayakamee, Podjanee Jittamala, Kasia Stepniewska, Niklas Lindegardh, Sunee Chueasuwanchai, Wattana Leowattana, Aphiradee Phakdeeraj, Sutatip Permpunpanich, Warunee Hanpithakpong, Wirichada Pan-Ngum, Caroline Fukuda, Salwaluk Panapipat, Pratap Singhasivanon, Nicholas J White, Nicholas P J Day. An open-label crossover study to evaluate potential pharmacokinetic interactions between oral oseltamivir and intravenous zanamivir in healthy Thai adults.
Antimicrobial agents and chemotherapy.
2011 Sep; 55(9):4050-7. doi:
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Indian journal of pharmacology.
2011 Sep; 43(5):536-40. doi:
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Virology journal.
2011 Aug; 8(?):411. doi:
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Chonnam medical journal.
2011 Aug; 47(2):127-9. doi:
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The Korean journal of internal medicine.
2011 Jun; 26(2):160-7. doi:
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Journal of clinical pharmacology.
2011 Feb; 51(2):243-51. doi:
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PloS one.
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