Rimantadine (BioDeep_00000002491)
Secondary id: BioDeep_00000399007
human metabolite blood metabolite Chemicals and Drugs
代谢物信息卡片
Forest brand OF rimantadine hydrochloride
化学式: C12H21N (179.1674)
中文名称: 左旋氧氟沙星, 金刚乙胺
谱图信息:
最多检出来源 Homo sapiens(plant) 15.92%
分子结构信息
SMILES: CC(C12CC3CC(C1)CC(C3)C2)N
InChI: InChI=1S/C12H21N/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H3
描述信息
Rimantadine is only found in individuals that have used or taken this drug. It is an RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza. [PubChem]The mechanism of action of rimantadine is not fully understood. Rimantadine appears to exert its inhibitory effect early in the viral replicative cycle, possibly inhibiting the uncoating of the virus. Genetic studies suggest that a virus protein specified by the virion M2 gene plays an important role in the susceptibility of influenza A virus to inhibition by rimantadine.
J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AC - Cyclic amines
D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
C254 - Anti-Infective Agent > C281 - Antiviral Agent
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3149
同义名列表
数据库引用编号
23 个数据库交叉引用编号
- ChEBI: CHEBI:94440
- KEGG: C07236
- KEGGdrug: D08483
- PubChem: 5071
- HMDB: HMDB0014621
- Metlin: METLIN43325
- DrugBank: DB00478
- ChEMBL: CHEMBL1201272
- ChEMBL: CHEMBL959
- Wikipedia: Rimantadine
- MeSH: Rimantadine
- chemspider: 4893
- CAS: 13392-28-4
- MoNA: EQ314905
- MoNA: EQ314901
- MoNA: EQ314903
- MoNA: EQ314902
- MoNA: EQ314906
- MoNA: EQ314904
- PMhub: MS000002790
- PubChem: 9445
- NIKKAJI: J8.105A
- RefMet: Rimantadine
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。
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文献列表
- Jiří Sedlák, Jaroslava Přibylová, Igor Koloňuk, Josef Špak, Ondřej Lenz, Matěj Semerák. Elimination of Solanum nigrum ilarvirus 1 and Apple Hammerhead Viroid from Apple Cultivars Using Antivirals Ribavirin, Rimantadine, and Zidovudine.
Viruses.
2023 Aug; 15(8):. doi:
10.3390/v15081684. [PMID: 37632025] - Trine Lisberg Toft-Bertelsen, Mads Gravers Jeppesen, Eva Tzortzini, Kai Xue, Karin Giller, Stefan Becker, Amer Mujezinovic, Bo Hjorth Bentzen, Loren B Andreas, Antonios Kolocouris, Thomas Nitschke Kledal, Mette Marie Rosenkilde. Amantadine has potential for the treatment of COVID-19 because it inhibits known and novel ion channels encoded by SARS-CoV-2.
Communications biology.
2021 12; 4(1):1347. doi:
10.1038/s42003-021-02866-9. [PMID: 34853399] - Yuyong Zhou, Karen A Gammeltoft, Andrea Galli, Anna Offersgaard, Ulrik Fahnøe, Santseharay Ramirez, Jens Bukh, Judith M Gottwein. Efficacy of Ion-Channel Inhibitors Amantadine, Memantine and Rimantadine for the Treatment of SARS-CoV-2 In Vitro.
Viruses.
2021 10; 13(10):. doi:
10.3390/v13102082. [PMID: 34696509] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Irina V Ilyina, Oksana S Patrusheva, Vladimir V Zarubaev, Maria A Misiurina, Alexander V Slita, Iana L Esaulkova, Dina V Korchagina, Yuri V Gatilov, Sophia S Borisevich, Konstantin P Volcho, Nariman F Salakhutdinov. Influenza antiviral activity of F- and OH-containing isopulegol-derived octahydro-2H-chromenes.
Bioorganic & medicinal chemistry letters.
2021 01; 31(?):127677. doi:
10.1016/j.bmcl.2020.127677. [PMID: 33171219] - Tatyana M Khomenko, Vladimir V Zarubaev, Marina V Kireeva, Alexandrina S Volobueva, Alexander V Slita, Sophia S Borisevich, Dina V Korchagina, Nina I Komarova, Konstantin P Volcho, Nariman F Salakhutdinov. New type of anti-influenza agents based on benzo[d][1,3]dithiol core.
Bioorganic & medicinal chemistry letters.
2020 12; 30(24):127653. doi:
10.1016/j.bmcl.2020.127653. [PMID: 33129992] - Radoslav Chayrov, Nikolaos A Parisis, Maria V Chatziathanasiadou, Eleni Vrontaki, Kalliopi Moschovou, Georgia Melagraki, Hristina Sbirkova-Dimitrova, Boris Shivachev, Michaela Schmidtke, Yavor Mitrev, Martin Sticha, Thomas Mavromoustakos, Andreas G Tzakos, Ivanka Stankova. Synthetic Analogues of Aminoadamantane as Influenza Viral Inhibitors-In Vitro, In Silico and QSAR Studies.
Molecules (Basel, Switzerland).
2020 Sep; 25(17):. doi:
10.3390/molecules25173989. [PMID: 32883012] - Hafsa Iftikhar, Hafiza Nayyer Ali, Sadia Farooq, Hammad Naveed, Syed Shahzad-Ul-Hussan. Identification of potential inhibitors of three key enzymes of SARS-CoV2 using computational approach.
Computers in biology and medicine.
2020 07; 122(?):103848. doi:
10.1016/j.compbiomed.2020.103848. [PMID: 32658735] - E N Ulomskiy, A V Ivanova, E B Gorbunov, I L Esaulkova, A V Slita, E O Sinegubova, E K Voinkov, R A Drokin, I I Butorin, E R Gazizullina, E L Gerasimova, V V Zarubaev, V L Rusinov. Synthesis and biological evaluation of 6-nitro-1,2,4-triazoloazines containing polyphenol fragments possessing antioxidant and antiviral activity.
Bioorganic & medicinal chemistry letters.
2020 07; 30(13):127216. doi:
10.1016/j.bmcl.2020.127216. [PMID: 32360104] - Constantinos K Zacharis, Paraskevas D Tzanavaras. Trace analysis of rimantadine in human urine after dispersive liquid liquid microextraction followed by liquid chromatography-post column derivatization.
Journal of separation science.
2020 Feb; 43(3):631-638. doi:
10.1002/jssc.201900903. [PMID: 31680400] - T M Garaev, A I Odnovorov, E S Kirillova, E I Burtseva, M P Finogenova, E A Mukasheva, T V Grebennikova. [Adamantan derivatives capable of inhibiting the reproduction of a Rimantadine resistant strain of influenza A(H1N1)pdm09 virus (Influenza A virus, Alphainfluenzavirus, Orthomyxoviridae).].
Voprosy virusologii.
2020 ; 65(1):16-20. doi:
10.36233/0507-4088-2020-65-1-16-20. [PMID: 32496716] - Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964. [PMID: 31515284] - Beili Ying, Shichao Pang, Junchen Yang, Yang Zhong, Jingfang Wang. Computational Study of HCV p7 Channel: Insight into a New Strategy for HCV Inhibitor Design.
Interdisciplinary sciences, computational life sciences.
2019 Jun; 11(2):292-299. doi:
10.1007/s12539-018-0306-3. [PMID: 30194627] - Dmitry Dar'in, Vladimir Zarubaev, Anastasia Galochkina, Maxim Gureev, Mikhail Krasavin. Non-chelating p-phenylidene-linked bis-imidazoline analogs of known influenza virus endonuclease inhibitors: Synthesis and anti-influenza activity.
European journal of medicinal chemistry.
2019 Jan; 161(?):526-532. doi:
10.1016/j.ejmech.2018.10.063. [PMID: 30390440] - Tatyana M Khomenko, Vladimir V Zarubaev, Iana R Orshanskaya, Renata A Kadyrova, Victoria A Sannikova, Dina V Korchagina, Konstantin P Volcho, Nariman F Salakhutdinov. Anti-influenza activity of monoterpene-containing substituted coumarins.
Bioorganic & medicinal chemistry letters.
2017 07; 27(13):2920-2925. doi:
10.1016/j.bmcl.2017.04.091. [PMID: 28501512] - Oleg I Artyushin, Elena V Sharova, Natalya M Vinogradova, Galina K Genkina, Aleksandra A Moiseeva, Zinaida S Klemenkova, Iana R Orshanskaya, Anna A Shtro, Renata A Kadyrova, Vladimir V Zarubaev, Olga I Yarovaya, Nariman F Salakhutdinov, Valery K Brel. Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity.
Bioorganic & medicinal chemistry letters.
2017 05; 27(10):2181-2184. doi:
10.1016/j.bmcl.2017.03.051. [PMID: 28366530] - Marta Barniol-Xicota, Sabrina Gazzarrini, Eva Torres, Yanmei Hu, Jun Wang, Lieve Naesens, Anna Moroni, Santiago Vázquez. Slow but Steady Wins the Race: Dissimilarities among New Dual Inhibitors of the Wild-Type and the V27A Mutant M2 Channels of Influenza A Virus.
Journal of medicinal chemistry.
2017 05; 60(9):3727-3738. doi:
10.1021/acs.jmedchem.6b01758. [PMID: 28418242] - V A Shibnev, T M Garaev, P G Deryabin, M P Finogenova, A G Botikov, D V Mishin. New Carbocyclic Amino Acid Derivatives Inhibit Infection Caused by Highly Pathogenic Influenza A Virus Strain (H5N1).
Bulletin of experimental biology and medicine.
2016 Jun; 161(2):284-7. doi:
10.1007/s10517-016-3396-0. [PMID: 27383164] - Alexander N Geisman, Vladimir T Valuev-Elliston, Alexander A Ozerov, Anastasia L Khandazhinskaya, Alexander O Chizhov, Sergey N Kochetkov, Christophe Pannecouque, Lieve Naesens, Katherine L Seley-Radtke, Mikhail S Novikov. 1,6-Bis[(benzyloxy)methyl]uracil derivatives-Novel antivirals with activity against HIV-1 and influenza H1N1 virus.
Bioorganic & medicinal chemistry.
2016 06; 24(11):2476-85. doi:
10.1016/j.bmc.2016.04.010. [PMID: 27112451] - O P Zhirnov, A A Manykin, J S Rossman, H D Klenk. Intravirion cohesion of matrix protein M1 with ribonucleocapsid is a prerequisite of influenza virus infectivity.
Virology.
2016 May; 492(?):187-96. doi:
10.1016/j.virol.2016.02.021. [PMID: 26954078] - Lidia A Baltina, Vladimir V Zarubaev, Lia A Baltina, Iana A Orshanskaya, Alina I Fairushina, Oleg I Kiselev, Marat S Yunusov. Glycyrrhizic acid derivatives as influenza A/H1N1 virus inhibitors.
Bioorganic & medicinal chemistry letters.
2015 Apr; 25(8):1742-1746. doi:
10.1016/j.bmcl.2015.02.074. [PMID: 25801933] - Nathania J Leong, Richard J Prankerd, David M Shackleford, Michelle P Mcintosh. The effect of intravenous sulfobutylether7 -β-cyclodextrin on the pharmacokinetics of a series of adamantane-containing compounds.
Journal of pharmaceutical sciences.
2015 Apr; 104(4):1492-8. doi:
10.1002/jps.24331. [PMID: 25573540] - Nathania J Leong, Richard J Prankerd, David M Shackleford, Michelle P Mcintosh. Evaluation of the impact of sulfobutylether7 -β-cyclodextrin on the liquid chromatography-mass spectrometry analysis of biological samples arising from in vivo pharmacokinetic studies.
Journal of pharmaceutical sciences.
2015 Apr; 104(4):1561-2. doi:
10.1002/jps.24348. [PMID: 25583633] - Ilona Bereczki, Máté Kicsák, Laura Dobray, Anikó Borbás, Gyula Batta, Sándor Kéki, Éva Nemes Nikodém, Eszter Ostorházi, Ferenc Rozgonyi, Evelien Vanderlinden, Lieve Naesens, Pál Herczegh. Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: synthesis and antiviral studies.
Bioorganic & medicinal chemistry letters.
2014 Aug; 24(15):3251-4. doi:
10.1016/j.bmcl.2014.06.018. [PMID: 24974341] - Antonios Kolocouris, Christina Tzitzoglaki, F Brent Johnson, Roland Zell, Anna K Wright, Timothy A Cross, Ian Tietjen, David Fedida, David D Busath. Aminoadamantanes with persistent in vitro efficacy against H1N1 (2009) influenza A.
Journal of medicinal chemistry.
2014 Jun; 57(11):4629-39. doi:
10.1021/jm500598u. [PMID: 24793875] - P G Deryabin, T M Garaev, M P Finogenova, A G Botikov, V A Shibnev. Amino acid derivatives of adamantane carbocycle are capable of inhibiting replication of highly virulent avian influenza A/H5N1 virus.
Bulletin of experimental biology and medicine.
2014 May; 157(1):62-5. doi:
10.1007/s10517-014-2492-2. [PMID: 24909717] - Matias Rey-Carrizo, Eva Torres, Chunlong Ma, Marta Barniol-Xicota, Jun Wang, Yibing Wu, Lieve Naesens, William F DeGrado, Robert A Lamb, Lawrence H Pinto, Santiago Vázquez. 3-Azatetracyclo[5.2.1.1(5,8).0(1,5)]undecane derivatives: from wild-type inhibitors of the M2 ion channel of influenza A virus to derivatives with potent activity against the V27A mutant.
Journal of medicinal chemistry.
2013 Nov; 56(22):9265-74. doi:
10.1021/jm401340p. [PMID: 24237039] - Constantinos K Zacharis, Paraskevas D Tzanavaras, Athanasios G Vlessidis. Determination of rimantadine in human urine by HPLC using a monolithic stationary phase and on-line post-column derivatization.
Journal of separation science.
2013 Jun; 36(11):1720-5. doi:
10.1002/jssc.201300106. [PMID: 23650193] - Edward E Korshin, Lyubov G Zakharova, Yakov A Levin, Marina P Shulaeva, Oskar K Pozdeev. Anti-influenza active and low toxic N-phenyl-substituted β-amidoamidines structurally related to natural antibiotic amidinomycin.
Bioorganic & medicinal chemistry letters.
2013 Apr; 23(8):2357-61. doi:
10.1016/j.bmcl.2013.02.053. [PMID: 23489622] - 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] - Dmitriy N Sokolov, Vladimir V Zarubaev, Anna A Shtro, Marina P Polovinka, Olga A Luzina, Nina I Komarova, Nariman F Salakhutdinov, Oleg I Kiselev. Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009.
Bioorganic & medicinal chemistry letters.
2012 Dec; 22(23):7060-4. doi:
10.1016/j.bmcl.2012.09.084. [PMID: 23099095] - Guang-Quan Wang, Yan-Fang Qin, Li-Ming Du, Jun-Fei Li, Xu Jing, Yin-Xia Chang, Hao Wu. Determination of amantadine and rimantadine using a sensitive fluorescent probe.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2012 Dec; 98(?):275-81. doi:
10.1016/j.saa.2012.08.016. [PMID: 22959366] - Georgina Cirrincione-Dall, Barbara J Brennan, Rosa M Ballester-Sanchis, Mercidita T Navarro, Brian E Davies. Pharmacokinetics and safety of coadministered oseltamivir and rimantadine in healthy volunteers: an open-label, multiple-dose, randomized, crossover study.
Journal of clinical pharmacology.
2012 Aug; 52(8):1255-64. doi:
10.1177/0091270011412960. [PMID: 22039289] - Sander A A Kooijmans, Danielle Senyschyn, Muguntha M Mezhiselvam, Julia Morizzi, Susan A Charman, Babette Weksler, Ignacio-Andres Romero, Pierre-Olivier Couraud, Joseph A Nicolazzo. The involvement of a Na⁺- and Cl⁻-dependent transporter in the brain uptake of amantadine and rimantadine.
Molecular pharmaceutics.
2012 Apr; 9(4):883-93. doi:
10.1021/mp2004127. [PMID: 22352408] - Rafal M Pielak, Kirill Oxenoid, James J Chou. Structural investigation of rimantadine inhibition of the AM2-BM2 chimera channel of influenza viruses.
Structure (London, England : 1993).
2011 Nov; 19(11):1655-63. doi:
10.1016/j.str.2011.09.003. [PMID: 22078564] - Belen Puente, Esther Hernandez, Susana Perez, Luis Pablo, Esther Prieto, Maria Angeles Garcia, Miguel Angel Bregante. Determination of memantine in plasma and vitreous humour by HPLC with precolumn derivatization and fluorescence detection.
Journal of chromatographic science.
2011 Nov; 49(10):745-52. doi:
10.1093/chrsci/49.10.745. [PMID: 22080801] - Joe Liu, Daniel Obando, Vivian Liao, Tulip Lifa, Rachel Codd. The many faces of the adamantyl group in drug design.
European journal of medicinal chemistry.
2011 Jun; 46(6):1949-63. doi:
10.1016/j.ejmech.2011.01.047. [PMID: 21354674] - V G Belolipetskaia, S V Blagodatskikh, E A Zhabina, D A Kibalchich, D F Guranda, N A Belolipetskiĭ, L I Rudenko. [Comparative pharmacokinetics of antigrippin-maximum administered in capsules and powder for preparing solutions].
Eksperimental'naia i klinicheskaia farmakologiia.
2011; 74(7):38-40. doi:
NULL. [PMID: 21894768] - Ann L Wozniak, Stephen Griffin, David Rowlands, Mark Harris, MinKyung Yi, Stanley M Lemon, Steven A Weinman. Intracellular proton conductance of the hepatitis C virus p7 protein and its contribution to infectious virus production.
PLoS pathogens.
2010 Sep; 6(9):e1001087. doi:
10.1371/journal.ppat.1001087. [PMID: 20824094] - Loren B Andreas, Matthew T Eddy, Rafal M Pielak, James Chou, Robert G Griffin. Magic angle spinning NMR investigation of influenza A M2(18-60): support for an allosteric mechanism of inhibition.
Journal of the American Chemical Society.
2010 Aug; 132(32):10958-60. doi:
10.1021/ja101537p. [PMID: 20698642] - Inna Karpenko, Sergey Deev, Oleg Kiselev, Valerey Charushin, Vladimir Rusinov, Eugeney Ulomsky, Ella Deeva, Dmitry Yanvarev, Alexander Ivanov, Olga Smirnova, Sergey Kochetkov, Oleg Chupakhin, Marina Kukhanova. Antiviral properties, metabolism, and pharmacokinetics of a novel azolo-1,2,4-triazine-derived inhibitor of influenza A and B virus replication.
Antimicrobial agents and chemotherapy.
2010 May; 54(5):2017-22. doi:
10.1128/aac.01186-09. [PMID: 20194696] - Pathumwadee Intharathep, Chittima Laohpongspaisan, Thanyada Rungrotmongkol, Arthorn Loisruangsin, Maturos Malaisree, Panita Decha, Ornjira Aruksakunwong, Krit Chuenpennit, Nopphorn Kaiyawet, Pornthep Sompornpisut, Somsak Pianwanit, Supot Hannongbua. How amantadine and rimantadine inhibit proton transport in the M2 protein channel.
Journal of molecular graphics & modelling.
2008 Oct; 27(3):342-8. doi:
10.1016/j.jmgm.2008.06.002. [PMID: 18620883] - Meijuan Xu, Wenzheng Ju, Xiaoyan Xia, Hengshan Tan, Min Chen, Jun Zhang, Ningning Xiong, Meng Jiang, Lei Chen, Lixiu Gong. Determination of rimantadine in rat plasma by liquid chromatography/electrospray mass spectrometry and its application in a pharmacokinetic study.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 Mar; 864(1-2):123-8. doi:
10.1016/j.jchromb.2008.01.053. [PMID: 18316252] - Jason R Schnell, James J Chou. Structure and mechanism of the M2 proton channel of influenza A virus.
Nature.
2008 Jan; 451(7178):591-5. doi:
10.1038/nature06531. [PMID: 18235503] - Sang Ho Park, Stanley J Opella. Conformational changes induced by a single amino acid substitution in the trans-membrane domain of Vpu: implications for HIV-1 susceptibility to channel blocking drugs.
Protein science : a publication of the Protein Society.
2007 Oct; 16(10):2205-15. doi:
10.1110/ps.073041107. [PMID: 17766368] - Cui Shuangjin, Feng Fang, Liu Han, Ma Ming. New method for high-performance liquid chromatographic determination of amantadine and its analogues in rat plasma.
Journal of pharmaceutical and biomedical analysis.
2007 Sep; 44(5):1100-5. doi:
10.1016/j.jpba.2007.04.021. [PMID: 17553649] - T Jefferson, V Demicheli, C Di Pietrantonj, D Rivetti. Amantadine and rimantadine for influenza A in adults.
The Cochrane database of systematic reviews.
2006 Apr; ?(2):CD001169. doi:
10.1002/14651858.cd001169.pub3. [PMID: 16625539] - D K L'vov, A G Prilipov, M Iu Shchelkanov, P G Deriabin, A A Shilov, T V Grebennikova, G K Sadykova, O V Liapina. [Molecular genetic analysis of the biological properties of highly pathogenic influenza A/H5N1 virus strains isolated from wild birds and poultry during epizooty in Western Siberia (July 2005)].
Voprosy virusologii.
2006 Mar; 51(2):15-9. doi:
. [PMID: 16756172] - D K L'vov, I T Fediakina, M Iu Shchelkanov, A G Prilipov, P G Deriabin, G A Galegov. [In vitro effects of antiviral drugs on the reproduction of highly pathogenic influenza A/H5N1 virus strains that induce epizooty among poultry in the summer of 2005].
Voprosy virusologii.
2006 Mar; 51(2):20-2. doi:
NULL. [PMID: 16756173] - Angel S Galabov, Lora Simeonova, Galina Gegova. Rimantadine and oseltamivir demonstrate synergistic combination effect in an experimental infection with type A (H3N2) influenza virus in mice.
Antiviral chemistry & chemotherapy.
2006; 17(5):251-8. doi:
10.1177/095632020601700502. [PMID: 17176629] - Yasuhiko Higashi, Izumi Uemori, Youichi Fujii. Simultaneous determination of amantadine and rimantadine by HPLC in rat plasma with pre-column derivatization and fluorescence detection for pharmacokinetic studies.
Biomedical chromatography : BMC.
2005 Nov; 19(9):655-62. doi:
10.1002/bmc.492. [PMID: 15803448] - F Chen, K H Chan, Y Jiang, R Y T Kao, H T Lu, K W Fan, V C C Cheng, W H W Tsui, I F N Hung, T S W Lee, Y Guan, J S M Peiris, K Y Yuen. In vitro susceptibility of 10 clinical isolates of SARS coronavirus to selected antiviral compounds.
Journal of clinical virology : the official publication of the Pan American Society for Clinical Virology.
2004 Sep; 31(1):69-75. doi:
10.1016/j.jcv.2004.03.003. [PMID: 15288617] - Julia Serkedjieva, Maria Velcheva. In vitro anti-influenza virus activity of isoquinoline alkaloids from thalictrum species.
Planta medica.
2003 Feb; 69(2):153-4. doi:
10.1055/s-2003-37720. [PMID: 12624821] - Donald F Smee, Ann C Morrison, Dale L Barnard, Robert W Sidwell. Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.
Journal of virological methods.
2002 Oct; 106(1):71-9. doi:
10.1016/s0166-0934(02)00137-4. [PMID: 12367731] - M Schmidtke, U Schnittler, B Jahn, H Dahse, A Stelzner. A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1.
Journal of virological methods.
2001 Jun; 95(1-2):133-43. doi:
10.1016/s0166-0934(01)00305-6. [PMID: 11377720] - J Chládek, L Sispera, J Martinková, B Zaludek, P Sova, S Mièuda, J Grim, J Cermanová, B Zaludek, P Sova, A Franc. Bioequivalence of two rimantadine tablet formulations in healthy male volunteers after single dose administration.
International journal of clinical pharmacology and therapeutics.
2001 Apr; 39(4):179-84. doi:
10.5414/cpp39179. [PMID: 11332875] - L Tantcheva, E Pavlova, V Savov, A Galabov, M Mileva, A Braykova. Free radical lipid peroxidation and monooxygenase activity in experimental influenza virus infection after treatment with rimantadine.
Advances in experimental medicine and biology.
2001; 500(?):217-20. doi:
10.1007/978-1-4615-0667-6_30. [PMID: 11764939] - I A Leneva, N Roberts, E A Govorkova, O G Goloubeva, R G Webster. The neuraminidase inhibitor GS4104 (oseltamivir phosphate) is efficacious against A/Hong Kong/156/97 (H5N1) and A/Hong Kong/1074/99 (H9N2) influenza viruses.
Antiviral research.
2000 Nov; 48(2):101-15. doi:
10.1016/s0166-3542(00)00123-6. [PMID: 11114412] - M Mileva, V Hadjimitova, L Tantcheva, T Traykov, A S Galabov, V Savov, S Ribarov. Antioxidant properties of rimantadine in influenza virus infected mice and in some model systems.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2000 Sep; 55(9-10):824-9. doi:
10.1515/znc-2000-9-1025. [PMID: 11098838] - S K Sarin. What should we advise about adjunctive therapies, including herbal medicines, for hepatitis C?.
Journal of gastroenterology and hepatology.
2000 May; 15 Suppl(?):E164-71. doi:
10.1046/j.1440-1746.2000.02117.x. [PMID: 10921401] - W A Rees, J D Harkins, M Lu, R E Holland, A F Lehner, T Tobin, T M Chambers. Pharmacokinetics and therapeutic efficacy of rimantadine in horses experimentally infected with influenza virus A2.
American journal of veterinary research.
1999 Jul; 60(7):888-94. doi:
NULL. [PMID: 10407485] - T L Fong, M W Fried, J Clarke-Platt. A pilot study of rimantadine for patients with chronic hepatitis C unresponsive to interferon therapy.
The American journal of gastroenterology.
1999 Apr; 94(4):990-3. doi:
10.1111/j.1572-0241.1999.01001.x. [PMID: 10201471] - K E Sherman, J Sickler, J Aranda-Michel, F L Weber, S Martin, J Whiting, D Hanto. Rimantadine for treatment of hepatitis C infection in liver transplant recipients.
Liver transplantation and surgery : official publication of the American Association for the Study of Liver Diseases and the International Liver Transplantation Society.
1999 Jan; 5(1):25-8. doi:
10.1002/lt.500050103. [PMID: 9873088] - NULL. Drugs for non-HIV viral infections.
The Medical letter on drugs and therapeutics.
1997 Aug; 39(1006):69-76. doi:
NULL. [PMID: 9255238] - S M Wintermeyer, M C Nahata. Rimantadine: a clinical perspective.
The Annals of pharmacotherapy.
1995 Mar; 29(3):299-310. doi:
10.1177/106002809502900312. [PMID: 7606077] - C Schroeder, C M Ford, S A Wharton, A J Hay. Functional reconstitution in lipid vesicles of influenza virus M2 protein expressed by baculovirus: evidence for proton transfer activity.
The Journal of general virology.
1994 Dec; 75 ( Pt 12)(?):3477-84. doi:
10.1099/0022-1317-75-12-3477. [PMID: 7527837] - F G Hayden, B S Rollins, L K Madren. Anti-influenza virus activity of the neuraminidase inhibitor 4-guanidino-Neu5Ac2en in cell culture and in human respiratory epithelium.
Antiviral research.
1994 Oct; 25(2):123-31. doi:
10.1016/0166-3542(94)90101-5. [PMID: 7847874] - D R Guay. Amantadine and rimantadine prophylaxis of influenza A in nursing homes. A tolerability perspective.
Drugs & aging.
1994 Jul; 5(1):8-19. doi:
10.2165/00002512-199405010-00002. [PMID: 7919641] - V K Natsina, V P Drinevskiĭ, K K Milkint. [Remantadine in the treatment of influenza in children].
Vestnik Rossiiskoi akademii meditsinskikh nauk.
1994; ?(9):51-5. doi:
NULL. [PMID: 7532497] - J Serkedjieva, I Zgorniak-Nowosielska. Combined antiinfluenza activity of a plant preparation SHS-174 and amantadine derivatives.
Acta virologica.
1993 Aug; 37(4):258-64. doi:
. [PMID: 7905240] - D Rakestraw. Determination of amantadine in human plasma by capillary gas chromatography using electron-capture detection following derivatization with pentafluorobenzoyl chloride.
Journal of pharmaceutical and biomedical analysis.
1993 Aug; 11(8):699-703. doi:
10.1016/0731-7085(93)80177-3. [PMID: 8257734] - B S Rollins, A H Elkhatieb, F G Hayden. Comparative anti-influenza virus activity of 2'-deoxy-2'-fluororibosides in vitro.
Antiviral research.
1993 Aug; 21(4):357-68. doi:
10.1016/0166-3542(93)90013-9. [PMID: 8215305] - G Gegova, N Manolova, Iu Serkedzhieva, V Maksimova, S Uzunov, D Dzeguze, M Indulen. Combined effect of selected antiviral substances of natural and synthetic origin. II. Anti-influenza activity of a combination of a polyphenolic complex isolated from Geranium sanguineum L. and rimantadine in vivo.
Acta microbiologica Bulgarica.
1993; 30(?):37-40. doi:
. [PMID: 8285131] - S Grambas, A J Hay. Maturation of influenza A virus hemagglutinin--estimates of the pH encountered during transport and its regulation by the M2 protein.
Virology.
1992 Sep; 190(1):11-8. doi:
10.1016/0042-6822(92)91187-y. [PMID: 1529523] - A L Bruu, I Orstavik. [Amantadine and rimantadine against influenza A].
Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke.
1992 Jun; 112(16):2102-4. doi:
NULL. [PMID: 1523633] - N Choma, P P Davis, R W Edom, E K Fukuda. Quantitation of the enantiomers of rimantadine and its hydroxylated metabolites in human plasma by gas chromatography/mass spectrometry.
Biomedical chromatography : BMC.
1992 Jan; 6(1):12-5. doi:
10.1002/bmc.1130060105. [PMID: 1600368] - Sh R Olimov, L T Ikramov, A K Saidvaliev. [The forensic chemical determination of remantadine in biological material].
Sudebno-meditsinskaia ekspertiza.
1992 Jan; 35(1):34-6. doi:
NULL. [PMID: 1589893] - M V Kamyshentsev, I V Volchek, V G Platonov, V A Isakov, N N Zolotukhin. [Concept of the mechanism of the therapeutic effect of flu chemotherapy].
Doklady Akademii nauk.
1992; 326(4):722-4. doi:
". [PMID: 1486335] - R D Clover, J L Waner, L Becker, A Davis. Effect of rimantadine on the immune response to influenza A infections.
Journal of medical virology.
1991 May; 34(1):68-73. doi:
10.1002/jmv.1890340112. [PMID: 1885945] - A C Loh, A J Szuna, T H Williams, G J Sasso, F J Leinweber. The metabolism of [14C]rimantadine hydrochloride in rats and dogs.
Drug metabolism and disposition: the biological fate of chemicals.
1991 Mar; 19(2):381-7. doi:
NULL. [PMID: 1676641] - R L Atmar, S B Greenberg, J M Quarles, S Z Wilson, B Tyler, S Feldman, R B Couch. Safety and pharmacokinetics of rimantadine small-particle aerosol.
Antimicrobial agents and chemotherapy.
1990 Nov; 34(11):2228-33. doi:
10.1128/aac.34.11.2228. [PMID: 2073113] - T Hianik, G Laputková, K Poláková. Rimantadine effects on the elasticity of bilayer lipid membranes and on ion transport through gramicidin D channels.
General physiology and biophysics.
1990 Aug; 9(4):391-402. doi:
". [PMID: 1703099] - I A Leneva, P V Gulak, Iu N Dubrov, A S Sobolev. [Effects of remantadine on fusion of lipid membranes of influenza A virus with plasma and internal membranes of lymphoblastic cells].
Biulleten' eksperimental'noi biologii i meditsiny.
1990 May; 109(5):483-5. doi:
NULL. [PMID: 2378964] - F A Rubio, N Choma, E K Fukuda. Determination of rimantadine and its hydroxylated metabolites in human plasma and urine.
Journal of chromatography.
1989 Dec; 497(?):147-57. doi:
10.1016/0378-4347(89)80014-3. [PMID: 2625452] - V I Votiakov, I R Erokhina, T V Amvros'eva, V A Rusiaev. [Pathology of the reproductive apparatus of cells under the action of remantadine and deitiforin].
Biulleten' eksperimental'noi biologii i meditsiny.
1989 Sep; 108(9):356-8. doi:
. [PMID: 2611400] - A A Holazo, N Choma, S Y Brown, L F Lee, R J Wills. Effect of cimetidine on the disposition of rimantadine in healthy subjects.
Antimicrobial agents and chemotherapy.
1989 Jun; 33(6):820-3. doi:
10.1128/aac.33.6.820. [PMID: 2764530] - V I Votiakov, I R Erokhina, T V Amvros'eva. [The 3-phase reaction of cells of an MDCK culture to long-term exposure to antiviral chemical preparations].
Biulleten' eksperimental'noi biologii i meditsiny.
1989 May; 107(5):595-8. doi:
NULL. [PMID: 2736297] - V V Cherny, M Paulitschke, M V Simonova, E Hessel, Ermakov YuA, V S Sokolov, D Lerche, V S Markin. The effect of rimantadine on the structure of model and biological membranes.
General physiology and biophysics.
1989 Feb; 8(1):23-37. doi:
". [PMID: 2737460] - R L Tominack, R J Wills, L E Gustavson, F G Hayden. Multiple-dose pharmacokinetics of rimantadine in elderly adults.
Antimicrobial agents and chemotherapy.
1988 Dec; 32(12):1813-9. doi:
10.1128/aac.32.12.1813. [PMID: 3245694] - H E Hoffman, J C Gaylord, J W Blasecki, L M Shalaby, C C Whitney. Pharmacokinetics and metabolism of rimantadine hydrochloride in mice and dogs.
Antimicrobial agents and chemotherapy.
1988 Nov; 32(11):1699-704. doi:
10.1128/aac.32.11.1699. [PMID: 3252751] - B J Miwa, N Choma, S Y Brown, N Keigher, W A Garland, E K Fukuda. Quantitation of the enantiomers of rimantadine in human plasma and urine by gas chromatography-mass spectrometry.
Journal of chromatography.
1988 Oct; 431(2):343-52. doi:
10.1016/s0378-4347(00)83102-3. [PMID: 3243789] - F R Rubio, E K Fukuda, W A Garland. Urinary metabolites of rimantadine in humans.
Drug metabolism and disposition: the biological fate of chemicals.
1988 Sep; 16(5):773-7. doi:
NULL. [PMID: 2906605] - D A Herold, P K Anonick, M Kinter, F G Hayden. Measurement of rimantadine in plasma by capillary gas chromatography/mass spectrometry with a deuterium-labeled internal standard.
Clinical chemistry.
1988 Aug; 34(8):1597-9. doi:
NULL. [PMID: 3402062] - E V Capparelli, R C Stevens, M S Chow, M Izard, R J Wills. Rimantadine pharmacokinetics in healthy subjects and patients with end-stage renal failure.
Clinical pharmacology and therapeutics.
1988 May; 43(5):536-41. doi:
10.1038/clpt.1988.69. [PMID: 3365917] - I G Kharitonenkov, S El Karadaghi, A N Fedorov, Iu A Zakomyrdin, V A Tverdislov. [Effect of remantadine and amantadine on the interaction of influenza virus proteins with model lipid membranes].
Voprosy virusologii.
1988 Jan; 33(1):22-6. doi:
". [PMID: 3369145] - R J Wills, N Choma, G Buonpane, A Lin, N Keigher. Relative bioavailability of rimantadine HCl tablet and syrup formulations in healthy subjects.
Journal of pharmaceutical sciences.
1987 Dec; 76(12):886-8. doi:
10.1002/jps.2600761208. [PMID: 3440931] - P E Hermans, F R Cockerill. Antiviral agents.
Mayo Clinic proceedings.
1987 Dec; 62(12):1108-15. doi:
10.1016/s0025-6196(12)62505-1. [PMID: 3500376] - E K Fukuda, L C Rodriguez, N Choma, N Keigher, F De Grazia, W A Garland. Quantitative determination of rimantadine in human plasma and urine by GC-MS.
Biomedical & environmental mass spectrometry.
1987 Oct; 14(10):549-53. doi:
10.1002/bms.1200141004. [PMID: 2962655] - R J Wills, R Belshe, D Tomlinsin, F De Grazia, A Lin, S Wells, J Milazzo, C Berry. Pharmacokinetics of rimantadine hydrochloride in patients with chronic liver disease.
Clinical pharmacology and therapeutics.
1987 Oct; 42(4):449-54. doi:
10.1038/clpt.1987.176. [PMID: 3665342]
