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Chemical Compound Review

Remantadine     1-(1-adamantyl)ethanamine

Synonyms: RIMANTADIN, Rimant, Rimantadina, rimantadine, Riamantadine, ...
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Disease relevance of Flumadine


High impact information on Flumadine


Chemical compound and disease context of Flumadine


Biological context of Flumadine


Anatomical context of Flumadine

  • Only 10 (8.7%) of 114 rimantadine recipients and 5 (4.4%) of 114 placebo control recipients reported one or more mild to moderate adverse symptoms, most of which were related to the gastrointestinal or central nervous system [17].
  • However, at concentrations of 16 and 32 micrograms/ml, rimantadine was toxic to the ciliated epithelium after 10 to 21 days of continuous exposure [18].
  • Virus-neutralizing-antibody titers were reduced only by rimantadine treatment, which included prophylaxis, whereas the cytotoxic T lymphocyte (CTL) response was depressed by treatment given with or without prophylaxis [16].
  • Both patients are receiving rimantadine therapy and performing well, with functioning kidney and pancreas grafts and no evidence of recurrent PV interstitial nephritis 22 and 37 months after retransplantation [19].
  • Both rimantadine and, to a lesser extent, amantadine were transported principally across the blood-brain barrier by a saturable transport system with a one-half saturation concentration of about 1.0 mM (either rimantadine or amantadine) [20].

Associations of Flumadine with other chemical compounds


Gene context of Flumadine


Analytical, diagnostic and therapeutic context of Flumadine

  • A combination of antiviral drugs and immunotherapy may need to be considered for their potential additive effect as well as to prevent the emergence of resistant virus, as occurs during monotherapy for influenza with amantadine or rimantadine [28].
  • Hemodialysis did not appreciably remove rimantadine [5].
  • Elimination half-lives were similar after both aerosol and oral administration (24.1 and 25.2 h, respectively), and rimantadine urinary excretion was less than 1% per 24 h in both groups [29].
  • Rimantadine appeared to provide an additional protective effect beyond vaccination in reducing the risk of clinical and laboratory-confirmed influenza-like illness; however, the efficacy estimates were never statistically significant [30].
  • Susceptible adults (n = 105) were enrolled into a randomized double-blind study of rimantadine treatment of experimental influenza A infection [31].


  1. Emergence and apparent transmission of rimantadine-resistant influenza A virus in families. Hayden, F.G., Belshe, R.B., Clover, R.D., Hay, A.J., Oakes, M.G., Soo, W. N. Engl. J. Med. (1989) [Pubmed]
  2. Rimantadine inhibits reproduction of influenza virus A/USSR/77. Galegov, G.A., Pushkarskaya, N.L., Smirnova, N.R., Lvov, N.D., Yatsina, A.A., Zhdanov, V.M. Lancet (1979) [Pubmed]
  3. Amantadine-resistant influenza A in nursing homes. Identification of a resistant virus prior to drug use. Houck, P., Hemphill, M., LaCroix, S., Hirsh, D., Cox, N. Arch. Intern. Med. (1995) [Pubmed]
  4. Influence of membrane (M) protein on influenza A virus virion transcriptase activity in vitro and its susceptibility to rimantadine. Zvonarjev, A.Y., Ghendon, Y.Z. J. Virol. (1980) [Pubmed]
  5. Rimantadine pharmacokinetics in healthy subjects and patients with end-stage renal failure. Capparelli, E.V., Stevens, R.C., Chow, M.S., Izard, M., Wills, R.J. Clin. Pharmacol. Ther. (1988) [Pubmed]
  6. Safety and efficacy of nebulized zanamivir in hospitalized patients with serious influenza. Ison, M.G., Gnann, J.W., Nagy-Agren, S., Treannor, J., Paya, C., Steigbigel, R., Elliott, M., Weiss, H.L., Hayden, F.G. Antivir. Ther. (Lond.) (2003) [Pubmed]
  7. Comparison of central nervous system adverse effects of amantadine and rimantadine used as sequential prophylaxis of influenza A in elderly nursing home patients. Keyser, L.A., Karl, M., Nafziger, A.N., Bertino, J.S. Arch. Intern. Med. (2000) [Pubmed]
  8. Prevention and treatment of influenza in immunocompromised patients. Hayden, F.G. Am. J. Med. (1997) [Pubmed]
  9. Neuraminidase inhibitor-rimantadine combinations exert additive and synergistic anti-influenza virus effects in MDCK cells. Govorkova, E.A., Fang, H.B., Tan, M., Webster, R.G. Antimicrob. Agents Chemother. (2004) [Pubmed]
  10. 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid is a highly effective inhibitor both of the sialidase (neuraminidase) and of growth of a wide range of influenza A and B viruses in vitro. Woods, J.M., Bethell, R.C., Coates, J.A., Healy, N., Hiscox, S.A., Pearson, B.A., Ryan, D.M., Ticehurst, J., Tilling, J., Walcott, S.M. Antimicrob. Agents Chemother. (1993) [Pubmed]
  11. Rimantadine and oseltamivir demonstrate synergistic combination effect in an experimental infection with type A (H3N2) influenza virus in mice. Galabov, A.S., Simeonova, L., Gegova, G. Antivir. Chem. Chemother. (2006) [Pubmed]
  12. The influenza virus ion channel and maturation cofactor M2 is a cholesterol-binding protein. Schroeder, C., Heider, H., Möncke-Buchner, E., Lin, T.I. Eur. Biophys. J. (2005) [Pubmed]
  13. Virulence of rimantadine-resistant human influenza A (H3N2) viruses in ferrets. Sweet, C., Hayden, F.G., Jakeman, K.J., Grambas, S., Hay, A.J. J. Infect. Dis. (1991) [Pubmed]
  14. Antivirals for pandemic influenza. Hayden, F.G. J. Infect. Dis. (1997) [Pubmed]
  15. Susceptibilities to rimantadine of influenza A/H1N1 and A/H3N2 viruses isolated during the epidemics of 1988 to 1989 and 1989 to 1990. Valette, M., Allard, J.P., Aymard, M., Millet, V. Antimicrob. Agents Chemother. (1993) [Pubmed]
  16. Effect of rimantadine on cytotoxic T lymphocyte responses and immunity to reinfection in mice infected with influenza A virus. Herrmann, J.E., West, K., Bruns, M., Ennis, F.A. J. Infect. Dis. (1990) [Pubmed]
  17. Safety and prophylactic efficacy of low-dose rimantadine in adults during an influenza A epidemic. Brady, M.T., Sears, S.D., Pacini, D.L., Samorodin, R., DePamphilis, J., Oakes, M., Soo, W., Clements, M.L. Antimicrob. Agents Chemother. (1990) [Pubmed]
  18. Anti-influenza A virus activity of amantadine hydrochloride and rimantadine hydrochloride in ferret tracheal ciliated epithelium. Burlington, D.B., Meiklejohn, G., Mostow, S.R. Antimicrob. Agents Chemother. (1982) [Pubmed]
  19. Renal allograft loss as the result of polyomavirus interstitial nephritis after simultaneous kidney-pancreas transplantation: results with kidney retransplantation. Al-Jedai, A.H., Honaker, M.R., Trofe, J., Egidi, M.F., Gaber, L.W., Gaber, A.O., Stratta, R.J. Transplantation (2003) [Pubmed]
  20. Transport of amantadine and rimantadine through the blood-brain barrier. Spector, R. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
  21. Enhancement of activity against influenza viruses by combinations of antiviral agents. Hayden, F.G., Douglas, R.G., Simons, R. Antimicrob. Agents Chemother. (1980) [Pubmed]
  22. Children with influenza A infection: treatment with rimantadine. Hall, C.B., Dolin, R., Gala, C.L., Markovitz, D.M., Zhang, Y.Q., Madore, P.H., Disney, F.A., Talpey, W.B., Green, J.L., Francis, A.B. Pediatrics (1987) [Pubmed]
  23. Dansylcadaverine and rimantadine inhibition of phagocytosis, PAF-acether release, and phosphatidylcholine synthesis in human polymorphonuclear leukocytes. Garcia Gil, M., Sanchez Crespo, M. Immunopharmacology (1983) [Pubmed]
  24. Influence of an additional 2-amino substituent of the 1-aminoethyl pharmacophore group on the potency of rimantadine against influenza virus A. Tataridis, D., Fytas, G., Kolocouris, A., Fytas, C., Kolocouris, N., Foscolos, G.B., Padalko, E., Neyts, J., De Clercq, E. Bioorg. Med. Chem. Lett. (2007) [Pubmed]
  25. Evidence for cytokine mediation of disease expression in adults experimentally infected with influenza A virus. Skoner, D.P., Gentile, D.A., Patel, A., Doyle, W.J. J. Infect. Dis. (1999) [Pubmed]
  26. Selective proton permeability and pH regulation of the influenza virus M2 channel expressed in mouse erythroleukaemia cells. Chizhmakov, I.V., Geraghty, F.M., Ogden, D.C., Hayhurst, A., Antoniou, M., Hay, A.J. J. Physiol. (Lond.) (1996) [Pubmed]
  27. A single amino acid substitution within the transmembrane domain of the human immunodeficiency virus type 1 Vpu protein renders simian-human immunodeficiency virus (SHIV(KU-1bMC33)) susceptible to rimantadine. Hout, D.R., Gomez, L.M., Pacyniak, E., Miller, J.M., Hill, M.S., Stephens, E.B. Virology (2006) [Pubmed]
  28. Community respiratory virus infections in immunocompromised patients with cancer. Whimbey, E., Englund, J.A., Couch, R.B. Am. J. Med. (1997) [Pubmed]
  29. Safety and pharmacokinetics of rimantadine small-particle aerosol. Atmar, R.L., Greenberg, S.B., Quarles, J.M., Wilson, S.Z., Tyler, B., Feldman, S., Couch, R.B. Antimicrob. Agents Chemother. (1990) [Pubmed]
  30. Safety and efficacy of long-term use of rimantadine for prophylaxis of type A influenza in nursing homes. Monto, A.S., Ohmit, S.E., Hornbuckle, K., Pearce, C.L. Antimicrob. Agents Chemother. (1995) [Pubmed]
  31. Effect of rimantadine treatment on clinical manifestations and otologic complications in adults experimentally infected with influenza A (H1N1) virus. Doyle, W.J., Skoner, D.P., Alper, C.M., Allen, G., Moody, S.A., Seroky, J.T., Hayden, F.G. J. Infect. Dis. (1998) [Pubmed]
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