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Chemical Compound Review

Symadine     adamantan-1-amine

Synonyms: Mantadine, Symmetrel, Wiregyt, Amantadina, amantadine, ...
 
 
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Disease relevance of Adamantylamine

 

Psychiatry related information on Adamantylamine

 

High impact information on Adamantylamine

 

Chemical compound and disease context of Adamantylamine

  • The effect of weak bases (NH4Cl and amantadine) and carboxylic ionophores (monensin) on the infection of CD4 (T4) positive human cell lines by HIV-1 is examined [16].
  • Tremulous jaw movements are induced by many of the conditions that are associated with parkinsonism, and suppressed by several different antiparkinsonian drugs, including scopolamine, benztropine, L-DOPA, apomorphine, bromocriptine, amantadine and clozapine [17].
  • Four hundred previously untreated patients with histologically proven chronic hepatitis C were randomly allocated to treatment with amantadine sulphate (100 mg twice daily orally) or a matched placebo together with IFN-alpha induction plus ribavirin (1,000-1,200 mg/day orally) for 48 weeks [18].
  • For example, amantadine, given as an adjuvant to levodopa, has been shown to improve dyskinesias, but larger, controlled studies are required [19].
  • This case report of neuroleptic malignant syndrome following withdrawal of neuroleptics and amantadine suggests that dopamine agonists should not be discontinued in hyperpyrexic patients at risk for this syndrome [20].
 

Biological context of Adamantylamine

 

Anatomical context of Adamantylamine

 

Associations of Adamantylamine with other chemical compounds

  • Reversal by mM concentrations of amines and 0.1 microM monensin indicates that amantadine action causes a reduction in intravesicular pH which triggers the conformational change in HA [29].
  • Vaccinating hospital personnel with influenza vaccine and, if influenza A is prevalent, giving amantadine hydrochloride to high-risk patients or personnel should both be considered [30].
  • In temporal association with ribavirin administration, viral shedding diminished in one patient and ceased in two patients, one of whom had developed virus resistant to amantadine [31].
  • Cyclosporin A, benzyloxycarbonyl-D-Phe-L-Phe-Gly, and amantadine inhibit the dilution of fluorescently labeled lipids, as measured with the resonance energy exchange assay for membrane fusion [32].
  • Four "amadoriase" enzyme fractions, which oxidatively degrade glycated low molecular weight amines and amino acids under formation of hydrogen peroxide and glucosone, were isolated from an Aspergillus sp. soil strain selected on fructosyl adamantanamine as sole carbon source [33].
 

Gene context of Adamantylamine

 

Analytical, diagnostic and therapeutic context of Adamantylamine

  • In a boarding school for boys, where routine influenza vaccination is carried out annually, 267 boys were given amantadine (100 mg daily) and 269 received no specific treatment during an influenza A (H1N1) outbreak [38].
  • A double-blind study was carried out to assess the efficacy (and adverse effects) of amantadine hydrochloride--an agent without appreciable anticholinergic activity--for the treatment of drug-induced EPS [39].
  • We present guidelines for use of amantadine in patients with impaired renal function, including those on maintenance hemodialysis [21].
  • The virologic on-treatment response rate in week 24 was significantly higher in the amantadine group as compared with the control group (70% vs. 59%, respectively, P =.016) [18].
  • In a double-blind placebo-controlled crossover study of 39 psychiatric inpatients, amantadine and trihexyphenidyl were equally effective in treating drug-induced parkinsonism, and amantadine produced fewer and less severe side effects [40].

References

  1. Persistent hiccup cured by amantadine. Askenasy, J.J., Boiangiu, M., Davidovitch, S. N. Engl. J. Med. (1988) [Pubmed]
  2. Influenza virus. Amantadine blocks the channel. Skehel, J.J. Nature (1992) [Pubmed]
  3. Influenza virus neuraminidase inhibitors. Gubareva, L.V., Kaiser, L., Hayden, F.G. Lancet (2000) [Pubmed]
  4. Depression, Borna disease, and amantadine. Lieb, K., Hufert, F.T., Bechter, K., Bauer, J., Kornhuber, J. Lancet (1997) [Pubmed]
  5. Letter: Amantadine in chorea. Gray, M.W., Herzberg, L., Lerman, J.A., Turnbull, M.J., Victoratos, G. Lancet (1975) [Pubmed]
  6. Amantadine and human Borna disease virus in vitro and in vivo in an infected patient with bipolar depression. Bode, L., Dietrich, D.E., Stoyloff, R., Emrich, H.M., Ludwig, H. Lancet (1997) [Pubmed]
  7. Four-year treatment of patients with parkinsonism using amantadine alone or with levodopa. Timberlake, W.H., Vance, M.A. Ann. Neurol. (1978) [Pubmed]
  8. Amantadine in the treatment of cocaine-dependent patients with severe withdrawal symptoms. Kampman, K.M., Volpicelli, J.R., Alterman, A.I., Cornish, J., O'Brien, C.P. The American journal of psychiatry. (2000) [Pubmed]
  9. Amantadine treatment is an independent predictor of improved survival in Parkinson's disease. Uitti, R.J., Rajput, A.H., Ahlskog, J.E., Offord, K.P., Schroeder, D.R., Ho, M.M., Prasad, M., Rajput, A., Basran, P. Neurology (1996) [Pubmed]
  10. Huntington's disease: a randomized, controlled trial using the NMDA-antagonist amantadine. Verhagen Metman, L., Morris, M.J., Farmer, C., Gillespie, M., Mosby, K., Wuu, J., Chase, T.N. Neurology (2002) [Pubmed]
  11. A controlled trial of amantadine and rimantadine in the prophylaxis of influenza A infection. Dolin, R., Reichman, R.C., Madore, H.P., Maynard, R., Linton, P.N., Webber-Jones, J. N. Engl. J. Med. (1982) [Pubmed]
  12. Activity of a monoclonal antibody-saporin-6 conjugate against B-lymphoma cells. Bregni, M., Lappi, D.A., Siena, S., Formosa, A., Villa, S., Soria, M., Bonadonna, G., Gianni, A.M. J. Natl. Cancer Inst. (1988) [Pubmed]
  13. Neuraminidase inhibitor and amantadine. Dawson, J. Lancet (2000) [Pubmed]
  14. Amantadine in chronic granulomatous disease. Warner, J.O. Lancet (1985) [Pubmed]
  15. Letter: Cardiovascular maldevelopment associated with maternal exposure to amantadine. Nora, J.J., Nora, A.H., Way, G.L. Lancet (1975) [Pubmed]
  16. Human immunodeficiency virus infection of CD4-bearing cells occurs by a pH-independent mechanism. McClure, M.O., Marsh, M., Weiss, R.A. EMBO J. (1988) [Pubmed]
  17. Tremulous jaw movements in rats: a model of parkinsonian tremor. Salamone, J.D., Mayorga, A.J., Trevitt, J.T., Cousins, M.S., Conlan, A., Nawab, A. Prog. Neurobiol. (1998) [Pubmed]
  18. Triple therapy with amantadine in treatment-naive patients with chronic hepatitis C: a placebo-controlled trial. Berg, T., Kronenberger, B., Hinrichsen, H., Gerlach, T., Buggisch, P., Herrmann, E., Spengler, U., Goeser, T., Nasser, S., Wursthorn, K., Pape, G.R., Hopf, U., Zeuzem, S. Hepatology (2003) [Pubmed]
  19. Medical treatment of levodopa-induced dyskinesias. Rascol, O. Ann. Neurol. (2000) [Pubmed]
  20. Case report of neuroleptic malignant syndrome associated with withdrawal from amantadine. Simpson, D.M., Davis, G.C. The American journal of psychiatry. (1984) [Pubmed]
  21. Pharmacokinetics of amantadine hydrochloride in subjects with normal and impaired renal function. Horadam, V.W., Sharp, J.G., Smilack, J.D., McAnalley, B.H., Garriott, J.C., Stephens, M.K., Prati, R.C., Brater, D.C. Ann. Intern. Med. (1981) [Pubmed]
  22. Amantadine and dansylcadaverine inhibit vesicular stomatitis virus uptake and receptor-mediated endocytosis of alpha 2-macroglobulin. Schlegel, R., Dickson, R.B., Willingham, M.C., Pastan, I.H. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  23. Amino acid variations in hepatitis C virus p7 and sensitivity to antiviral combination therapy with amantadine in chronic hepatitis C. Mihm, U., Grigorian, N., Welsch, C., Herrmann, E., Kronenberger, B., Teuber, G., von Wagner, M., Hofmann, W.P., Albrecht, M., Lengauer, T., Zeuzem, S., Sarrazin, C. Antivir. Ther. (Lond.) (2006) [Pubmed]
  24. Amantadine inhibits the function of an ion channel encoded by GB virus B, but fails to inhibit virus replication. Premkumar, A., Dong, X., Haqshenas, G., Gage, P.W., Gowans, E.J. Antivir. Ther. (Lond.) (2006) [Pubmed]
  25. Synthesis and characterization of an antihuman T-lymphocyte saporin immunotoxin (OKT1-SAP) with in vivo stability into nonhuman primates. Siena, S., Lappi, D.A., Bregni, M., Formosa, A., Villa, S., Soria, M., Bonadonna, G., Gianni, A.M. Blood (1988) [Pubmed]
  26. The active oligomeric state of the minimalistic influenza virus M2 ion channel is a tetramer. Sakaguchi, T., Tu, Q., Pinto, L.H., Lamb, R.A. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  27. Amantadine potentiates T lymphocyte killing by an anti-pan-T cell (CD5) ricin A-chain immunotoxin. Siena, S., Villa, S., Bregni, M., Bonnadonna, G., Gianni, A.M. Blood (1987) [Pubmed]
  28. Amantadine-induced afterpotentials and automaticity in guinea pig ventricular myocytes. Hiraoka, M., Hirano, Y., Kawano, S., Fan, Z., Sawanobori, T. Circ. Res. (1989) [Pubmed]
  29. Specific structural alteration of the influenza haemagglutinin by amantadine. Sugrue, R.J., Bahadur, G., Zambon, M.C., Hall-Smith, M., Douglas, A.R., Hay, A.J. EMBO J. (1990) [Pubmed]
  30. Control of influenza in the hospital. Hoffman, P.C., Dixon, R.E. Ann. Intern. Med. (1977) [Pubmed]
  31. Intravenous ribavirin by constant infusion for serious influenza and parainfluenzavirus infection. Hayden, F.G., Sable, C.A., Connor, J.D., Lane, J. Antivir. Ther. (Lond.) (1996) [Pubmed]
  32. Effects of viral chemotherapeutic agents on membrane properties. Studies of cyclosporin A, benzyloxycarbonyl-D-Phe-L-Phe-Gly and amantadine. Epand, R.M., Epand, R.F., McKenzie, R.C. J. Biol. Chem. (1987) [Pubmed]
  33. Isolation, purification, and characterization of amadoriase isoenzymes (fructosyl amine-oxygen oxidoreductase EC 1.5.3) from Aspergillus sp. Takahashi, M., Pischetsrieder, M., Monnier, V.M. J. Biol. Chem. (1997) [Pubmed]
  34. Effects of amantadine treatment on in vitro production of interleukin-2 in de-novo patients with idiopathic Parkinson's disease. Wandinger, K.P., Hagenah, J.M., Klüter, H., Rothermundt, M., Peters, M., Vieregge, P. J. Neuroimmunol. (1999) [Pubmed]
  35. Trapping channel block of NMDA-activated responses by amantadine and memantine. Blanpied, T.A., Boeckman, F.A., Aizenman, E., Johnson, J.W. J. Neurophysiol. (1997) [Pubmed]
  36. Amantadine inhibits RANTES production by influenzavirus-infected human bronchial epithelial cells. Asai, Y., Hashimoto, S., Kujime, K., Gon, Y., Mizumura, K., Shimizu, K., Horie, T. Br. J. Pharmacol. (2001) [Pubmed]
  37. Amantadine acetylation may be effected by acetyltransferases other than NAT1 or NAT2. Bras, A.P., Hoff, H.R., Aoki, F.Y., Sitar, D.S. Can. J. Physiol. Pharmacol. (1998) [Pubmed]
  38. Influenza A prophylaxis with amantadine in a boarding school. Payler, D.K., Purdham, P.A. Lancet (1984) [Pubmed]
  39. A controlled trial of amantadine in drug-induced extrapyramidal disorders. DiMascio, A., Bernardo, D.L., Greenblatt, D.J., Marder, J.E. Arch. Gen. Psychiatry (1976) [Pubmed]
  40. Amantadine versus trihexyphenidyl in the treatment of neuroleptic-induced parkinsonism. Fann, W.E., Lake, C.R. The American journal of psychiatry. (1976) [Pubmed]
 
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