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Chemical Compound Review

ADAMANTANE     adamantane

Synonyms: Adamantan, Adamantine, ACMC-1CCIJ, AG-E-90056, CHEMBL1230831, ...
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Disease relevance of adamantane


Psychiatry related information on adamantane


High impact information on adamantane

  • Recovery of dP/dt at 30 minutes of reperfusion, expressed as a percentage of preischemic control, was 80% +/- 3% for the methyl adamantane hearts and 61% +/- 3% for the crystalloid hearts (p less than 0.05) [8].
  • In the present study, memantine, an adamantane derivative similar to the antiviral drug amantadine, is shown to block the channels activated by NMDA receptor stimulation [9].
  • The first single-crystal diffraction studies on methane, propane, methane/propane, and adamantane gas hydrates SI, SII, and SH have been performed [10].
  • FTIR spectra and normal-mode analysis of a tetranuclear manganese adamantane-like complex in two electrochemically prepared oxidation states: relevance to the oxygen-evolving complex of photosystem II [11].
  • 3) Fourier transform ion cyclotron resonance (FT-ICR) spectroscopy was used to determine the rate constants for proton transfer from 16 protonated reference bases to adamantane in the gas phase [12].

Chemical compound and disease context of adamantane

  • Among 470 strains tested, Streptomyces griseoplanus was highly regioselective to give 1-adamantanol (0.096 mmol) from adamantane (0.3 mmol) in a 32% molar conversion yield after 72-h cultivation in the presence of 3% (v/v) Tween 60 [13].
  • The main categories of antiherpes agents presently used in chemotherapy area reviewed according to the phase of virus replication affected : 1) virus adsorption (adamantane, nonionic surfactants) ; 2) eclipse (interferon) ; 3) virion maturation (nucleoside and nucleotide analogues and phosphonic acid derivatives) [14].

Biological context of adamantane

  • We report solid-state deuterium magic angle spinning NMR spectra of perdeuterated adamantane bound to the active site of microcrystalline cytochrome P450cam (CP450cam) in its resting state [15].
  • The basic region peptide derived from the basic leucine zipper protein GCN4 bound specifically to the native GCN4 binding sequences in a dimeric form when the beta-cyclodextrin/adamantane dimerization domain was introduced at the C-terminus of the GCN4 basic region peptide [16].
  • On the other hand, the binding of adamantane and norcamphor does not affect the kinetics [17].
  • With the beta-cyclodextrin/adamantane dimerization domain, the basic region peptide dimer preferred to bind to a palindromic 5'-ATGACGTCAT-3' sequence over the sequence lacking the central G.C base pair and that with an additional G.C base pair in the middle [16].
  • 4. It is concluded that the presence of the edited GluR2 subunit in recombinant AMPA receptors and native AMPA/kainate receptors inhibits channel block by organic cations and that adamantane derivatives are potentially valuable tools for identifying classes of AMPA/kainate receptors and their roles in synaptic transmission [18].

Anatomical context of adamantane

  • In addition, the data show that the location of the substituent group on the adamantane ring altered the molecule's capacity to modulate lymphocyte activity [19].
  • An adamantane derivative, 2, 2-Bis (4-(4-amino-3-hydroxyphenoxy) phenyl) adamantane (DPA), was found to inhibit the growth of several cancer cell lines in the National Cancer Institute (NCI) Anticancer Drug Screen system [20].
  • This result suggests that the introduction of the lipophilic adamantane moiety into [D-Ala2]Leu-enkephalin would improve the permeation of the poorly absorbed parent peptide through the blood-brain-barrier (BBB) without loss of antinociceptive effect [21].
  • Based on the physicochemical and pharmacological properties of drugs having an adamantane skeleton, an adamantane-based moiety was evaluated as a drug carrier for poorly absorbed compounds, including peptides, active towards the central nervous system (CNS) [21].
  • Newly developed antiviral compounds consisting of an adamantane derivative chemically linked to a water-soluble polyanionic matrix were shown to inhibit HIV-1 infection in lymphoblastoid cells, HeLa CD4+ beta-galactosidase (MAGI) cells and macrophages [22].

Associations of adamantane with other chemical compounds

  • Interatomic distances determined from the EXAFS data were compared to the distances observed by X-ray crystallographic analysis of adamantane-like clusters containing four and five copper atoms and a cubic cluster containing four copper atoms, structurally similar to the 4Fe-4S clusters in some ferredoxins [23].
  • Chorismate-5,6-epoxide, chorismate-5,6-diol, various adamantane derivatives and 2-hydroxy-phenyl acetate are structural analogues of chorismate that act as competitive inhibitors of both the chorismate mutase and prephenate dehydrogenase activities of the bifunctional enzyme, hydroxyphenylpyruvate synthase [24].
  • The barriers for interconverting the conformational enantiomers (stereolabile atropisomers) of pyridine-substituted adamantane derivatives have been determined by dynamic 13C NMR spectroscopy [25].
  • Using the patch-clamp technique, we studied the effect of two novel adamantane derivatives, N-[2-(3,5-dimethyl-1-adamantyl)ethyl] guanidine (CR 3391) and N-[2-(3,5-dimethyl-1-adamantyl) ethyl]acetamidine (CR 3394), on NMDA receptors expressed in cortical neuron cultures [26].
  • The fastest rates of adamantane hydroxylation with 2,6-dichloropyridine N-oxide were achieved by the reductive activation of Ru(IV)(TPFPP)Cl(2) with a zinc amalgam [27].

Gene context of adamantane

  • 2. We investigated the interaction of the adamantane derivative IEM-1460 with human wild-type and mutant AMPA-type GluR channels [28].
  • The transferrin conjugate retains high receptor binding and self-assembles with the nanoparticles by adamantane (host) and particle surface cyclodextrin (guest) inclusion complex formation [29].
  • The ratio of the 13C resonance frequencies for the two carbons in solid adamantane to the 1H resonance of TMS is reported [30].
  • The low reactivity and high selectivity (tert/sec = 8) obtained in the oxidation of adamantane suggests that the present type of peroxo species is not directly involved in catalytic Gif-type oxygenations of adamantane [31].
  • Data obtained show that adamantane and its derivative amantadine are able to inhibit the 'in vivo' interferon synthesis only when viral inductors are used; possibly by impairing the necessary stimulative action of the viral nucleic acid at the replication level [32].

Analytical, diagnostic and therapeutic context of adamantane


  1. The adamantane-derived bananins are potent inhibitors of the helicase activities and replication of SARS coronavirus. Tanner, J.A., Zheng, B.J., Zhou, J., Watt, R.M., Jiang, J.Q., Wong, K.L., Lin, Y.P., Lu, L.Y., He, M.L., Kung, H.F., Kesel, A.J., Huang, J.D. Chem. Biol. (2005) [Pubmed]
  2. Chorismate mutase-prephenate dehydrogenase from Escherichia coli: positive cooperativity with substrates and inhibitors. Christopherson, R.I., Morrison, J.F. Biochemistry (1985) [Pubmed]
  3. Biologically active polycycloalkanes. 1. Antiviral adamantane derivatives. Aigami, K., Inamoto, Y., Takaishi, N., Hattori, K., Takatsuki, A. J. Med. Chem. (1975) [Pubmed]
  4. Different modes of inhibition by adamantane amine derivatives and natural polyamines of the functionally reconstituted influenza virus M2 proton channel protein. Lin, T.I., Heider, H., Schroeder, C. J. Gen. Virol. (1997) [Pubmed]
  5. How to overcome resistance of influenza A viruses against adamantane derivatives. Scholtissek, C., Quack, G., Klenk, H.D., Webster, R.G. Antiviral Res. (1998) [Pubmed]
  6. Solutes probe hydration in specific association of cyclodextrin and adamantane. Harries, D., Rau, D.C., Parsegian, V.A. J. Am. Chem. Soc. (2005) [Pubmed]
  7. Dementia of Alzheimer's disease and other neurodegenerative disorders--memantine, a new hope. Sonkusare, S.K., Kaul, C.L., Ramarao, P. Pharmacol. Res. (2005) [Pubmed]
  8. New pluronic-free perfluorocarbon cardioplegia improves myocardial oxygenation. Johnson, D.L., Greene, P.S., Gott, V.L., Gardner, T.J. Circulation (1988) [Pubmed]
  9. Open-channel block of N-methyl-D-aspartate (NMDA) responses by memantine: therapeutic advantage against NMDA receptor-mediated neurotoxicity. Chen, H.S., Pellegrini, J.W., Aggarwal, S.K., Lei, S.Z., Warach, S., Jensen, F.E., Lipton, S.A. J. Neurosci. (1992) [Pubmed]
  10. Gas hydrate single-crystal structure analyses. Kirchner, M.T., Boese, R., Billups, W.E., Norman, L.R. J. Am. Chem. Soc. (2004) [Pubmed]
  11. FTIR spectra and normal-mode analysis of a tetranuclear manganese adamantane-like complex in two electrochemically prepared oxidation states: relevance to the oxygen-evolving complex of photosystem II. Visser, H., Dubé, C.E., Armstrong, W.H., Sauer, K., Yachandra, V.K. J. Am. Chem. Soc. (2002) [Pubmed]
  12. Ab initio and experimental thermodynamic and kinetic study of proton-assisted bond activation in gaseous hydrocarbons: deconvolution of reaction efficiencies in the case of adamantane. Dávalos, J.Z., Herrero, R., Quintanilla, E., Jiménez, P., Gal, J.F., Maria, P.C., Abboud, J.L. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  13. Regioselective hydroxylation of adamantane by Streptomyces griseoplanus cells. Mitsukura, K., Kondo, Y., Yoshida, T., Nagasawa, T. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  14. Recent advances in the chemotherapy of herpes virus infections. Eşanu, V. Virologie. (1981) [Pubmed]
  15. Deuterium magic angle spinning studies of substrates bound to cytochrome P450. Lee, H., Ortiz de Montellano, P.R., McDermott, A.E. Biochemistry (1999) [Pubmed]
  16. Stability of the dimerization domain effects the cooperative DNA binding of short peptides. Aizawa, Y., Sugiura, Y., Ueno, M., Mori, Y., Imoto, K., Makino, K., Morii, T. Biochemistry (1999) [Pubmed]
  17. High-pressure flash photolysis study of hemoprotein: effects of substrate analogues on the recombination of carbon monoxide to cytochrome P450CAM. Unno, M., Ishimori, K., Ishimura, Y., Morishima, I. Biochemistry (1994) [Pubmed]
  18. Block of open channels of recombinant AMPA receptors and native AMPA/kainate receptors by adamantane derivatives. Magazanik, L.G., Buldakova, S.L., Samoilova, M.V., Gmiro, V.E., Mellor, I.R., Usherwood, P.N. J. Physiol. (Lond.) (1997) [Pubmed]
  19. Inhibition of lymphocyte proliferation by amantadine and its isomer, 2-aminoadamantane; impact on Lyt-2+ T cells while sparing L3T4+ T cells. Clark, C., Woodson, M.M., Nagasawa, H.T. Immunopharmacology (1991) [Pubmed]
  20. The antitumor effect of a novel differentiation inducer, 2, 2-Bis (4-(4-amino-3-hydroxyphenoxy) phenyl) adamantane (DPA), in combinatory therapy on human colon cancer. Wang, J.J., Lee, J.Y., Chen, Y.C., Chern, Y.T., Chi, C.W. Int. J. Oncol. (2006) [Pubmed]
  21. Synthesis and antinociceptive activity of [D-Ala2]Leu-enkephalin derivatives conjugated with the adamantane moiety. Kitagawa, K., Mizobuchi, N., Hama, T., Hibi, T., Konishi, R., Futaki, S. Chem. Pharm. Bull. (1997) [Pubmed]
  22. Inhibition of HIV-1 replication by newly developed adamantane-containing polyanionic agents. Burstein, M.E., Serbin, A.V., Khakhulina, T.V., Alymova, I.V., Stotskaya, L.L., Bogdan, O.P., Manukchina, E.E., Jdanov, V.V., Sharova, N.K., Bukrinskaya, A.G. Antiviral Res. (1999) [Pubmed]
  23. Structure of the copper cluster in canine hepatic metallothionein using X-ray absorption spectroscopy. Freedman, J.H., Powers, L., Peisach, J. Biochemistry (1986) [Pubmed]
  24. Partial inactivation of chorismate mutase-prephenate dehydrogenase from Escherichia coli in the presence of analogues of chorismate. Christopherson, R.I. Int. J. Biochem. Cell Biol. (1997) [Pubmed]
  25. Conformational studies by dynamic NMR. 100. Enantiomerization process of stereolabile atropisomers in pyridine-substituted adamantane derivatives. Casarini, D., Coluccini, C., Lunazzi, L., Mazzanti, A., Rompietti, R. J. Org. Chem. (2004) [Pubmed]
  26. Functional in vitro characterization of CR 3394: a novel voltage dependent N-methyl-D-aspartate (NMDA) receptor antagonist. Losi, G., Lanza, M., Makovec, F., Artusi, R., Caselli, G., Puia, G. Neuropharmacology (2006) [Pubmed]
  27. Fast catalytic hydroxylation of hydrocarbons with ruthenium porphyrins. Wang, C., Shalyaev, K.V., Bonchio, M., Carofiglio, T., Groves, J.T. Inorganic chemistry. (2006) [Pubmed]
  28. Two mechanisms of action of the adamantane derivative IEM-1460 at human AMPA-type glutamate receptors. Schlesinger, F., Tammena, D., Krampfl, K., Bufler, J. Br. J. Pharmacol. (2005) [Pubmed]
  29. Transferrin-containing, cyclodextrin polymer-based particles for tumor-targeted gene delivery. Bellocq, N.C., Pun, S.H., Jensen, G.S., Davis, M.E. Bioconjug. Chem. (2003) [Pubmed]
  30. Chemical shift referencing in MAS solid state NMR. Morcombe, C.R., Zilm, K.W. J. Magn. Reson. (2003) [Pubmed]
  31. Synthesis, characterization, and reactivity of ferrous and ferric oxo/peroxo pivalate complexes in relation to Gif-type oxygenation of substrates. Celenligil-Cetin, R., Staples, R.J., Stavropoulos, P. Inorganic chemistry. (2000) [Pubmed]
  32. 'In vivo' variations in serum interferon levels produced by antiviral compounds. Minguez, F., Alonso, M.L., Moya, P., Ronda, E. Chemotherapy. (1983) [Pubmed]
  33. Bilayer vesicles of amphiphilic cyclodextrins: host membranes that recognize guest molecules. Falvey, P., Lim, C.W., Darcy, R., Revermann, T., Karst, U., Giesbers, M., Marcelis, A.T., Lazar, A., Coleman, A.W., Reinhoudt, D.N., Ravoo, B.J. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  34. Phase transition in a lipid bilayer. II. Influence of adamantane derivatives. Jain, M.K., Wu, N.Y., Morgan, T.K., Briggs, M.S., Murray, R.K. Chem. Phys. Lipids (1976) [Pubmed]
  35. Controlled synthesis and inclusion ability of a hyaluronic acid derivative bearing beta-cyclodextrin molecules. Charlot, A., Heyraud, A., Guenot, P., Rinaudo, M., Auzély-Velty, R. Biomacromolecules (2006) [Pubmed]
  36. Molecular, crystal and solution structure of a beta-cyclodextrin complex with the bromide salt of 2-(3-dimethylaminopropyl)tricyclo[,7)]decan-2-ol, a potent antimicrobial drug. Perrakis, A., Antoniadou-Vyza, E., Tsitsa, P., Lamzin, V.S., Wilson, K.S., Hamodrakas, S.J. Carbohydr. Res. (1999) [Pubmed]
  37. Towards nanomedicine with a supramolecular approach: a review. Cao, R., Villalonga, R., Fragoso, A. IEE proceedings. Nanobiotechnology. (2005) [Pubmed]
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