Adapromine is anantiviral drug of theadamantane group related toamantadine (1-aminoadamantane),rimantadine (1-(1-aminoethyl)adamantane), andmemantine (1-amino-3,5-dimethyladamantane) that is marketed inRussia for the treatment and prevention ofinfluenza.[1][2][3][4] It is analkylanalogue of rimantadine and is similar to rimantadine in its antiviral activity but possesses a broader spectrum of action, being effective against influenza viruses of both type A and B.[1][2][5] Strains of type A influenza virus withresistance to adapromine and rimantadine and the related drugdeitiforine were encountered inMongolia and theSoviet Union in the 1980s.[6][7]
Electroencephalography (EEG) studies of animals suggest that adapromine and related adamantanes including amantadine,bromantane (1-amino-2-bromophenyladamantane), and memantine havepsychostimulant-like and possiblyantidepressant-like effects, and that these effects may be mediated viacatecholaminergic processes.[8][9][10][11] These psychostimulant effects differ qualitatively from those of conventional psychostimulants likeamphetamine however, and the adamantane derivatives have been described contrarily as "adaptogens" and as "actoprotectors".[12]
In 2004, it was discovered thatamantadine andmemantine bind to and act asagonists of theσ1 receptor (Ki = 7.44 μM and 2.60 μM, respectively) and that activation of the σ1 receptor is involved in thedopaminergic effects of amantadine at therapeutically relevant concentrations.[13] These findings might also extend to the other adamantanes such as adapromine,rimantadine, andbromantane and could explain the psychostimulant-like effects of this family of compounds.[13]
^abSpasov AA, Khamidova TV, Bugaeva LI, Morozov IS (2000). "Adamantane derivatives: Pharmacological and toxicological properties (review)".Pharmaceutical Chemistry Journal.34 (1):1–7.doi:10.1007/BF02524549.ISSN0091-150X.S2CID41620120.
^abLavrova LN, Indulen MK, Ryazantseva GM, Korytnyi VS, Yashunskii VG (1990). "Synthesis and biological activity of some 1-hydroxy-3-aminoalkyladamantanes and their derivatives".Pharmaceutical Chemistry Journal.24 (1):35–39.doi:10.1007/BF00769383.ISSN0091-150X.S2CID8544357.
^Gavrilova NA, Frolenko TA, Semichenko ES, Suboch GA (2010). "Synthesis of naphtho[1,2-d]imidazoles containing an adamantyl fragment".Russian Journal of Organic Chemistry.46 (5):777–778.doi:10.1134/S1070428010050349.ISSN1070-4280.S2CID94469430.
^Rodionov VN, Sklyarova AS, Shamota TV, Schreiner PR, Fokin AA (2011). "Selective reductive dimerization of homocubane series oximes".Russian Journal of Organic Chemistry.47 (11):1695–1702.doi:10.1134/S1070428011110078.ISSN1070-4280.S2CID94472143.
^Leneva IA, Glushkov RG, Gus'kova TA (2004). "Drugs for chemotherapy and prophylaxis of influenza: Mechanisms, efficacy, and safety (a review)".Pharmaceutical Chemistry Journal.38 (11):590–596.doi:10.1007/s11094-005-0036-9.ISSN0091-150X.S2CID9442971.
^Kozeletskaia KN, Grinbaum EB, Zhamsrangiĭn M, Burmistrova VV, Kiselev OI (1990). "[The isolation and study of the properties of current influenza A viruses (H1N1) with a natural resistance to remantadine]".Voprosy Virusologii (in Russian).35 (4):289–293.PMID1701588.
^Kozeletskaia KN, Karginov VA, Kiseleva OI, Mishin VP, Grinbaum EB, Burmistrova VV (1995). "[The origin of resistance to chemicals of naturally occurring isolates of influenza A virus]".Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (in Russian) (9):36–41.PMID7580412.
^Krapivin SV, Sergeeva SA, Morozov IS (1992). "[A spectral analysis of the effect of adapromine on brain bioelectrical activity]".Eksperimental'naia i Klinicheskaia Farmakologiia (in Russian).55 (3):6–8.PMID1458170.
^Krapivin SV, Sergeeva SA, Morozov IS (1998). "Comparative analysis of the effects of adapromine, midantane, and bromantane on bioelectrical activity of rat brain".Bulletin of Experimental Biology and Medicine.125 (2):151–155.doi:10.1007/BF02496845.ISSN0007-4888.S2CID21940190.
^Krapivin SV, Voronina TA (1995). "[Comparative quantitative pharmacological-EEG analysis of the effects of psychostimulants]".Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (in Russian) (6):7–16.PMID7627000.
^Krapivin SV, Sergeeva SA, Morozov IS, Dulpe IU (1991). "Spectral analysis of the effect of midantane on bioelectrical activity of the rat brain".Bulletin of Experimental Biology and Medicine.112 (1):975–978.doi:10.1007/BF00841147.ISSN0007-4888.S2CID22469427.
^Morozov IS, Ivanova IA, Lukicheva TA (2001). "Actoprotector and Adaptogen Properties of Adamantane Derivatives (A Review)".Pharmaceutical Chemistry Journal.35 (5):235–238.doi:10.1023/A:1011905302667.ISSN0091-150X.S2CID29475883.
^abPeeters M, Romieu P, Maurice T, Su TP, Maloteaux JM, Hermans E (April 2004). "Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine".The European Journal of Neuroscience.19 (8):2212–2220.doi:10.1111/j.0953-816X.2004.03297.x.PMID15090047.S2CID19479968.
^abUS patent 3352912, Prichard WW, "Adamantanes and tricyclo[4. 3. 1. 1 3.8] undecanes", issued 1967-11-14, assigned to EI Du Pont de Nemours and Co
^Aldrich PE, Hermann EC, Meier WE, Paulshock M, Prichard WW, Snyder JA, et al. (June 1971). "Antiviral agents. 2. Structure-activity relationships of compounds related to 1-adamantanamine".Journal of Medicinal Chemistry.14 (6):535–543.doi:10.1021/jm00288a019.PMID5091970.
