Chemistry:Adapromine
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| Other names | JP-62, MK-3 |
| Routes of administration | Oral |
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| Formula | C13H23N |
| Molar mass | 193.334 g·mol−1 |
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Adapromine is an antiviral drug of the adamantane group related to amantadine (1-aminoadamantane), rimantadine (1-(1-aminoethyl)adamantane), and memantine (1-amino-3,5-dimethyladamantane) that is marketed in Russia for the treatment and prevention of influenza.[1][2][3][4] It is an alkyl analogue 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 with resistance to adapromine and rimantadine and the related drug deitiforine were encountered in Mongolia and the Soviet 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 have psychostimulant-like and possibly antidepressant-like effects, and that these effects may be mediated via catecholaminergic processes.[8][9][10][11] These psychostimulant effects differ qualitatively from those of conventional psychostimulants like amphetamine however, and the adamantane derivatives have been described contrarily as "adaptogens" and as "actoprotectors".[12]
In 2004, it was discovered that amantadine and memantine bind to and act as agonists of the σ1 receptor (Ki = 7.44 μM and 2.60 μM, respectively) and that activation of the σ1 receptor is involved in the dopaminergic effects of amantadine at therapeutically relevant concentrations.[13] These findings might also extend to the other adamantanes such as adapromine, rimantadine, and bromantane and could explain the psychostimulant-like effects of this family of compounds.[13]
See also
References
- ↑ 1.0 1.1 "Adamantane derivatives: Pharmacological and toxicological properties (review)". Pharmaceutical Chemistry Journal 34 (1): 1–7. 2000. doi:10.1007/BF02524549. ISSN 0091-150X.
- ↑ 2.0 2.1 "Synthesis and biological activity of some 1-hydroxy-3-aminoalkyladamantanes and their derivatives". Pharmaceutical Chemistry Journal 24 (1): 35–39. 1990. doi:10.1007/BF00769383. ISSN 0091-150X.
- ↑ "Synthesis of naphtho[1,2-d]imidazoles containing an adamantyl fragment". Russian Journal of Organic Chemistry 46 (5): 777–778. 2010. doi:10.1134/S1070428010050349. ISSN 1070-4280.
- ↑ "Selective reductive dimerization of homocubane series oximes". Russian Journal of Organic Chemistry 47 (11): 1695–1702. 2011. doi:10.1134/S1070428011110078. ISSN 1070-4280.
- ↑ "Drugs for chemotherapy and prophylaxis of influenza: Mechanisms, efficacy, and safety (a review)". Pharmaceutical Chemistry Journal 38 (11): 590–596. 2004. doi:10.1007/s11094-005-0036-9. ISSN 0091-150X.
- ↑ "[The isolation and study of the properties of current influenza A viruses (H1N1) with a natural resistance to remantadine]" (in ru). Voprosy Virusologii 35 (4): 289–293. 1990. PMID 1701588.
- ↑ "[The origin of resistance to chemicals of naturally occurring isolates of influenza A virus]" (in ru). Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (9): 36–41. 1995. PMID 7580412.
- ↑ "[A spectral analysis of the effect of adapromine on brain bioelectrical activity]" (in ru). Eksperimental'naia i Klinicheskaia Farmakologiia 55 (3): 6–8. 1992. PMID 1458170.
- ↑ "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. 1998. doi:10.1007/BF02496845. ISSN 0007-4888.
- ↑ "[Comparative quantitative pharmacological-EEG analysis of the effects of psychostimulants]" (in ru). Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (6): 7–16. 1995. PMID 7627000.
- ↑ "Spectral analysis of the effect of midantane on bioelectrical activity of the rat brain". Bulletin of Experimental Biology and Medicine 112 (1): 975–978. 1991. doi:10.1007/BF00841147. ISSN 0007-4888.
- ↑ "Actoprotector and Adaptogen Properties of Adamantane Derivatives (A Review)". Pharmaceutical Chemistry Journal 35 (5): 235–238. 2001. doi:10.1023/A:1011905302667. ISSN 0091-150X.
- ↑ 13.0 13.1 "Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine". The European Journal of Neuroscience 19 (8): 2212–2220. April 2004. doi:10.1111/j.0953-816X.2004.03297.x. PMID 15090047.
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