Amantadine: an antiviral and antiparkinsonian agent

Abstract

ABSTRACT:In this article, we deal with the 80th birthday of Prof. Jozef Vodrážka, M.V.D., D.Sc., and also with 52-year history of the Department of Pharmacology, since the establishment of the University of Veterinary Medicine in Košice, Slovak Republic, in the academic year 1949/1950. Our goal is to provide the basic information about the history of the Department of Pharmacology. We also describe the activity of its full-time staff as well as some other people (undergraduate and postgraduate home students, and some foreign visiting teachers and scientists) in a summary form. In conclusion we can say that the history of this department and its people has been very rich and highly productive, not only in their scientific and publishing activities but also in the pedagogical and intellectual orientation of the section. We hope that this tendency will remain not only in the nearest but also in more distant future to enhance the reputation of the University of Veterinary Medicine, Košice.

A Convenient Road to 1‐Chloropentacycloundecanes – A Joint Experimental and Computational Investigation

“…Subsequent addition of pyridine (19.7 g, 0.25 mol) at 0°C immediately gave pyridinium chlorochromate as yellow-orange solid (45 g, 84 %). ]-undecane-8,11-dione was prepared accord-ing to a literature method, [56] which uses the Diels-Alder reaction of p-benzoquinone and cyclopentadiene to yield endo-tricyclo[6.2.1.0 2,7 ]undeca-4,9-dien-3,6-dione. Irradiation (low-pressure mercury UV lamp, 300 W) of the diene-dione in ethyl acetate gave 4 in 90 % yield; m.p.…”

“…Interest in the pharmacology of polycyclic cage amines was stimulated by early findings that adamantane amine, 1-amino-adamantane or amantadine, had antiviral activity against a variety of viruses, including influenza, [1,2] hepatitis C [3,4] and herpes zoster neuralgia. [5,6] Amantadine is a specific inhibitor of the M2 ion channel of the influenza virus and is believed to form a hydrogen bond with a histidine residue (His-37) in the M2 protein, effectively blocking the ion channel.…”

“…It was recently suggested that, "the polycyclic cage structure seems to be ideally suited for developing multiple mechanism drugs, as it can both serve as a scaffold for the drug molecule proper, or as a moiety that may be added to improve the pharmacokinetic properties of drugs currently used in the clinic, or drug candidates under development." [24] Both, adamantane (1) (T d symmetry) and D 3 -symmetrical trishomocubane, pentacyclo[6.3.0.0 2,6 .0 3,10 .0 5,9 ]-undecane (2), have a relatively large hydrocarbon cage size (ca. 5.5 Å), high lipophilicity and are conformationally rigid.…”

“…The reasons for this are limited synthetic methods, harsh reaction conditions, and often unsatisfactory yields of the desired D 3 -trishomocubane derivatives. The majority of synthetic routes to 2 and its derivatives are based on rearrangements of the carbon cage of isomeric cage structures, usually pentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane (C strishomocubane, 3).…”

NMR elucidation of novel SQ109 derivatives

“…However, its pharmaceutical importance only drew increased attention after the discovery of 1-amino-adamantane or amantadine. This molecule possesses anti-viral activity against several species including hepatitis C [11] and the influenza virus [12,13]. Memantine is another important amino-adamantane used in the clinical treatment of Alzheimer's disease ( Fig.…”