<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE root>
<article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" article-type="research-article" dtd-version="1.1d1" xml:lang="en"><front><journal-meta><journal-id journal-id-type="publisher">Problems of Social Hygiene, Public Health and History of Medicine</journal-id><journal-title-group><journal-title>Problems of Social Hygiene, Public Health and History of Medicine</journal-title></journal-title-group><issn publication-format="print">0869-866X</issn><issn publication-format="electronic">2412-2106</issn><publisher><publisher-name>Joint-Stock Company Chicot</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="publisher-id">420</article-id><article-id pub-id-type="doi">10.32687/0869-866X-2020-28-s2-1118-1122</article-id><article-categories><subj-group subj-group-type="heading"><subject>Научная статья</subject></subj-group></article-categories><title-group><article-title>History of aminoquinoline preparations: from cinchona bark to chloroquine and hydroxychloroquinon</article-title></title-group><contrib-group><contrib contrib-type="author"><name name-style="western"><surname>Tolkushin</surname><given-names>A. G.</given-names></name><bio></bio><email>-</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author"><name name-style="western"><surname>Luchinin</surname><given-names>E. A.</given-names></name><bio></bio><email>-</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author"><name name-style="western"><surname>Kholovnya-Voloskova</surname><given-names>M. E.</given-names></name><bio></bio><email>kholovnyame@zdrav.mos.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author"><name name-style="western"><surname>Zavyalov</surname><given-names>A. A.</given-names></name><bio></bio><email>-</email><xref ref-type="aff" rid="aff-1"/></contrib></contrib-group><aff id="aff-1">State Budgetary Institution “Research Institute for Healthcare Organization and Medical Management of Moscow Healthcare Department”</aff><pub-date date-type="epub" iso-8601-date="2020-12-15" publication-format="electronic"><day>15</day><month>12</month><year>2020</year></pub-date><volume>28</volume><fpage>1118</fpage><lpage>1122</lpage><history><pub-date date-type="received" iso-8601-date="2021-04-06"><day>06</day><month>04</month><year>2021</year></pub-date></history><permissions><copyright-statement>Copyright © 2020,</copyright-statement><copyright-year>2020</copyright-year></permissions><abstract>The article presents a review of the historical facts related to the discovery and introduction of chloroquine and hydroxychloroquine. The history of studying aminoquinoline preparations is associated with the discovery of the antimalarial action of the bark of the quinine tree, the isolation of quinine from other active substances - alkaloids and the determination of their structure. The structural similarity of quinine and one of the first chemically synthesized dyes - methylene blue-was an important factor at the beginning of the synthesis of molecules with antimalarial activity in the 1930s in Germany. Pamaquin (plasmoquin, plasmoсid), quinacrine (quinacrine, Atebrin, Mepacrine), sontoquine (sontochin), chloroquine, primaquine, hydroxychloroquine, and mefloquine (Lariam) were consistently introduced in medical practice. Many of these medications are no longer widely used. However, chloroquine and hydroxychloroquine have not lost their relevance. The scope of their use has been expanded.</abstract><kwd-group xml:lang="en"><kwd>chloroquine</kwd><kwd>hydroxychloroquine</kwd><kwd>history of antimalarial aminoquinoline medicines</kwd></kwd-group><kwd-group xml:lang="ru"><kwd>хлорохин</kwd><kwd>гидроксихлорохин</kwd><kwd>история противомалярийных аминохинолиновых лекарственных препаратов</kwd></kwd-group></article-meta></front><body></body><back><ref-list><ref id="B1"><label>1.</label><mixed-citation>Flückiger F. A., Hanbury D. Pharmacographia: a history of the principle drugs of vegetable origin, met with in Great Britain and British India. London: MacMillan and Co.; 1874:302-31.</mixed-citation></ref><ref id="B2"><label>2.</label><mixed-citation>Guerra F. The introduction of Cinchona in the treatment of malaria, parts 1 and 2. J. Trop. Med. Hyg. 1977;80(6):112-8;135-40.</mixed-citation></ref><ref id="B3"><label>3.</label><mixed-citation>Yalcindag E., Elguero E., Arnathau C., Durand P., Akiana J., Anderson T. J., et al. Multiple independed introductions of Plasmodium falciparum in South America. PNAS. 2012;109(2):511-6. doi: 10.1073/pnas.1119058109</mixed-citation></ref><ref id="B4"><label>4.</label><mixed-citation>Jarcho S. Quinine's Predecessor: Francesco Torti and the Early History of Cinchona. Baltimore, Maryland: Johns Hopkins University Press; 1993.</mixed-citation></ref><ref id="B5"><label>5.</label><mixed-citation>Поляков В. Е. Открытия Самуэля Ганемана и история зарождения гомеопатии. Педиатрия. Журнал им. Г. Н. Сперанского. 2015;94(4):99-104.</mixed-citation></ref><ref id="B6"><label>6.</label><mixed-citation>Sappington J., Stith F. The Theory and Treatment of Fevers. Arrow Rock [Mo.]; 1844. Режим доступа: https://historicmissourians.shsmo.org/historicmissourians/name/s/sappington/</mixed-citation></ref><ref id="B7"><label>7.</label><mixed-citation>Pelletier P., Caventou J. B. Recherches chimiques sur les quinquinas. Ann. Chim. Phys. 1820;15:289-318.</mixed-citation></ref><ref id="B8"><label>8.</label><mixed-citation>Chopra R. N. Anti-malarial remedies: natural and synthetic. Calcutta Med. J. 1938;34:183-93.</mixed-citation></ref><ref id="B9"><label>9.</label><mixed-citation>Dickson D. J.H. On the febrifuge power of the sulphate of quinine. Edinb. Med. Surg. J. 1823;19(77):571-3.</mixed-citation></ref><ref id="B10"><label>10.</label><mixed-citation>Grove to be sold to bristol-myers. New York Times. Section Business Finance. 1957. P. 35. Режим доступа: https://www.nytimes.com/1957/11/09/archives/grove-to-be-sold-to-bristolmyers-bromoquinine-4way-and-fitch-line.html Режим доступа: https://mycompanies.fandom.com/wiki/Grove_Laboratories https://tennesseeencyclopedia.net/entries/edwin-wiley-grove/</mixed-citation></ref><ref id="B11"><label>11.</label><mixed-citation>Taylor N. Cinchona in Java: the story of quinine. New York: Greenburg; 1945.</mixed-citation></ref><ref id="B12"><label>12.</label><mixed-citation>Strecker A. Untersuchungenüber die Constitution des Chinins. Liebigs Ann. 1854;1:155-70.</mixed-citation></ref><ref id="B13"><label>13.</label><mixed-citation>Schulemann W. Synthetic anti-malarial preparations: a discussion of the various steps which led to the synthesis and discovery of «plasmoquine» and a brief account of its use in tropical medicine. Proc. Roy. Soc. Med. 1932;25:897-905.</mixed-citation></ref><ref id="B14"><label>14.</label><mixed-citation>Горелова Л. Е. Из истории борьбы с малярией. Русский медицинский журнал. 2009;(7):503-4.</mixed-citation></ref><ref id="B15"><label>15.</label><mixed-citation>Campbell N. A., Reece J. B., Heyden R. «Biology» Seventh edition. Menlo Park,: Addison Wesley Longman, Inc; 2005.</mixed-citation></ref><ref id="B16"><label>16.</label><mixed-citation>Hückel W. Vorlesungen über Pharmazeutische Chemie und Arzneimittelsynthese, II. Band, Organische Teil. Stuttgart: Enke; 1962.</mixed-citation></ref><ref id="B17"><label>17.</label><mixed-citation>Guttmann P., Ehrlich P. Über die Wirkung des Methylenblaubei Malaria. Klin. Wochenschr. 1891;28:953-6.</mixed-citation></ref><ref id="B18"><label>18.</label><mixed-citation>An epitome of current medical literature. Suppl. BMJ. 1892;47.</mixed-citation></ref><ref id="B19"><label>19.</label><mixed-citation>Funk E., Potter S. L. Potter's therapeutics, materia medica, and pharmacy. Philadelphia: P. Blakiston's Son &amp; Co.; 1917. 733 p.</mixed-citation></ref><ref id="B20"><label>20.</label><mixed-citation>Kikuth W. Zur Frage der Malaria Prophylaxe. Hoppe Seylers Z. Physiol. Chem. 1942;274:9-18.</mixed-citation></ref><ref id="B21"><label>21.</label><mixed-citation>Covell G., Nicol W. D. Clinical, chemotherapeutic, and immunological studies on induced malaria. Br. Med. Bull. 1951;8(1):51-5.</mixed-citation></ref><ref id="B22"><label>22.</label><mixed-citation>Chernin E. The malaria therapy of neurosyphilis. J. Parasitol. 1984;70(5):611-7.</mixed-citation></ref><ref id="B23"><label>23.</label><mixed-citation>Burrows J. N., Chibale K., Wells T. N.C. The state of the art in anti-malarial drug discovery and development. Curr. Top. Med. Chem. 2011;11:1226-54.</mixed-citation></ref><ref id="B24"><label>24.</label><mixed-citation>Chopra R. N. Anti-malarial remedies: natural and synthetic. Calcutta Med. J. 1938;34:183-93.</mixed-citation></ref><ref id="B25"><label>25.</label><mixed-citation>Кнунянц И. Л., Топчиев К. С., Челинцев Г. В. Строение и синтез новых антималярийных веществ. I. Плазмохин. Известия Академии наук СССР. VII серия. Отделение математических и естественных наук. 1934;(1):153-64.</mixed-citation></ref><ref id="B26"><label>26.</label><mixed-citation>Elderfield R. C., Gensler W. J., Head J. D., Hageman H. A., Kremer C. B., Wright J. B., et al. Alkylaminoalkyl derivatives of 8-aminoquinoline. J. Am. Chem. Soc. 1946;68(8):1524-9.</mixed-citation></ref><ref id="B27"><label>27.</label><mixed-citation>Mauss H., Mietzsch F. Atebrin, ein neues Heilmittel gegen Malaria. Klin. Wochenschr. 1933;12(33):1276-8.</mixed-citation></ref><ref id="B28"><label>28.</label><mixed-citation>Mietzsch F. Entwicklungslinien der Chemotherapie (vom chemischen Standpunktgesehen). Klin. Wochenschr. 1951;29(7-8):125-35.</mixed-citation></ref><ref id="B29"><label>29.</label><mixed-citation>Greenwood D. Conflicts of interest: the genesis of synthetic antimalarial agents in peace and war. J. Antimicrobial Chem. 1995;36:857-72.</mixed-citation></ref><ref id="B30"><label>30.</label><mixed-citation>Kodak to Sell Drug Unit for $1.68 Billion. Los Angeles Times. June 24, 1994 (accessed 03.05.2013).</mixed-citation></ref><ref id="B31"><label>31.</label><mixed-citation>Olmos D. German firm to reclaim Bayer aspirin name: drugs: it will acquire Sterling Winthrop's over-the-counter business and recover the rights it lost after WWI. Los Angeles Times. September 14, 1994 (accessed 03.05.2013).</mixed-citation></ref><ref id="B32"><label>32.</label><mixed-citation>Кнунянц И. Л., Челинцев Г. В., Беневоленская З. В., Осетрова Е. Д., Курсанова А. И. Строение и синтез новых антималярийных веществ. III. Синтез «Атебрина». Известия Академии наук СССР. VII серия. Отделение математических и естественных наук. 1934;(1):165-76.</mixed-citation></ref><ref id="B33"><label>33.</label><mixed-citation>«Акрихин» - гордость второй пятилетки. Очерки по истории предприятия. Исторический вестник РХТУ. 2016;48:9-14.</mixed-citation></ref><ref id="B34"><label>34.</label><mixed-citation>Andersag H. Antimalariamittel aus der Gruppehalogensubstitutierter Chinolinverbindungen. Chem. Ber. 1948;81:499-507.</mixed-citation></ref><ref id="B35"><label>35.</label><mixed-citation>Wiselogle F. Y. A survey of antimalarial drugs, 1941-1945. Ann Arbor: Edwards, 1946: 987 р.</mixed-citation></ref><ref id="B36"><label>36.</label><mixed-citation>Slater L. B. War and disease: biomedical research on malaria in the twentieth century. New Brunswick, New Jersey: Rutgers University Press; 2009.</mixed-citation></ref><ref id="B37"><label>37.</label><mixed-citation>Schlitzer M. Malaria chemotherapeutics. Рart I: History of antimalarial drug development, currently used therapeutics, and drugs in clinical development. Chem. Med. Chem. 2007;2:944-86.</mixed-citation></ref><ref id="B38"><label>38.</label><mixed-citation>Vale N., Moreira R., Gomes P. Primaquine revisited six decades after its discovery. Eur. J. Med. Chem. 2009;44(3):937-53. doi:10.1016/j.ejmech.2008.08.011</mixed-citation></ref><ref id="B39"><label>39.</label><mixed-citation>Ashley E. A., Recht J., White N. J. Primaquine: the risks and the benefits. Malar. J. 2014;13:418.</mixed-citation></ref><ref id="B40"><label>40.</label><mixed-citation>Haston J. C., Hwang J., Tan K. R. Guidance for using tafenoquine for prevention and antirelapse therapy for malaria - United States. Morbid. Mortal. Weekly Rep. 2019;68(46):1062-8. doi: 10.15585/mmwr.mm6846a4</mixed-citation></ref><ref id="B41"><label>41.</label><mixed-citation>Hounkpatin A. B., Kreidenweiss A., Held J. Clinical utility of tafenoquine in the prevention of relapse of Plasmodium vivax malaria: a review on the mode of action and emerging trial data. Infect. Drug Resist. 2019;12:553-70. doi:10.2147/IDR.S151031</mixed-citation></ref><ref id="B42"><label>42.</label><mixed-citation>Avina-Zubieta J. A., Galindo-Rodriguez G., Newman S., Suarez-Almazor M. E., Russell A. S. Long term effectiveness of antimalarial drugs in rheumatic diseases. Ann. Rheum. Dis. 1998;57:582-7. doi: 10.1136/ard.57.10.582</mixed-citation></ref><ref id="B43"><label>43.</label><mixed-citation>Quinacrine sterilization: reports on 40,252 cases. Int. J. Gynaecol. Obstet. 2003;83Suppl2:S1-S159.</mixed-citation></ref></ref-list></back></article>
