THE DEVELOPMENTAL PATH OF QUININE: WHAT CAN WE LEARN FROM HISTORY?

  • Aleksandar Jovanović Univerzitet u Nišu – Medicinski fakultet, Katedra za farmaciju
  • Dušanka Krajnović University of Belgrade - Faculty of Pharmacy, Department of Social Pharmacy and Pharmaceutical Legislation
Keywords: quinine, history of pharmacy, drug development, antimalarial drugs

Abstract


Almost 200 years have passed since the pure substance was first isolated, but scientists still face similar challenges. Quinine—the first chemotherapeutic agent in the treatment of malaria—is one of the good examples from history that testifies to the challenges in drug development.

The aim of the paper was to present the history of the discovery and synthesis of quinine and its importance in medicine.

Descriptive research was conducted using secondary data sources during September and October 2022.

Quinine is one of the first active substance whose effectiveness has been proven in clinical research. Its widespread consumption soon led to a shortage of quinine, and new sources of this valuable active substance had to be provided. The challenges of plantation cultivation were solved by developing botany and its chemical synthesis through organic chemistry. By researching quinine, numerous pharmacologically active substances such as caffeine and methylene blue were found, which would start a revolution in the chemical industry and the industry of organic synthesis. With the development of resistance to antimalarials, quinine experienced its heyday again because it proved to be effective even in resistant strains.

Quinine represents a significant historical discovery that influenced the development of many scientific disciplines, primarily pharmacy, medicine, and organic chemistry. The history of quinine provides us with an important historical lesson that we need to be aware of in today's time when the pharmacy is facing the significant challengesof developing new drugs. 

References

Achan J, Talisuna AO, Erhart A, Yeka A, Tibenderana JK, Baliraine FN, et al. Quinine, an old anti-malarial drug in a modern world: role in the treatment of malaria. Malar J 2011;10(1):1-12. [CrossRef][PubMed]

Anderson S. Making medicines: a brief history of pharmacy and pharmaceuticals. London: Pharmaceutical Press; 2005.

Aregawi M, Cibulskis RE, Otten M, Williams R. World malaria report 2009. Geneva: World Health Organization; 2009.

Ashley E, McGready R, Proux S, Nosten F. Malaria. Travel Med Infect Dis 2006;4(3-4):159-73. [CrossRef][PubMed]

Askitopoulou H, Ramoutsaki IA, Konsolaki E. Analgesia and anesthesia: etymology and literary history of related Greek words. Anesth Analg 2000;91(2):486-91. [CrossRef][PubMed]

Ball P. History of science: Quinine steps back in time. Nature 2008;451(7182):1065-6. [CrossRef][PubMed]

Butler AR, Khan S, Ferguson E. A brief history of malaria chemotherapy. J R Coll Physicians Edinb 2010;40(2):172-7. [CrossRef][PubMed]

Butler MS. Natural products to drugs: natural product-derived compounds in clinical trials. Nat Prod Rep 2008;25(3):475-516. [CrossRef][PubMed]

Coatney GR. Pitfalls in a discovery: the chronicle of chloroquine. Am J Trop Med Hyg 1963;12:121-8. [CrossRef][PubMed]

Coatney GR. Pitfalls in a discovery: the chronicle of chloroquine. Am J Trop Med Hyg 1963;12:121-8. [CrossRef][PubMed]

Cova TFGG, Pais AACC, Seixas de Melo JS. Reconstructing the historical synthesis of mauveine from Perkin and Caro: procedure and details. Sci Rep 2017;7(1):6806. [CrossRef][PubMed]

Dagani R. Quinine. Chem Eng News 2005;83(25):106. [CrossRef]

Dobson SMaM: The history of antimalarial drugs. In: Totowa PJ R, editor. Antimalarial Chemotherapy: Mechanisms of Action, Resistance, and New Directions in Drug Discovery. New Jersey: Humana Press; 2001. p. 15-25.

Drews J. Drug discovery: a historical perspective. Science. 2000;287(5460):1960-4. [CrossRef][PubMed]

Eiden F. Ausflug in die Vergangenheit: Chinin und andere Chinaalkaloide. 1. Teil: Von der Isolierung der Chinaalkaloide bis zur Konstitutions aufklärung [A trip to the past: quinine and quinine alkaloids. 1. The isolation of quinine alkaloids and clarification of its chemistry]. Pharm Unserer Zeit 1998;27(6):257-271. [CrossRef][PubMed]

Findlay G, Stevenson A. Investigations in the chemotherapy of malaria in west Africa. II. Malaria suppression: quinine and mepacrine. Ann Trop Med Parasitol 1944;38:168–187. [CrossRef]

Frankenburg FR, Baldessarini RJ. Neurosyphilis, malaria, and the discovery of antipsychotic agents. Harv Rev Psychiatry 2008;16(5):299-307. [CrossRef][PubMed]

Gachelin G, Garner P, Ferroni E, Tröhler U, Chalmers I. Evaluating Cinchona bark and quinine for treating and preventing malaria. J R Soc Med 2017;110(1):31-40. [CrossRef][PubMed]

Ganesan A. The impact of natural products upon modern drug discovery. Curr Opin Chem Biol 2008;12(3):306-17. [CrossRef][PubMed]

Gensini GF, Conti AA, Lippi D. The contributions of Paul Ehrlich to infectious disease. J Infect 2007;54(3):221-224. [CrossRef][PubMed]

Gibaud S, Jaouen G. Arsenic-based drugs: from fowler’s solution to modern anticancer chemotherapy. Medicinal organometallic chemistry 2010:1-20. [CrossRef]

Goss A. Building the world's supply of quinine: Dutch colonialism and the origins of a global pharmaceutical industry. Endeavour 2014;38(1):8-18. [CrossRef][PubMed]

Greenwood D. Conflicts of interest: the genesis of synthetic antimalarial agents in peace and war. J Antimicrob Chemother 1995;36(5):857-2. [CrossRef][PubMed]

Greenwood D. The quinine connection. J Antimicrob Chemother 1992;30(4):417-27. [CrossRef][PubMed]

Hamilton GR, Baskett TF. In the arms of Morpheus the development of morphine for postoperative pain relief. Can J Anaesth 2000;47(4):367-74. [CrossRef][PubMed]

Harvey AL. Natural products in drug discovery. Drug Discov Today 2008;13(19-20):894-901. [CrossRef][PubMed]

Hellgren U, Ericsson O, Gustafsson LL. Handbook of drugs for tropical parasitic infections. 2nd ed. London: CRC Press; 2003. [CrossRef]

Holmstedt B, Liljestrand G. Readings in Pharmacology. London: Pergamon Press; 1963.

Institute of Medicine (US) Committee on the Economics of Antimalarial Drugs. Saving Lives, Buying Time: Economics of Malaria Drugs in an Age of Resistance. Arrow KJ, Panosian C, Gelband H, editors. Washington (DC): National Academies Press (US); 2004.

Jacoby DB, Youngson RM. Encyclopedia of family health. New York: Marshall Cavendish; 2004.

Johnston WT. The discovery of aniline and the origin of the term "aniline dye". Biotech Histochem 2008;83(2):83-7. [CrossRef][PubMed]

Kaufman TS, Rúveda EA. The quest for quinine: those who won the battles and those who won the war. Angew Chem Int Ed Engl 2005;44(6):854-85. [CrossRef][PubMed]

Kingston DGI, Cassera MB. Antimalarial Natural Products. Prog Chem Org Nat Prod 2022;117:1-106. [CrossRef][PubMed]

Lam KS. New aspects of natural products in drug discovery. Trends Microbiol 2007;15(6):279-89. [CrossRef][PubMed]

Li JW, Vederas JC. Drug discovery and natural products: end of an era or an endless frontier? Science 2009;325(5937):161-5. [CrossRef][PubMed]

Loeb RF, Clarke WM, Coatney GR, Coggeshall LT, Dieuaide FR, Dochez AR, et al. Activity of a new antimalarial agent, chloroquine (SN 7618). J Am Med Assoc 1946;130:1069. [CrossRef][PubMed]

Lombardino JG, Lowe JA 3rd. The role of the medicinal chemist in drug discovery--then and now. Nat Rev Drug Discov 2004;3(10):853-62. [CrossRef][PubMed]

López-Muñoz F, Ucha-Udabe R, Alamo C. The history of barbiturates a century after their clinical introduction. Neuropsychiatr Dis Treat 2005;1(4):329-43. [PubMed]

Magendie F. Formulaire pour la pre ´parationetl’emploi de plusieurs me ´dicaments [Formulations for the preparation and the usage of several drugs]. Paris: Imprimerie de Plassan. 1822 [1829, 2nd edn] [cited 2022 Nov 02]. Available from: URL: http://gallica.bnf.fr/ark:/12148/bpt6k5832713d.r¼Magendie%2CþFran%C3%A7ois.langEN

Malik NN. Drug discovery: past, present and future. Drug Discov Today 2008;13(21-22):909-12. [CrossRef][PubMed]

Markham CR, Blanchard P, editors. Markham in Peru: The Travels of Clement R. Markham, 1852-1853. Austin: University of Texas Press; 1991.

Mühlens P. Die Behandlung der natürlichen menschlichen Malaria-infektion mit Plasmochin. Naturwissenschaften 1926;14(48):1162-6. [CrossRef]

Nanayakkara NP, Tekwani BL, Herath HM, Sahu R, Gettayacamin M, Tungtaeng A, et al. Scalable preparation and differential pharmacologic and toxicologic profiles of primaquine enantiomers. Antimicrob Agents Chemother 2014;58(8):4737-44. [CrossRef][PubMed]

Nowruzi B. Cyanobacteria Natural Products as Sources for Future Directions in Antibiotic Drug Discovery. In: Tiwari A, editor. Cyanobacteria - Recent Advances and New Perspectives. IntechOpen; 2022. [CrossRef]

Parojčić D, Stupar D. Istorijski osvrt na lekovito bilje i njegovu upotrebu u farmakologiji. Timočki medicinski glasnik 2003;28(3-4):101-9.

Renslo AR. Antimalarial drug discovery: from quinine to the dream of eradication. ACS Med Chem Lett 2013;4(12):1126-8. [CrossRef][PubMed]

Ross R K C B K C M G. Report on the Treatment of Malaria: Abstract of 2,460 Cases-War Office Investigations. Ind Med Gaz 1918;53(7):241-9. [PubMed]

Sanders NG, Meyers DJ, Sullivan DJ. Antimalarial efficacy of hydroxyethylapoquinine (SN-119) and its derivatives. Antimicrob Agents Chemother 2014;58(2):820-7. [CrossRef][PubMed]

Sayang C, Gausseres M, Vernazza-Licht N, Malvy D, Bley D, Millet P. Treatment of malaria from monotherapy to artemisinin-based combination therapy by health professionals in rural health facilities in southern Cameroon. Malar J 2009;8:174. [CrossRef][PubMed]

Schlitzer M. Malaria chemotherapeutics part I: History of antimalarial drug development, currently used therapeutics, and drugs in clinical development. Chem Med Chem 2007;2(7):944-86. [CrossRef][PubMed]

Seeman JI. The Woodward-Doering/Rabe-Kindler total synthesis of quinine: setting the record straight. Angew Chem Int Ed Engl 2007;46(9):1378-413. [CrossRef][PubMed]

Shanks GD. Historical Review: Problematic Malaria Prophylaxis with Quinine. Am J Trop Med Hyg 2016;95(2):269-72. [CrossRef][PubMed]

Shanks GD. Historical Review: Problematic Malaria Prophylaxis with Quinine. Am J Trop Med Hyg 2016;95(2):269-72. [CrossRef][PubMed]

Shanks GD. Historical Review: Problematic Malaria Prophylaxis with Quinine. Am J Trop Med Hyg 2016;95(2):269-72. [CrossRef][PubMed]

Souza KAF, Porto PA. History and Epistemology of Science in the Classroom: The Synthesis of Quinine as a Proposal. J ChemEduc 2012;89(1):58-63. [CrossRef]

Stork G, Niu D, Fujimoto RA, Koft ER, Balkovec JM, Tata JR, et al. The first stereoselective total synthesis of quinine. J Am Chem Soc 2001;123(14):3239-42. [CrossRef][PubMed]

Sullivan DJ. Cinchona alkaloids: quinine and quinidine. In: Staines HM, Krishna S, editors. Treatment and prevention of malaria. Basel: Springer; 2011. p. 45-68. [CrossRef]

Sweeney T. Malaria Frontline: Australian Army Research during World War II. Melbourne: Melbourne University Press; 2003.

Taylor N. Cinchona in Java: The Story of Quinine. New York; Greenberg; 1945.

Thomas G, editor. Medicinal chemistry: an introduction. Chichester: John Wiley & Sons; 2011.

Triunfol ML. More bark than bites.(Books: medicine). Science 2002;297(5580):342-3. [CrossRef]

Worthen DB. The national quinine pool: when quinine went to war. Pharm Hist 1996;38(3):143-7. [PubMed]

Wyler DJ. Malaria--resurgence, resistance, and research. (First of two parts). N Engl J Med 1983;308(15):875-8. [CrossRef][PubMed]

Published
2023/06/16
Section
Review article