Skip to main content
SpringerLink
Log in

8-Aminoquinolines

  • Chapter
Antimalarial Drug II

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 68 / 2))

Abstract

The role of the 8-aminoquinolines against malaria is currently focused on their activity as tissue schizontocides in the treatment and prophylaxis of vivax and ovale malaria. In addition they are gametocytocidal and sporontocidal and can prevent transmission of falciparum malaria. Of the two 8-aminoquinolines presently in use primaquine is the most generally available and quinocide, a structural isomer of primaquine, is used in the USSR. Although primaquine is the safest available 8-aminoquinoline it does have significant toxic effects, the best known being the induction of haemolytic anaemia in individuals with glucose-6-phosphate dehydrogenase (G6PD) deficiency. Furthermore, the radical cure of vivax and ovale malaria requires the administration of primaquine even in partially immune individuals over a period of at least several days. Nevertheless, because no other available tissue schizontocide is more effective or less toxic than primaquine there is a recognised need for investigations to differentiate the efficacy and the toxicity of prima-quine as well as to discover new, less toxic, tissue schizontocides. Thus the Third Meeting of the Scientific Working Group on the Chemotherapy of Malaria of the World Health Organization held in Geneva, Switzerland in October 1980 was entirely devoted to the field of tissue schizontocidal drugs.

The author wishes to dedicate this chapter in memory of Alf S. Alfing, M.D. who has leader and mentor made this work posible

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Ajmar F, Scharrer B, Hashimoto F, Carson PE (1968) Interrelation of stromal NAD(P)ase and human erythrocytic 6-phosphogluconic dehydrogenase. Proc Natl Acad Sci USA 59:538–545

    Article  PubMed  CAS  Google Scholar 

  • Alving AS (1948) Pentaquine (SN-13,276) and isopentaquine (SN-13,274), therapeutic agents effective in reducing relapse rate in vivax malaria. Proc of the fourth intl cong on trop med and malaria, Washington, DC, May 1948. Vol I, pp 734–741. Available from:Department of State, Washington

    Google Scholar 

  • Alving AS, Arnold J, Hockwald RS, Clayman CB, Dem RJ, Beutler E, Flanagan CL (1955) Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. J Lab Clin Med 46:301–306

    PubMed  CAS  Google Scholar 

  • Alving AS, Arnold J, Robinson DH (1952) Status of primaquine. 1. Mass therapy of sub-clinical vivax malaria with primaquine. JAMA 149:1558–1570

    CAS  Google Scholar 

  • Alving AS, Craige B Jr, Jones R Jr, Whorton CM, Pullman TN, Eichelberger L (1948b) Pentaquine (SN-13,276), a therapeutic agent effective in reducing the relapse rate in vivax malaria. J Clin Invest 27:25–33

    Article  Google Scholar 

  • Alving AS, Hankey DD, Coatney GR, Jones R Jr, Coker WG, Garrison PL, Donovan WN (1953) Korean vivax malaria. II. Curative treatment with pamaquine and primaquine. Am J Trop Med Hyg 2:970–976

    Article  Google Scholar 

  • Alving AS, Johnson CF, Tarlow AR, Brewer GJ, Kellermeyer RW, Carson PE (1960) Mitigation of the hemolytic effect of primaquine and enhancement of its action against exoerythrocytic forms of the Chesson strain of Plasmodium vivax by intermittent regimes of drug administration. Bull WHO 22:621–631

    PubMed  CAS  Google Scholar 

  • Alving AS, Powell RD, Brewer GJ, Arnold JD (1962) Malaria, 8-aminoquinolines and haemolysis. In: Goodwin LG and Nimmo-Smith RH (eds) Drugs, parasites, and hosts, pp 83–94. Churchill, London

    Google Scholar 

  • Alving AS, Pullman TN, Craige B Jr, Jones R Jr, Whorton CM, Eichelberger L ( 1948 a) The clinical trial of eighteen analogues of pamaquine (plasmochin) in vivax malaria ( Chesson strain ). J Clin Invest 27:34–35

    Google Scholar 

  • Alving AS, Rucker K, Flanagan CL, Carson PE, Schrier SL, Kellermeyer RW, Tarlov AR (1959) Obervations on primaquine in the prophylaxis and cure of vivax malaria. Proc of the sixth internl congresses on trop med and malaria, Lisbon Sept 1958. vol 7, pp 203–209.

    Google Scholar 

  • Appel L (1917) Zur Behandlung der Malaria mit Methylenblau und Salvarsan. Dtsch Med Wochenschr 43:1359–1360

    Article  Google Scholar 

  • Arnold J, Alving AS, Clayman CB, Hockwald RS (1961) Induced primaquine resistance in vivax malaria. Trans R Soc Trop Med Hyg 55:345–350

    Article  PubMed  CAS  Google Scholar 

  • Arnold J, Alving AS, Hockwald RS, Clayman CB, Dem RJ, Beutler E, Jeffery GM (1954) The effect of continuous and intermittent primaquine therapy on the relapse rate of Chesson strain vivax malaria. J Lab Clin Med 43:429–438

    Google Scholar 

  • Arnold J, Alving AS, Hockwald RS, Clayman CB, Dem RJ, Beutler E, Flanagan CL, Jeffery GM (1955) The antimalarial action of primaquine against the blood and tissue stages of falciparum malaria (Panama, P-F-6 strain). J Lab Clin Med 43:391–397

    Google Scholar 

  • Atchley JA, Yount EH, Husted JR, Pullman TN, Alving AS, Eichelberger L (1948) Reactions observed during treatment with pentaquine, administered with quinacrine (atabrine), metachloridine (SN-11,437), and with sulfadiazine. J Nat Mal Soc 7:118–124

    CAS  Google Scholar 

  • Baty JD, Price-Evans DA, Robinson PA (1975) The identification of 6-methoxy 8-amino quinoline as a metabolite of primaquine in man. Biomed Mass Spectrom 2:304–306

    Article  CAS  Google Scholar 

  • Berliner RW, Earle DP Jr, Taggart JV, Welch WJ, Zubrod CG, Knowlton P, Atchley JA, Shannon JA (1948) Studies on the chemotherapy of the human malarias. VII. The antimalarial activity of pamaquine. J Clin Invest (Suppl) 27:108–113

    Google Scholar 

  • Beutler E (1957) The glutathione instability of drug-sensitive red cells. J Lab Clin Med 49:84–95

    PubMed  CAS  Google Scholar 

  • Beutler E (1978) Glucose-6-phosphate dehydrogenase deficiency. In: Stanbury JB, Wyngaarden JB, Predrickson DS (eds) The metabolic basis of inherited disease, 4th edn. McGraw-Hill, New York, pp 1430–1451

    Google Scholar 

  • Beutler E, Dem RJ, Alving AS (1954a) The hemolytic effect of primaquine. III. A study of primaquine-sensitive erythrocytes. J Lab Clin Med 44:177–184

    Google Scholar 

  • Beutler E, Dem RJ, Alving AS (1954b) The hemolytic effect of primaquine. IV. The relationship of cell age to hemolysis. J Lab Clin Med 44:439–442

    Google Scholar 

  • Beutler E, Dern RJ, Alving AS (1955a) The hemolytic effect of primaquine. VI. An in vitro test for sensitivity of erythrocytes to primaquine. J Lab Clin Med 45:40–50

    Google Scholar 

  • Beutler E, Dem RJ, Flanagan CL, Alving AS (1955b) The hemolytic effect of primaquine. VII. Biochemical studies of drug-sensitive erythrocytes. J Lab Clin Med 45:286–295

    Google Scholar 

  • Brewer GJ, Tarlov AR, Alving AS (1960) Methaemoglobin reduction test. A new, simple, in vitro test for identifying primaquine-sensitivity. Bull WHO 22:633–640

    Google Scholar 

  • Brewer GJ, Tarlov AR, Alving AS (1961a) The toxicity of the 8-aminoquinoline antimalarial drugs. Bull Nat Soc Ind Mal Mosq Dis 9:331–351

    Google Scholar 

  • Brewer GJ, Tarlov AR, Alving AS (1962a) The methemoglobin reduction test for primaquine-type sensitivity of erythrocytes. A simplified procedure for detecting a specific hypersusceptibility to drug hemolysis. JAMA 180:386–388

    Google Scholar 

  • Brewer GJ, Tarlov AR (1961) Studies on the mechanism of primaquine-type hemolysis:the effect of methylene blue. Clin Res 9:65

    Google Scholar 

  • Brewer GJ, Tarlov AR, Kellermeyer RW (1961b) The hemolytic effect of primaquine. XII. Shortened erythrocyte life span in primaquine-sensitive male Negroes in the absence of drug administration. J Lab Clin Med 58:217–224

    Google Scholar 

  • Brewer GJ, Tarlov AR, Kellermeyer RW, Alving AS (1962b) The hemolytic effect of primaquine. XV. Role of methemoglobin. J Lab Clin Med 59:905–917

    Google Scholar 

  • Brodie BB, Udenfriend S, Taggart JV (1946) Analysis of basic organic compounds in biological tissues:4. Coupling with diazonium salts. Fed Proc 5:125–126

    Google Scholar 

  • Brodie BB, Udenfriend S, Taggart JV (1947) The estimation of basic organic compounds in biological fluids. IV. Estimation by coupling with diazonium salts. J Biol Chem 168:327

    Google Scholar 

  • Burgess RW, Bray RS (1961) The effect of a single dose of primaquine on the gametocytes, gametogony, and sporogony of Laveraniafalciparum. Bull WHO 24:451–456

    PubMed  CAS  Google Scholar 

  • Campbell GD Jr, Steinberg MH, Bower JD (1975) Ascorbic acid induced hemolysis in glu cose-6-phosphate dehydrogenase deficiency. Ann Intern Med 82:810

    PubMed  Google Scholar 

  • Carson PE (1960) Glucose-6-phosphate dehydrogenase deficiency in hemolytic anemia. Fed Proc 19:995–1006

    PubMed  CAS  Google Scholar 

  • Carson PE (1968) Hemolysis due to inherited erythrocyte enzyme deficiencies. In: Conference on pharmacogenetics. Ann NY Acad Sci 151:765–776

    Google Scholar 

  • Carson PE (1970) Clinical metabolic and molecular consequences of disorders of the pentose phosphate pathway. International symposium on pharmacogenetics, Royal Society of Medicine (1969) Proc R Soc Med 63:175–176

    CAS  Google Scholar 

  • Carson, PE, Ajmar F, Hashimoto F, Bowman JE (1966) Electrophoretic demonstration of stromal effects on haemolysate glucose-6-phosphate dehydrogenase and 6-phosphogluconic dehydrogenase. Nature 210:813–815

    Article  PubMed  CAS  Google Scholar 

  • Carson PE, Flanagan CL, Ickes CE, Alving AS (1956) Enzymatic deficiency in primaquinesensitive erythrocytes. Science 124:484–485

    Article  PubMed  CAS  Google Scholar 

  • Carson PE, Frischer H (1966) Glucose-6-phosphate dehydrogenase deficiency and related disorders of the pentose phosphate pathway. Am J Med 41:744–761

    Article  PubMed  CAS  Google Scholar 

  • Carson PE, Hohl R, Nora MV, Parkhurst GW, Ahmad T, Scanlan S, Frischer H (1981) Toxicology of the 8-aminoquinolines and genetic factors associated with their toxicity in man. Bull WHO 59:427–437

    PubMed  CAS  Google Scholar 

  • Carson PE, Okita GT, Frischer H, Hirasa J, Long WK, Brewer GJ (1963) Patterns of hemolytic susceptibility and metabolism. Proc 9th congr Europ Soc Haemat, Lisbon 1963, pp 655–665. Karger, Basel

    Google Scholar 

  • Carson PE, Schrier SL, Kellermeyer RW (1959) Glucose-6-phosphate dehydrogenase and human erythrocytes:characteristics of glucose-6-phosphate dehydrogenase from normal and primaquine-sensitive erythrocytes. Nature 184:1291–1293

    Article  Google Scholar 

  • Carson PE, Tarlov AR (1962) Biochemistry of hemolysis. Ann Rev Med 13:105–126 Cedillos RA, Warren M, Jeffery GM (1978) Field evaluation of primaquine in the control of Plasmodium vivax. Am J Trop Med Hyg 27:466–472

    Google Scholar 

  • Clayman CB, Arnold J, Hockwold RS, Yount EH, Edgcomb JH, Alving AS (1952) Toxicity of primaquine in Caucasians. JAMA 149:1563–1568

    CAS  Google Scholar 

  • Clyde DF, McCarthy VC (1977) Brief communications. Radical cure of Chesson strain vivax malaria in man by 7, not 14 days of treatment with primaquine. Am J Trop Med Hyg 26:562–563

    PubMed  CAS  Google Scholar 

  • Coatney GR, Alving AS, Jones R Jr, Hankey DD, Robinson DH, Garison PL, Coker WG, Donovan WN, DiLorenzo A, Marx RL, Simmons IH (1953) Korean vivax malaria. V. Cure of the infection by primaquine administered during long-term latency. Am J Trop Med Hyg 2:985–988

    Google Scholar 

  • Coggeshall LT, Rice FA, Yount ER Jr (1948) The cure of recurrent vivax malaria and status of immunity thereafter. Proc fourth intl congresses of trop med and mal. Washington DC May 1948. vol I, pp 749–755. Available from:Department of State, Washington

    Google Scholar 

  • Coggeshall LT, Rice FA (1949) Cure of chronic vivax malaria with pentaquine. JAMA 139:437–439

    CAS  Google Scholar 

  • Cohen G, Hochstein P (1963) Gluthathione peroxidase:the primary agent for the elimination of hydrogen peroxide in erythrocytes. Biochemistry 2:1420–1428

    Article  PubMed  CAS  Google Scholar 

  • Cohen RJ, Sachs JR, Wicker DJ, Conrad ME (1968) Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam. N Engl J Med 279:1127–1131

    Article  PubMed  CAS  Google Scholar 

  • Cooper WC, Myatt AV, Hernandez T, Jeffery GM, Coatney GR (1953) Studies in human malaria. XXXI. Comparison of primaquine, isopentaquine, SN-3883, and pamaquine as curative agents against Chesson strain vivax malaria. Am J Trop Med Hyg 2:949–957

    PubMed  CAS  Google Scholar 

  • Craige B Jr, Eichelberger L, Jones R Jr, Alving AS, Pullman TN, Whorton CM (1947 b) The toxicity of large doses of pentaquine (SN-13,276), a new antimalarial drug. J Clin Invest 27:17–24

    Google Scholar 

  • Craige B Jr, Jones R Jr, Whorton CM, Pullman TN, Alving AS, Eichelberger L (1947a) Clinical standardization of pamaquine (plasmochin) in mosquito-induced vivax malaria, Chesson strain. A preliminary report. Am J Trop Med 27:309–315

    Google Scholar 

  • Crosby WH (1956) Newsletter. Favism in Sardinia. Blood 11:91

    Google Scholar 

  • Dem RJ, Beutler E, Alving AS (1954) Clinical and experimental. The hemolytic effect of primaquine. The natural course of the hemolytic anemia and the mechanism of its self-limited character. J Lab Clin Med 44:171–176

    Google Scholar 

  • Dem RJ, Beutler E, Alving AS (1955) The hemolytic effect of primaquine. V. Primaquine sensitivity as a manifestation of a multiple drug sensitivity. J Lab Clin Med 45:30–39.

    Google Scholar 

  • Dem RJ, Beutler E, Alving AS (1955) The hemolytic effect of primaquine. V. Primaquine sensitivity as a manifestation of a multiple drug sensitivity. (1981) J Lab Clin Med 97:750–759

    Google Scholar 

  • Dem RJ, Weinstein IM, LeRoy GV, Talmage DW, Alving AS (1953) The hemolytic effect of primaquine. I. The localization of the drug-induced hemolytic defect in primaquinesensitive individuals. J Lab Clin Med 43:303–309

    Google Scholar 

  • DiLorenzo A, Marx RL, Alving AS, Jones R Jr (1953) Korean vivax malaria. IV. Curative effect of 15 milligrams of primaquine daily for 7 days. Am J Trop Med Hyg 2:983–984

    CAS  Google Scholar 

  • Earle DP Jr, Bigelow FS, Zubrod CG, Kane CA (1948) Studies on the chemotherapy of the human malarias. IX. Effect of pamaquine on the blood cells of man. J Clin Invest (Suppl) 27:121–129

    Google Scholar 

  • Edgecomb JH, Arnold J, Yount EH Jr, Alving AS, Eichelberger L (1950) Primaquine, SN-13,272, a new curative agent in vivax malaria:A preliminary report. J Nat Mal Soc 9:285–292

    Google Scholar 

  • Eppes RB, Brewer CJ, DeGowin RL, McNamara JV, Flanagan CL, Schrier SL, Tarlov AR, Powell RD, Carson PE (1966) Oral glucose tolerance in Negro men deficient in glucose6-phosphate dehydrogenase. N Engl J Med 275:855–861

    Article  PubMed  CAS  Google Scholar 

  • Eppes RB, Lawrence AM, McNamara JV, Powell RD, Carson PE (1969) Intravenous glucose tolerance in Negro men deficient in glucose-6-phosphate dehydrogenase. N Engl J Med 281:60–63

    Article  PubMed  CAS  Google Scholar 

  • Ehrman FC, Ellis JM, Young MD (1945) Plasmodium vivax Chesson strain. Science 101:377

    Article  PubMed  CAS  Google Scholar 

  • Fairley NH (1945) Chemotherapeutic suppression and prophylaxis in malaria. An experimental investigation undertaken by medical research teams in Australia. Trans R Soc Trop Med Hyg 38:311–355

    Article  PubMed  CAS  Google Scholar 

  • Fairley NH (1947) Sidelights on malaria in man obtained by subinoculation experiments. Trans R Soc Trop Med Hyg 40:621–676

    Article  PubMed  CAS  Google Scholar 

  • Farbenindustrie IG (1928) Redaktionelle Notiz. Archiv für Schiffs-und Tropen-Hygiene 32:382

    Google Scholar 

  • Feldman HA, Packer H, Murphy FD, Watson RB (1946) Pamaquine naphthoate as a prophylactic for malarial infections. The American Association of Immunologists. Thirtieth annual meeting. Fed Proc 5:244

    Google Scholar 

  • Flanagan CL, Beutler E, Dern RJ, Alving AS (1955) Biochemical changes in erythrocytes during hemolysis induced by aniline derivatives. J Lab Clin Med 46:814

    Google Scholar 

  • Flanagan CL, Schrier SL, Carson PE, Alving AS (1958) The hemolytic effect of primaquine. VIII. The effect of drug administration on parameters of primaquine sensitivity. J Lab Clin Med 51:600–608

    Google Scholar 

  • Fletcher W (1933) New drugs in the treatment of malaria. Trop Dis Bull 30:193–202

    Google Scholar 

  • Fraser IM, Vesell ES (1968) Effects of metabolites of primaquine and acetanilid on normal and glucose-6-phosphate dehydrogenase deficient erythrocytes. J Pharmacol Exp Ther 162:155–165

    PubMed  CAS  Google Scholar 

  • Frischer H (1977) Erythrocytic glutathione reductase deficiency in a hospital population in the United States. Am J Hematol 2:327–344

    Article  PubMed  CAS  Google Scholar 

  • Frischer H, Ahmad T (1977) Severe generalized glutathione reductase deficiency after antitumor chemotherapy with BCNU [1,3-bis(chlorethyl)-1-nitrosourea]. J Lab Clin Med 89:1080–1091

    PubMed  CAS  Google Scholar 

  • Frischer H, Carson PE (1981) Multiple gene interactions in pharmacogenetics. J Lab Clin Med 97:760–763

    PubMed  CAS  Google Scholar 

  • Frischer H, Bowman JE (1975) Hemoglobin E, an oxidatively unstable mutation. J Lab Clin Med 85:531–539

    PubMed  CAS  Google Scholar 

  • Frischer H, Bowman JE, Carson PE, Rieckmann KH, Willerson D Jr, Colwell EJ (1973a) Erythrocytic glutathione reductase, glucose-6-phosphate dehydrogenase and 6-phosphogluconic dehydrogenase deficiencies in populations of the USA, South Vietnam, Iran, and Ethiopia. J Lab Clin Med 81:603–612

    Google Scholar 

  • Frischer H, Carson PE, Bowman JE, Rieckmann KH (1973b) Visual test for erythrocytic glucose-6-phosphate dehydrogenase, 6-phosphogluconic dehydrogenase, and glutathione reductase deficiencies. J Lab Clin Med 81:613–624

    PubMed  CAS  Google Scholar 

  • Frischer H, McNamara J, Rieckmann KH, Stockert T, Powell RD, Carson PE (1968) H2O2 effects on intracellular enzymes and glutathione; activation of glutathione reductase. Clin Res 16:303

    Google Scholar 

  • Frischer H, Nelson R, Noyes C, Carson PE, Bowman JE, Rieckmann KH, Ajmar F (1973c) NAD(P)-glycohydrolase deficiency in human erythrocytes and alteration of cytosol NADH-methemoglobin diaphorase by membrane NAD-glycohydrolase activity. Proc Natl Acad Sci USA 70:2406–2410

    Article  PubMed  CAS  Google Scholar 

  • Garrison PL, Hankey DD, Coker WG, Donovan WM, Jastranski B, Coatney GR, Alving AS, Jones R Jr (1952) Cure of Korean vivax malaria with pamaquine and primaquine. JAMA 149:1562–1563

    CAS  Google Scholar 

  • Goodman L, Gilman A (1941) Methylene blue. Cyanosis. In: The pharmacological basis of therapeutics, 1st edn. MacMillan, New York, pp 868–870, 1031–1033

    Google Scholar 

  • Greaves J, Evans DAP, Gilles HM, Fletcher KA, Bunnag D, Harinasuta T (1980 b) Plasma kinetics and urinary excretion of primaquine in man. Br J Clin Pharmacol 10:399–405

    Google Scholar 

  • Greaves J, Evans DAP, Fletcher KA (1980a) Urinary primaquine excretion and red cell methaemoglobin levels in man following a primaquine:chloroquine regimen. Br J Clin Pharmacol 10:293–295

    PubMed  CAS  Google Scholar 

  • Greaves J, Price-Evans DA, Gilles HM, Baty JD (1979) A selected ion monitoring assay for primaquine in plasma and urine. Biomed Mass Spectrom 6:109–112

    Article  PubMed  CAS  Google Scholar 

  • Gunders AE (1961) The effect of a single dose of pyrimethamine and primaquine in combination upon gametocytes and sporogony of Laverania falcipara (Plasmodium falciparum) in Liberia. Bull WHO 24:650–653

    PubMed  CAS  Google Scholar 

  • Guttman P, Ehrlich P (1981) Ãœber die Wirkung des Methylenblau bei Malaria. Berl Klin Wochenschr 28:953–956

    Google Scholar 

  • Hankey DD, Jones R Jr, Coatney GR, Alving AS, Coker WG, Garrison PL, Donovan WN (1953) Korean vivax malaria. I. Natural history and response to chloroquine. Am J Trop Med Hyg 2:958–969

    Google Scholar 

  • Hawking F, Perry WLM, Thurston JP (1948) Tissue forms of a malaria parasite, Plasmodium cynomolgi. Lancet 1:783–789

    Google Scholar 

  • Hockwald RS, Arnold J, Clayman CB, Alving AS (1952) 4. Toxicity of primaquine in negroes. JAMA 149:1568–1570

    Google Scholar 

  • Holbrook DJ Jr, Griffin JB, Fowler L, Gibson BR (1981) Tissue distribution of primaquine in the rat. Pharmacology 22:330–336

    Article  PubMed  CAS  Google Scholar 

  • Horlein (1926) Ãœber die chemischen Grundlagen und die Entwicklungs-Geschichte des Plas mochins. Archiv für Schiffs-und Tropen-Hygiene 30 (Suppl 1–3):305–310

    Google Scholar 

  • Hughes HB, Schmidt LH (1950) Metabolism of various 8-aminoquinolines in rhesus mon key. Proc Soc Exp Biol Med 73:581–585

    CAS  Google Scholar 

  • James SP (1931a) Some general results of a study of induced malaria in England. Trans R Soc Trop Med Hyg 24:477–525

    Article  Google Scholar 

  • James SP (1931b) On the prevention of malaria with plasmoquine. Lancet:341–345

    Google Scholar 

  • James SP, Nicol WD, Shute PG (1931) A drug which prevents malaria. Lancet:1248–1249

    Google Scholar 

  • Jarvis OD (1932) Further researches into the treatment of chronic B.T. malaria with plas moquine and quinine. Indian J Med Res 20:627, and J R Army Med Corps 59:190

    Google Scholar 

  • Jeffery GM, Collins WE, Skinner JC (1963) Antimalarial drug trials on a multi-resistant strain of Plasmodium falciparum. Am J Trop Med Hyg 12:844–850

    PubMed  CAS  Google Scholar 

  • Jeffery GM, Wolcott GB, Young MD, Williams D Jr (1952) Exoerythrocytic stages of Plasmodium falciparum. Am J Trop Med Hyg 1:917–926

    PubMed  CAS  Google Scholar 

  • Jeffery GM, Young MD, Eyles DE (1956) The treatment of Plasmodium falciparum infection with chloroquine, with a note on infectivity to mosquitoes of primaquine-and pyrimethamine-treated cases. Am J Hyg 64:1–11

    PubMed  CAS  Google Scholar 

  • Jones R Jr, Craige B Jr, Alving AS, Whorton MC, Pullman TN, Eichelberger L ( 1948 b) A study of the prophylactic effectiveness of several 8-aminoquinolines in sporozoite-induced vivax malaria ( Chesson strain ). J Clin Invest (Suppl) 27:6–11

    Google Scholar 

  • Jones R Jr, Pullman TN, Whorton CM, Craige B Jr, Alving AS, Eichelberger L ( 1948 a) The therapeutic effectiveness of large doses of paludrine in acute attacks of sporozoite-induced vivax malaria ( Chesson strain ). J Clin Invest 27:51–55

    Google Scholar 

  • Jones R Jr, Jackson LS, DiLorenzo A, Marx RL, Levy BL, Kenney EC, Gilbert M, Johnston MN, Alving AS (1953) Korean vivax malaria. III. Curative effect and toxicity of primaquine in doses from 10 to 30 mg daily. Am J Trop Med Hyg 2:977–982

    PubMed  Google Scholar 

  • Josephson ES, Greenberg J, Taylor DJ, Bami HL (1951a) A metabolite of pamaquine from chickens. J Pharmacol Exp Ther 103:7–9

    PubMed  CAS  Google Scholar 

  • Josephson ES, Taylor DJ, Greenberg J, Amar PR (1951b) A metabolic intermediate of pamaquine for chickens. Proc Soc Exp Biol Med 96:700–703

    Google Scholar 

  • Kass L, Willerson D Jr, Rieckmann KH, Carson PE, Becker RP (1971a) Plasmodium falciparum gametocytes. Electron microscopic observations on material obtained by a new method. Am Soc Trop Med Hyg 20:187–194

    Google Scholar 

  • Kass L, Willerson D Jr, Rieckmann KH, Carson PE (1971b) Blastoid transformation of lymphocytes in falciparum malaria. Am Soc Trop Med Hyg 20:195–198

    CAS  Google Scholar 

  • Kelleher MFH, Thompson K (1945) Treatment of malaria. Lancet 2:217

    Article  Google Scholar 

  • Kellermeyer RW, Tarlov AR, Brewer GJ, Carson PE, Alving AS (1962) Hemolytic effect of therapeutic drugs. Clinical considerations of the primaquine-type hemolysis. JAMA 180:388–394

    PubMed  CAS  Google Scholar 

  • Kellermeyer RW, Tarlov AR, Schrier SL, Carson PE, Alving AS (1961) The hemolytic effect of primaquine. XIII. Gradient susceptibility to hemolysis of primaquine-sensitive erythrocytes. J Lab Clin Med 58:225–233

    PubMed  CAS  Google Scholar 

  • Kirkman HN, Rosenthal IM, Simon ER, Carson PE (1964) Chicago P type of glucose-6-phos phate dehydrogenase in congenital hemolytic disease. J Lab Clin Med 63:715–725

    PubMed  CAS  Google Scholar 

  • Kirkman HN, Wilson WG, Clemons EH (1980) Regulations of glucose-6-phosphate dehy drogenase. I. Intact red cells. J Lab Clin Med 95:876–887

    Google Scholar 

  • Krotoski WA, Garnham PCC, Bray RS, Krotoski DM, Killick-Kendrick R, Draper CC, Targett GAT, Guy MW (1982) Observations on early and late post-sporozoite tissue stages in primate malaria. I. Discovery of a new latent form of Plasmodium cynomolgi (the hypnozoite), and failure to detect hepatic forms within the first 24 h after infection. Am J Trop Med Hyg 31:24–35

    PubMed  CAS  Google Scholar 

  • Krotoski WA, Krotoski DM, Garnham PCC, Bray RS, Killick-Kendrick R, Draper CC, Targett GAT, Guy MW (1980) Relapse in primate malaria:discovery of two populations of exoerythrocytic stages. Preliminary note. Br Med J (Jan):153–154

    Google Scholar 

  • Lehmann H, Kynoch PAM (1976) Human hemoglobin variants and their characteristics. Elsevier, Amsterdam

    Google Scholar 

  • Ljachowetzky AM (1924) Combined treatment of malaria by intravenous injections of methylene-blue and neosalvarsan. Russian J Trop Med 2:3–10

    Google Scholar 

  • Ljachowetzky AM (1927) Treatment of chronic malaria. Russian J Trop Med 5:202–204

    Google Scholar 

  • Loos H, Roos D, Weening R (1976) Familial deficiency of glutathione reductase in human blood cells. Blood 48:53–62

    PubMed  CAS  Google Scholar 

  • Lyle DJ, Schmidt IG (1962) The selective effect of drugs upon nuclei of the oculogyric system. Am J Opthalmol 54:706–716

    CAS  Google Scholar 

  • Manifold JA (1931) Report on trial of plasmoquine and quinine in treatment of of benign tertian malaria. J R Army Med Corp 56:321, 410

    Google Scholar 

  • Malaria Commission (1933) Third General Report Therapeutics of Malaria. I. General aims. In: League of Nations. Bull WHO 2:185–285

    Google Scholar 

  • Malaria Commission (1937) Fourth General Report. The treatment of malaria. In: League of Nations. Bull WHO 6:1011–1012

    Google Scholar 

  • McNamara JV, Eppes RB, Powell RD, Carson PE (1966) The effects of para-aminobenzoic acid on the hemolytic effects of 4,4’-diaminodiphenylsulfone. Milit Med 131:1057–1060

    CAS  Google Scholar 

  • Most H, Kane CA, Lavietes PH, London IM, Schroeder FE, Hayman JM (1946) Combined quinine-plasmochin treatment of vivax malaria:effect on relapse rate. Am J Med Sci 212:550–560

    Article  PubMed  CAS  Google Scholar 

  • Murphy JR (1960) Erythrocyte metabolism. II. Glucose metabolism and pathways. J Lab Clin Med 55:286–302

    PubMed  CAS  Google Scholar 

  • Peters W (1970) Experimental drug resistance II 8-aminoquinolines and other compounds. Pamaquine. Quinine, mepacrine, 8-aminoquinolines and hydroxynaphthalenes. Prima-quine, quinine, mepacrine, 8-aminoquinolines, and hydroxynaphthalenes. WIN 5037; 6methoxy-8-(5-propylaminoamylamino) quinoline phosphate. In: Chemotherapy and drug resistance in malaria. Academic, London, pp 286, 449, 453

    Google Scholar 

  • Pitschugin PI (1925) Das Methylenblau bei Behandlung von Malaria bei Kindern. Jahrb f Kinderheilkunde 108 (5–6):347–353

    Google Scholar 

  • Powell RD, Brewer GJ (1967) Effects of pyrimethamine, chlorguanide, and primaquine against exoerythrocytic forms of a strain of chloroquine-resistant Plasmodium falciparum from Thailand. Am J Trop Med Hyg 16:693–698

    PubMed  CAS  Google Scholar 

  • Powell RD, Brewer GJ, DeGowin RL, Carson PE (1966) Effects of glucose-6-phosphate dehydrogenase deficiency upon the host and upon host-drug-malaria parasite interactions. Milit Med 131:1039–1056

    CAS  Google Scholar 

  • Prins HK, Oort M, Loos JA, Zurcher C, Beckers T (1966) Congenital non-spherocytic he molytic anemia, associated with glutathione deficiency of the erythrocytes. Blood 27:145

    PubMed  CAS  Google Scholar 

  • Raffaele G, Carrescia PM (1961) Efficacia dosi di sintesi Azione della primachina. Riv Ma lar 41:51–59

    Google Scholar 

  • Rajagopalan TG, Anjaneyulu B, Shanbag VD, Grewal RS (1981) Electron-capture gas chromatographic assay for primaquine in blood. J Chromatogr 224:265–273

    Article  CAS  Google Scholar 

  • Rieckmann KH, McNamara JV, Frischer H, Stockert TA, Carson PE, Powell RD (1968) Gametocytocidal and sporontocidal effects of primaquine and of sulfadiazine with pyrimethamine in a chloroquine-resistant strain of Plasmodium falciparum. Bull WHO 38:625–632

    PubMed  CAS  Google Scholar 

  • Rieckmann KH, McNamara JV, Kass L, Powell RD (1969) Gametocytocidal and sporontocidal effects of primaquine upon two strains of Plasmodium falciparum. Milit Med 134:802–819

    CAS  Google Scholar 

  • Rieckmann KH, Trenholme GM, Williams RL, Carson PE, Frischer H, Desjardins RE (1974) Prophylactic activity of mefloquine hydrochloride (WR 142490) in drug-resistant malaria. Bull WHO 51:375–377

    PubMed  CAS  Google Scholar 

  • Richter RB (1949) The effect of certain quinoline compounds upon the nervous system of monkeys. J Neuropathol Exp Neurol 8:155–169

    Article  PubMed  CAS  Google Scholar 

  • Roehl (1926) Die Wirkung des Plasmochins auf die Vogel Malaria. Naturwissenschaften 14:1156–1159

    Article  CAS  Google Scholar 

  • Ruhe DS, Cooper WC, Coatney GR, Josephson ES (1949) Studies in human malaria XV. The therapeutic action of pamaquine (Plasmochin) against St. Elizabeth strain vivax malaria. Am J Hyg 49:367–373

    Google Scholar 

  • Ryer HF (1971) The distribution, excretion and retention of primaquine-o-methyl-3H-diphosphate following oral administration to rats. Fed Proc 30:335

    Google Scholar 

  • Salvidio E, Pannacciulli I, Tizianello A, Ajmar (1967) Nature of hemolytic crises and the fate of G-6-PD deficient, drug-damaged erythrocytes in Sardinians. N Engl J Med 276:1339–1344

    CAS  Google Scholar 

  • Sansone G, Segni G (1957) Sensitivity to broad beans. Lancet 2:295

    Article  Google Scholar 

  • Schmidt IG, Schmidt LH (1949a) Neurotoxicity of the 8-aminoquinolines. I. Lesions in the central nervous system of the rhesus monkey induced by administration of plasmocid J Neuropathol Exp Neurol 7:368–393

    Google Scholar 

  • Schmidt IG, Schmidt LH (1949b) Neurotoxicity of the 8-aminoquinolines. II. Reactions of various experimental animals to plasmocid. J Comp Neurol 91:337–367

    Google Scholar 

  • Schmidt IG, Schmidt LH (1951) Neurotoxicity of the 8-aminoquinolines. III. The effects of pentaquine, isopentaquine, primaquine, and pamaquine on the central nervous system of the rhesus monkey. J Neuropathol Exp Neurol 10:231–256

    Google Scholar 

  • Schmidt LH (1981) Comparative efficacies of quinine and chloroquine as companions to primaquine in a curative drug regimen. Am J Trop Med Hyg 30:20–25

    PubMed  CAS  Google Scholar 

  • Schmidt LH (1982) Plasmodium cynomolgi infections in the rhesus monkey. Background of studies. Am J Trop Med Hyg 31:Part 2, pp 609–611

    Google Scholar 

  • Schmidt LH, Alexander S, Allen L, Rasco J (1977a) Comparison of the curative antimalarial activities and toxicities of primaquine and its d and l isomers. Antimicrob Agents Chemother 12:51–60

    PubMed  CAS  Google Scholar 

  • Schmidt LH, Coatney GR (1955) Review of investigations in malaria chemotherapy (USA) 1946 to 1954. Am J Trop Med Hyg 4:203–216

    Google Scholar 

  • Schmidt LH, Fradkin R, Genther CS, Hughes HB (1982c) III. Delineation of the potentials of primaquine as a radical curative and prophylactic drug. Am J Trop Med Hyg 31:666–680

    Google Scholar 

  • Schmidt LH, Fradkin R, Genther CS, Rossan R, Squires W (1982a) I. The characteristics of untreated sporozoite-induced and trophozoite-induced infections. Am J Trop Med Hyg 31:612–645

    Google Scholar 

  • Schmidt LH, Fradkin R, Genther CS, Rossan R, Squires W (1982b) II. Responses of sporozoite-induced and trophozoite-induced infections to standard antimalarial drugs. Am J Trop Med Hyg 31:646–665

    Google Scholar 

  • Schmidt LH, Fradkin R, Vaughan D, Rasco J (1977b) Radical cure of infections with Plasmodium cynomolgi:A function of total 8-aminoquinoline dose. Am J Trop Med Hyg 26:1116–1128

    PubMed  CAS  Google Scholar 

  • Schmidt LH, Genther CS, Rosan RN (1982d) IV. Acquisition of Anopheles quadrimaculatus infected with the M strain and Anopheles freeborni infected with the M, B, or Ro strain. Am J Trop Med Hyg 31:681–698

    Google Scholar 

  • Schulemann W (1932) Synthetic anti-malarial preparations. Proc Roy Soc Med 25:897–905

    PubMed  CAS  Google Scholar 

  • Schwartz JM, Jaffe ER (1978) Hereditary methemoglobinemia with deficiency of NADH dehydrogenase. In: Stanbury JB, Wyngaarden JB, Fredrickson DS (eds) The metabolic basis of inherited disease, 4th edn. McGraw-Hill, New York, p 1430

    Google Scholar 

  • Shortt HE, Fairley NH, Covell G, Shute PG, Garnham PCC (1949) The pre-erythrocytic stage of Plasmodium falciparum. Trans R Soc Trop Med Hyg 44:405–419

    Article  Google Scholar 

  • Shortt HE, Garnham PCC (1948) Demonstration of a persisting exoerythrocytic cycle in Plasmodium cynomolgi and its bearing on the production of relapses. Br Med J 1:1225–1232

    Article  Google Scholar 

  • Shortt HE, Garnham PCC, Covell G, Shute PG (1948) The pre-erythrocytic stage of human malaria, Plasmodium vivax. Br Med J 1:1547

    Article  Google Scholar 

  • Sinton JA, Bird W (1928) Studies in malaria, with special reference to treatment. Part IX. Plasmoquine in the treatment of malaria. Indian J Med Res 16:159–177

    Google Scholar 

  • Sinton JA, Smith S, Pottinger D (1930) Studies in malaria, with special reference to treatment. Part XII. Further researches into the treatment of chronic benign tertian malaria with plasmoquine and quinine. Indian J Med Res 17:793–814

    Google Scholar 

  • Sipe JC, Vick NA, Schulman S, Fernandez C (1973) Plasmocid encephalopathy in the rhesus monkey:a study of selective vulnerability. J Neuropathol Exp Neurol 32:446–457

    Article  PubMed  CAS  Google Scholar 

  • Smith CC (1956) Metabolism of pentaquine in the rhesus monkey. J Pharmacol 116:67–76

    CAS  Google Scholar 

  • Steck EA (1972) Pamaquine. In: The chemotherapy of protozoan diseases. vol III, sect 4–5, pp 23, 147–23, 151. Division of medicinal chemistry, Walter Reed Army Institute of Research, Washington

    Google Scholar 

  • Strother A, Fraser IM, Allahyari R, Tilton BE (1981) Metabolism of 8-aminoquinoline antimalarial agents. Bull WHO 59:413–425

    PubMed  CAS  Google Scholar 

  • Thaeler AD Jr, Arnold J, Alving AS (1953) A clinical study of primaquine (SN-13,272) in the treatment of malaria among the Miskito Indians of Nicaragua. Am J Trop Med Hyg 2:989–999

    PubMed  Google Scholar 

  • Thompson PE, Werbel LM (1972) 8-Aminoquinolines. In: Antimalarial agents, chemistry and pharmacology. Medicinal chemistry, vol 12. Academic, New York, p 101

    Google Scholar 

  • Thomson D (1912) The destruction of crescents:conclusions regarding the prevention of malaria by the administration of quinine. Ann Trop Med Parasitol 6:223–230

    Google Scholar 

  • Trenholme GM, Williams RL, Frischer H, Carson PE, Rieckmann KH (1975a) Host failure in treatment of malaria with sulfalene and pyrimethamine. Ann Intern Med 82:219–223

    PubMed  CAS  Google Scholar 

  • Trenholme GM, Williams RL, Desjardins RE, Canfield CJ, Carson PE, Frischer H, Rieckmann KH (1975b) Mefloquine in the treatment of human malaria. Science 190:792–795

    Article  PubMed  CAS  Google Scholar 

  • Vivona S, Brewer GJ, Conrad M, Alving AS (1961) The concurrent weekly administration of chloroquine and primaquine for the prevention of Korean vivax malaria. Bull WHO 25:267–269

    PubMed  CAS  Google Scholar 

  • Vorobiew (1927) Appel’s method for the treatment of malaria. Russ J Trop Med 5:406–414

    Google Scholar 

  • Wilson W, Kirkman HN, Clemons EH (1980) Regulation of glucose-6-phosphate dehydrogenase. II. Resealed red cell ghosts. J Lab Clin Med 95:888–896

    CAS  Google Scholar 

  • Wiselogle FY (ed) (1946) A survey of antimalarial drugs 1941–1945, vol I. Edwards Brothers, Ann Arbor, pp 1–536

    Google Scholar 

  • Young MD (1959) The effect of small doses of primaquine upon malarial infections. Indian J Malar 13:69–74

    CAS  Google Scholar 

  • Ziai M, Amirhakim GH, Reinhold JG, Tabatabaee M, Gettner M, Bowman JE (1967) Malaria prophylaxis and treatment in G-6-PD deficiency. An observation on the toxicity of primaquine and chloroquine. Clin Pediatr (Phila) 6:242–243

    Article  CAS  Google Scholar 

  • Zubrod CG, Kennedy TJ, Shannon JA (1947) Studies on the chemotherapy of the human malarias. VIII. The physiological disposition of pamaquine. J Clin Invest 27:114–120

    Article  Google Scholar 

Download references

Authors
  1. P. E. Carson
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. London School of Hygiene and Tropical Medicine, Keppel Street, London, WC1E 7HT, Great Britain

    Wallace Peters M.D., DSc, FRCP, DTM & H (Professor of Medical Protozoology) (Professor of Medical Protozoology)

  2. Wellcome Research Laboratories, Ravens Lane, Berkhamsted, Herts., HP4 2DY, Great Britain

    William H. G. Richards BSc, Ph. D. (Manager, Scientific Advisory Services) (Manager, Scientific Advisory Services)

Rights and permissions

Reprints and permissions

Copyright information

© 1984 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Carson, P.E. (1984). 8-Aminoquinolines. In: Peters, W., Richards, W.H.G. (eds) Antimalarial Drug II. Handbook of Experimental Pharmacology, vol 68 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-69254-3_3

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-69254-3_3

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-69256-7

  • Online ISBN: 978-3-642-69254-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation