Cinchona alkaloids: Quinine and quinidine

Milestones in Drug Therapy

Volumn 41, Issue , 2012, Pages 45-68

  Sullivan, David J ^a  

^a JOHNS HOPKINS BLOOMBERG SCHOOL OF PUBLIC HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTEMISININ; ARTESUNATE; BENZODIAZEPINE; CHARCOAL; CHLOROQUINE; CINCHONA ALKALOID; CINCHONIDINE; CLINDAMYCIN; DIHYDROQUINIDINE; DOXYCYCLINE; FLUNARIZINE; FOLIC ACID ANTAGONIST; HALOFANTRINE; KENENE SOL; MAL CAPS; MALONIC ACID PLUS OXALIC ACID; MEFLOQUINE; MULTIDRUG RESISTANCE PROTEIN 1; NO KO TAB; QUINARSINE; QUINIDINE; QUININE; RYZALEN; TREPONYL; UNCLASSIFIED DRUG; VERARD SOL;

ABDOMINAL PAIN; ANTIMALARIAL DRUG RESISTANCE; ARTICLE; BLINDNESS; CARDIOTOXICITY; CLINICAL EFFECTIVENESS; DISEASE SEVERITY; DOSE RESPONSE; DRUG ABSORPTION; DRUG APPROVAL; DRUG BINDING; DRUG BLOOD LEVEL; DRUG DOSE INCREASE; DRUG EFFECT; DRUG EFFICACY; DRUG ELIMINATION; DRUG HALF LIFE; DRUG ISOLATION; DRUG MECHANISM; DRUG METABOLISM; DRUG OVERDOSE; DRUG POTENCY; DRUG QUALITY; DRUG SAFETY; DRUG SYNTHESIS; DRUG TOLERABILITY; DRUG TREATMENT FAILURE; DRUG URINE LEVEL; DRUG WITHDRAWAL; GINGIVA BLEEDING; HEADACHE; HEARING IMPAIRMENT; HISTORY OF MEDICINE; HUMAN; HYPOGLYCEMIA; IC 50; INTOXICATION; LEG CRAMP; LOADING DRUG DOSE; MALARIA; MALARIA FALCIPARUM; MAXIMUM PLASMA CONCENTRATION; MOLECULAR DYNAMICS; NAUSEA; NONHUMAN; PARASITE CLEARANCE; PARASITEMIA; PATIENT COMPLIANCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PURPURA; STRUCTURE ACTIVITY RELATION; TASTE DISORDER; THROMBOCYTOPENIA; TINNITUS; TREATMENT DURATION; VISUAL DISORDER; VISUAL IMPAIRMENT;

EID: 84867018113     PISSN: None     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-0346-0480-2_3     Document Type: Article

References (145)

1. Bruce-Chwatt LJ (1988) Three hundred and fifty years of the Peruvian fever bark. Br Med J (Clin Res Ed) 296:1486-1487
2. Petithory JC (1995) On the discovery of the parasite of malaria by A. Laveran: Bone 1878-Constantine 1880. Hist Sci Med 29:57-62
3. Guttmann P, Ehrlich P (1891) Ueber die Wirkung des Methylenblau bei Malaria. Berlin Klin Wochenschr 28:953-956
4. Vennerstrom JL, Makler MT, Angerhofer CK, Williams JA (1995) Antimalarial dyes revisited: xanthenes, azines, oxazines, and thiazines. Antimicrob Agents Chemother 39:2671-2677
5. Greenwood D (1992) The quinine connection. J Antimicrob Chemother 30:417-427
6. Guerra F (1977) The introduction of cinchona in the treatment of malaria. Part II. J Trop Med Hyg 80:135-140
7. Guerra F (1977) The introduction of Cinchona in the treatment of malaria. Part I. J Trop Med Hyg 80:112-118
8. Garnham PC (1966) Malaria parasites and other haemosporidia. Blackwell Scientific, Oxford
9. Bruce-Chwatt LJ (1982) Oliver Cromwell's medical history. Trans Stud Coll Physicians Phila 4:98-121
10. Vane JR (2000) The fight against rheumatism: from willow bark to COX-1 sparing drugs. J Physiol Pharmacol 51:573-586
11. Greenwood D (1995) Conflicts of interest: the genesis of synthetic antimalarial agents in peace and war. J Antimicrob Chemother 36:857-872
12. Gramiccia G (1987) Ledger's cinchona seeds: a composite of field experience, chance, and intuition. Parassitologia 29:207-220
13. Delepine M (1951) Joseph Pelletier and Joseph Caventou. J Chem Educ 28:454-461
14. (1890) CXXVIII-Manufacture of quinine in India. Bull Misc Inf (Royal Gardens, Kew) 1890:29-34; www.jstororg/stable/4118253
15. Rocco F (2003) Quinine, malaria and the quest for a cure that changed the world. Perrenial, New York
16. Strecker A (1854) On the constitution of quinine. Lond Edinb Dublin Philos Mag J Sci 8:123-125
17. Johnston WT (2008) The discovery of aniline and the origin of the term "aniline dye". Biotech Histochem 83:83-87
18. Steverding D (2010) The development of drugs for treatment of sleeping sickness: a historical review. Parasit Vectors 3:15
19. Gensini GF, Conti AA, Lippi D (2007) The contributions of Paul Ehrlich to infectious disease. J Infect 54:221-224
20. Frankenburg FR, Baldessarini RJ (2008) Neurosyphilis, malaria, and the discovery of antipsychotic agents. Harv Rev Psychiatry 16:299-307
21. Horlein H (1936) The chemotherapy of infectious diseases caused by protozoa and bacteria: (Section of tropical diseases and parasitology). Proc R Soc Med 29:313-324
22. Lesher GY, Froelich EJ, Gruett MD, Bailey JH, Brundage RP (1962) 1,8-Naphthyridine derivatives: a new class of chemotherapeutic agents. J Med Pharm Chem 91:1063-1065
23. Andriole VT (2005) The quinolones: past, present, and future. Clin Infect Dis 41(Suppl 2): S113-119
24. Krishna S, Davis TM, Chan PC, Wells RA, Robson KJ (1988) Ciprofloxacin and malaria. Lancet 1:1231-1232
25. Mahmoudi N, Ciceron L, Franetich JF, Farhati K, Silvie O, Eling W, Sauerwein R, Danis M, Mazier D, Derouin F (2003) In vitro activities of 25 quinolones and fluoroquinolones against liver and blood stage Plasmodium spp. Antimicrob Agents Chemother 47:2636-2639
26. Seeman J (2007) The Woodward-Doering/Rabe-Kindler total synthesis of quinine: setting the record straight. Angew Chem Int Ed Engl 46:1378-1413
27. Stork G, Niu D, Fujimoto RA, Koft ER, Balkovec JM, Tata JR, Dake GR (2001) The first stereoselective total synthesis of quinine. J Am Chem Soc 123:3239-3242
28. Woodward RB, Doering WE (1944) The total synthesis of quinine. JACS 66:849
29. ter Kuile F, White NJ, Holloway P, Pasvol G, Krishna S (1993) Plasmodium falciparum: in vitro studies of the pharmacodynamic properties of drugs used for the treatment of severe malaria. Exp Parasitol 76:85-95
30. Price RN, Nosten F, Luxemburger C, ter Kuile FO, Paiphun L, Chongsuphajaisiddhi T, White NJ (1996) Effects of artemisinin derivatives on malaria transmissibility. Lancet 347:1654-1658
31. Fink E (1974) Assessment of causal prophylactic activity in Plasmodium berghei yoelii and its value for the development of new antimalarial drugs. Bull World Health Organ 50:213-222
32. Brown PJ (1997) Malaria, miseria, and underpopulation in Sardinia: the "malaria blocks development" cultural model. Med Anthropol 17:239-254
33. Davies EE, Warhurst DC, Peters W (1975) The chemotherapy of rodent malaria, XXI. Action of quinine and WR 122 (a 9-phenanthrenemethanol) on the fine structure of Plasmodium berghei in mouse blood. Ann Trop Med Parasitol 69:147-153
34. Gligorijevic B, Purdy K, Elliott DA, Cooper RA, Roepe PD (2008) Stage independent chloroquine resistance and chloroquine toxicity revealed via spinning disk confocal microscopy. Mol Biochem Parasitol 159:7-23
35. Slater AF (1993) Chloroquine: mechanism of drug action and resistance in Plasmodium falciparum. Pharmacol Ther 57:203-235
36. Warhurst DC, Craig JC, Adagu IS, Meyer DJ, Lee SY (2003) The relationship of physicochemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids. Malar J 2:26
37. Ginsburg H, Geary TG (1987) Current concepts and new ideas on the mechanism of action of quinoline-containing antimalarials. Biochem Pharmacol 36:1567-1576
38. Ginsburg H, Golenser J (2003) Glutathione is involved in the antimalarial action of chloroquine and its modulation affects drug sensitivity of human and murine species of Plasmodium. Redox Rep 8:276-279
39. Sullivan DJ Jr, Matile H, Ridley RG, Goldberg DE (1998) A common mechanism for blockade of heme polymerization by antimalarial quinolines. J Biol Chem 273:31103-31107
40. Sullivan DJ Jr, Gluzman IY, Russell DG, Goldberg DE (1996) On the molecular mechanism of chloroquine's antimalarial action. Proc Natl Acad Sci USA 93:11865-11870
41. Egan TJ, Mavuso WW, Ross DC, Marques HM (1997) Thermodynamic factors controlling the interaction of quinoline antimalarial drugs with ferriprotoporphyrin IX. J Inorg Biochem 68:137-145
42. de Villiers KA, Marques HM, Egan TJ (2008) The crystal structure of halofantrine-ferriprotoporphyrin IX and the mechanism of action of arylmethanol antimalarials. J Inorg Biochem 102:1660-1667
43. Leed A, DuBay K, Ursos LM, Sears D, De Dios AC, Roepe PD (2002) Solution structures of antimalarial drug-heme complexes. Biochemistry 41:10245-10255
44. Alumasa JN, Gorka AP, Casabianca LB, Comstock E, de Dios AC, Roepe PD (2011) The hydroxyl functionality and a rigid proximal N are required for forming a novel non-covalent quinine-heme complex. J Inorg Biochem 105:467-475
45. Chong CR, Sullivan DJ Jr (2003) Inhibition of heme crystal growth by antimalarials and other compounds: implications for drug discovery. Biochem Pharmacol 66:2201-2212
46. + channel in Plasmodium berghei transmission revealed by targeted gene disruption. Proc Natl Acad Sci USA 105:6398-6402
47. Waller KL, Kim K, McDonald TV (2008) Plasmodium falciparum: growth response to potassium channel blocking compounds. Exp Parasitol 120:280-285
48. Waller KL, McBride SM, Kim K, McDonald TV (2008) Characterization of two putative potassium channels in Plasmodium falciparum. Malar J 7:19
49. Sanchez-Chapula JA, Ferrer T, Navarro-Polanco RA, Sanguinetti MC (2003) Voltagedependent profile of human ether-a-go-go-related gene channel block is influenced by a single residue in the S6 transmembrane domain. Mol Pharmacol 63:1051-1058
50. + channel. Eur J Neurosci 16:415-428
51. Kuryshev YA, Ficker E, Wang L, Hawryluk P, Dennis AT, Wible BA, Brown AM, Kang J, Chen XL, Sawamura K et al (2005) Pentamidine-induced long QT syndrome and block of hERG trafficking. J Pharmacol Exp Ther 312:316-323
52. White NJ (2004) Antimalarial drug resistance. J Clin Invest 113:1084-1092
53. Le Jouan M, Jullien V, Tetanye E, Tran A, Rey E, Treluyer JM, Tod M, Pons G (2005) Quinine pharmacokinetics and pharmacodynamics in children with malaria caused by Plasmodium falciparum. Antimicrob Agents Chemother 49:3658-3662
54. Pukrittayakamee S, Wanwimolruk S, Stepniewska K, Jantra A, Huyakorn S, Looareesuwan S, White NJ (2003) Quinine pharmacokinetic-pharmacodynamic relationships in uncomplicated falciparum malaria. Antimicrob Agents Chemother 47:3458-3463
55. Karbwang J, Harinasuta T (1992) Overview: clinical pharmacology of antimalarials. SE Asian J Trop Med Public Health 23(Suppl 4):95-109
56. Caramello P, Canta F, Cavecchia I, Sergi G, Lipani F, Calleri G, Gobbi F, Di Perri G (2005) Pharmacodynamic analysis of antimalarials used in Plasmodium falciparum imported malaria in northern Italy. J Travel Med 12:127-132
57. Mapaba E, Hellgren U, Landberg-Lindgren A, Rombo L (1995) Susceptibility of Plasmodium falciparum to quinine in vitro: effects of drug concentrations and time of exposure. Trans R Soc Trop Med Hyg 89:85-89
58. Cooper RA, Lane KD, Deng B, Mu J, Patel JJ, Wellems TE, Su X, Ferdig MT (2007) Mutations in transmembrane domains 1, 4 and 9 of the Plasmodium falciparum chloroquine resistance transporter alter susceptibility to chloroquine, quinine and quinidine. Mol Microbiol 63:270-282
59. Karle JM, Karle IL, Gerena L, Milhous WK (1992) Stereochemical evaluation of the relative activities of the cinchona alkaloids against Plasmodium falciparum. Antimicrob Agents Chemother 36:1538-1544
60. Karle JM, Bhattacharjee AK (1999) Stereoelectronic features of the cinchona alkaloids determine their differential antimalarial activity. Bioorg Med Chem 7:1769-1774
61. Brocks DR, Mehvar R (2003) Stereoselectivity in the pharmacodynamics and pharmacokinetics of the chiral antimalarial drugs. Clin Pharmacokinet 42:1359-1382
62. Basco LK, Le Bras J (1992) In vitro activity of halofantrine and its relationship to other standard antimalarial drugs against African isolates and clones of Plasmodium falciparum. Am J Trop Med Hyg 47:521-527
63. White NJ (1998) Why is it that antimalarial drug treatments do not always work? Ann Trop Med Parasitol 92:449-458
64. Weinke T, Held T, Trautmann M, Rogler G, Mravak S, Alexander M, Pohle HD (1992) Malaria therapy in 452 patients, with special reference to the use of quinine. J Infect 25:173-180
65. Newton PN, Green MD, Fernandez FM (2010) Impact of poor-quality medicines in the 'developing' world. Trends Pharmacol Sci 31:99-101
66. Basco LK (2004) Molecular epidemiology of malaria in Cameroon. XIX. Quality of antimalarial drugs used for self-medication. Am J Trop Med Hyg 70:245-250
67. Fletcher W (1923) Notes on the treatment of malaria with the alkaloids of cinchona. John Bale, London
68. Looareesuwan S, Charoenpan P, Ho M, White NJ, Karbwang J, Bunnag D, Harinasuta T (1990) Fatal Plasmodium falciparum malaria after an inadequate response to quinine treatment. J Infect Dis 161:577-580
69. Peters W (1969) Drug resistance in malaria-a perspective. Trans R Soc Trop Med Hyg 63:25-45
70. Mu J, Ferdig MT, Feng X, Joy DA, Duan J, Furuya T, Subramanian G, Aravind L, Cooper RA, Wootton JC et al (2003) Multiple transporters associated with malaria parasite responses to chloroquine and quinine. Mol Microbiol 49:977-989
71. Brandicourt O, Druilhe P, Diouf F, Brasseur P, Turk P, Danis M (1986) Decreased sensitivity to chloroquine and quinine of some Plasmodium falciparum strains from Senegal in September 1984. Am J Trop Med Hyg 35:717-721
72. Benito A, Roche J, Molina R, Amela C, Alvar J (1995) In vitro susceptibility of Plasmodium falciparum to chloroquine, amodiaquine, quinine, mefloquine, and sulfadoxine/pyrimethamine in Equatorial Guinea. Am J Trop Med Hyg 53:526-531
73. Pradines B, Rogier C, Fusai T, Tall A, Trape JF, Doury JC (1996) In vitro sensitivity of 85 Plasmodium falciparum isolates in the Fatick region, Senegal. Med Trop (Mars) 56:141-145
74. Pradines B, Tall A, Parzy D, Spiegel A, Fusai T, Hienne R, Trape JF, Doury JC (1998) Invitro activity of pyronaridine and amodiaquine against African isolates (Senegal) of Plasmodium falciparum in comparison with standard antimalarial agents. J Antimicrob Chemother 42:333-339
75. Takechi M, Matsuo M, Ziba C, MacHeso A, Butao D, Zungu IL, Chakanika I, Bustos MD (2001) Therapeutic efficacy of sulphadoxine/pyrimethamine and susceptibility in vitro of P. falciparum isolates to sulphadoxine-pyremethamine and other antimalarial drugs in Malawian children. Trop Med Int Health 6:429-434
76. Pradines B, Tall A, Rogier C, Spiegel A, Mosnier J, Marrama L, Fusai T, Millet P, Panconi E, Trape JF et al (2002) In vitro activities of ferrochloroquine against 55 Senegalese isolates of Plasmodium falciparum in comparison with those of standard antimalarial drugs. Trop Med Int Health 7:265-270
77. Pradines B, Fusai T, Daries W, Laloge V, Rogier C, Millet P, Panconi E, Kombila M, Parzy D (2001) Ferrocene-chloroquine analogues as antimalarial agents: in vitro activity of ferrochloroquine against 103 Gabonese isolates of Plasmodium falciparum. J Antimicrob Chemother 48:179-184
78. Agnamey P, Brasseur P, de Pecoulas PE, Vaillant M, Olliaro P (2006) Plasmodium falciparum in vitro susceptibility to antimalarial drugs in Casamance (southwestern Senegal) during the first 5 years of routine use of artesunate-amodiaquine. Antimicrob Agents Chemother 50:1531-1534
79. Tinto H, Rwagacondo C, Karema C, Mupfasoni D, Vandoren W, Rusanganwa E, Erhart A, Van Overmeir C, Van Marck E, D'Alessandro U (2006) In-vitro susceptibility of Plasmodium falciparum to monodesethylamodiaquine, dihydroartemisinin and quinine in an area of high chloroquine resistance in Rwanda. Trans R Soc Trop Med Hyg 100:509-514
80. Pradines B, Hovette P, Fusai T, Atanda HL, Baret E, Cheval P, Mosnier J, Callec A, Cren J, Amalvict R et al (2006) Prevalence of in vitro resistance to eleven standard or new antimalarial drugs among Plasmodium falciparum isolates from Pointe-Noire, Republic of the Congo. J Clin Microbiol 44:2404-2408
81. Nsobya SL, Kiggundu M, Nanyunja S, Joloba M, Greenhouse B, Rosenthal PJ (2010) In vitro sensitivities of Plasmodium falciparum to different antimalarial drugs in Uganda. Antimicrob Agents Chemother 54:1200-1206
82. + exchanger (Pfnhe-1) gene with reduced in vitro susceptibility to quinine: lack of confirmation in clinical isolates from Africa. Am J Trop Med Hyg 82:782-787
83. Smrkovski LL, Buck RL, Alcantara AK, Rodriguez CS, Uylangco CV (1985) Studies of resistance to chloroquine, quinine, amodiaquine and mefloquine among Philippine strains of Plasmodium falciparum. Trans R Soc Trop Med Hyg 79:37-41
84. Hombhanje FW (1998) In vitro susceptibility of Plasmodium falciparum to four antimalarial drugs in the Central Province of Papua New Guinea. P N G Med J 41:51-58
85. Noedl H, Faiz MA, Yunus EB, Rahman MR, Hossain MA, Samad R, Miller RS, Pang LW, Wongsrichanalai C (2003) Drug-resistant malaria in Bangladesh: an in vitro assessment. Am J Trop Med Hyg 68:140-142
86. Chaijaroenkul W, Bangchang KN, Mungthin M, Ward SA (2005) In vitro antimalarial drug susceptibility in Thai border areas from 1998-2003. Malar J 4:37
87. Lim P, Chim P, Sem R, Nemh S, Poravuth Y, Lim C, Seila S, Tsuyuoka R, Denis MB, Socheat D et al (2005) In vitro monitoring of Plasmodium falciparum susceptibility to artesunate, mefloquine, quinine and chloroquine in Cambodia: 2001-2002. Acta Trop 93:31-40
88. Chaijaroenkul W, Wisedpanichkij R, Na-Bangchang K (2010) Monitoring of in vitro susceptibilities and molecular markers of resistance of Plasmodium falciparum isolates from Thai-Myanmar border to chloroquine, quinine, mefloquine and artesunate. Acta Trop 113:190-194
89. Legrand E, Volney B, Meynard JB, Mercereau-Puijalon O, Esterre P (2008) In vitro monitoring of Plasmodium falciparum drug resistance in French Guiana: a synopsis of continuous assessment from 1994 to 2005. Antimicrob Agents Chemother 52:288-298
90. Cerutti Junior C, Marques C, Alencar FE, Durlacher RR, Alween A, Segurado AA, Pang LW, Zalis MG (1999) Antimalarial drug susceptibility testing of Plasmodium falciparum in Brazil using a radioisotope method. Mem Inst Oswaldo Cruz 94:803-809
91. Lim P, Wongsrichanalai C, Chim P, Khim N, Kim S, Chy S, Sem R, Nhem S, Yi P, Duong S et al (2010) Decreased in vitro susceptibility of Plasmodium falciparum isolates to artesunate, mefloquine, chloroquine, and quinine in Cambodia from 2001 to 2007. Antimicrob Agents Chemother 54:2135-2142
92. Young MD, Eyles DE (1948) The efficacy of chloroquine, quinacrine, quinine and totaquine in the treatment of Plasmodium malariae infections (quartan malaria). Am J Trop Med Hyg 28:23-28
93. Sanchez CP, Stein WD, Lanzer M (2008) Dissecting the components of quinine accumulation in Plasmodium falciparum. Mol Microbiol 67:1081-1093
94. Cabrera M, Paguio MF, Xie C, Roepe PD (2009) Reduced digestive vacuolar accumulation of chloroquine is not linked to resistance to chloroquine toxicity. Biochemistry 48:11152-11154
95. Nkrumah LJ, Riegelhaupt PM, Moura P, Johnson DJ, Patel J, Hayton K, Ferdig MT, Wellems TE, Akabas MH, Fidock DA (2009) Probing the multifactorial basis of Plasmodium falciparum quinine resistance: evidence for a strain-specific contribution of the sodiumproton exchanger PfNHE. Mol Biochem Parasitol 165:122-131
96. Ursing J, Zakeri S, Gil JP, Bjorkman A (2006) Quinoline resistance associated polymorphisms in the pfcrt, pfmdr1 and pfmrp genes of Plasmodium falciparum in Iran. Acta Trop 97:352-356
97. Sanchez CP, Rotmann A, Stein WD, Lanzer M (2008) Polymorphisms within PfMDR1 alter the substrate specificity for anti-malarial drugs in Plasmodium falciparum. Mol Microbiol 70:786-798
98. Pleeter P, Lekostaj JK, Roepe PD (2010) Purified Plasmodium falciparum multi-drug resistance protein (PfMDR 1) binds a high affinity chloroquine analogue. Mol Biochem Parasitol 173:158-161
99. Cooper RA, Ferdig MT, Su XZ, Ursos LM, Mu J, Nomura T, Fujioka H, Fidock DA, Roepe PD, Wellems TE (2002) Alternative mutations at position 76 of the vacuolar transmembrane protein PfCRT are associated with chloroquine resistance and unique stereospecific quinine and quinidine responses in Plasmodium falciparum. Mol Pharmacol 61:35-42
100. + exchanger 1 transporter is involved in reduced susceptibility to quinine. Antimicrob Agents Chemother 53:1926-1930
101. Langford NJ, Good AM, Laing WJ, Bateman DN (2003) Quinine intoxications reported to the Scottish Poisons Information Bureau 1997-2002: a continuing problem. Br J Clin Pharmacol 56:576-578
102. Taylor WR, White NJ (2004) Antimalarial drug toxicity: a review. Drug Saf 27:25-61
103. Touze JE, Heno P, Fourcade L, Deharo JC, Thomas G, Bohan S, Paule P, Riviere P, Kouassi E, Buguet A (2002) The effects of antimalarial drugs on ventricular repolarization. Am J Trop Med Hyg 67:54-60
104. Gous P, Haus M (1990) Intravenous flunarizine therapy for acute toxicity in malaria. S Afr Med J 77:217
105. Bacon P, Spalton DJ, Smith SE (1988) Blindness from quinine toxicity. Br J Ophthalmol 72:219-224
106. Dyson EH, Proudfoot AT, Prescott LF, Heyworth R (1985) Death and blindness due to overdose of quinine. Br Med J (Clin Res Ed) 291:31-33
107. Dickinson P, Sabto J, West RH (1981) Management of quinine toxicity. Trans Ophthalmol Soc N Z 33:56-58
108. Hill J (1963) Part 2: The antimalarial drugs. In: Schnitzer RJ, Hawking F (eds) Experimental chemotherapy, vol 1. Academic, New York, pp 513-602
109. George CR (2009) Blackwater fever: the rise and fall of an exotic disease. J Nephrol 22 (Suppl 14):120-128
110. Bruce-Chwatt LJ (1987) Quinine and the mystery of blackwater fever. Acta Leiden 55:181-196
111. Rogier C, Imbert P, Tall A, Sokhna C, Spiegel A, Trape JF (2003) Epidemiological and clinical aspects of blackwater fever among African children suffering frequent malaria attacks. Trans R Soc Trop Med Hyg 97:193-197
112. Bruneel F, Gachot B, Wolff M, Regnier B, Danis M, Vachon F (2001) Resurgence of blackwater fever in long-term European expatriates in Africa: report of 21 cases and review. Clin Infect Dis 32:1133-1140
113. Van den Ende J, Coppens G, Verstraeten T, Van Haegenborgh T, Depraetere K, Van Gompel A, Van den Enden E, Clerinx J, Colebunders R, Peetermans WE et al (1998) Recurrence of blackwater fever: triggering of relapses by different antimalarials. Trop Med Int Health 3:632-639
114. Vipan WH (1865) Quinine as a cause of purpura. Lancet 86:37
115. Aster RH (1999) Drug-induced immune thrombocytopenia: an overview of pathogenesis. Semin Hematol 36:2-6
116. Zakarija A, Bennett C (2005) Drug-induced thrombotic microangiopathy. Semin Thromb Hemost 31:681-690
117. Burgess JK, Lopez JA, Berndt MC, Dawes I, Chesterman CN, Chong BH (1998) Quininedependent antibodies bind a restricted set of epitopes on the glycoprotein Ib-IX complex: characterization of the epitopes. Blood 92:2366-2373
118. Park YA, Hay SN, King KE, Matevosyan K, Poisson J, Powers A, Sarode R, Shaz B, Brecher ME (2009) Is it quinine TTP/HUS or quinine TMA? ADAMTS13 levels and implications for therapy. J Clin Apher 24:115-119
119. Boehme MW, Werle E, Kommerell B, Raeth U (1994) Serum levels of adhesion molecules and thrombomodulin as indicators of vascular injury in severe Plasmodium falciparum malaria. Clin Investig 72:598-603
120. Kojouri K, Vesely SK, George JN (2001) Quinine-associated thrombotic thrombocytopenic purpura-hemolytic uremic syndrome: frequency, clinical features, and long-term outcomes. Ann Intern Med 135:1047-1051
121. Brinker AD, Beitz J (2002) Spontaneous reports of thrombocytopenia in association with quinine: clinical attributes and timing related to regulatory action. Am J Hematol 70:313-317
122. (2010) Safety of quinine. Med Lett Drugs Ther, 52:88
123. El-Tawil S, Al Musa T, Valli H, Lunn MP, El-Tawil T, Weber M (2010) Quinine for muscle cramps. Cochrane Database Syst Rev 12: CD005044
124. Yeager OW, Reider RF, Mc DG (1946) Evaluation of totaquine in treatment of malaria in an endemic malarious area. J Am Pharm Assoc Am Pharm Assoc 35:337
125. Taggart JV, Earle DP Jr et al (1948) Studies on the chemotherapy of the human malarias; the physiological disposition and antimalarial activity of the cinchona alkaloids. J Clin Invest 27:80-86
126. Earle DP Jr, Welch WJ, Shannon JA et al (1948) Studies on the chemotherapy of the human malarias the metabolism of cinchonine in relation to its antimalarial activity. J Clin Invest 27:87-92
127. White NJ (1985) Clinical pharmacokinetics of antimalarial drugs. Clin Pharmacokinet 10:187-215
128. White NJ, Looareesuwan S, Warrell DA, Warrell MJ, Bunnag D, Harinasuta T (1982) Quinine pharmacokinetics and toxicity in cerebral and uncomplicated falciparum malaria. Am J Med 73:564-572
129. Zhao XJ, Yokoyama H, Chiba K, Wanwimolruk S, Ishizaki T (1996) Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human live microsomes and nine recombinant human cytochromes P450. J Pharmacol Exp Ther 279:1327-1334
130. Hutzler JM, Walker GS, Wienkers LC (2003) Inhibition of cytochrome P450 2D6: structureactivity studies using a series of quinidine and quinine analogues. Chem Res Toxicol 16:450-459
131. Soyinka JO, Onyeji CO, Omoruyi SI, Owolabi AR, Sarma PV, Cook JM (2010) Pharmacokinetic interactions between ritonavir and quinine in healthy volunteers following concurrent administration. Br J Clin Pharmacol 69:262-270
132. Soyinka JO, Onyeji CO, Omoruyi SI, Owolabi AR, Sarma PV, Cook JM (2009) Effects of concurrent administration of nevirapine on the disposition of quinine in healthy volunteers. J Pharm Pharmacol 61:439-443
133. Nosten F, McGready R, D'Alessandro U, Bonell A, Verhoeff F, Menendez C, Mutabingwa T, Brabin B (2006) Antimalarial drugs in pregnancy: a review. Curr Drug Saf 1:1-15
134. Donovan JL, DeVane CL, Boulton D, Dodd S, Markowitz JS (2003) Dietary levels of quinine in tonic water do not inhibit CYP2D6 in vivo. Food Chem Toxicol 41:1199-1201
135. Taggart JV, Earle DP, Berliner RW, Zubrod CG, Welch WJ, Wise NB, Schroeder EF, London IM, Shannon JA (1948) Studies on the chemotherapy of the human malarias. III. The physiological disposition and antimalarial activity of the cinchona alkaloids. J Clin Invest 27:80-86
136. Krishna S, White NJ (1996) Pharmacokinetics of quinine, chloroquine and amodiaquine. Clinical implications. Clin Pharmacokinet 30:263-299
137. Krishna S, Nagaraja NV, Planche T, Agbenyega T, Bedo-Addo G, Ansong D, Owusu-Ofori A, Shroads AL, Henderson G, Hutson A et al (2001) Population pharmacokinetics of intramuscular quinine in children with severe malaria. Antimicrob Agents Chemother 45:1803-1809
138. Watt G, Loesuttivibool L, Shanks GD, Boudreau EF, Brown AE, Pavanand K, Webster HK, Wechgritaya S (1992) Quinine with tetracycline for the treatment of drug-resistant falciparum malaria in Thailand. Am J Trop Med Hyg 47:108-111
139. Pukrittayakamee S, Chantra A, Vanijanonta S, Clemens R, Looareesuwan S, White NJ (2000) Therapeutic responses to quinine and clindamycin in multidrug-resistant falciparum malaria. Antimicrob Agents Chemother 44:2395-2398
140. Sinclair D, Donegan S, Lalloo DG: (2011) Artesunate versus quinine for treating severe malaria. Cochrane Database Syst Rev 3:CD005967
141. Phu NH, Tuan PQ, Day N, Mai NT, Chau TT, Chuong LV, Sinh DX, White NJ, Farrar J, Hien TT (2010) Randomized controlled trial of artesunate or artemether in Vietnamese adults with severe falciparum malaria. Malar J 9:97
142. Lubell Y, Yeung S, Dondorp AM, Day NP, Nosten F, Tjitra E, Abul Faiz M, Yunus EB, Anstey NM, Mishra SK et al (2009) Cost-effectiveness of artesunate for the treatment of severe malaria. Trop Med Int Health 14:332-337
143. Jones KL, Donegan S, Lalloo DG: (2007) Artesunate versus quinine for treating severe malaria. Cochrane Database Syst Rev: CD005967
144. Dondorp AM, Nosten F, Yi P, Das D, Phyo AP, Tarning J, Lwin KM, Ariey F, Hanpithakpong W, Lee SJ et al (2009) Artemisinin resistance in Plasmodium falciparum malaria. N Engl J Med 361:455-467
145. Witkowski B, Lelievre J, Barragan MJ, Laurent V, Su XZ, Berry A, Benoit-Vical F (2010) Increased tolerance to artemisinin in Plasmodium falciparum is mediated by a quiescence mechanism. Antimicrob Agents Chemother 54:1872-1877