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Volumn 52, Issue 6, 2008, Pages 2130-2137

Antiparasitic activities and toxicities of individual enantiomers of the 8-aminoquinoline 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3,4- dichlorophenoxy]quinoline succinate

Author keywords

[No Author keywords available]

Indexed keywords

8 [(4 AMINO 1 METHYLBUTYL)AMINO] 6 METHOXY 4 METHYL 5 (3,4 DICHLOROPHENOXY)QUINOLINE SUCCINATE; 8 AMINOQUINOLINE 8 [(4 AMINO 1 METHYLBUTYL)AMINO] 6 METHOXY 4 METHYL 5 (3,4 DICHLOROPHENOXY)QUINOLINE SUCCINATE; 8 AMINOQUINOLINE DERIVATIVE; ANTIPARASITIC AGENT; METHEMOGLOBIN; NPC 1161A; NPC 1161B; NPC 1161C; PRIMAQUINE; SITAMAQUINE; TAFENOQUINE;

EID: 44449113132     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.00645-07     Document Type: Article
Times cited : (67)

References (49)
  • 1
    • 0024202763 scopus 로고
    • Susceptibility of glucose-6-phosphate dehydrogenase-deficient red cells to primaquine enantiomers and two putative metabolites. I. Effect on reduced glutathione, methemoglobin content and release of hemoglobin
    • Agarwal, S., U. R. Gupta, R. C. Gupta, N. Anand, and S. S. Agarwal. 1988. Susceptibility of glucose-6-phosphate dehydrogenase-deficient red cells to primaquine enantiomers and two putative metabolites. I. Effect on reduced glutathione, methemoglobin content and release of hemoglobin. Biochem. Pharmacol. 37:4605-4609.
    • (1988) Biochem. Pharmacol , vol.37 , pp. 4605-4609
    • Agarwal, S.1    Gupta, U.R.2    Gupta, R.C.3    Anand, N.4    Agarwal, S.S.5
  • 2
    • 7644226738 scopus 로고    scopus 로고
    • Primaquine therapy for malaria
    • Baird, J. K., and S. L. Hoffman. 2004. Primaquine therapy for malaria. Clin. Infect. Dis. 39:1336-1345.
    • (2004) Clin. Infect. Dis , vol.39 , pp. 1336-1345
    • Baird, J.K.1    Hoffman, S.L.2
  • 3
    • 0022504463 scopus 로고
    • Effects of nine synthetic putative metabolites of primaquine on activity of the hexose monophosphate shunt in intact human red blood cells in vitro
    • Baird, J. K., G. J. McCormick, and C. J. Canfield. 1986. Effects of nine synthetic putative metabolites of primaquine on activity of the hexose monophosphate shunt in intact human red blood cells in vitro. Biochem. Pharmacol. 35:1099-1106.
    • (1986) Biochem. Pharmacol , vol.35 , pp. 1099-1106
    • Baird, J.K.1    McCormick, G.J.2    Canfield, C.J.3
  • 4
    • 0024242183 scopus 로고
    • Differential metabolism of the enantiomers of primaquine
    • Baker, J. K., and J. D. McChesney. 1988. Differential metabolism of the enantiomers of primaquine. J. Pharm. Sci. 77:380-382.
    • (1988) J. Pharm. Sci , vol.77 , pp. 380-382
    • Baker, J.K.1    McChesney, J.D.2
  • 5
    • 0026081818 scopus 로고
    • 8-Aminoquinolines from Walter Reed Army Institute for Research for treatment and prophylaxis of Pneumocystis pneumonia in rat models
    • Bartlett, M. S., S. F. Queener, R. R. Tidwell, W. K. Milhous, J. D. Berman, W. Y. Ellis, and J. W. Smith. 1991. 8-Aminoquinolines from Walter Reed Army Institute for Research for treatment and prophylaxis of Pneumocystis pneumonia in rat models. Antimicrob. Agents Chemother. 35:277-282.
    • (1991) Antimicrob. Agents Chemother , vol.35 , pp. 277-282
    • Bartlett, M.S.1    Queener, S.F.2    Tidwell, R.R.3    Milhous, W.K.4    Berman, J.D.5    Ellis, W.Y.6    Smith, J.W.7
  • 8
    • 0025289722 scopus 로고
    • In vitro effects of primaquine and primaquine metabolites on exoerythrocytic stages of Plasmodium berghei
    • Bates, M. D., S. R. Meshnick, C. I. Sigler, P. Leland, and M. R. Hollingdale. 1990. In vitro effects of primaquine and primaquine metabolites on exoerythrocytic stages of Plasmodium berghei. Am. J. Trop. Med. Hyg. 42:532-537.
    • (1990) Am. J. Trop. Med. Hyg , vol.42 , pp. 532-537
    • Bates, M.D.1    Meshnick, S.R.2    Sigler, C.I.3    Leland, P.4    Hollingdale, M.R.5
  • 10
    • 0025854115 scopus 로고
    • Clindamycin and primaquine as primary treatment for mild and moderately severe Pneumocystis carinii pneumonia in patients with AIDS
    • Black, J. R., J. Feinberg, R. L. Murphy, R. J. Fass, J. Carey, and F. R. Sattler. 1991. Clindamycin and primaquine as primary treatment for mild and moderately severe Pneumocystis carinii pneumonia in patients with AIDS. Eur. J. Clin. Microbiol. Infect. Dis. 10:204-207.
    • (1991) Eur. J. Clin. Microbiol. Infect. Dis , vol.10 , pp. 204-207
    • Black, J.R.1    Feinberg, J.2    Murphy, R.L.3    Fass, R.J.4    Carey, J.5    Sattler, F.R.6
  • 11
    • 0028335216 scopus 로고
    • Clindamycin and primaquine therapy for mild-to-moderate episodes of Pneumocystis carinii pneumonia in patients with AIDS: AIDS Clinical Trials Group 044
    • Black, J. R., J. Feinberg, R. L. Murphy, R. J. Fass, D. Finkelstein, B. Akil, S. Safrin, J. T. Carey, J. Stansell, and J. F. Plouffe. 1994. Clindamycin and primaquine therapy for mild-to-moderate episodes of Pneumocystis carinii pneumonia in patients with AIDS: AIDS Clinical Trials Group 044. Clin. Infect. Dis. 18:905-913.
    • (1994) Clin. Infect. Dis , vol.18 , pp. 905-913
    • Black, J.R.1    Feinberg, J.2    Murphy, R.L.3    Fass, R.J.4    Finkelstein, D.5    Akil, B.6    Safrin, S.7    Carey, J.T.8    Stansell, J.9    Plouffe, J.F.10
  • 12
    • 0036896929 scopus 로고    scopus 로고
    • Primaquine-induced hemolytic anemia: Formation of free radicals in rat erythrocytes exposed to 6-methoxy-8-hydroxylaminoquinoline
    • Bolchoz, L. J. C., A. K. Gelasco, D. J. Jollow, and D. C. McMillan. 2002. Primaquine-induced hemolytic anemia: formation of free radicals in rat erythrocytes exposed to 6-methoxy-8-hydroxylaminoquinoline. J. Pharmacol. Exp. Ther. 303:1121-1129.
    • (2002) J. Pharmacol. Exp. Ther , vol.303 , pp. 1121-1129
    • Bolchoz, L.J.C.1    Gelasco, A.K.2    Jollow, D.J.3    McMillan, D.C.4
  • 13
    • 1642292958 scopus 로고    scopus 로고
    • Primaquine-induced hemolytic anemia: Susceptibility of normal versus glutathione-depleted rat erythrocytes to 5-hydroxyprimaquine
    • Bowman, Z. S., J. E. Oatis, Jr., J. L. Whelan, D. J. Jollow, and D. C. McMillan. 2004. Primaquine-induced hemolytic anemia: susceptibility of normal versus glutathione-depleted rat erythrocytes to 5-hydroxyprimaquine. J. Pharmacol. Exp. Ther. 309:79-85.
    • (2004) J. Pharmacol. Exp. Ther , vol.309 , pp. 79-85
    • Bowman, Z.S.1    Oatis Jr., J.E.2    Whelan, J.L.3    Jollow, D.J.4    McMillan, D.C.5
  • 14
    • 0023190257 scopus 로고
    • Antimalarial activity and inhibition of monoamine oxidases A and B by exo-erythrocytic antimalarials. Optical isomers of primaquine, N-acylated congeners, primaquine metabolites and 5-phenoxy-substituted analogs
    • Brossi, A., P. Millet, I. Landau, M. E. Bembenek, and C. W. Abell. 1987. Antimalarial activity and inhibition of monoamine oxidases A and B by exo-erythrocytic antimalarials. Optical isomers of primaquine, N-acylated congeners, primaquine metabolites and 5-phenoxy-substituted analogs. FEBS Lett. 214:291-294.
    • (1987) FEBS Lett , vol.214 , pp. 291-294
    • Brossi, A.1    Millet, P.2    Landau, I.3    Bembenek, M.E.4    Abell, C.W.5
  • 15
    • 9044222890 scopus 로고
    • Quinoline series. III. Preparation of some 8-(ω- alkylaminoalkylamino)-quinolines
    • Campbell, K. N., A. H. Sommers, J. H. Kerwin, and B. K. Campbell. 1946. Quinoline series. III. Preparation of some 8-(ω- alkylaminoalkylamino)-quinolines. J. Am. Chem. Soc. 68:1556-1559.
    • (1946) J. Am. Chem. Soc , vol.68 , pp. 1556-1559
    • Campbell, K.N.1    Sommers, A.H.2    Kerwin, J.H.3    Campbell, B.K.4
  • 16
    • 0014425983 scopus 로고
    • Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam
    • Cohen, R. J., J. R. Sachs, D. J. Wicker, and M. E. Conrad. 1968. Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam. N. Engl. J. Med. 279:1127-1131.
    • (1968) N. Engl. J. Med , vol.279 , pp. 1127-1131
    • Cohen, R.J.1    Sachs, J.R.2    Wicker, D.J.3    Conrad, M.E.4
  • 17
    • 0035687445 scopus 로고    scopus 로고
    • Phase 2 trial of WR6026, an orally administered 8-aminoquinoline, in the treatment of visceral leishmaniasis caused by Leishmania chagasi
    • Dietze, R., S. F. G. Carvalho, L. C. Valli, J. Berman, T. Brewer, W. Milhous, J. Sanchez, B. Schuster, and M. Grogl. 2001. Phase 2 trial of WR6026, an orally administered 8-aminoquinoline, in the treatment of visceral leishmaniasis caused by Leishmania chagasi. Am. J. Trop. Med. Hyg. 65:685-689.
    • (2001) Am. J. Trop. Med. Hyg , vol.65 , pp. 685-689
    • Dietze, R.1    Carvalho, S.F.G.2    Valli, L.C.3    Berman, J.4    Brewer, T.5    Milhous, W.6    Sanchez, J.7    Schuster, B.8    Grogl, M.9
  • 18
    • 44449093000 scopus 로고    scopus 로고
    • GC-MS analysis of the 8-aminoquinoline antimalarial [NPC1161] and its carboxy metabolite in plasma and red blood cells of primates
    • Elsohly, M. A., W. Gul, S. Feng, N. P. D. Nanayakkara, A. M. Clark, S. Khan, F. B. Cogswell, and L. A. Walker. 2006. GC-MS analysis of the 8-aminoquinoline antimalarial [NPC1161] and its carboxy metabolite in plasma and red blood cells of primates. Chromatographia 64:199-205.
    • (2006) Chromatographia , vol.64 , pp. 199-205
    • Elsohly, M.A.1    Gul, W.2    Feng, S.3    Nanayakkara, N.P.D.4    Clark, A.M.5    Khan, S.6    Cogswell, F.B.7    Walker, L.A.8
  • 19
    • 0023924545 scopus 로고
    • Studies on the mechanisms of oxidation in the erythrocyte by metabolites of primaquine
    • Fletcher, K. A., P. F. Barton, and J. A. Kelly. 1988. Studies on the mechanisms of oxidation in the erythrocyte by metabolites of primaquine. Biochem. Pharmacol. 37:2683-2690.
    • (1988) Biochem. Pharmacol , vol.37 , pp. 2683-2690
    • Fletcher, K.A.1    Barton, P.F.2    Kelly, J.A.3
  • 21
    • 29844441606 scopus 로고    scopus 로고
    • A phase II dose-ranging study of sitamaquine for the treatment of visceral leishmaniasis in India
    • Jha, T. K., S. Sundar, C. P. Thakur, J. M. Felton, A. J. Sabin, and J. Horton. 2005. A phase II dose-ranging study of sitamaquine for the treatment of visceral leishmaniasis in India. Am. J. Trop. Med. Hyg. 73:1005-1011.
    • (2005) Am. J. Trop. Med. Hyg , vol.73 , pp. 1005-1011
    • Jha, T.K.1    Sundar, S.2    Thakur, C.P.3    Felton, J.M.4    Sabin, A.J.5    Horton, J.6
  • 22
    • 0026478821 scopus 로고
    • Primaquine-induced methemoglobinemia during treatment of Pneumocystis carinii pneumonia
    • Kantor, G. S. 1992. Primaquine-induced methemoglobinemia during treatment of Pneumocystis carinii pneumonia. N. Engl. J. Med. 327:1461.
    • (1992) N. Engl. J. Med , vol.327 , pp. 1461
    • Kantor, G.S.1
  • 23
    • 0025373992 scopus 로고
    • Clindamycin/ primaquine therapy and secondary prophylaxis against Pneumocystis carinii pneumonia in patients with AIDS
    • Kay, R., and R. E. DuBois. 1990. Clindamycin/ primaquine therapy and secondary prophylaxis against Pneumocystis carinii pneumonia in patients with AIDS. South. Med. J. 83:403-404.
    • (1990) South. Med. J , vol.83 , pp. 403-404
    • Kay, R.1    DuBois, R.E.2
  • 24
    • 0029907471 scopus 로고    scopus 로고
    • Primaquine analogs that are potent anti-Trypanosoma cruzi agents in a mouse model
    • Kinnamon, K. E., B. T. Poon, W. L. Hanson, and V. B. Waits. 1996. Primaquine analogs that are potent anti-Trypanosoma cruzi agents in a mouse model. Ann. Trop. Med. Parasitol. 90:467-474.
    • (1996) Ann. Trop. Med. Parasitol , vol.90 , pp. 467-474
    • Kinnamon, K.E.1    Poon, B.T.2    Hanson, W.L.3    Waits, V.B.4
  • 26
    • 0020384171 scopus 로고
    • Antimalarials. 14. 5-(Aryloxy)-4-methylprimaquine analogs. A highly effective series of blood and tissue schizonticidal agents
    • LaMontagne, M. P., P. Blumbergs, and R. E. Strube. 1982. Antimalarials. 14. 5-(Aryloxy)-4-methylprimaquine analogs. A highly effective series of blood and tissue schizonticidal agents. J. Med. Chem. 25:1094-1097.
    • (1982) J. Med. Chem , vol.25 , pp. 1094-1097
    • LaMontagne, M.P.1    Blumbergs, P.2    Strube, R.E.3
  • 27
    • 0022342389 scopus 로고
    • Structure-activity relationships of putative primaquine metabolites causing methemoglobin formation in canine hemolyzates
    • Link, C. M., A. D. Theoharides, J. C. Anders, H. Chung, and C. J. Canfield. 1985. Structure-activity relationships of putative primaquine metabolites causing methemoglobin formation in canine hemolyzates. Toxicol. Appl. Pharmacol. 81:192-202.
    • (1985) Toxicol. Appl. Pharmacol , vol.81 , pp. 192-202
    • Link, C.M.1    Theoharides, A.D.2    Anders, J.C.3    Chung, H.4    Canfield, C.J.5
  • 28
    • 0023719353 scopus 로고
    • Primaquine is lethal for intracellular but not extracellular Trypanosoma cruzi
    • McCabe, R. E. 1988. Primaquine is lethal for intracellular but not extracellular Trypanosoma cruzi. J. Parasitol. 74:748-753.
    • (1988) J. Parasitol , vol.74 , pp. 748-753
    • McCabe, R.E.1
  • 29
    • 44449179223 scopus 로고    scopus 로고
    • McChesney, J. D, N. P. D. Nanayakkara, M. Bartlett, and A. L. Ager. April 2002. 8-Aminoquinolines. U.S. patent 6,376,511
    • McChesney, J. D., N. P. D. Nanayakkara, M. Bartlett, and A. L. Ager. April 2002. 8-Aminoquinolines. U.S. patent 6,376,511.
  • 30
    • 0023475202 scopus 로고
    • The disposition of primaquine in the isolated perfused rat liver. Stereoselective formation of the carboxylic acid metabolite
    • Nicholl, D. D., G. Edwards, S. A. Ward, M. L. Orme, and A. M. Breckenridge. 1987. The disposition of primaquine in the isolated perfused rat liver. Stereoselective formation of the carboxylic acid metabolite. Biochem. Pharmacol. 36:3365-3369.
    • (1987) Biochem. Pharmacol , vol.36 , pp. 3365-3369
    • Nicholl, D.D.1    Edwards, G.2    Ward, S.A.3    Orme, M.L.4    Breckenridge, A.M.5
  • 32
    • 0027491678 scopus 로고
    • 8-Amino-quinolines effective against Pneumocystis carinii in vitro and in vivo
    • Queener, S. F., M. S. Bartlett, M. Nasr, and J. W. Smith. 1993. 8-Amino-quinolines effective against Pneumocystis carinii in vitro and in vivo. Antimicrob. Agents Chemother. 37:2166-2172.
    • (1993) Antimicrob. Agents Chemother , vol.37 , pp. 2166-2172
    • Queener, S.F.1    Bartlett, M.S.2    Nasr, M.3    Smith, J.W.4
  • 34
    • 0026647832 scopus 로고
    • Efficacy of intermittent dosage of 8-aminoquinolines for therapy or prophylaxis of Pneumocystis carinii pneumonia in rats
    • Queener, S. F., R. A. Deen, M. S. Bartlett, W. K. Milhous, J. D. Berman, W. Y. Ellis, and J. W. Smith. 1992. Efficacy of intermittent dosage of 8-aminoquinolines for therapy or prophylaxis of Pneumocystis carinii pneumonia in rats. J. Infect. Dis. 165:764-768.
    • (1992) J. Infect. Dis , vol.165 , pp. 764-768
    • Queener, S.F.1    Deen, R.A.2    Bartlett, M.S.3    Milhous, W.K.4    Berman, J.D.5    Ellis, W.Y.6    Smith, J.W.7
  • 36
    • 0017372529 scopus 로고
    • Comparison of the curative antimalarial activities and toxicities of primaquine and its d and l isomers
    • Schmidt, L. H., S. Alexander, L. Allen, and J. Rasco. 1977. Comparison of the curative antimalarial activities and toxicities of primaquine and its d and l isomers. Antimicrob. Agents Chemother. 12:51-60.
    • (1977) Antimicrob. Agents Chemother , vol.12 , pp. 51-60
    • Schmidt, L.H.1    Alexander, S.2    Allen, L.3    Rasco, J.4
  • 38
    • 0036010751 scopus 로고    scopus 로고
    • Methemoglobin reductase activity and in vitro sensitivity towards oxidant induced methemoglobinemia in Swiss mice and beagle dogs erythrocytes
    • Srivastava, S., A. S. Alhomida, N. J. Siddiqi, S. K. Puri, and V. C. Pandey. 2002. Methemoglobin reductase activity and in vitro sensitivity towards oxidant induced methemoglobinemia in Swiss mice and beagle dogs erythrocytes. Mol. Cell. Biochem. 232:81-85.
    • (2002) Mol. Cell. Biochem , vol.232 , pp. 81-85
    • Srivastava, S.1    Alhomida, A.S.2    Siddiqi, N.J.3    Puri, S.K.4    Pandey, V.C.5
  • 39
    • 0027208841 scopus 로고
    • Biodegradable microspheres: XIV. Effect of microparticle-bound primaquine on Leishmania donovani in mice
    • Stjaernkvist, P. 1993. Biodegradable microspheres: XIV. Effect of microparticle-bound primaquine on Leishmania donovani in mice. Int. J. Pharm. 96:23-32.
    • (1993) Int. J. Pharm , vol.96 , pp. 23-32
    • Stjaernkvist, P.1
  • 41
    • 33750512152 scopus 로고    scopus 로고
    • 8-Aminoquinolines: Future role as antiprotozoal drugs
    • Tekwani, B. L., and L. A. Walker. 2006. 8-Aminoquinolines: future role as antiprotozoal drugs. Curr. Opin. Infect. Dis. 19:623-631.
    • (2006) Curr. Opin. Infect. Dis , vol.19 , pp. 623-631
    • Tekwani, B.L.1    Walker, L.A.2
  • 42
    • 0014065863 scopus 로고
    • Relations among antimalarial drugs: Results of studies with cycloquanil-, sulfone-, or chloroquine-resistant Plasmodium berghei in mice
    • Thompson, P. E., B. Olszewski, A. Bayles, and J. A. Waitz. 1967. Relations among antimalarial drugs: results of studies with cycloquanil-, sulfone-, or chloroquine-resistant Plasmodium berghei in mice. Am. J. Trop. Med. Hyg. 16:133-145.
    • (1967) Am. J. Trop. Med. Hyg , vol.16 , pp. 133-145
    • Thompson, P.E.1    Olszewski, B.2    Bayles, A.3    Waitz, J.A.4
  • 43
    • 0025806312 scopus 로고
    • Clindamycin/primaquine for treatment of Pneumocystis carinii pneumonia in AIDS
    • Toma, E. 1991. Clindamycin/primaquine for treatment of Pneumocystis carinii pneumonia in AIDS. Eur. J. Clin. Microbiol. Infect. Dis. 10:210-213.
    • (1991) Eur. J. Clin. Microbiol. Infect. Dis , vol.10 , pp. 210-213
    • Toma, E.1
  • 44
    • 0027248912 scopus 로고
    • Clindamycin/primaquine versus trimethoprim-sulfamethoxazole as primary therapy for Pneumocystis carinii pneumonia in AIDS: A randomized, double-blind pilot trial
    • Toma, E., S. Fournier, M. Dumont, P Bolduc, and H. Deschamps. 1993. Clindamycin/primaquine versus trimethoprim-sulfamethoxazole as primary therapy for Pneumocystis carinii pneumonia in AIDS: a randomized, double-blind pilot trial. Clin. Infect. Dis. 17:178-184.
    • (1993) Clin. Infect. Dis , vol.17 , pp. 178-184
    • Toma, E.1    Fournier, S.2    Dumont, M.3    Bolduc, P.4    Deschamps, H.5
  • 45
    • 0024604644 scopus 로고
    • Clindamycin with primaquine for Pneumocystis carinii pneumonia
    • Toma, E., S. Fournier, M. Poisson, R. Morisset, D. Phaneuf, and C. Vega. 1989. Clindamycin with primaquine for Pneumocystis carinii pneumonia. Lancet i:1046-1048.
    • (1989) Lancet , vol.1 , pp. 1046-1048
    • Toma, E.1    Fournier, S.2    Poisson, M.3    Morisset, R.4    Phaneuf, D.5    Vega, C.6
  • 46
    • 0030855768 scopus 로고    scopus 로고
    • Cytosolic arylamine N-acetyltransferase (NAT) deficiency in the dog and other canids due to an absence of NAT genes
    • Trepanier, L. A., K. Ray, N. J. Winand, S. P. Spielberg, and A. E. Cribb. 1997. Cytosolic arylamine N-acetyltransferase (NAT) deficiency in the dog and other canids due to an absence of NAT genes. Biochem. Pharmacol. 54:73-80.
    • (1997) Biochem. Pharmacol , vol.54 , pp. 73-80
    • Trepanier, L.A.1    Ray, K.2    Winand, N.J.3    Spielberg, S.P.4    Cribb, A.E.5
  • 47
    • 0023777973 scopus 로고
    • Oxidants, oxidant drugs, and malaria
    • Vennerstrom, J. L., and J. W. Eaton. 1988. Oxidants, oxidant drugs, and malaria. J. Med. Chem. 31:1269-1277.
    • (1988) J. Med. Chem , vol.31 , pp. 1269-1277
    • Vennerstrom, J.L.1    Eaton, J.W.2


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