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Chemical Compound Review

PRIMAQUINE     N-(6-methoxyquinolin-8- yl)pentane-1,4-diamine

Synonyms: Kanaprim, Primachin, Primaquin, Primachina, Primaquina, ...
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Disease relevance of PRIMAQUINE


Psychiatry related information on PRIMAQUINE


High impact information on PRIMAQUINE


Chemical compound and disease context of PRIMAQUINE


Biological context of PRIMAQUINE

  • Subtherapeutic primaquine doses, the shorter extrinsic cycle of P vivax in the insect vector, and the timing of MDA at a high-transmission period of the year may explain the limited effects of the campaign [17].
  • DAB cytochemistry showed that sorting between endocytosed 131I-transferrin and 125I-ASOR/HRP was also blocked in the presence of primaquine [18].
  • Previously, we showed that drug-induced endocytosis, which can occur in adult RBCs exposed to amphipathic cations like primaquine, is greatly enhanced in all density-defined fractions of neonatal RBCs [19].
  • However, enzymatic assays show that the rate of MTX hydrolysis was unaltered in the MTX-resistant R1000-3 line and the primaquine-resistant PQ-R30 line (which is 24-fold cross-resistant to MTX) [20].
  • In this assay, primaquine inhibits protein transport at a half-maximal concentration of 50 microM, similar to the concentration previously reported to disrupt protein secretion in cultured cells [21].

Anatomical context of PRIMAQUINE

  • Following internalization CD4DAF recycles through a primaquine-insensitive compartment, whereas the recycling of transmembrane CD4 is inhibited by primaquine, suggesting that the two receptors may recycle from distinct populations of early endosomes [22].
  • The intracellular transport to the Golgi complex of the membrane protein VSV-G was not affected by primaquine as it acquires resistance to endo-beta-N-acetylglucosaminidase H at the same rate as in control cells [23].
  • Primaquine specifically accumulated within endocytotic compartments (including CURL vesicles, multivesicular bodies and lysosomes) [4].
  • Agents that induce endocytosis in intact erythrocytes (primaquine, vinblastine, and chlorpromazine) caused a prompt movement of 45Ca from cytosol to membrane-associated sites [24].
  • We also found a significant decrease in the ability of the immunized animals to express iNOS in response to sporozoite challenge by accelerating the removal of pre-existing irradiated-attenuated parasites from hepatocytes with the antimalarial drug, primaquine [25].

Associations of PRIMAQUINE with other chemical compounds


Gene context of PRIMAQUINE


Analytical, diagnostic and therapeutic context of PRIMAQUINE


  1. Frequency of relapse and primaquine resistance in Southeast Asian vivax malaria. Krotoski, W.A. N. Engl. J. Med. (1980) [Pubmed]
  2. Primaquine-induced methemoglobinemia during treatment of Pneumocystis carinii pneumonia. Kantor, G.S. N. Engl. J. Med. (1992) [Pubmed]
  3. High rate of Plasmodium vivax relapse following treatment of falciparum malaria in Thailand. Looareesuwan, S., White, N.J., Chittamas, S., Bunnag, D., Harinasuta, T. Lancet (1987) [Pubmed]
  4. Immunoelectron microscopic localization of acidic intracellular compartments in hepatoma cells. Schwartz, A.L., Strous, G.J., Slot, J.W., Geuze, H.J. EMBO J. (1985) [Pubmed]
  5. Primaquine prophylaxis against malaria in nonimmune Colombian soldiers: efficacy and toxicity. A randomized, double-blind, placebo-controlled trial. Soto, J., Toledo, J., Rodriquez, M., Sanchez, J., Herrera, R., Padilla, J., Berman, J. Ann. Intern. Med. (1998) [Pubmed]
  6. The impact of Malarone and primaquine on psychomotor performance. Paul, M.A., McCarthy, A.E., Gibson, N., Kenny, G., Cook, T., Gray, G. Aviation, space, and environmental medicine. (2003) [Pubmed]
  7. In vitro cultivation of the exoerythrocytic stage of Plasmodium berghei from sporozoites. Hollingdale, M.R., Leef, J.L., McCullough, M., Beaudoin, R.L. Science (1981) [Pubmed]
  8. Therapy and prophylaxis of malaria. Trenholme, G.H., Carson, P.E. JAMA (1978) [Pubmed]
  9. Carl Jung. Kyle, R.A., Shampo, M.A. JAMA (1978) [Pubmed]
  10. Randomised placebo-controlled trial of primaquine for prophylaxis of falciparum and vivax malaria. Fryauff, D.J., Baird, J.K., Basri, H., Sumawinata, I., Purnomo, n.u.l.l., Richie, T.L., Ohrt, C.K., Mouzin, E., Church, C.J., Richards, A.L. Lancet (1995) [Pubmed]
  11. Clindamycin/primaquine for Pneumocystis carinii pneumonia. Ruf, B., Pohle, H.D. Lancet (1989) [Pubmed]
  12. Toxicity of clindamycin and primaquine treatment of AIDS-related Pneumocystis carinii pneumonia. Smith, N., Blanshard, C., Smith, D., Gazzard, B. AIDS (1993) [Pubmed]
  13. Lymphocyte response to tetanus toxoid among Indonesian men immunized with tetanus-diphtheria during extended chloroquine or primaquine prophylaxis. Fryauff, D.J., Church, L.W., Richards, A.L., Widjaja, H., Mouzin, E., Ratiwayanto, S., Hadiputranto, H., Sutamihardja, M.A., Richie, T.L., Subianto, B., Tjitra, E., Hoffman, S.L. J. Infect. Dis. (1997) [Pubmed]
  14. Primaquine as prophylaxis for malaria for nonimmune travelers: A comparison with mefloquine and doxycycline. Schwartz, E., Regev-Yochay, G. Clin. Infect. Dis. (1999) [Pubmed]
  15. Malaria chemoprophylaxis in the age of drug resistance. II. Drugs that may be available in the future. Shanks, G.D., Kain, K.C., Keystone, J.S. Clin. Infect. Dis. (2001) [Pubmed]
  16. Role of aniline metabolites in aniline-induced hemolytic anemia. Harrison, J.H., Jollow, D.J. J. Pharmacol. Exp. Ther. (1986) [Pubmed]
  17. Changes in malaria incidence after mass drug administration in Nicaragua. Garfield, R.M., Vermund, S.H. Lancet (1983) [Pubmed]
  18. Sorting of endocytosed transferrin and asialoglycoprotein occurs immediately after internalization in HepG2 cells. Stoorvogel, W., Geuze, H.J., Strous, G.J. J. Cell Biol. (1987) [Pubmed]
  19. Comparison of transferrin receptor-mediated endocytosis and drug-induced endocytosis in human neonatal and adult RBCs. Thatte, H.S., Schrier, S.L. Blood (1988) [Pubmed]
  20. Wild-type and drug-resistant Leishmania major hydrolyze methotrexate to N-10-methyl-4-deoxy-4-aminopteroate without accumulation of methotrexate polyglutamates. Ellenberger, T.E., Wright, J.E., Rosowsky, A., Beverley, S.M. J. Biol. Chem. (1989) [Pubmed]
  21. Primaquine blocks transport by inhibiting the formation of functional transport vesicles. Studies in a cell-free assay of protein transport through the Golgi apparatus. Hiebsch, R.R., Raub, T.J., Wattenberg, B.W. J. Biol. Chem. (1991) [Pubmed]
  22. Endocytosis of glycophospholipid-anchored and transmembrane forms of CD4 by different endocytic pathways. Keller, G.A., Siegel, M.W., Caras, I.W. EMBO J. (1992) [Pubmed]
  23. Effect of lysosomotropic amines on the secretory pathway and on the recycling of the asialoglycoprotein receptor in human hepatoma cells. Strous, G.J., Du Maine, A., Zijderhand-Bleekemolen, J.E., Slot, J.W., Schwartz, A.L. J. Cell Biol. (1985) [Pubmed]
  24. Calcium distribution within human erythrocytes during endocytosis. Schrier, S.L., Johnson, M., Junga, I., Krueger, J. Blood (1980) [Pubmed]
  25. Co-localization of inducible-nitric oxide synthase and Plasmodium berghei in hepatocytes from rats immunized with irradiated sporozoites. Klotz, F.W., Scheller, L.F., Seguin, M.C., Kumar, N., Marletta, M.A., Green, S.J., Azad, A.F. J. Immunol. (1995) [Pubmed]
  26. Ligand- and weak base-induced redistribution of asialoglycoprotein receptors in hepatoma cells. Zijderhand-Bleekemolen, J.E., Schwartz, A.L., Slot, J.W., Strous, G.J., Geuze, H.J. J. Cell Biol. (1987) [Pubmed]
  27. Invariant chain retains MHC class II molecules in the endocytic pathway. Loss, G.E., Sant, A.J. J. Immunol. (1993) [Pubmed]
  28. Glucosidase II, a protein of the endoplasmic reticulum with high mannose oligosaccharide chains and a rapid turnover. Strous, G.J., Van Kerkhof, P., Brok, R., Roth, J., Brada, D. J. Biol. Chem. (1987) [Pubmed]
  29. Oxidative stress participates in the breakdown of neuronal phenotype in experimental diabetic neuropathy. Hounsom, L., Corder, R., Patel, J., Tomlinson, D.R. Diabetologia (2001) [Pubmed]
  30. Cytochrome 1A1 induction by primaquine in human hepatocytes and HepG2 cells: absence of binding to the aryl hydrocarbon receptor. Fontaine, F., Delescluse, C., de Sousa, G., Lesca, P., Rahmani, R. Biochem. Pharmacol. (1999) [Pubmed]
  31. Reversal of MRP-mediated doxorubicin resistance with quinoline-based drugs. Vezmar, M., Georges, E. Biochem. Pharmacol. (2000) [Pubmed]
  32. Differentiation-inducing quinolines as experimental breast cancer agents in the MCF-7 human breast cancer cell model. Martirosyan, A.R., Rahim-Bata, R., Freeman, A.B., Clarke, C.D., Howard, R.L., Strobl, J.S. Biochem. Pharmacol. (2004) [Pubmed]
  33. Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Bapiro, T.E., Egnell, A.C., Hasler, J.A., Masimirembwa, C.M. Drug Metab. Dispos. (2001) [Pubmed]
  34. The gap junction protein connexin43 is degraded via the ubiquitin proteasome pathway. Laing, J.G., Beyer, E.C. J. Biol. Chem. (1995) [Pubmed]
  35. Humoral immune response to tetanus-diphtheria vaccine given during extended use of chloroquine or primaquine malaria chemoprophylaxis. Fryauff, D.J., Cryz, S.J., Widjaja, H., Mouzin, E., Church, L.W., Sutamihardja, M.A., Richards, A.L., Subianto, B., Hoffman, S.L. J. Infect. Dis. (1998) [Pubmed]
  36. Carrier-linked primaquine in the chemotherapy of malaria. Hofsteenge, J., Capuano, A., Altszuler, R., Moore, S. J. Med. Chem. (1986) [Pubmed]
  37. Primaquine: metabolism by microorganisms and 13C nuclear magnetic resonance assignments. Clark, A.M., Huford, C.D., McChesney, J.D. Antimicrob. Agents Chemother. (1981) [Pubmed]
  38. Enantioselective analysis of primaquine and its metabolite carboxyprimaquine by capillary electrophoresis. Bortocan, R., Bonato, P.S. Electrophoresis (2004) [Pubmed]
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