Scalable preparation and differential pharmacologic and toxicologic profiles of primaquine enantiomers

Antimicrobial Agents and Chemotherapy

Volumn 58, Issue 8, 2014, Pages 4737-4744

  Nanayakkara, N P Dhammika ^a   Tekwani, Babu L ^a,b   Herath, H M T Bandara ^a   Sahu, Rajnish ^a   Gettayacamin, Montip ^c   Tungtaeng, Anchalee ^c   Van Gessel, Yvonne ^c   Baresel, Paul ^d   Wickham, Kristina S ^d   Bartlett, Marilyn S ^e   Fronczek, Frank R ^f   Melendez, Victor ^g   Ohrt, Colin ^g   Reichard, Gregory A ^g   McChesney, James D ^h   Rochford, Rosemary ^d   Walker, Larry A ^a,b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c Army Medical Department Center and School   (United States)

^d State University of New York Upstate Medical University: College of Medicine   (United States)

^e INDIANA UNIVERSITY   (United States)

^f LOUISIANA STATE UNIVERSITY   (United States)

^g WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^h Ironstone Separations Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; PRIMAQUINE;

ANIMAL; BAGG ALBINO MOUSE; DOG; DRUG EFFECTS; ERYTHROCYTE; ERYTHROCYTE TRANSFUSION; FEMALE; GLUCOSE 6 PHOSPHATE DEHYDROGENASE DEFICIENCY; HEMOLYSIS; HUMAN; INSTITUTE FOR CANCER RESEARCH MOUSE; ISOLATION AND PURIFICATION; LD50; MALARIA; METABOLISM; MICROBIOLOGY; MOUSE; NONOBESE DIABETIC MOUSE; PARASITOLOGY; PHYSIOLOGY; PLASMODIUM BERGHEI; PNEUMOCYSTIS CARINII; PNEUMONIA, PNEUMOCYSTIS; SCID MOUSE; STEREOISOMERISM; XENOGRAFT;

ANIMALS; ANTIMALARIALS; DOGS; ERYTHROCYTE TRANSFUSION; ERYTHROCYTES; FEMALE; GLUCOSEPHOSPHATE DEHYDROGENASE DEFICIENCY; HEMOLYSIS; HUMANS; LETHAL DOSE 50; MALARIA; MICE; MICE, INBRED BALB C; MICE, INBRED ICR; MICE, INBRED NOD; MICE, SCID; PLASMODIUM BERGHEI; PNEUMOCYSTIS CARINII; PNEUMONIA, PNEUMOCYSTIS; PRIMAQUINE; STEREOISOMERISM; TRANSPLANTATION, HETEROLOGOUS;

EID: 84905386803     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.02674-13     Document Type: Article

References (40)

1. Tekwani BL, Walker L. 2006. A8-Aminoquinolines: future role as antiprotozoal drugs. Curr. Opin. Infect. Dis. 19:623-631. http://dx.doi.org/10. 1097/QCO.0b013e328010b848.
2. Vale N, Moreira R, Gomes P. 2009. Primaquine revisited six decades after its discovery. Eur. J. Med. Chem. 44:937-953. http://dx.doi.org/10.1016/j. ejmech.2008.08.011.
3. Fernando D, Rodrigo C, Rajapakse S. 2011. Primaquine in vivax malaria: an update and review on management issues. Malar. J. 10:351. http://dx.doi.org/10. 1186/1475-2875-10-351.
4. Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ. 2006. Primaquine: report from CDC expert meeting on malaria chemoprophylaxis. Am. J. Trop. Med. Hyg. 75:402-415.
5. Safrin SD, Finkelstein M, Feinberg J, Frame P, Simpson G, Wu A, Cheung T, Soeiro R, Hojczyk P, Black JR. 1996. Comparison of three regimens for treatment of mild to moderate Pneumocystis carinii pneumonia in patients with AIDS. A double-blind, randomized trial of oral trimethoprimsulfamethoxazole, dapsone-trimethoprim, and clindamycinprimaquine. Ann. Intern. Med. 124:792-802.
6. McCabe RE. 1988. Primaquine is lethal for intracellular but not extracellular Trypanosoma cruzi. J. Parasitol. 74:748-753. http://dx.doi.org/10. 2307/3282248.
7. Trotter ER, Peters W, Robinson BL. 1980. The experimental chemotherapy of leishmaniasis. VI. The development of rodent models for cutaneous infection with L. major and L. mexicana amazonensis. Ann. Trop. Med. Parasitol. 74:299-319.
8. Cowan WK, Evans DA. 1964. Primaquine and methemoglobin. Clin. Pharmacol. Ther. 5:307-309.
9. Tarlov AR, Brewer GL, Carson PE, Alving AS. 1962. Primaquine sensitivity. Arch. Intern. Med. 109:209-234. http://dx.doi.org/10.1001/archinte.1962. 03620140081013.
10. Brewer GJ, Tarlov AR, Kellermeyer RW, Alving AS. 1962. The hemolytic effect of primaquine. XV. Role of methemoglobin. J. Lab. Clin. Med. 59:905-917.
11. Nanayakkara NPD, Ager AL, Jr, Bartlett MS, Yardley V, Croft SL, Khan IA, McChesney JD, Walker LA. 2008. 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. Antimicrob. Agents Chemother. 52:2130-2137. http://dx.doi.org/10.1128/AAC.00645- 07.
12. Carroll FI, Berrang B, Linn CP. 1978. Resolution of antimalarial agents via complex formation with alpha.-(2, 4, 5, 7-tetranitro-9- fluorenylideneaminooxy) propionic acid. J. Med. Chem. 21:326-330. http://dx.doi.org/10.1021/jm00202a002.
13. Schmidt LH, Alexander S, Allen L, Rasco J. 1977. Comparison of the curative antimalarial activities and toxicities of primaquine and its d and l isomers. Antimicrob. Agents Chemother. 12:51-60. http://dx.doi.org/10.1128/AAC. 12.1.51.
14. Brossi A, Millet P, Landau I, Bembenek ME, Abell CW. 1987. Antimalarial activity and inhibition of monoamine oxidases A and B by exoerythrocytic antimalarials. Optical isomers of primaquine, N-acylated congeners, primaquine metabolites and 5-phenoxy-substituted analogs. FEBS Lett. 214:291-294.
15. Agarwal SU, Gupta R, Gupta RC, Anand N, Agarwal SS. 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.
16. Nicholl DD, Edwards G, Ward SA, Orme ML, Breckenridge AM. 1987. The disposition of primaquine in the isolated perfused rat liver. Stereoselective formation of the carboxylic acid metabolite. Biochem. Pharmacol. 36:3365-3369.
17. Baker JK, McChesney JD. 1988. Differential metabolism of the enantiomers of primaquine. J. Pharm. Sci. 77:380-382. http://dx.doi.org/10.1002/jps. 2600770503.
18. Avula B, Khan SI, Tekwani BL, Nanayakkara NPD, McChesney JD, Walker LA, Khan IA. 2011. Analysis of primaquine and its metabolite carboxyprimaquine in biological samples: enantiomeric separation, method validation and quantification. Biomed. Chromatogr. 25:1010-1017. http://dx.doi.org/10.1002/bmc. 1557.
19. Bartlett MS, Queener SF, Shaw MM, Durant PJ, Lee CH, Smith JW. 1997. In vitro and in vivo models of Pneumocystis carinii. J. Eukaryot. Microbiol. 44:51S. http://dx.doi.org/10.1111/j.1550-7408.1997.tb05772.x.
20. Rochford R, Ohrt C, Baresel P, Othoro C, Sampath A, Magill AJ, Tekwani BL, Walker LA. 2013. Humanized mouse model of glucose 6-phosphate dehydrogenase deficiency for in vivo assessment of hemolytic toxicity. Proc. Natl. Acad. Sci. U. S. A. 110:17486-17491. http://dx.doi.org/10.1073/pnas.1310402110.
21. Brocks DR, Mehvar R. 2003. Stereoselectivity in the pharmacodynamics and pharmacokinetics of the chiral antimalarial drugs. Clin. Pharmacokinet. 42:1359-1382. http://dx.doi.org/10.2165/00003088-200342150-00004.
22. Pybus BS, Sousa JC, Jin X, Ferguson JA, Christian RE, Barnhart R, Vuong C, Sciotti RJ, Reichard GA, Kozar MP, Walker LA, Ohrt C, Melendez V. 2012. CYP450 phenotyping and accurate mass identification of metabolites of the 8-aminoquinoline, anti-malarial drug primaquine. Malar. J. 11:259. http://dx.doi.org/10.1186/1475-2875-11-259.
23. Ganesan S, Tekwani BL, Sahu R, Tripathi LM, Walker LA. 2009. Cytochrome P (450)-dependent toxic effects of primaquine on human erythrocytes. Toxicol. Appl. Pharmacol. 241:14-22. http://dx.doi.org/10.1016/j.taap.2009.07.012.
24. Pybus BS, Marcsisin SR, Jin X, Deye G, Sousa JC, Li Q, Caridha D, Zeng Q, Reichard GA, Ockenhouse C, Bennett J, Walker LA, Ohrt C, Melendez V. 2013. The metabolism of primaquine to its active metabolite is dependent on CYP 2D6. Malar. J. 12:212. http://dx.doi.org/10.1186/1475-2875-12-212.
25. Mihaly GW, Ward SA, Edwards G, Orme ML, Breckenridge AM. 1984. Pharmacokinetics of primaquine in man: identification of the carboxylic acid derivative as a major plasma metabolite. Br. J. Clin. Pharmacol. 17:441-446. http://dx.doi.org/10.1111/j.1365-2125.1984.tb02369.x.
26. Clark AM, McChesney JD, Baker JK. 1984. Excretion, distribution, and metabolism of primaquine in rats. J. Pharm. Sci. 73:502-506. http://dx.doi.org/10.1002/jps.2600730418.
27. Baker JK, Bedford JA, Clark AM, McChesney JD. 1984. Metabolism and distribution of primaquine in monkeys. Pharm. Res. 1:98-100. http://dx.doi.org/10.1023/A:1016363600790.
28. Peters W, Robinson BL. 1984. The activity of primaquine and its possible metabolites against rodent malaria, p 93-101. In Wernsdorfer WH, Trigg PI (ed), Primaquine: pharmacokinetics, metabolism, toxicity and activity. John Wiley, Chichester, United Kingdom.
29. Link CM, Theoharides AD, Anders JC, Chung H, Canfield CJ. 1985. Structure-activity relationships of putative primaquine metabolites causing methemoglobin formation in canine hemolysates. Toxicol. Appl. Pharmacol. 81:192-202. http://dx.doi.org/10.1016/0041-008X(85)90155-3.
30. Vasquez-Vivar J, Augusto O. 1992. Hydroxylated metabolites of the antimalarial drug primaquine: oxidation and redox cycling. J. Biol. Chem. 267:6848-6854.
31. Vennerstrom JL, Eaton JW. 1988. Oxidants, oxidant drugs, and malaria. J. Med. Chem. 31:1269-1277. http://dx.doi.org/10.1021/jm00402a001.
32. Fletcher KA, Barton PF, Kelly JA. 1988. Studies on the mechanisms of oxidation in the erythrocyte by metabolites of primaquine. Biochem. Pharmacol. 37:2683-2690. http://dx.doi.org/10.1016/0006-2952(88)90263-8.
33. Avula B, Tekwani BL, Nanayakkara NPD, Wang Y-H, Chaurasiya ND, Khan SI, Adelli VR, Sahu RK, Elsohly MA, McChesney JD, Khan Walker IA LA. 2013. Profiling primaquine metabolites in primary human hepatocytes by UPLC-QTOF-MS with 13C stable isotope labeling. J. Mass Spectrom. 48:276-285. http://dx.doi.org/10. 1002/jms.3122.
34. Bates MD, Meshnick SR, Sigler CI, Leland P, Hollingdale MR. 1990. In vitro effects of primaquine and primaquine metabolites on exoerythrocytic stages of Plasmodium berghei. Am. J. Trop. Med. Hyg. 42:532-537.
35. Allahyari R, Strother A, Fraser IM, Verbiscar AJ. 1984. Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes. J. Med. Chem. 27:407-410. http://dx.doi.org/10.1021/jm00369a031.
36. Bowman ZS, Morrow JD, Jollow DJ, McMillan DC. 2005. Primaquineinduced hemolytic anemia: role of membrane lipid peroxidation and cytoskeletal protein alterations in the hemotoxicity of 5-hydroxyprimaquine. J. Pharmacol. Exp. Ther. 314:838-845. http://dx.doi.org/10.1124/jpet.105.086488.
37. Shetty RV, Wetter WP, Blanton CD, Jr. 1977. Synthesis of 2-benzyloxy and 2-benzylthio analogues of primaquine as potential antimalarials. J. Med. Chem. 20:1349-1351. http://dx.doi.org/10.1021/jm00220a025.
38. LaMontagne MP, Markovac A, Menke JR. 1977. Antimalarials. 10. Synthesis of 4-substituted primaquine analogues as candidate antimalarials. J. Med. Chem. 20:1123-1127.
39. Walker LA, Avula B, Chaurasiya ND, Sahu R, Herath HMTB, Stanford DS, Khan SI, Nanayakkara NPD, Khan IA, McChesney JD, Yates TW, Elsohly MA, Tekwani BL. 2012. Enantioselective pharmacokinetics of primaquine by healthy human volunteers. Am. J. Trop. Med. Hyg. 87(Suppl 1):204.
40. Shekalaghe S, Drakeley C, Gosling R, Ndaro A, Meegeren Mvan Enevold A, Alifrangis M, Mosha F, Sauerwein Bousema RT. 2007. Primaquine clears submicroscopic Plasmodium falciparum gametocytes that persist after treatment with sulphadoxine-pyrimethamine and artesunate. PLoS On. 2:e1023. http://dx.doi.org/10.1371/journal.pone.0001023.