Experimental and clinical studies on rifacinna® - The new effective antituberculous drug (review)

Recent Patents on Anti-Infective Drug Discovery

Volumn 5, Issue 1, 2010, Pages 76-90

  Velichka, Dimova ^a   Ivana, Atanasova ^a   Haruaki, Tomioka ^b   Katsumasa, Sato ^b   Venkata, Reddy ^c   Nadadhur, Geeta ^c   Donna, Daneluzzi ^c   Patisapu, Gangadharam ^c   Todor, Kantardjiev ^d   Arvind, Dhople ^e   Yurii, Feshchenko ^f   Ljudmila, Yashina ^f   Andrei, Toumanov ^f   Zvetana, Zhivkova ^g   Chiaki, Sano ^b  

^a Res Inst Pharmacology   (Bulgaria)

^b SHIMANE UNIVERSITY   (Japan)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d National Centerof Infectious and Parasitic Diseases   (Bulgaria)

^e FLORIDA INSTITUTE OF TECHNOLOGY   (United States)

^f National Institute of Pulmology and Tuberculosis Kiev   (Ukraine)

^g Trakia University Medical College   (Bulgaria)

Author keywords

Clinical study; Experimental tuberculosis; In vitro; In vivo; Mycobacterium tuberculosis; Pharmacokinetics; Rifacinna; Rifamycins; T11; T9; Toxicology; Tuberculosis

Indexed keywords

1 (6 BROMO 2 METHOXY 3 QUINOLINYL) 4 DIMETHYLAMINO 2 (1 NAPHTHYL) 1 PHENYL 2 BUTANOL; 2,3 DIHYDRO 2 METHYL 6 NITRO 2 [4 [4 (4 TRIFLUOROMETHOXYPHENOXY) 1 PIPERIDINYL]PHENOXYMETHYL]IMIDAZO[2,1 B]OXAZOLE; 3 (4 CINNAMYL 1 PIPERAZINYLIMINOMETHYL)RIFAMYCIN SV SODIUM; 3 (4 CINNAMYLPIPERAZINYLIMINOMETHYL)RIFAMYCIN SV; 6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; ETHAMBUTOL; GATIFLOXACIN; ISONIAZID; LL 3858; MOXIFLOXACIN; N (2 ADAMANTYL) N' GERANYLETHYLENEDIAMINE; PYRAZINAMIDE; PYRROLE DERIVATIVE; RIFABUTIN; RIFACINNA; RIFALAZIL; RIFAMPICIN; RIFAMYCIN DERIVATIVE; RIFAPENTINE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

AEROBIC BACTERIUM; ANAEROBIC BACTERIUM; ANTIBACTERIAL ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CLINICAL TRIAL; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG EFFECT; DRUG EFFICACY; DRUG HALF LIFE; DRUG SAFETY; DRUG TOLERABILITY; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HUMAN; LD 50; LUNG TUBERCULOSIS; MAXIMUM PLASMA CONCENTRATION; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MILIARY TUBERCULOSIS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM AVIUM; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PATENT; PHAGOCYTOSIS; PRIORITY JOURNAL; SINGLE DRUG DOSE; STAPHYLOCOCCUS; STREPTOCOCCUS; TOXICITY TESTING; TUBERCULOSIS;

ANIMALS; ANTIBIOTICS, ANTITUBERCULAR; DISEASE MODELS, ANIMAL; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM; RIFAMYCINS; STRUCTURE-ACTIVITY RELATIONSHIP; TOXICITY TESTS; TREATMENT OUTCOME; TUBERCULOSIS;

EID: 77953760910     PISSN: 1574891X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157489110790112572     Document Type: Article

References (81)

1. Heifets L. Drug susceptibility in the chemotherapy of mycobacterial infections. CRC Press: Boca Raton, Fla 1991; 103-109.
2. Tiruviluamala P, Reichman L. Tuberculosis. Annu Rev Public Health 2002; 23: 403-426.
3. Frieden T, Sterling T, Munsiff S, Watt C, Dye C. Tuberculosis. Lancet 2003; 362: 887-899.
4. Marcus V, de Souza N. Promising drugs against tuberculosis. Rec Pat Anti-Infective Drug Discov 2006; 1: 33-44.
5. O'Brien R, Nunn P. The need for new drugs against tuberculosis. Obstacles, opportunities, and next steps. Am J Respir Crit Care Med 2001; 163: 1055-1058.
6. American Thoracic Society/Centers for disease control and prevention/infectious diseases society of America treatment of tuberculosis. Am J Resp Crit Care Med 2003; 167: 603-662.
7. Tomioka H, Namba K. Development of antituberculous drugs: Current status and future prospects. Kekkaku. Tuberculosis 2006; 81(12): 753-774.
8. Mitnick C, McGee B, Peloquin C. Tuberculosis pharmacotherapy: Strategies to optimize patient care. Expert Opin Pharmacother 2009; 10(3): 381-340.
9. Palomino J, Ramos D, Silva PA. New antituberculosis drugs: Strategies, sources and new molecules Curr Med Chem 2009; 16(15): 1898-1904.
10. Tomioka H. Development of new antituberculous drugs: Strategies for new drug targets and drug delivery. Drug Des Rev 2006; 2(6): 427-434.
11. Tomioka H. Current status of some antituberculosis drugs and the development of new antituberculous agents with special reference to their in vitro and in vivo antimicrobial activities. Curr Pharm Des 2006; 12(31): 4047-4070.
12. Binda G, Domenichini E, Gottardi A, Ortelli E, Pacini B, Fowst G. Rifampicin, a general view. Arzneim Forsch/Drug Res 1971; 21: 1907-1977.
13. Acocella G. Clinical pharmacokinetics of Rifampicin. Clin Pharmacokinet 1978; 3: 108-127.
14. Rustomjee R, Diacon H, Allen J, et al. Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis. Antimicrob Agents Chemother 2008; 52(8): 2831-2835.
15. Dimova V, Sapunjieva E, Pencheva P, Toshcova K, Atanasova I. in vitro Antibacterial activity of new rifamycin derivative, separately and in combinations with other antibacterial agents. 18 ICC, Montreal, 16-21. Can J Infect Dis 1995; 6 (Suppl C): 2276.
16. Brogden RN, Fitton A. Rifabutin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 1994; 47: 983-1009.
17. th Int Congress Chemotherap, Stockholm June-July 1993; Abstr. no 302: 1323.
18. O'Brien RJ, Lyle MA, Snider DE Jr. Rifabutin (ansamycin LM 427): A new rifamycin-S derivative for the treatment of mycobacterial diseases. Rev Infect Dis 1987; 9: 519-530.
19. Sullam PM. Rifabutin therapy for disseminated Mycobacterium avium complex infection. Clin Infect Dis 1996; 22 (Suppl 1): S37-41.
20. Tomioka H, Sato K, Hidaka T, Saito H. in vitro and in vivo Antimycobacterial activities of KRM-1648, a new benzoxa-zinorifamycin. In: Pandali SG, Ed. Recent research developments in antimicrobial agents and chemotherapy, Trivandrum. Res Signpost 1997; 37-68.
21. Tomioka H. Prospects for development of new antimycobacterial drugs, with special reference to a new benzoxazinorifamycin, KRM-1648. Arch Immunol Ther Exp 2000; 48: 183-188.
22. Grassi C, Peona V. Use of rifabutin in the treatment of pulmonary tuberculosis. Clin Infect Dis 1996; 22 (Suppl 1): S50-54.
23. Van Duzer, J., Michaelis, A., Geiss, W., Stafford, D., Raker, J., Yu X., Siedlecki J., Yang, Y.: WO2006012443 (2006).
24. Protopopova, M., Lee, R., Slayden, R., Barry, III C., Bogatcheva, E., Einck, L.: US20097456222 (2009).
25. van Duzer; J., Michaelis, A., Geiss, W., Stafford, D., Yu, X., Siedlecki, J., Yang, Y.S.: US20097494991 (2009).
26. Van Duzer, J., Michaelis, A., Geiss, W., Stafford, D.G., Yu, X., Siedlecki, J., Yingfei, Y.: US20090068168 (2009).
27. Takaoki, S., Masaki, I., Shinji, H., Masaji, K., Kazunori, H.: US20040147597 (2004), WO2007148713 & WO200720070620 & JP623840620 (2007).
28. Ma, Z.; Li, J., Harran, S., He, Y., Minor, K., Kim, I., Ding, C., Longgood, J., Jin, Y., Combrink, K.: US20060019985 (2006).
29. Dimova V, Again I, Radanov R, et al. Experimental Studies of some derivative of rifamycin SV. In: Ishigami J, Ed. Recent advances in chemotherapy, Antimicrobial section. Proceed of 14 th Int Congress of Chemother. University of Tokyo Press 1985; 1915-1916.
30. Feschenko Y, Yashina L, Tumanov A. Open clinical study on efficacy and tolerability of Rifacinna caps. 150mg, 300mg, production of "Ecopharm 2002", Bulgaria, in treatment of pulmonary tuberculosis" Academy of Medicinal Sciency "F.G.Yanovski", Institut of pulmonology and tuberculosis. Kiev, Ukraine 2006.
31. Simon H, Yin E. Microbioassay of antimicrobial agents. Appl Microbiol 1970; 19: 573-579.
32. th ed. Approved Stand M11-A5 2001; 21(2): NCCLS.
33. Dimova V, Kantardjiev T, Bachiiska E, Marina M, Panajotov S, Bachvarova A. National center for infectious and parasitic diseases, Sofia, Bulgaria, Company dossier 2005.
34. th ed. Belmont, California: Star Publishing 1993.
35. Reddy V, Nadadhur G, Daneluzzi D, Dimova V, Gangadharam P. Antimycobacterial activity of a new rifamycin derivative, 3-(4-Cinnamylpiperazinyl Iminomethyl) rifamycin sv (t9). antimic. Agent Chemother 1995; 39(10): 2320-2324.
36. Reddy V, Srinivasan S, Andersen B, Gangadharam P. Rapid assessment of mycobacterial growth inside macrophages and mice, using radiometric (BACTEC) method. Tubercle Lung Dis 1994; 75: 127-131.
37. Kanyok T, Reddy V, Chinnaswamy J, Danziger L, Gangadharam P. in vivo Activity of paromomycin against susceptible and multidrug-resistant Mycobacterium tuberculosis and M. avium complex strains. Antimicrob Agents Chemother 1994; 38: 170-173.
38. Shimizu T, Dimova V, Tomioka H. Antimicrobial activities of cinnamyl rifamycin derivatives against M. tuberculosis and M. Avium complex (MAC) with special reference to the activities against intracellular MAC. Microbiol Immunol 2008; 50(8): 621-623.
39. Sato K, Akaki T, Tomioka H. Antimicrobial activities of benzoxazinorifamycin KRM-1648, clarithromycin and levofloxacin against intracellular Mycobacterium avium complex phagocytosed by murine peritoneal macrophages. J Antimicrob Chemother 1998; 41: 77-83.
40. Luna-Herrera J, Reddy V, Gangadharam P. in vitro Activity of the benzoxazinorifamycin KRM-1648 against drug-susceptible and multidrug-resistant Tubercle bacilli. Antimicrob Agents Chemother 1995; 39: 440-444.
41. Luna-Herrera J, Reddy MV, Gangadharam PRJ. in vitro Activity of the benzoxazinorifamycin KRM-1648 against drug-susceptible and multidrug-resistant Tubercle bacilli. Antimicrob Agents Chemother 1995; 39: 440-444.
42. Dhople A. in vitro Activity of a new rifamycin derivative against Mycobacterium leprae. Arzneimittelforschung 1996; 46(2): 210-212.
43. Dhople A, Dimova V. Comparative in vitro activities of rifamycin analogues against Mycobacterium leprae. Florida Institute of Technology, Melbourne. USA. Indian J Lepr 1997; 69(4): 377-384.
44. Joseph L, Thappa D. Recent therapeutic advances in leprosy and their implications in clinical practice. Ind J Practising Doctor 2008; 5(1).
45. Tomioka H, Saito H, Sato K, et al. Chemotherapeutic efficacy of a newly synthesized benzoxazinorifamycin, KRM-1648, against M. avium complex infection induced in mice. Antimicrob Agents Chemother 1992; 36: 378-393.
46. Tomioka H, Sato K, Sano C, Sano K, Shimizu T. Intramacrophage passage of Mycobacterium tuberculosis and M. avium complex alters the drug susceptibilities of the organisms as determined by intracellular susceptibility testing using macrophages and type II alveolar epithelial cells. Antimicrob Agents Chemother 2002; 46: 519-521.
47. Dimova V, Dobrev P, Kalfin E, Vlasov V. Therapeutic effect of 3/4-cinamyl-1-piperazinyl/iminomethyl rifamycin SV on generalized tuberculosism in guinea pigs. In: Einhorn J, Nord CE, Norrby SR, Eds. Recent advances in chemotherapy: Proceedings of the 18th Int. Congress of Chemother Am Soc Microbiol Washington, D.C. 1994; 711-714.
48. Omura T, Sato R. The carbon monoxide binding pigment of liver microsomes. J Biol Chem 1964; 239: 2370-2378.
49. Van den Broek J, Wolde-Kraamwinkel H, Kleinbloesem C, Breimer D. Effect of rifampicin treatment on in vitro drug-metabolizing activities in the pig. Biochem Pharmacol 1984; 15: 33(2): 325-327.
50. Karuzina P, Arachkov A. Contemporary methods in biochemistry. M Medicine 1977; 56.
51. Dallner G. Studies on the structural and enzymic organizationof the membrane elements of liver microsomes. Acta Pathol Microb Scand 1963; 166: 94.
52. Rosenbrough L, Farr A, Randle R. Protein mesurment with the Folinphenol reagent. J Biol Chem 1951; 193: 265-275.
53. Pogell B, Leloir L. Nucleotide activation of liver microsomal glucoronidation. J Biol Chem 1961; 236: 293-298.
54. Dimova V, Markova S. The chemical pharmaceutical research institute. Sofia, Bulgaria, Company dossier.
55. DimovaV, Ivanova D, Valova N. Pharmacokinetic study on 3-4(- cinnamyl-1-piperazinyl) iminomethyl rifamicin SV (T9) in experimental animals. Proceedings of 3rd Congress of Bulgarian Pharmacologists 1990; 64(65): 159.
56. Delev D, Dimova V. Proceedings of the Chemical Pharmaceutical Research Institute. Sofia, Bulgaria 1989; 512-514.
57. Tomioka H, Tatano Y, Yasumoto K, Shimizu T. Recent advances in antituberculous drug development and novel drug targets. Expert Rev Respir Med 2008; 24: 455-471.
58. Sarade W. A wish list of new anti- tuberculous candidate agents. Tuberculosis. Siriraj Med J 2009; 61(1).
59. Ginsberg A. Emerging drugs for active tuberculosis. Semin Respir Crit Care Med 2008; 29: 552-559.
60. Spigelman M. New tuberculosis therapies: A growing pipeline. J Infect Dis 2007; 196(Suppl 1): S28-34.
61. Ginsberg A, Spigelman M. Challenges in tuberculosis drug research and development. Nat Med 2007; 13: 290-294.
62. Barry C III, Slayden R, Sampson AE, Lee R. Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs. Biochem Pharmacol 2000; 59: 221-231.
63. Tomioka H. Current status of some antituberculosis drugs and the development of new antituberculous agents with special reference to their in vitro and in vivo antimicrobial activities. Curr Pharm Des 2006; 12: 4047-4070.
64. Pletz M, De Roux A, Roth A, Neumann K, Mauch H, Lode H. Early bactericidal activity of moxifloxacin in treatment of pul- monary tuberculosis: A prospective, randomized study. Antimicrob Agents Chemother 2004; 48(3): 780-782.
65. Gradelski E, Kolek B, Bonner D, Fung-Tomc J. Bactericidal mechanism of gatifloxacin compared with other quinolones. J Antimicrob Chemother 2002; 49(1): 185-188.
66. Sato K, Tomioka H, Sano C, et al. Comparative antimicrobial activities of gatifloxacin, sitafloxacin and levofloxacin against Mycobacterium tuberculosis replicating within Mono Mac 6 human macrophage and A-549 type II alveolar cell lines. J Antimicrob Chemother 2003; 52(2): 199-203.
67. Ruiz-Serrano M, Alcala L, Martinez L, et al. Antimicrob Agents Chemother 2002; 44: 2567.
68. Barry C. Preclinical candidates and targets for tuberculosis therapy III. Curr Opin Investigat Drugs 2001; 2: 198-201.
69. Protopopova M, Bogatcheva E, Nikonenko B, Hundert S, Einck L, Nacy C. In search of new cures for tuberculosis. Med Chem 2007; 3: 301-316.
70. Yoshimatsu S, Tyagi K, Williams I, et al. Moxifloxacin-containing regimens of reduced duration produce a stable cure in murine tuberculosis. Am J Respir Crit Care Med 2004; 170: 1131-1134.
71. Ji B, Lounis N, Maslo C, Truffot-Pernot C, Bonnafous P, Grosset J. in vitro and in vivo Activities of moxifloxacin and clinafloxacin against Mycobacterium tuberculosis. Antimicrob Agents Chemother 1998; 42: 2066-2069.
72. Lenaerts A, Gruppo V, Marietta K, et al. Preclinical testing of the nitroimidazopyran PA-824 for activity against Mycobacterium tuberculosis in a series of - in vitro and in vivo. Models Antimicrob Agents Chemother 2005; 49(6): 2294-2301.
73. Stover C, Warrener P, van Devanter D. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature 2000; 405: 962-966.
74. Tyagi S, Nuermberger E, Yoshimatsu T, et al. Bactericidal activity of the nitroimidazopyran PA-824 in a murine model of tuberculosis. Antimicrob Agents Chemother 2005; 49(6): 2289-2293.
75. Matsumoto M, Hashizume H, Tomishige T. OPC-67683, a nitro- dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice. PLoS Med 2006; 3: e466.
76. Andries K, Verhasselt P, Guillemount J. A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis. Science 2005; 307: 223-227.
77. Chen P, Gearhart G, Protopopova M, Einck L, Nacy CA. Synergic interaction of SQ109, a new ethylene diamine, with front-line antitubercular drugs in vitro. J Antimicrob Chemother 2006; 51(4): 1563-1565.
78. Nikonenko B, Protopopova M, Samala R, Einck L, Nacy C. Drug therapy of experimental tuberculosis (TB): Improved outcome by combining SQ109, a new diamine antibiotic, with existing TB drugs. Antimicrob Agents Chemother 2007; 51(4): 1563-1565.
79. Jia L, Noker P, Coward L, Gorman G, Protopopova M, Tomaszewski J. Interspecies pharmacokinetics and in vitro metabolism of SQ109. Br J Pharmacol 2006; 147(5): 476-485.
80. Jia L, Tomaszewski J, Hanrahan C, et al. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Br J Pharmacol 2005; 144(1): 80-87.
81. th Annual Meeting of IDSA, San Diego (2007).