The broad-spectrum antimycobacterial activities of phenothiazines, in vitro: Somewhere in all of this there may be patentable potentials

Recent Patents on Anti-Infective Drug Discovery

Volumn 6, Issue 2, 2011, Pages 104-109

  van Ingen, Jakko ^a  

^a RADBOUD UNIVERSITY MEDICAL CENTER   (Netherlands)

Author keywords

Chlorpromazine; Mycobacteria; Mycobacterium avium; Nontuberculous mycobacteria; Phenothiazines; Thioridazine; Tuberculosis

Indexed keywords

CHLORPROMAZINE; PHENOTHIAZINE DERIVATIVE; PROMETHAZINE; THIORIDAZINE; TRIFLUOPERAZINE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; DRUG POTENTIATION; DRUG STRUCTURE; DRUG TARGETING; HUMAN; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM AVIUM; MYCOBACTERIUM TUBERCULOSIS; NAUSEA AND VOMITING; NONHUMAN; PATENT; PRIORITY JOURNAL; TUBERCULOSIS;

ANIMALS; ANTITUBERCULAR AGENTS; DRUG DISCOVERY; DRUG RESISTANCE, MULTIPLE, BACTERIAL; DRUG THERAPY, COMBINATION; EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS; HUMANS; MICROBIAL SENSITIVITY TESTS; MICROBIOLOGICAL TECHNIQUES; MYCOBACTERIUM TUBERCULOSIS; PATENTS AS TOPIC; PHENOTHIAZINES; RISK ASSESSMENT; THIORIDAZINE; TREATMENT OUTCOME; TUBERCULOSIS, MULTIDRUG-RESISTANT;

EID: 79959995954     PISSN: 1574891X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157489111796064623     Document Type: Article

References (51)

1. Amaral L, Boeree MJ, Gillespie SH, Udwadia ZF, van Soolingen D. Thioridazine cures extensively drug-resistant tuberculosis (XDR-TB) and the need for global trials is now. Int J Antimicrob Agents 2010; 35: 524-6.
2. World Health Organization. Multidrug-and extensively drug resistant TB (M/XDR-TB); 2010 global report on surveillance and response. WHO Press, Geneva, 2010. http://whqlibdoc.who.int/publications/2010/9789241599191_eng.pdf
3. Hollister LE, Eikenberry DT, Raffel S. Chlorpromazine in nonpsychotic patients with pulmonary tuberculosis. Am Rev Respir Dis 1960; 81: 562-6.
4. Geiger H, Finkelstein BA. Largactil in der Behandlung der Tuberkulose. Schweiz Med Wochenschr 1954; 84: 1063-4.
5. Dobkin AB, Wehling B, Gross G, Mendelsohn H. Chlorpromazine in anesthesia; for surgical treatment of pulmonary tuberculosis. Anaesthesia 1955; 10: 328-45.
6. Tello F. Results of combined use of cycloserine in pulmonary tuberculosis. Scand J Respir Dis Suppl 1970; 71: 162-7.
7. Gover DM. Thioridazine and chlorprothixene in the management of anxiety in tuberculous patients. Am Rev Respir Dis 1962; 85: 587-90.
8. van Soolingen D, Hernandez Pando R, Orozco H, Aguilar D, Magis-Escurra C, et al. The antipsychotic thioridazine shows promising therapeutic activity in a mouse model of multidrugresistant tuberculosis. PLoS One 2010; 5: e12640. doi:10.1371/journal.pone.0012640
9. Gadre DV, Talwar V, Gupta HC, Murthy PS. Effect of trifluoperazine, a potential drug for tuberculosis with psychotic disorders, on the growth of clinical isolates of drug resistant Mycobacterium tuberculosis. Int Clin Psychopharmacol 1998; 13: 129-31.
10. Gadre DV, Talwar V. In vitro susceptibility testing of Mycobacterium tuberculosis strains to trifluoperazine. J Chemother 1999; 11: 203-6.
11. Ratnakar P, Rao SP, Sriramarao P, Murthy PS. Structureantitubercular activity relationship of phenothiazine-type calmodulin antagonists. Int Clin Psychopharmacol 1995; 10: 39-43.
12. Ratnakar P, Murthy PS. Antitubercular trifluoperazine, a calmodulin antagonist. FEMS Microbiol Lett 1992; 76: 73-6.
13. Raffel S, Kochan I, Poland N, Hollister LE. The action of chlorpromazine upon Mycobacterium tuberculosis. Am Rev Respir Dis 1960; 81: 555-61.
14. Molnár J, Béládi I, Földes I. Studies on antituberculotic action of some phenothiazine derivatives in vitro. Zentralbl Bakteriol Orig A 1977; 239: 521-6.
15. Kristiansen JE, Vergmann B. The antibacterial effect of selected phenothiazines and thioxanthenes on slow-growing mycobacteria. Acta Pathol Microbiol Immunol Scand B 1986; 94: 393-8.
16. van Ingen J, van der Laan T, Amaral L, Dekhuijzen R, Boeree MJ, van Soolingen D. In vitro activity of thioridazine against mycobacteria. Int J Antimicrob Agents 2009; 34: 190-1.
17. Amaral L, Kristiansen JE, Abebe LS, Millett W. Inhibition of the respiration of multi-drug resistant clinical isolates of Mycobacterium tuberculosis by thioridazine: Potential use for initial therapy of freshly diagnosed tuberculosis. J Antimicrob Chemother 1996; 38: 1049-53.
18. Viveiros MB, Bosne-David S, Amaral L. Comparative in vitro activity of phenothiazines against multidrug-resistant Mycobacterium tuberculosis. Int J Antimicrob Agents 2000; 16: 69-71.
19. Viveiros M, Martins M, Couto I, Kristiansen JE, Molnar J, Amaral L. The in vitro activity of phenothiazines against Mycobacterium avium: Potential of thioridazine for therapy of the co-infected AIDS patient. In vivo 2005; 19: 733-6.
20. Reddy MV, Nadadhur G, Gangadharam PR. In vitro and intracellular antimycobacterial activity of trifluoperazine. J Antimicrob Chemother 1996; 37: 196-7.
21. Weinstein EA, Yano T, Li LS, Avarbock D, Avarbock A, Helm D, et al. Inhibitors of type II NADH: Menaquinone oxidoreductase represents a class of antitubercular drugs. PNAS 2005; 102: 4548-53.
22. Dhople AM. In vitro activities of phenothiazine-type calmodulin antagonists against Mycobacterium leprae. Microbios 1999; 98: 113-21.
23. Ordway D, Viveiros M, Leandro C, Bettencourt R, Almeida J, Martins M, et al. Clinical concentrations of thioridazine kill intracellular multidrug-resistant Mycobacterium tuberculosis. Antimicrob Agents Chemother 2003; 47: 917-22.
24. Crowle AJ, Douvas GS, May MH. Chlorpromazine: A drug potentially useful for treating mycobacterial infections. Chemotherapy 1992; 38: 410-9.
25. Martins M, Viveiros M, Kristiansen JE, Molnar J, Amaral L. The curative activity of thioridazine on mice infected with Mycobacterium tuberculosis. In vivo 2007; 21: 771-5.
26. Yano T, Li LS, Weinstein E, Teh JS, Rubin H. Steady-state kinetics and inhibitory action of antitubercular phenothiazines on Mycobacterium tuberculosis type-II NADH-menaquinone oxidoreductase (NDH-2). J Biol Chem 2006; 281: 11456-63.
27. Viveiros M, Amaral L. Enhancement of antibiotic activity against poly-drug resistant Mycobacterium tuberculosis by phenothiazines. Int J Antimicrob Agents 2001; 17: 225-8.
28. Manion RE, Bradley SG, Hall WH. Retardation of the emergence of isoniazid-resistant mycobacteria by phenothiazines and quinacrine. Proc Soc Exp Biol Med 1969; 130: 206-9.
29. Rodrigues L, Sampaio D, Couto I, Machado D, Kern WV, Amaral L, Viveiros M. The role of efflux pumps in macrolide resistance in Mycobacterium avium complex. Int J Antimicrob Agents 2009; 34: 529-33.
30. Rodrigues L, Wagner D, Viveiros M, Sampaio D, Couto I, Vavra M, et al. Thioridazine and chlorpromazine inhibition of ethidium bromide efflux in Mycobacterium avium and Mycobacterium smegmatis. J Antimicrob Chemother 2008; 61: 1076-82.
31. Griffith DE, Aksamit T, Brown-Elliot BA, Catanzaro A, Daley C, Gordin F, et al. An official ATS/IDSA statement: Diagnosis, treatment, and prevention of nontuberculous mycobacterial diseases. Am J Respir Crit Care Med 2007; 175: 367-416.
32. Venulet J, Jakimowska K, Janowiec M, Urbanska A. The accumulation of isoniazid in tissues, and the course of experimental tuberculosis. Br J Pharmacol Chemother 1960; 15: 4-9.
33. Figueras ER. Chlorpromazine in the control of side effects of paraaminosalicylic acid administration. Dis Chest 1956; 30: 429-34.
34. Boshoff, HIM, Myers TG, Copp BR, McNeil MR, Wilson MA, Barry CEI. The transcriptional responses of Mycobacterium tuberculosis to inhibitors of metabolism. J Biol Chem 2004; 279: 40174-84.
35. Sohaskey CD. Nitrate enhances the survival of Mycobacterium tuberculosis during inhibition of respiration. J Bacteriol 2008; 190: 2981-6.
36. Zakharov SD, Li X, Red'ko TP, Dilley RA. Calcium binding to the subunit C of E. coli ATP-synthase and possible functional implications in energy coupling. J Bioenerg Biomembr 1996; 28: 483-94.
37. Faguet M. On the antimicrobial activity of chlorpromazine, the antagonistic action of adenosine-5-triphosphate (ATP) and some electron aspects of such actions. CR Hebd Seances Acad Sci 1962; 255: 155-7.
38. Lieberman LA, Higgins DE. Inhibition of Listeria monocytogenes infection by neurological drugs. Int J Antimicrob Agents 2010; 35: 292-6.
39. van der Wel N, Hava D, Houben D, Fluitsma D, van Zon M, Pierson J, et al. M. tuberculosis and M. leprae translocate from the phagolysosome to the cytosol in myeloid cells. Cell 2007; 129: 1287-98.
40. Kristiansen JE. Experiments to illustrate the effect of chlorpromazine on the permeability of the bacterial cell wall. Acta Pathol Microbiol Scand (B) 1979; 87: 317-9.
41. Dutta NK, Mehra S, Kaushal D. A Mycobacterium tuberculosis sigma factor network responds to cell-envelope damage by the promising anti-mycobacterial thioridazine. PLoS One 2010; 5: e10069. doi:10.1371/journal.pone.0010069
42. Sinha I, Dick T. Role for malonyl coenzyme A: Acyl carrier protein transacylase (MCAT) in the growth-inhibitory effect of the calmodulin antagonist trifluoperazine in Mycobacterium bovis BCG. J Antimicrob Chemother 2004; 53: 1072-5.
43. Ratnakar P, Murthy PS. Trifluoperazine inhibits the incorporation of labelled precursors into lipids, proteins and DNA of Mycobacterium tuberculosis H37Rv. FEMS Microbiol Lett 1993; 110; 291-4.
44. Glassman AH, Bigger JT Jr. Antipsychotic drugs: Prolonged QTc interval, torsade de pointes, and sudden death. Am J Psychiatry 2001; 158: 1774-82.
45. Poluzzi E, Raschi E, Motola D, Moretti U, De Ponti F. Antimicrobials and the risk of torsades de pointes: the contribution from data mining of the US FDA Adverse Event Reporting System. Drug Saf 2010; 33: 303-14.
46. Iannini PB. Cardiotoxicity of macrolides, ketolides and fluoroquinolones that prolong the QTc interval. Expert Opin Drug Saf 2002; 1: 121-8.
47. Bate AB, Kalin JH, Fooksman EM, Amorose EL, Price CM, Williams HM, et al. Synthesis and antitubercular activity of quaternized promazine and promethazine derivatives. Bioorg Med Chem Lett 2007; 17: 1346-8.
48. Madrid PB, Polgar WE, Toll L, Tange MJ. Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonin receptors. Bioorg Med Chem Lett 2007; 17: 3014-7.
49. Giwercman, B.K. New thioxanthene and phenothiazine derivatives useful for treatment or prophylaxis of an infectious disease caused by a drug resistant infectious agent such as bacterium, virus, or fungi. WO2005105145 (2005).
50. Giwercman, B.K. New thioxanthene and phenothiazine derivatives useful for treatment or prophylaxis of an infectious disease caused by a drug resistant infectious agent such as bacterium, virus, or fungi. WO2010122012 (2010).
51. Amaral L, Molnar J. Potential therapy of XDRTB with Thioridazine a drug beyond patent protection but eligible for patent as ''New Use''. Recent Pat Antiinfect Drug Discov 2010; 5: 109-14.