Nitazoxanide analogues as antimicrobial agents against nosocomial pathogens

Medicinal Chemistry

Volumn 12, Issue 6, 2016, Pages 544-552

  Gau, Jia Suey ^a   Lin, Wen Pao ^a   Kuo, Li Ching ^a   Hu, Ming Kuan ^a  

^a NATIONAL DEFENSE MEDICAL CENTER   (Taiwan)

Author keywords

Antimicrobial agents; Electronic resonance effects; Nitazoxanide; Nosocomial pathogens

Indexed keywords

2 ACETOXY N (6 NITRO 1,3 BENZOTHIAZOL 2 YL)BENZAMIDE; 2 HYDROXY N (6 NITRO 1,3 BENZOTHIAZOL 2 YL)BENZAMIDE; 4 CHLORO N (5 NITRO 1,3 THIAZOL 2 YL)BENZENESULFONAMIDE; 4 CHLORO N (6 NITRO 1,3 BENZOTHIAZOL 2 YL)BENZENESULFONAMIDE; ANTIINFECTIVE AGENT; BENZENESULFONAMIDE DERIVATIVE; CIPROFLOXACIN; NITAZOXANIDE; SULFAMERAZINE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG; PHTHALIMIDE DERIVATIVE; SULFONAMIDE; THIAZOLE DERIVATIVE;

ACINETOBACTER BAUMANNII; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; HOSPITAL INFECTION; MINIMUM BACTERICIDAL CONCENTRATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION; CROSS INFECTION; DRUG EFFECTS; ENDOSPORE-FORMING RODS AND COCCI; GRAM NEGATIVE BACTERIUM; MICROBIAL SENSITIVITY TEST; MICROBIOLOGY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CIPROFLOXACIN; CROSS INFECTION; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE ENDOSPORE-FORMING RODS; MICROBIAL SENSITIVITY TESTS; PHTHALIMIDES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; THIAZOLES;

EID: 84983661956     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/1573406412666160129105719     Document Type: Article

References (28)

1. Bereket, W.; Hemalatha, K.; Getenet, B.; Wondwossen, T.; Solomon, A.; Zeynudin, A.; Kannan, S. Update on bacterial nosocomial infections. Eur. Rev. Med. Pharmacol. Sci., 2012, 16, 1039- 44.
2. Hsueh, P.; Chen, W.; Luh, K. Relationship between antimicrobial use and antimicrobial resistance in Gram-negative bacteria causing nosocomial infections from 1991-2003 at a university hospital in Taiwan. Inter. J. Antimicrob. Agents, 2005, 26, 463-72.
3. Jarvis, W.R.; Martooe, W.J. Predominant pathogens in hospital infections. J. Antimicrob. Chemother., 1992, 29, (Suppl A), 19-24.
4. Navon-Venezia, S.; Ben-Ami, R.; Carmeli, Y. Update on Pseudomonas aeruginosa and Acinetobacter baumannii infections in the healthcare setting Curr. Opin. Infect. Dis., 2005, 18, 306-13.
5. Van Looveren, M.; Goossens, H. Antimicrobial resistance of Acinetobacter spp. in Europe. Clin. Microbiol. Infect., 2004, 10, 684-704.
6. Li, J.; Nation, R.L.; Turnidge, J.D.; Milne, R.W.; Coulthard, K.; Rayner, C.R.; Paterson, D.L. Colistin: The re-emerging antibiotic for multidrug resistant Gram-negative bacterial infections. Lancet Infect. Dis., 2006, 6, 589-601.
7. Yuan, Z.; Tam, V.H. Polymyxin B: A new strategy for multidrugresistant Gram-negative organisms. Expert Opin. Investig. Drugs, 2008, 17, 661-8.
8. Fox, L.M.; Saravolatz, L.D. Nitazoxanide: A new thiazolide antiparasitic agent. Clin. Infect. Dis., 2005, 40, 1173-80.
9. Adagu, I.S.; Nolder, D.; Warhurst, D.C.; Rossignol, J.F. In vitro activity of nitazoxanide and related compounds against isolates of Giardia intestinalis, Entamoeba histolytica and Trichomonas vaginalis. J. Antimicrob. Chemother., 2002, 49, 103-11.
10. Dubreuil, L.; Houcke, I.; Mouton, Y.; Rossignol, J.F. In vitro evaluation of activities of nitazoxanide and tizoxanide against anaerobes and aerobic organisms. Antimicrob. Agents Chemother., 1996, 40, 2266-70.
11. McVay, C.S.; Rolfe, R.D. In vitro and in vivo activities of nitazoxanide against Clostridium difficile. Antimicrob. Agents Chemother., 2000, 44, 2254-8.
12. Hoffman, P.S.; Sisson, G.; Croxen, M.A.; Welch, K.; Harman, W.D.; Cremades, N.; Morash, M.G. Antiparasitic drug nitazoxanide inhibits the pyruvate oxidoreductases of Helicobacter pylori, selected anaerobic bacteria and parasites, and Campylobacter jejuni. Antimicrob. Agents Chemother., 2007, 51, 868-76.
13. Rossignol, J.F.; Frazia, S.L.; Lucia Chiappa, L.; Ciucci, A.; Santoro, M.G. Thiazolides, a New Class of Anti-influenza Molecules Targeting Viral Hemagglutinin at the Post-translational Level. J. Biol. Chem., 2009, 284, 20798-808.
14. Basu, P.P.; Rayapudi, K.; Shah, N.J., Krishnaswamy, N.; Brown, R.S. Effects of triple-drug therapy with nitazoxanide, high-dose ribavirin and peginterferon 2a in patients with chronic hepatitis C. Hepatol. Res., 2013, 43, 589-95.
15. de Carvalho, L.P.S.; Lin, G.; Jiang, X.; Nathan, C. Nitazoxanide kills replicating and nonreplicating Mycobacterium tuberculosis and evades resistance. J. Med. Chem., 2009, 52, 5789-92.
16. Ballard, T.E.; Wang, X.; Olekhnovich, I.; Koerner, T.; Seymour, C.; Salamoun, J.; Warthan, M.; Hoffman, P.S.; Macdonald, T.L. Synthesis and antimicrobial evaluation of nitazoxanide-based analogues: identification of selective and broad spectrum activity. Chem. Med. Chem., 2011, 6, 362-77.
17. Megraud, F.; Occhialini, A.; Rossignol, J.F. Nitazoxanide, a potential drug for eradicating of Helicobacter pylori with no crossresistance to metronidazole. Antimicrob. Agents Chemother., 1998, 42, 2836-40.
18. Anderson, V.R.; Curran, M.P. Nitazoxanide: A review of its use in the treatment of gastrointestinal infections. Drugs, 2007, 67, 1947- 67.
19. Ballard, T.E.; Wang X.; Olekhnovich I.; Koerner T.; Seymour C.; Hoffman P.S.; Macdonald, T.L. Biological activity of modified and zoxanide. Bioorg. Med. Chem. Lett., 2010, 20, 3537-9.
20. Wermuth, C.G. The Practice of Medicinal Chemistry, 3rd Ed.; Academic Press: London, 2008, 283-7.
21. Meanwell, N.A. Synopsis of some recent tactical applications of bioisosteres in drug design. J. Med. Chem., 2011, 54, 2529-91.
22. Wikler, M.A.; Cockerill, F.R.; Craig, W.A.; Dudley, M.N.; Eliopoulos, G.M.; Hecht, D.W.; Hindler, J.F.; Low, D.E.; Sheehan, D.J.; Tenover, F.C.; Turnidge, J.D.; Weinstein, M.P.; Zimmer, B.L; Ferraro, M.J.; Swenson, J.M. Clinical and laboratory standards institute: Performance standards for antimicrobial susceptibility testing. CLSI Document M100 S17 17th ed., Wayne, PA, USA, 2007.
23. Moody, J.A.; Knapp, C. Tests to assess bactericidal activity. In: Isenber H.D. ed. Clinical Microbiology Procedures Handbook. Vol. 2, 2nd ed. Washington: ASM Press, 2004, 5.10.1.1-5.10.1.17.
24. http://146.107.217.178/lab/alogps/start.html.
25. Navarrete-Vazquez, G; Chavez-Silva, F.; Argotte-Ramos, R.; Rodriguez- Gutierrez, M. del C.; Chan-Bacab, M.J.; Cedillo-Rivera, R.; Moo-Puc, R.; Hernandez-Nunez, E. Synthesis of benzologues of nitazoxanide and tizoxanide: A comparative study of their in vitro broad-spectrum antiprotozoal activity. Bioorg. Med. Chem. Lett., 2011, 21, 3168-71.
26. Werbel, L.M.; Battaglia, J.R. Derivatives of 2- Amino-5- nitrothiazole as potential schistosomicides. J. Med. Chem., 1971, 14, 10-6.
27. Navarrete-Vazquez, G.; Paoli, P.; Leon-Rivera, I.; Villalobos- Molina, R.; Medina-Franco, J. L.; Ortiz-Andrade, R.; Estrada-Soto, S.; Camici, G.; Diaz-Coutino, D.; Gallardo-Ortiz, I.; Martinez- Mayorga, K.; Moreno-Diaz, H. Synthesis, in vitro and computational studies of protein tyrosine phosphatase 1B inhibition of a small library of 2- Arylsulfonylaminobenzothiazoles with antihyperglycemic activity. Bioorg. Med. Chem., 2009, 17, 3332- 41.
28. Chen, P.T.; Lin, W.P.; Lee, A.R.; Hu, M.K. New 7-[4-(4- (un)Substituted)piperazine-1-carbonyl]-piperazin-1-yl]derivatives of fluoroquinolone: Synthesis and antimicrobial evaluation. Molecules, 2013, 18, 7557-69.