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Chemical Compound Review

Tisamid     pyrazine-2-carboxamide

Synonyms: Dipimide, Lynamide, Pyramide, Pyrazide, Tebrazid, ...
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Disease relevance of pyrazinamide


Psychiatry related information on pyrazinamide


High impact information on pyrazinamide


Chemical compound and disease context of pyrazinamide


Biological context of pyrazinamide


Anatomical context of pyrazinamide


Associations of pyrazinamide with other chemical compounds


Gene context of pyrazinamide

  • Characterization of pncA mutations in pyrazinamide-resistant Mycobacterium tuberculosis in Brazil [28].
  • Escherichia coli isolates expressing individually five of the eight katG mutations showed loss of catalase and INH oxidation activities, and isolates carrying any of the five pncA mutations showed no pyrazinamidase activity, indicating that these mutations are associated with INH and PZA resistance, respectively [29].
  • Allopurinol or pyrazinamide was administered to rats treated with BOF-4272 (a potent xanthine oxidase inhibitor) to investigate to what degree xanthine dehydrogenase participates in the oxidation of these agents [30].
  • Besides biochemical (sensitivity to pyrazinamide) and epidemiological features, strains of this unusual member of the M. tuberculosis complex show a special combination of pncA, oxyR, katG and gyrA gene polymorphisms [31].
  • In Mycobacterium tuberculosis there is a strong correlation between in-vitro resistance to rifampicin (RIF) and pyrazinamide (PZA) and mutations in rpoB and pncA, respectively [32].

Analytical, diagnostic and therapeutic context of pyrazinamide


  1. Pulmonary tuberculosis in HIV-infected patients in Zaire. A controlled trial of treatment for either 6 or 12 months. Perriëns, J.H., St Louis, M.E., Mukadi, Y.B., Brown, C., Prignot, J., Pouthier, F., Portaels, F., Willame, J.C., Mandala, J.K., Kaboto, M. N. Engl. J. Med. (1995) [Pubmed]
  2. Mutations in pncA, a gene encoding pyrazinamidase/nicotinamidase, cause resistance to the antituberculous drug pyrazinamide in tubercle bacillus. Scorpio, A., Zhang, Y. Nat. Med. (1996) [Pubmed]
  3. Rifampin and pyrazinamide vs isoniazid for prevention of tuberculosis in HIV-infected persons: an international randomized trial. Terry Beirn Community Programs for Clinical Research on AIDS, the Adult AIDS Clinical Trials Group, the Pan American Health Organization, and the Centers for Disease Control and Prevention Study Group. Gordin, F., Chaisson, R.E., Matts, J.P., Miller, C., de Lourdes Garcia, M., Hafner, R., Valdespino, J.L., Coberly, J., Schechter, M., Klukowicz, A.J., Barry, M.A., O'Brien, R.J. JAMA (2000) [Pubmed]
  4. Drug-resistant tuberculosis: inconsistent results of pyrazinamide susceptibility testing. Hewlett, D., Horn, D.L., Alfalla, C. JAMA (1995) [Pubmed]
  5. Acute hypertension as an adverse effect of pyrazinamide. Goldberg, J., Moreno, F., Barbara, J. JAMA (1997) [Pubmed]
  6. Pharmacokinetic interaction between rifampicin and the once-daily combination of saquinavir and low-dose ritonavir in HIV-infected patients with tuberculosis. Ribera, E., Azuaje, C., Lopez, R.M., Domingo, P., Curran, A., Feijoo, M., Pou, L., Sánchez, P., Sambeat, M.A., Colomer, J., Lopez-Colomes, J.L., Crespo, M., Falcó, V., Ocaña, I., Pahissa, A. J. Antimicrob. Chemother. (2007) [Pubmed]
  7. A trial of three regimens to prevent tuberculosis in Ugandan adults infected with the human immunodeficiency virus. Uganda-Case Western Reserve University Research Collaboration. Whalen, C.C., Johnson, J.L., Okwera, A., Hom, D.L., Huebner, R., Mugyenyi, P., Mugerwa, R.D., Ellner, J.J. N. Engl. J. Med. (1997) [Pubmed]
  8. Controlled trial of prednisolone as adjuvant in treatment of tuberculous constrictive pericarditis in Transkei. Strang, J.I., Kakaza, H.H., Gibson, D.G., Girling, D.J., Nunn, A.J., Fox, W. Lancet (1987) [Pubmed]
  9. Reduced plasma concentrations of antituberculosis drugs in patients with HIV infection. Sahai, J., Gallicano, K., Swick, L., Tailor, S., Garber, G., Seguin, I., Oliveras, L., Walker, S., Rachlis, A., Cameron, D.W. Ann. Intern. Med. (1997) [Pubmed]
  10. Deleterious influence of pyrazinamide on the outcome of patients with fulminant or subfulminant liver failure during antituberculous treatment including isoniazid. Durand, F., Bernuau, J., Pessayre, D., Samuel, D., Belaiche, J., Degott, C., Bismuth, H., Belghiti, J., Erlinger, S., Rueff, B. Hepatology (1995) [Pubmed]
  11. Clinical and radiographic findings in disseminated tuberculosis of the brain. Eide, F.F., Gean, A.D., So, Y.T. Neurology (1993) [Pubmed]
  12. Effect of steroids on cerebrospinal fluid penetration of antituberculous drugs in tuberculous meningitis. Kaojarern, S., Supmonchai, K., Phuapradit, P., Mokkhavesa, C., Krittiyanunt, S. Clin. Pharmacol. Ther. (1991) [Pubmed]
  13. Crystal structure and mechanism of catalysis of a pyrazinamidase from Pyrococcus horikoshii. Du, X., Wang, W., Kim, R., Yakota, H., Nguyen, H., Kim, S.H. Biochemistry (2001) [Pubmed]
  14. Structure-function relations in the inhibition of murine contact hypersensitivity by amiloride. Lindgren, A.M., Granstein, R.D., Hosoi, J., Gallo, R.L. J. Invest. Dermatol. (1995) [Pubmed]
  15. Synergistic activities of clarithromycin and pyrazinamide against Mycobacterium tuberculosis in human macrophages. Mor, N., Esfandiari, A. Antimicrob. Agents Chemother. (1997) [Pubmed]
  16. Reduced pyrazinamidase activity and the natural resistance of Mycobacterium kansasii to the antituberculosis drug pyrazinamide. Sun, Z., Zhang, Y. Antimicrob. Agents Chemother. (1999) [Pubmed]
  17. Phenotypic characterization of pncA mutants of Mycobacterium tuberculosis. Morlock, G.P., Crawford, J.T., Butler, W.R., Brim, S.E., Sikes, D., Mazurek, G.H., Woodley, C.L., Cooksey, R.C. Antimicrob. Agents Chemother. (2000) [Pubmed]
  18. Isoniazid interaction with tyrosine as a possible mode of action of the drug in mycobacteria. Herman, R.P., Weber, M.M. Antimicrob. Agents Chemother. (1980) [Pubmed]
  19. Activity and penetration of antituberculosis drugs in mouse peritoneal macrophages infected with Mycobacterium microti OV254. Dhillon, J., Mitchison, D.A. Antimicrob. Agents Chemother. (1989) [Pubmed]
  20. Study of the structure-activity relationships for the pyrazinamidase (PncA) from Mycobacterium tuberculosis. Lemaitre, N., Callebaut, I., Frenois, F., Jarlier, V., Sougakoff, W. Biochem. J. (2001) [Pubmed]
  21. Moxifloxacin versus ethambutol in the first 2 months of treatment for pulmonary tuberculosis. Burman, W.J., Goldberg, S., Johnson, J.L., Muzanye, G., Engle, M., Mosher, A.W., Choudhri, S., Daley, C.L., Munsiff, S.S., Zhao, Z., Vernon, A., Chaisson, R.E. Am. J. Respir. Crit. Care Med. (2006) [Pubmed]
  22. Bactericidal and sterilizing activities of antituberculosis drugs during the first 14 days. Jindani, A., Doré, C.J., Mitchison, D.A. Am. J. Respir. Crit. Care Med. (2003) [Pubmed]
  23. Evaluation of rifapentine in long-term treatment regimens for tuberculosis in mice. Lenaerts, A.M., Chase, S.E., Chmielewski, A.J., Cynamon, M.H. Antimicrob. Agents Chemother. (1999) [Pubmed]
  24. Hypouricemia by defect in the tubular reabsorption. Barrientos, A., Perez-Diaz, V., Diaz-Gonzalez, R., Rodicio, J.L. Arch. Intern. Med. (1979) [Pubmed]
  25. Clinical and molecular analysis of patients with renal hypouricemia in Japan-influence of URAT1 gene on urinary urate excretion. Ichida, K., Hosoyamada, M., Hisatome, I., Enomoto, A., Hikita, M., Endou, H., Hosoya, T. J. Am. Soc. Nephrol. (2004) [Pubmed]
  26. Mycobacterium malmoense infections in Scotland: an increasing problem. France, A.J., McLeod, D.T., Calder, M.A., Seaton, A. Thorax (1987) [Pubmed]
  27. In vitro oxidation of pyrazinamide and allopurinol by rat liver aldehyde oxidase. Moriwaki, Y., Yamamoto, T., Nasako, Y., Takahashi, S., Suda, M., Hiroishi, K., Hada, T., Higashino, K. Biochem. Pharmacol. (1993) [Pubmed]
  28. Characterization of pncA mutations in pyrazinamide-resistant Mycobacterium tuberculosis in Brazil. Rodrigues, V.d.e. .F., Telles, M.A., Ribeiro, M.O., Cafrune, P.I., Rossetti, M.L., Zaha, A. Antimicrob. Agents Chemother. (2005) [Pubmed]
  29. Detection of Multidrug Resistance in Mycobacterium tuberculosis. Sekiguchi, J., Miyoshi-Akiyama, T., Augustynowicz-Kopec, E., Zwolska, Z., Kirikae, F., Toyota, E., Kobayashi, I., Morita, K., Kudo, K., Kato, S., Kuratsuji, T., Mori, T., Kirikae, T. J. Clin. Microbiol. (2007) [Pubmed]
  30. Effect of BOF-4272 on the oxidation of allopurinol and pyrazinamide in vivo. Is xanthine dehydrogenase or aldehyde oxidase more important in oxidizing both allopurinol and pyrazinamide? Yamamoto, T., Moriwaki, Y., Suda, M., Nasako, Y., Takahashi, S., Hiroishi, K., Nakano, T., Hada, T., Higashino, K. Biochem. Pharmacol. (1993) [Pubmed]
  31. Elevation of Mycobacterium tuberculosis subsp. caprae Aranaz et al. 1999 to species rank as Mycobacterium caprae comb. nov., sp. nov. Aranaz, A., Cousins, D., Mateos, A., Domínguez, L. Int. J. Syst. Evol. Microbiol. (2003) [Pubmed]
  32. Simultaneous identification and typing of multi-drug-resistant Mycobacterium tuberculosis isolates by analysis of pncA and rpoB. Brown, T.J., Tansel, O., French, G.L. J. Med. Microbiol. (2000) [Pubmed]
  33. Survey of drug resistance of Mycobacterium tuberculosis in 3 Mexican states, 1997. Granich, R.M., Balandrano, S., Santaella, A.J., Binkin, N.J., Castro, K.G., Marquez-Fiol, A., Anzaldo, G., Zarate, M., Jaimes, M.L., Velazquez-Monroy, O., Salazar, L., Alvarez-Lucas, C., Kuri, P., Flisser, A., Santos-Preciado, J., Ruiz-Matus, C., Tapia-Conyer, R., Tappero, J.W. Arch. Intern. Med. (2000) [Pubmed]
  34. Intrapulmonary concentrations of pyrazinamide. Conte, J.E., Golden, J.A., Duncan, S., McKenna, E., Zurlinden, E. Antimicrob. Agents Chemother. (1999) [Pubmed]
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