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Chemical Compound Review

FANFT     N-[4-(5-nitro-2-furyl)-1,3- thiazol-2...

Synonyms: CCRIS 308, CHEMBL82444, AG-E-73336, LS-1055, NSC-155010, ...
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Disease relevance of FANFT

  • Rats fed FANFT for 10 weeks and then the control diet developed hyperplastic epithelial lesions and carcinomas by week 52, whereas those fed FANFT for 6 weeks had normal bladders through 52 weeks [1].
  • FANFT administration increased the incidences of mesothelioma of the peritoneum and thyroid tumors [2].
  • PB significantly increased the incidence of transitional cell carcinoma of the bladder of the rats that had been treated with FANFT (P = 0.027) [3].
  • By the 50th week the rats fed FANFT for 8 weeks all had moderate to marked hyperplasia, but the rats fed FANFT for 10 weeks had transitional cell tumors, one of which was invasive through the entire thickness of the bladder wall [4].
  • Of 26 rats fed SAC for 100 weeks after FANFT, two developed papillomas, and five developed carcinomas (p less than 0.03) [5].

High impact information on FANFT

  • Numerical but not structural changes of chromosomes were significantly greater in the FANFT group than in the BBN group [6].
  • There is substantial evidence that N-[4-(5-nitro-2-furyl)-2-thiazolyl] formamide (FANFT) is deformylated to 2-amino-4-(5-nitro-2-furyl)thiazole (ANFT) in the process of FANFT-induced bladder cancer [7].
  • Neither aspirin nor probenecid altered the urinary excretion or half-life of FANFT or ANFT [7].
  • The carcinogen N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide (CAS: 24554-26-5) was fed to male and female CD-1 mice in the diet as a positive control [8].
  • The epithelial lesions present after 6 and 10 weeks of FANFT feeding also regressed and the mucosa returned to normal as observed by light microscopy [1].

Chemical compound and disease context of FANFT


Biological context of FANFT


Anatomical context of FANFT

  • Hyperplastic mucosa with pleomorphic microvilli was also observed at 52 weeks in rats fed 0.1% and 0.05% FANFT [19].
  • The present study was designed to evaluate whether chronic urinary tract infection could enhance tumor development in FANFT-induced urinary tract carcinogenesis [20].
  • Rats fed FANFT for 6 weeks show regression of the moderately hyperplastic epithelium to normal within 4 weeks after being placed on control diet which persists through 50 weeks [4].
  • One wk after completion of FANFT administration, a suspension of heat-killed E. coli (06K13H1) was injected into the bladder through the urethra [20].
  • FANFT alone had no effect on hepatic cytosol or microsomal nitroreductase activity but increased hepatic and blood acid-soluble thiol content [21].

Associations of FANFT with other chemical compounds

  • However, the hyperplastic effects induced in the bladder epithelium by saccharin without prior FANFT administration were inhibited by coadministration with aspirin [22].
  • N-[4-(5-Nitro-2-furyl)-2-thiazolyl]formamide (FANFT), a potent urinary bladder carcinogen, is metabolically activated in vitro by a variety of enzyme systems including aerobic cooxidation by prostaglandin H synthase which is present in the rat bladder mucosa [23].
  • Both chemicals significantly increased the incidence of bladder tumors following FANFT feeding compared to six weeks of FANFT feeding followed by control diet, and the results were similar whether saccharin or tryptophan feeding was started immediately after FANFT feeding was concluded or after a six-week delay [24].
  • The effects of aspirin on N-[4-(5-nitro-2-furyl)-2-thiazolyl]-formamide (FANFT) -induced urinary bladder lesions, endogenous bladder prostaglandin E2 synthesis, and the metabolism of FANFT by bladder epithelial microsomes were examined [25].
  • The effects of allopurinol on the induction of bladder cancer by N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide (FANFT), excretion of urinary tryptophan metabolites, hepatic nitroreductase activity, and the acid-soluble thiol content of liver and blood in weanling female Fischer rats were investigated [21].

Gene context of FANFT

  • Mice given FANFT p.o. demonstrated a significant increase over controls in ornithine decarboxylase activity within 12 hr, followed by a gradual decline to control levels by 72 hr [26].
  • Further investigations using immunohistochemical staining with a different pan-reactive p21 monoclonal antibody (Cetus Corporation) specific for this method, however, showed two groups of cells from FANFT-induced rat bladder tumors had enhanced immunoreactivity [10].
  • Screening by Western blotting revealed no enhanced levels of p21ras in ANFT-transformed cells nor in cells established in culture from FANFT-induced rat bladder carcinomas [10].
  • With monoclonal antibody PAb421 (which detects mutant and wild-type p53), p53 antigen was also detected in cells from F542, a bladder tumor induced by FANFT in which no p53 mutations were found [27].
  • Using a standard clonogenic assay and the AY-27 FANFT tumor line, photoactivation of CDS1 was shown to be cytotoxic [28].

Analytical, diagnostic and therapeutic context of FANFT

  • Urine specimens obtained periodically from weanling male F344 rats fed 0.2% N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide (FANFT) for 25 weeks followed by control diet for an additional 35 weeks, were examined by light microscopy (LM) and scanning electron microscopy (SEM) [29].
  • Control groups consisted of rats that received tap water with or without prior administration of FANFT [2].
  • Histological appearance and biological behavior of tumor isografts closely resembled those of the original FANFT tumors [30].
  • Using low (less than 10) and high (greater than 80) passages of these cell strains, tumorigenicity experiments in syngeneic rats showed that the normal in vivo progression of FANFT tumors was interrupted by the isolation of carcinoma cells to cell culture [30].
  • The effect on urothelial proliferation of a urinary bladder carcinogen, N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide (FANFT), fed to male F344 rats at doses of 0.2, 0.1, 0.05, 0.01, 0.005 and 0.001% of diet for 4 or 10 weeks was evaluated by autoradiography, using [3H-methyl]thymidine, and by histopathology [31].


  1. Neovascularization in rats during urinary bladder carcinogenesis induced by N-[4-(5-Nitro-2-furyl)-2-thiazolyl]formamide. Cohen, S.M., Tatematsu, M., Shinohara, Y., Nakanishi, K., Ito, N. J. Natl. Cancer Inst. (1980) [Pubmed]
  2. Evaluation of the effects of cotinine and nicotine-N'-oxides on the development of tumors in rats initiated with N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide. LaVoie, E.J., Shigematsu, A., Rivenson, A., Mu, B., Hoffmann, D. J. Natl. Cancer Inst. (1985) [Pubmed]
  3. Effect of sodium phenobarbital and sodium saccharin in AIN-76A diet on carcinogenesis initiated with N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide and N,N-dibutylnitrosamine in male F344 rats. Imaida, K., Wang, C.Y. Cancer Res. (1986) [Pubmed]
  4. Early lesions in experimental bladder cancer: experimental design and light microscopic findings. Cohen, S.M., Jacobs, J.B., Arai, M., Johansson, S., Friedell, G.H. Cancer Res. (1976) [Pubmed]
  5. Effect of L-tryptophan and sodium saccharin on urinary tract carcinogenesis initiated by N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide. Fukushima, S., Friedell, G.H., Jacobs, J.B., Cohen, S.M. Cancer Res. (1981) [Pubmed]
  6. Chromosomal characteristics and malignancy of urothelial cells from carcinogen-treated rats. Debiec-Rychter, M., Zukowski, K., Wang, C.Y. J. Natl. Cancer Inst. (1989) [Pubmed]
  7. Role of renal metabolism and excretion in 5-nitrofuran-induced uroepithelial cancer in the rat. Spry, L.A., Zenser, T.V., Cohen, S.M., Davis, B.B. J. Clin. Invest. (1985) [Pubmed]
  8. Carcinogenicity of the antischistosomal nitrofuran trans-5-amino-3-[2-(5-nitro-2-furyl)vinyl]-1,2,4-oxadiazole. Dunsford, H.A., Keysser, C.H., Dolan, P.M., Seed, J.L., Bueding, E. J. Natl. Cancer Inst. (1984) [Pubmed]
  9. Effect of avitaminosis A and hypervitaminosis A on urinary bladder carcinogenicity of N-(4-(5-Nitro-2-furyl)-2-thiazolyl)formamide. Cohen, S.M., Wittenberg, J.F., Bryan, G.T. Cancer Res. (1976) [Pubmed]
  10. Ras involvement in cells transformed with 2-amino-4-(5-nitro-2-furyl)thiazole (ANFT) in vitro and with N-[4-(5-nitro-2-furyl)-2-thiazoyl]formamide in vivo. Mann, A.M., Asamoto, M., Chlapowski, F.J., Masui, T., Macatee, T.L., Cohen, S.M. Carcinogenesis (1992) [Pubmed]
  11. The effect of nitrofurantoin on bladder tumor cell lines: in vitro growth and implantation in the cauterized mouse bladder. Bulbul, M.A., Chin, J.L., Huben, R.P., Englander, L.S., Pontes, J.E. J. Urol. (1985) [Pubmed]
  12. N-[4-(5-nitro-2-furyl)-2-thiazolyl] formamide-induced bladder cancer in mice: augmentation by sutures through the bladder wall. Chester, J.F., Gaissert, H.A., Ross, J.S., Malt, R.A., Weitzman, S.A. J. Urol. (1987) [Pubmed]
  13. Action of nitrofurans on E. coli: mutation and induction and repair of daughter-strand gaps in DNA. Lu, C., McCalla, D.R., Bryant, D.W. Mutat. Res. (1979) [Pubmed]
  14. Biotransformation of the bladder carcinogen N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide in mice. Swaminathan, S., Bryan, G.T. Cancer Res. (1984) [Pubmed]
  15. Metabolism of N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide by prostaglandin endoperoxide synthetase. Zenser, T.V., Mattammal, M.B., Davis, B.B. Cancer Res. (1980) [Pubmed]
  16. Oncogene expression of FANFT- or BBN-induced rat urothelial cells. Debiec-Rychter, M., Jones, R.F., Zukowski, K., Wang, C.Y. Int. J. Cancer (1990) [Pubmed]
  17. Direct DNA sequencing of the rat neu oncogene transmembrane domain reveals no mutation in urinary bladder carcinomas induced by N-butyl-N-(4-hydroxybutyl)nitrosamine, N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide or N-methyl-N-nitrosourea. Masui, T., Mann, A.M., Macatee, T.L., Garland, E.M., Okamura, T., Smith, R.A., Cohen, S.M. Carcinogenesis (1991) [Pubmed]
  18. Effect of aspirin on N-[4-(5-nitro-2-furyl)-2-thiazolyl]-formamide-induced epithelial proliferation in the urinary bladder and forestomach of the rat. Hasegawa, R., St John, M., Murasaki, G., Fukushima, S., Cohen, S.M. Cancer Lett. (1984) [Pubmed]
  19. Effect of dose on urinary bladder carcinogenesis induced in F344 rats by N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide. Arai, M., Cohen, S.M., Jacobs, J.B., Friedell, G.H. J. Natl. Cancer Inst. (1979) [Pubmed]
  20. Enhancement of N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide-induced carcinogenesis by urinary tract infection in rats. Johansson, S.L., Anderström, C., von Schultz, L., Larsson, P. Cancer Res. (1987) [Pubmed]
  21. Enhancing effect of allopurinol on the induction of bladder cancer in rats by n-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide. Wang, C.Y., Hayashida, S., Pamukcu, A.M., Bryan, G.T. Cancer Res. (1976) [Pubmed]
  22. Inhibition by aspirin of N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide initiation and sodium saccharin promotion of urinary bladder carcinogenesis in male F344 rats. Sakata, T., Hasegawa, R., Johansson, S.L., Zenser, T.V., Cohen, S.M. Cancer Res. (1986) [Pubmed]
  23. Effect of aspirin on urinary bladder carcinogenesis initiated with N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide in rats. Cohen, S.M., Hasegawa, R., Sakata, T., Johansson, S.L. Cancer Res. (1989) [Pubmed]
  24. Promoting effect of saccharin and DL-tryptophan in urinary bladder carcinogenesis. Cohen, S.M., Arai, M., Jacobs, J.B., Friedell, G.H. Cancer Res. (1979) [Pubmed]
  25. Aspirin inhibition of N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide-induced lesions of the urinary bladder correlated with inhibition of metabolism by bladder prostaglandin endoperoxide synthetase. Cohen, S.M., Zenser, T.V., Murasaki, G., Fukushima, S., Mattammal, M.B., Rapp, N.S., Davis, B.B. Cancer Res. (1981) [Pubmed]
  26. Early induction of mouse urinary bladder ornithine decarboxylase activity by rodent vesical carcinogens. Matsushima, M., Bryan, G.T. Cancer Res. (1980) [Pubmed]
  27. Mutation and altered expression of p53 genes in experimental rat bladder tumor cells. Jones, R.F., Matuszyk, J., Debiec-Rychter, M., Wang, C.Y. Mol. Carcinog. (1994) [Pubmed]
  28. Iminium salt of copper benzochlorin (CDS1), a novel photosensitizer for photodynamic therapy: mechanism of cell killing. Hampton, J.A., Skalkos, D., Taylor, P.M., Selman, S.H. Photochem. Photobiol. (1993) [Pubmed]
  29. Light and scanning electron microscopy of exfoliated bladder epithelial cells in rats fed N-(4-(5-nitro-2-furyl)-2-thiazolyl)formamide. Jacobs, J.B., Arai, M., Cohen, S.M., Friedell, G.H. J. Natl. Cancer Inst. (1976) [Pubmed]
  30. Development of an in vitro and in vivo epithelial tumor model for the study of invasion. Pauli, B.U., Anderson, S.N., Memoli, V.A., Kuettner, K.E. Cancer Res. (1980) [Pubmed]
  31. Effect of dose on the induction of urothelial proliferation by N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide and its relationship to bladder carcinogenesis in the rat. Hasegawa, R., Cohen, S.M., St John, M., Cano, M., Ellwein, L.B. Carcinogenesis (1986) [Pubmed]
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