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Chemical Compound Review

Florafur     5-fluoro-1-(oxolan-2- yl)pyrimidine-2,4-dione

Synonyms: Ftorafur, Futraful, Fluorofur, tegafur, Sunfural S, ...
 
 
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Disease relevance of FT 207

 

High impact information on FT 207

  • The pharmacokinetics of FD-1 and FT-207 were compared in the livers and kidneys of control mice and in mice (DD males) pretreated with phenobarbital [4].
  • Oral administration of FD-1 to the mice pretreated with phenobarbital elevated the FT-207 and 3-T-F-FU levels in the livers to twice the levels in the control mice and further elevated the FUra levels in the livers to twice the levels in the controls [4].
  • These results indicate that FD-1 is catabolized in the liver by microsomal enzymes (including cytochrome P450) faster than is FT-207, which consequently enlarges the hepatic pool of the intermediates on the way to FUra formation [4].
  • PURPOSE: The conversion rate of tegafur (a component of S-1) to fluorouracil (FU) differs in Asians and whites because of polymorphic differences in the CYP2A6 gene [5].
  • Postoperative adjuvant therapy with tamoxifen, tegafur plus uracil, or both in women with node-negative breast cancer: a pooled analysis of six randomized controlled trials [6].
 

Chemical compound and disease context of FT 207

 

Biological context of FT 207

  • The number of FdUMP binding sites was significantly increased in patients who received tegafur and uracil preoperatively [UFT (+) group, n = 14] compared with those who did not [UFT (-) group, n = 36; P < 0.0001] [11].
  • The maximum tolerated dose (MTD) of FT and UFT, administered 3 times a day for 28 days, was 150 mg/kg/day and 60 mg/kg/day, respectively [12].
  • The purpose of the present study was to identify the human CYP isoform(s) involved in the metabolic activation of tegafur using human liver microsomes and cDNA-expressed human CYPs [13].
  • All the cyclic aminals provoked a G(o)/G(1)-phase cell cycle arrest, whereas Ftorafur, a known prodrug of 5-FU, and 1-[2-(2-hydroxymethyl-4-nitrophenoxy)-1-methoxyethyl]-5-fluorouracil (51) induced an S-phase cell cycle arrest [14].
  • A novel mutant allele of the CYP2A6 gene (CYP2A6*11 ) found in a cancer patient who showed poor metabolic phenotype towards tegafur [15].
 

Anatomical context of FT 207

  • A low dose of FT (100 mg/kg) also increased the therapeutic effect in combination with allogeneic lymphoid cell transfer (28.0%) [16].
  • L-dRib (20 mg/kg/day) was significantly (P < 0.05) more efficient than tegafur (100 mg/kg/day) in decreasing the number of metastatic nodules in organs in the abdominal cavity [17].
  • Transfected cells were also more sensitive to Tegafur than untransfected KB cells [18].
  • The S isomer of Ftorafur was synthesized and the ability of the latter to inhibit growth of cultured human fibroblasts was determined relative to both the R isomer and the racemic mixture (Ftorafur) that is presently used clinically [19].
  • In 14 human samples, the mean rates of 5-FU formation in liver microsomes were 5-fold and 2-fold higher than those in liver cytosol at substrate concentrations of 100 microM and 1 mM tegafur, respectively [20].
 

Associations of FT 207 with other chemical compounds

 

Gene context of FT 207

 

Analytical, diagnostic and therapeutic context of FT 207

References

  1. Randomized clinical trial of adjuvant mitomycin plus tegafur in patients with resected stage III gastric cancer. Cirera, L., Balil, A., Batiste-Alentorn, E., Tusquets, I., Cardona, T., Arcusa, A., Jolis, L., Saigí, E., Guasch, I., Badia, A., Boleda, M. J. Clin. Oncol. (1999) [Pubmed]
  2. Phase I-II studies of oral tegafur (ftorafur). Ansfield, F.J., Kallas, G.J., Singson, J.P. J. Clin. Oncol. (1983) [Pubmed]
  3. Phase I study of preoperative oral uracil and tegafur plus leucovorin and radiation therapy in rectal cancer. Hoff, P.M., Janjan, N., Saad, E.D., Skibber, J., Crane, C., Lassere, Y., Cleary, K.R., Benner, S., Randolph, J., Abbruzzese, J.L., Pazdur, R. J. Clin. Oncol. (2000) [Pubmed]
  4. Metabolism of 1,3-bis(tetrahydro-2-furanyl)-5-fluorouracil in mice. Fujimoto, S., Ishigami, H., Minami, T., Miyazaki, M., Itoh, K., Kimura, K. J. Natl. Cancer Inst. (1979) [Pubmed]
  5. Phase I pharmacokinetic study of S-1 plus cisplatin in patients with advanced gastric carcinoma. Ajani, J.A., Faust, J., Ikeda, K., Yao, J.C., Anbe, H., Carr, K.L., Houghton, M., Urrea, P. J. Clin. Oncol. (2005) [Pubmed]
  6. Postoperative adjuvant therapy with tamoxifen, tegafur plus uracil, or both in women with node-negative breast cancer: a pooled analysis of six randomized controlled trials. Noguchi, S., Koyama, H., Uchino, J., Abe, R., Miura, S., Sugimachi, K., Akazawa, K., Abe, O. J. Clin. Oncol. (2005) [Pubmed]
  7. Randomized comparative study of tegafur/uracil and oral leucovorin versus parenteral fluorouracil and leucovorin in patients with previously untreated metastatic colorectal cancer. Carmichael, J., Popiela, T., Radstone, D., Falk, S., Borner, M., Oza, A., Skovsgaard, T., Munier, S., Martin, C. J. Clin. Oncol. (2002) [Pubmed]
  8. Randomized phase III trial of fluorouracil alone versus fluorouracil plus cisplatin versus uracil and tegafur plus mitomycin in patients with unresectable, advanced gastric cancer: The Japan Clinical Oncology Group Study (JCOG9205). Ohtsu, A., Shimada, Y., Shirao, K., Boku, N., Hyodo, I., Saito, H., Yamamichi, N., Miyata, Y., Ikeda, N., Yamamoto, S., Fukuda, H., Yoshida, S. J. Clin. Oncol. (2003) [Pubmed]
  9. Tegafur/uracil + calcium folinate in colorectal cancer: double modulation of fluorouracil. Hoff, P.M., Lassere, Y., Pazdur, R. Drugs (1999) [Pubmed]
  10. Blood vessel density correlates with the effects of targeted intra-arterial carboplatin infusion with concurrent radiotherapy for squamous cell carcinomas of the oral cavity and oropharynx. Takagi, S., Inenaga, R., Oya, R., Nakamura, S., Ikemura, K. Br. J. Cancer (2006) [Pubmed]
  11. The number of 5-fluoro-2'-deoxyuridine-5'-monophosphate binding sites and reduced folate pool in human colorectal carcinoma tissues: changes after tegafur and uracil treatment. Omura, K., Kawakami, K., Kanehira, E., Nagasato, A., Kawashima, S., Tawaraya, K., Watanabe, S., Hirano, K., Shirasaka, T., Watanabe, Y. Cancer Res. (1995) [Pubmed]
  12. 5-Fluorouracil prodrug: role of anabolic and catabolic pathway modulation in therapy of colorectal cancer. Cao, S., Frank, C., Shirasaka, T., Rustum, Y.M. Clin. Cancer Res. (1995) [Pubmed]
  13. Bioactivation of tegafur to 5-fluorouracil is catalyzed by cytochrome P-450 2A6 in human liver microsomes in vitro. Ikeda, K., Yoshisue, K., Matsushima, E., Nagayama, S., Kobayashi, K., Tyson, C.A., Chiba, K., Kawaguchi, Y. Clin. Cancer Res. (2000) [Pubmed]
  14. New medium oxacyclic O,N-acetals and related open analogues: biological activities. Campos, J., Saniger, E., Marchal, J.A., Aiello, S., Súarez, I., Boulaiz, H., Aránega, A., A Gallo, M., Espinosa, A. Current medicinal chemistry. (2005) [Pubmed]
  15. A novel mutant allele of the CYP2A6 gene (CYP2A6*11 ) found in a cancer patient who showed poor metabolic phenotype towards tegafur. Daigo, S., Takahashi, Y., Fujieda, M., Ariyoshi, N., Yamazaki, H., Koizumi, W., Tanabe, S., Saigenji, K., Nagayama, S., Ikeda, K., Nishioka, Y., Kamataki, T. Pharmacogenetics (2002) [Pubmed]
  16. Effect of normal allogeneic lymphoid cell transfer in combination with chemotherapy on a transplantable tumor in rats. Yamada, Y., Kawamura, T., Gotohda, E., Akiyama, J., Hosokawa, M., Kodama, T., Kobayashi, H. Cancer Res. (1980) [Pubmed]
  17. Inhibition of metastasis of tumor cells overexpressing thymidine phosphorylase by 2-deoxy-L-ribose. Nakajima, Y., Gotanda, T., Uchimiya, H., Furukawa, T., Haraguchi, M., Ikeda, R., Sumizawa, T., Yoshida, H., Akiyama, S. Cancer Res. (2004) [Pubmed]
  18. Sensitivity of human KB cells expressing platelet-derived endothelial cell growth factor to pyrimidine antimetabolites. Haraguchi, M., Furukawa, T., Sumizawa, T., Akiyama, S. Cancer Res. (1993) [Pubmed]
  19. In vitro biological evaluation of the R and S isomers of 1-(Tetrahydrofuran-2-yl)-5-fluorouracil. Horwitz, J.P., McCormick, J.J., Philips, K.D., Maher, V.M., Otto, J.R., Kessel, D., Zemlicka, J. Cancer Res. (1975) [Pubmed]
  20. Involvement of microsomal cytochrome P450 and cytosolic thymidine phosphorylase in 5-fluorouracil formation from tegafur in human liver. Komatsu, T., Yamazaki, H., Shimada, N., Nagayama, S., Kawaguchi, Y., Nakajima, M., Yokoi, T. Clin. Cancer Res. (2001) [Pubmed]
  21. Uracil/tegafur plus cisplatin with concurrent radiotherapy for locally advanced non-small-cell lung cancer: a multi-institutional phase II trial. Ichinose, Y., Nakai, Y., Kudoh, S., Semba, H., Yoshida, S., Nukiwa, T., Yamamoto, H., Yamane, Y., Niitani, H. Clin. Cancer Res. (2004) [Pubmed]
  22. The effect of food on the pharmacokinetics of S-1 after single oral administration to patients with solid tumors. Peters, G.J., Noordhuis, P., Van Groeningen, C.J., Giaccone, G., Holwerda, U., Voorn, D., Schrijvers, A., Schornagel, J.H., Beijnen, J.H., Fumoleau, P., Schellens, J.H. Clin. Cancer Res. (2004) [Pubmed]
  23. Fluorinated pyrimidine nucleosides. 4. Synthesis and antitumor testing of a series of 2',5'-dideoxy- and 2',3',5'-trideoxynucleosides of 5-fluorouracil. Cook, A.F., Holman, M.J., Kramer, M.J. J. Med. Chem. (1980) [Pubmed]
  24. Combination of dihydropyrimidine dehydrogenase and thymidylate synthase gene expressions in primary tumors as predictive parameters for the efficacy of fluoropyrimidine-based chemotherapy for metastatic colorectal cancer. Ichikawa, W., Uetake, H., Shirota, Y., Yamada, H., Nishi, N., Nihei, Z., Sugihara, K., Hirayama, R. Clin. Cancer Res. (2003) [Pubmed]
  25. Cloning and characterization of the 5'-transcriptional regulatory region of the human intercellular adhesion molecule 1 gene. Degitz, K., Li, L.J., Caughman, S.W. J. Biol. Chem. (1991) [Pubmed]
  26. Genomic organization of the rat aromatic L-amino acid decarboxylase (AADC) locus: partial analysis reveals divergence from the Drosophila dopa decarboxylase (DDC) gene structure. Hahn, S.L., Hahn, M., Joh, T.H. Mamm. Genome (1991) [Pubmed]
  27. Randomized trial of adjuvant chemotherapy with mitomycin plus ftorafur versus mitomycin alone in resected locally advanced gastric cancer. Grau, J.J., Estapé, J., Fuster, J., Filella, X., Visa, J., Terés, J., Soler, G., Albiol, S., García-Valdecasas, J.C., Grande, L., Bombí, J., Bordas, J., Alcobendas, F. J. Clin. Oncol. (1998) [Pubmed]
  28. Protracted oral chemotherapy with fluorinated pyrimidines as an adjuvant to surgical treatment for stomach cancer. Fujimoto, S., Akao, T., Itoh, B., Koshizuka, I., Koyano, K. Ann. Surg. (1977) [Pubmed]
 
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