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Chemical Compound Review

FENRETINIDE     (2E,4E,6E,8E)-N-(4- hydroxyphenyl)-3,7...

Synonyms: Fenretinida, Fenretinidum, Fenretinimide, CHEMBL7301, McN-R-1967, ...
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Disease relevance of FENRETINIDE


Psychiatry related information on FENRETINIDE

  • When compared to control-fed animals, dietary fenretinide reduced the tumor incidence by 49% and the tumor mass by 52% of ras+myc-induced cancers in the mouse prostate reconstitution model system, which was modified to prolong the latency period before cancer development [9].
  • The younger were the women, the greater was the risk reduction associated with fenretinide, which attained 50% in women aged 40 years or younger and disappeared after age 55 (P-age*treatment interaction = 0.023) [10].

High impact information on FENRETINIDE


Chemical compound and disease context of FENRETINIDE


Biological context of FENRETINIDE


Anatomical context of FENRETINIDE


Associations of FENRETINIDE with other chemical compounds


Gene context of FENRETINIDE


Analytical, diagnostic and therapeutic context of FENRETINIDE


  1. Randomized trial of fenretinide to prevent second breast malignancy in women with early breast cancer. Veronesi, U., De Palo, G., Marubini, E., Costa, A., Formelli, F., Mariani, L., Decensi, A., Camerini, T., Del Turco, M.R., Di Mauro, M.G., Muraca, M.G., Del Vecchio, M., Pinto, C., D'Aiuto, G., Boni, C., Campa, T., Magni, A., Miceli, R., Perloff, M., Malone, W.F., Sporn, M.B. J. Natl. Cancer Inst. (1999) [Pubmed]
  2. N-(4-hydroxyphenyl)retinamide: a potent inducer of apoptosis in human neuroblastoma cells. Mariotti, A., Marcora, E., Bunone, G., Costa, A., Veronesi, U., Pierotti, M.A., Della Valle, G. J. Natl. Cancer Inst. (1994) [Pubmed]
  3. Can fenretinide protect women against ovarian cancer? De Palo, G., Veronesi, U., Camerini, T., Formelli, F., Mascotti, G., Boni, C., Fosser, V., Del Vecchio, M., Campa, T., Costa, A. J. Natl. Cancer Inst. (1995) [Pubmed]
  4. Growth inhibition and induction of apoptosis by fenretinide in small-cell lung cancer cell lines. Kalemkerian, G.P., Slusher, R., Ramalingam, S., Gadgeel, S., Mabry, M. J. Natl. Cancer Inst. (1995) [Pubmed]
  5. Increase of ceramide and induction of mixed apoptosis/necrosis by N-(4-hydroxyphenyl)- retinamide in neuroblastoma cell lines. Maurer, B.J., Metelitsa, L.S., Seeger, R.C., Cabot, M.C., Reynolds, C.P. J. Natl. Cancer Inst. (1999) [Pubmed]
  6. Analysis of gene expression identifies PLAB as a mediator of the apoptotic activity of fenretinide in human ovarian cancer cells. Appierto, V., Villani, M.G., Cavadini, E., Gariboldi, M., De Cecco, L., Pierotti, M.A., Lambert, J.R., Reid, J., Tiberio, P., Colombo, N., Formelli, F. Oncogene (2007) [Pubmed]
  7. The unhydrolyzable fenretinide analogue 4-hydroxybenzylretinone induces the proapoptotic genes GADD153 (CHOP) and Bcl-2-binding component 3 (PUMA) and apoptosis that is caspase- dependent and independent of the retinoic acid receptor. Anding, A.L., Chapman, J.S., Barnett, D.W., Curley, R.W., Clagett-Dame, M. Cancer Res. (2007) [Pubmed]
  8. Synergistic Activity of Fenretinide and the Bcl-2 Family Protein Inhibitor ABT-737 against Human Neuroblastoma. Fang, H., Harned, T.M., Kalous, O., Maldonado, V., Declerck, Y.A., Reynolds, C.P. Clin. Cancer Res. (2011) [Pubmed]
  9. Dietary fenretinide, a synthetic retinoid, decreases the tumor incidence and the tumor mass of ras+myc-induced carcinomas in the mouse prostate reconstitution model system. Slawin, K., Kadmon, D., Park, S.H., Scardino, P.T., Anzano, M., Sporn, M.B., Thompson, T.C. Cancer Res. (1993) [Pubmed]
  10. Fifteen-year results of a randomized phase III trial of fenretinide to prevent second breast cancer. Veronesi, U., Mariani, L., Decensi, A., Formelli, F., Camerini, T., Miceli, R., Di Mauro, M.G., Costa, A., Marubini, E., Sporn, M.B., De Palo, G. Ann. Oncol. (2006) [Pubmed]
  11. Effects of N-(4-hydroxyphenyl)retinamide on hTERT expression in the bronchial epithelium of cigarette smokers. Soria, J.C., Moon, C., Wang, L., Hittelman, W.N., Jang, S.J., Sun, S.Y., Lee, J.J., Liu, D., Kurie, J.M., Morice, R.C., Lee, J.S., Hong, W.K., Mao, L. J. Natl. Cancer Inst. (2001) [Pubmed]
  12. Effects of retinoids on cancerous phenotype and apoptosis in organotypic cultures of ovarian carcinoma. Guruswamy, S., Lightfoot, S., Gold, M.A., Hassan, R., Berlin, K.D., Ivey, R.T., Benbrook, D.M. J. Natl. Cancer Inst. (2001) [Pubmed]
  13. Re: Randomized trial of fenretinide to prevent second breast malignancy in women with early breast cancer. Ménard, S., Camerini, T., Mariani, L., Tomasic, G., Pilotti, S., Costa, A., De Palo, G., Veronesi, U. J. Natl. Cancer Inst. (2001) [Pubmed]
  14. Effects of dietary N-(4-hydroxyphenyl)retinamide on N-nitrosomethylbenzylamine metabolism and esophageal tumorigenesis in the Fischer 344 rat. Gupta, A., Nines, R., Rodrigo, K.A., Aziz, R.A., Carlton, P.S., Gray, D.L., Steele, V.E., Morse, M.A., Stoner, G.D. J. Natl. Cancer Inst. (2001) [Pubmed]
  15. Synergistic cytotoxicity in solid tumor cell lines between N-(4-hydroxyphenyl)retinamide and modulators of ceramide metabolism. Maurer, B.J., Melton, L., Billups, C., Cabot, M.C., Reynolds, C.P. J. Natl. Cancer Inst. (2000) [Pubmed]
  16. Differential expression of nuclear retinoid receptors in normal and malignant prostates. Lotan, Y., Xu, X.C., Shalev, M., Lotan, R., Williams, R., Wheeler, T.M., Thompson, T.C., Kadmon, D. J. Clin. Oncol. (2000) [Pubmed]
  17. American Society of Clinical Oncology technology assessment of pharmacologic interventions for breast cancer risk reduction including tamoxifen, raloxifene, and aromatase inhibition. Chlebowski, R.T., Col, N., Winer, E.P., Collyar, D.E., Cummings, S.R., Vogel, V.G., Burstein, H.J., Eisen, A., Lipkus, I., Pfister, D.G. J. Clin. Oncol. (2002) [Pubmed]
  18. Fenretinide cytotoxicity for Ewing's sarcoma and primitive neuroectodermal tumor cell lines is decreased by hypoxia and synergistically enhanced by ceramide modulators. Batra, S., Reynolds, C.P., Maurer, B.J. Cancer Res. (2004) [Pubmed]
  19. Synthetic retinoid fenretinide is effective against a human ovarian carcinoma xenograft and potentiates cisplatin activity. Formelli, F., Cleris, L. Cancer Res. (1993) [Pubmed]
  20. Chemopreventive activity of tamoxifen, N-(4-hydroxyphenyl)retinamide, and the vitamin D analogue Ro24-5531 for androgen-promoted carcinomas of the rat seminal vesicle and prostate. Lucia, M.S., Anzano, M.A., Slayter, M.V., Anver, M.R., Green, D.M., Shrader, M.W., Logsdon, D.L., Driver, C.L., Brown, C.C., Peer, C.W. Cancer Res. (1995) [Pubmed]
  21. Involvement of reactive oxygen species in N-(4-hydroxyphenyl)retinamide-induced apoptosis in cervical carcinoma cells. Oridate, N., Suzuki, S., Higuchi, M., Mitchell, M.F., Hong, W.K., Lotan, R. J. Natl. Cancer Inst. (1997) [Pubmed]
  22. Effect of the synthetic retinoid fenretinide on dark adaptation and the ocular surface. Decensi, A., Torrisi, R., Polizzi, A., Gesi, R., Brezzo, V., Rolando, M., Rondanina, G., Orengo, M.A., Formelli, F., Costa, A. J. Natl. Cancer Inst. (1994) [Pubmed]
  23. 4-oxo-fenretinide, a recently identified fenretinide metabolite, induces marked G2-M cell cycle arrest and apoptosis in fenretinide-sensitive and fenretinide-resistant cell lines. Villani, M.G., Appierto, V., Cavadini, E., Bettiga, A., Prinetti, A., Clagett-Dame, M., Curley, R.W., Formelli, F. Cancer Res. (2006) [Pubmed]
  24. Induction of apoptosis in primary meningioma cultures by fenretinide. Puduvalli, V.K., Li, J.T., Chen, L., McCutcheon, I.E. Cancer Res. (2005) [Pubmed]
  25. Enhanced expression of an insulin growth factor-like binding protein (mac25) in senescent human mammary epithelial cells and induced expression with retinoic acid. Swisshelm, K., Ryan, K., Tsuchiya, K., Sager, R. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  26. Fenretinide enhances rituximab-induced cytotoxicity against B-cell lymphoma xenografts through a caspase-dependent mechanism. Gopal, A.K., Pagel, J.M., Hedin, N., Press, O.W. Blood (2004) [Pubmed]
  27. Enhanced inhibition of mammary carcinogenesis by combined treatment with N-(4-hydroxyphenyl)retinamide and ovariectomy. McCormick, D.L., Mehta, R.G., Thompson, C.A., Dinger, N., Caldwell, J.A., Moon, R.C. Cancer Res. (1982) [Pubmed]
  28. Synthetic retinoids as inducers of apoptosis in ovarian carcinoma cell lines. Holmes, W.F., Soprano, D.R., Soprano, K.J. J. Cell. Physiol. (2004) [Pubmed]
  29. Isolation and characterization of an acute promyelocytic leukemia cell line selectively resistant to the novel antileukemic and apoptogenic retinoid 6-[3-adamantyl-4-hydroxyphenyl]-2-naphthalene carboxylic acid. Ponzanelli, I., Giannì, M., Giavazzi, R., Garofalo, A., Nicoletti, I., Reichert, U., Erba, E., Rambaldi, A., Terao, M., Garattini, E. Blood (2000) [Pubmed]
  30. Five-year administration of fenretinide: pharmacokinetics and effects on plasma retinol concentrations. Formelli, F., Clerici, M., Campa, T., Di Mauro, M.G., Magni, A., Mascotti, G., Moglia, D., De Palo, G., Costa, A., Veronesi, U. J. Clin. Oncol. (1993) [Pubmed]
  31. Prospects of chemoprevention of human cancers with the synthetic retinoid fenretinide. Costa, A., Formelli, F., Chiesa, F., Decensi, A., De Palo, G., Veronesi, U. Cancer Res. (1994) [Pubmed]
  32. Comparative activity of dietary or topical exposure to three retinoids in the promotion of skin tumor induction in mice. McCormick, D.L., Bagg, B.J., Hultin, T.A. Cancer Res. (1987) [Pubmed]
  33. Bak: a downstream mediator of fenretinide-induced apoptosis of SH-SY5Y neuroblastoma cells. Lovat, P.E., Oliverio, S., Corazzari, M., Rodolfo, C., Ranalli, M., Goranov, B., Melino, G., Redfern, C.P., Piacentini, M. Cancer Res. (2003) [Pubmed]
  34. Induction of retinoic acid receptor-beta suppresses cyclooxygenase-2 expression in esophageal cancer cells. Li, M., Song, S., Lippman, S.M., Zhang, X.K., Liu, X., Lotan, R., Xu, X.C. Oncogene (2002) [Pubmed]
  35. BBC3 mediates fenretinide-induced cell death in neuroblastoma. Wei, J.S., Whiteford, C.C., Cenacchi, N., Son, C.G., Khan, J. Oncogene (2005) [Pubmed]
  36. Relationships between plasma insulin-like growth factor-I and insulin-like growth factor binding protein-3 and second breast cancer risk in a prevention trial of fenretinide. Decensi, A., Veronesi, U., Miceli, R., Johansson, H., Mariani, L., Camerini, T., Di Mauro, M.G., Cavadini, E., De Palo, G., Costa, A., Perloff, M., Malone, W.F., Formelli, F. Clin. Cancer Res. (2003) [Pubmed]
  37. Cyclin d1 overexpression sensitizes breast cancer cells to fenretinide. Pirkmaier, A., Yuen, K., Hendley, J., O'Connell, M.J., Germain, D. Clin. Cancer Res. (2003) [Pubmed]
  38. Cell death induced by N-(4-hydroxyphenyl)retinamide in human epidermal keratinocytes is modulated by TGF-beta and diminishes during the progression of squamous cell carcinoma. Davies, M., Paterson, I.C., Ganapathy, A., Prime, S.S. Int. J. Cancer (2006) [Pubmed]
  39. Phase IIa study of fenretinide in superficial bladder cancer, using DNA flow cytometry as an intermediate end point. Decensi, A., Bruno, S., Costantini, M., Torrisi, R., Curotto, A., Gatteschi, B., Nicolò, G., Polizzi, A., Perloff, M., Malone, W.F. J. Natl. Cancer Inst. (1994) [Pubmed]
  40. GADD153 and 12-lipoxygenase mediate fenretinide-induced apoptosis of neuroblastoma. Lovat, P.E., Oliverio, S., Ranalli, M., Corazzari, M., Rodolfo, C., Bernassola, F., Aughton, K., Maccarrone, M., Hewson, Q.D., Pearson, A.D., Melino, G., Piacentini, M., Redfern, C.P. Cancer Res. (2002) [Pubmed]
  41. Identification of the genes involved in enhanced fenretinide-induced apoptosis by parthenolide in human hepatoma cells. Park, J.H., Liu, L., Kim, I.H., Kim, J.H., You, K.R., Kim, D.G. Cancer Res. (2005) [Pubmed]
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