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Chemical Compound Review

RETINAMIDE     (2E,4E,6E,8E)-3,7-dimethyl-9- (2,6,6...

Synonyms: AC1NSUDP, Retinoyl amid, Retinoyl Amide, LS-143458, FT-0674371, ...
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Disease relevance of Ro 4-3930


Psychiatry related information on Ro 4-3930


High impact information on Ro 4-3930


Chemical compound and disease context of Ro 4-3930


Biological context of Ro 4-3930


Anatomical context of Ro 4-3930


Associations of Ro 4-3930 with other chemical compounds

  • Beginning 1 week after a single i.p. dose of 0, 50 or 100 mg DEN per kg body wt, groups of 35 mice received dietary supplements of (per kg diet): 0.1 mmol all-trans-retinoic acid (RA), 0.5 or 1.0 mmol all-trans-ethyl retinamide (ER), 0.5 or 1.0 mmol 13-cis-ethyl retinamide (13-cis-ER), or vehicle only [19].
  • N-(4-hydroxphenyl) retinamide induced a dose-dependent decline in cell growth and survival associated with a maximal 10-fold increase in ceramide production at 10 microM [20].
  • The retinamide-mediated apoptosis of promyelocytic cells was investigated using pHi- and DNA-sensitive fluorescent probes (BCECF and Hoechst 33342) [21].
  • Differential effects of retinoic acid (RA) and N-(4-hydroxyphenyl) retinamide (4-HPR) on cell growth, induction of differentiation, and changes in p34cdc2, Bcl-2, and actin expression in the human promyelocytic HL-60 leukemic cells [22].
  • Cells were treated with either retinamide alone or in combination with the chemotherapy agent, BCNU [12].

Gene context of Ro 4-3930

  • Effects of N-(4-hydroxyphenyl) retinamide on urokinase-type plasminogen activator and plasminogen activator inhibitor-1 in prostate adenocarcinoma cell lines [23].
  • Retinamide treatment resulted in increased ratios of deamidated verses transamidated levels of Bcl-xL in U87 cells [12].
  • Clinical studies have demonstrated that N-4-(carboxyphenyl) retinamide is effective against oral leukoplakia, vulvar leukoplakia, and dysplasia of the uterine cervix and stomach [24].
  • The identification of agents that inhibit the progression of dysplastic lesions to esophageal SCC has proven difficult; however, the results of the trial with ATB and retinamide are encouraging [25].
  • Cis/trans isomerization of each retinamide at C13 occurred, but only 15-20% of the total dose could be accounted for as parent retinamide and its C13 isomer [26].

Analytical, diagnostic and therapeutic context of Ro 4-3930


  1. 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]
  2. Putative metabolites derived from dietary combinations of calcium glucarate and N-(4-hydroxyphenyl)retinamide act synergistically to inhibit the induction of rat mammary tumors by 7,12-dimethylbenz[a]anthracene. Abou-Issa, H.M., Duruibe, V.A., Minton, J.P., Larroya, S., Dwivedi, C., Webb, T.E. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  3. 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]
  4. N-(4-hydroxyphenyl)retinamide inhibits invasion, suppresses osteoclastogenesis, and potentiates apoptosis through down-regulation of I(kappa)B(alpha) kinase and nuclear factor-kappaB-regulated gene products. Shishodia, S., Gutierrez, A.M., Lotan, R., Aggarwal, B.B. Cancer Res. (2005) [Pubmed]
  5. N-(4-hydroxyphenyl) retinamide (4HPR) enhances TRAIL-mediated apoptosis through enhancement of a mitochondrial-dependent amplification loop in ovarian cancer cell lines. Cuello, M., Coats, A.O., Darko, I., Ettenberg, S.A., Gardner, G.J., Nau, M.M., Liu, J.R., Birrer, M.J., Lipkowitz, S. Cell Death Differ. (2004) [Pubmed]
  6. Anticarcinogenic effect of retinoids on 7,12-dimethylbenz(a)anthracene-induced mammary tumor induction, and its relationship to cyclic AMP-dependent protein kinase. Abou-Issa, H., Duruibe, V.A. Biochem. Biophys. Res. Commun. (1986) [Pubmed]
  7. Regulation of apoptosis induced by the retinoid N-(4-hydroxyphenyl) retinamide and effect of deregulated bcl-2. Delia, D., Aiello, A., Formelli, F., Fontanella, E., Costa, A., Miyashita, T., Reed, J.C., Pierotti, M.A. Blood (1995) [Pubmed]
  8. Involvement of mitochondrial and akt signaling pathways in augmented apoptosis induced by a combination of low doses of celecoxib and N-(4-hydroxyphenyl) retinamide in premalignant human bronchial epithelial cells. Schroeder, C.P., Kadara, H., Lotan, D., Woo, J.K., Lee, H.Y., Hong, W.K., Lotan, R. Cancer Res. (2006) [Pubmed]
  9. Influence of retinoids on growth and metastasis of hamster melanoma in athymic mice. Schleicher, R.L., Moon, R.C., Patel, M.K., Beattie, C.W. Cancer Res. (1988) [Pubmed]
  10. N-[4-hydroxyphenyl] retinamide in rheumatoid arthritis: a pilot study. Gravallese, E.M., Handel, M.L., Coblyn, J., Anderson, R.J., Sperling, R.I., Karlson, E.W., Maier, A., Ruderman, E.M., Formelli, F., Weinblatt, M.E. Arthritis Rheum. (1996) [Pubmed]
  11. N-(4-hydroxyphenyl)retinamide (4-HPR)-mediated biological actions involve retinoid receptor-independent pathways in human breast carcinoma. Sheikh, M.S., Shao, Z.M., Li, X.S., Ordonez, J.V., Conley, B.A., Wu, S., Dawson, M.I., Han, Q.X., Chao, W.R., Quick, T. Carcinogenesis (1995) [Pubmed]
  12. Retinamide-induced apoptosis in glioblastomas is associated with down-regulation of Bcl-xL and Bcl-2 proteins. Lytle, R.A., Jiang, Z., Zheng, X., Higashikubo, R., Rich, K.M. J. Neurooncol. (2005) [Pubmed]
  13. Role of antioxidants and intracellular free radicals in retinamide-induced cell death. Delia, D., Aiello, A., Meroni, L., Nicolini, M., Reed, J.C., Pierotti, M.A. Carcinogenesis (1997) [Pubmed]
  14. N-(4-hydroxyphenyl) retinamide induces cell cycle specific growth inhibition in PC3 cells. Igawa, M., Tanabe, T., Chodak, G.W., Rukstalis, D.B. Prostate (1994) [Pubmed]
  15. Effect of N-(4-hydroxyphenyl) retinamide on food intake, growth, and mammary gland development in rats. Radcliffe, J.D., Moon, R.C. Proc. Soc. Exp. Biol. Med. (1983) [Pubmed]
  16. Antisense BAG-1 sensitizes HeLa cells to apoptosis by multiple pathways. Xiong, J., Chen, J., Chernenko, G., Beck, J., Liu, H., Pater, A., Tang, S.C. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  17. Enhancement of acyl coenzyme A:retinol acyltransferase in rat liver and mammary tumor tissue by retinyl acetate and its competitive inhibition by N-(4-hydroxyphenyl) retinamide. Ball, M.D., Furr, H.C., Olson, J.A. Biochem. Biophys. Res. Commun. (1985) [Pubmed]
  18. Chemoprevention of cancer of uterine cervix: a study on chemoprevention of retinamide II from cervical precancerous lesions. Ruidi, C., Aihua, D., Peiyu, B., Zhongru, G., Huazao, L., Shifeng, S., Rui, H., Shiping, X. J. Cell. Biochem. Suppl. (1997) [Pubmed]
  19. Enhancement of murine hepatocarcinogenesis by all-trans-retinoic acid and two synthetic retinamides. McCormick, D.L., Hollister, J.L., Bagg, B.J., Long, R.E. Carcinogenesis (1990) [Pubmed]
  20. Fenretinide stimulates redox-sensitive ceramide production in breast cancer cells: potential role in drug-induced cytotoxicity. Rehman, F., Shanmugasundaram, P., Schrey, M.P. Br. J. Cancer (2004) [Pubmed]
  21. Early cytoplasmic acidification in retinamide-mediated apoptosis of human promyelocytic leukemia cells. Angoli, D., Delia, D., Wanke, E. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  22. Differential effects of retinoic acid (RA) and N-(4-hydroxyphenyl) retinamide (4-HPR) on cell growth, induction of differentiation, and changes in p34cdc2, Bcl-2, and actin expression in the human promyelocytic HL-60 leukemic cells. Dipietrantonio, A., Hsieh, T.C., Wu, J.M. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  23. Effects of N-(4-hydroxyphenyl) retinamide on urokinase-type plasminogen activator and plasminogen activator inhibitor-1 in prostate adenocarcinoma cell lines. Tanabe, T. Hiroshima J. Med. Sci. (2000) [Pubmed]
  24. Highlights of the cancer chemoprevention studies in China. Han, J. Preventive medicine. (1993) [Pubmed]
  25. Clinical models of chemoprevention for the esophagus. Beer, D.G., Stoner, G.D. Hematol. Oncol. Clin. North Am. (1998) [Pubmed]
  26. Pharmacokinetics, tissue distribution, and placental permeability of all-trans- and 13-cis-N-ethyl retinamides in pregnant hamsters. Howard, W.B., Willhite, C.C., Omaye, S.T., Sharma, R.P. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1989) [Pubmed]
  27. Breast tissue accumulation of retinamides in a randomized short-term study of fenretinide. Sabichi, A.L., Modiano, M.R., Lee, J.J., Peng, Y.M., Xu, M.J., Villar, H., Dalton, W.S., Lippman, S.M. Clin. Cancer Res. (2003) [Pubmed]
  28. Evaluation of biomarker modulation by fenretinide in prostate cancer patients. Urban, D., Myers, R., Manne, U., Weiss, H., Mohler, J., Perkins, D., Markiewicz, M., Lieberman, R., Kelloff, G., Marshall, M., Grizzle, W. Eur. Urol. (1999) [Pubmed]
  29. A retinoic acid resistant HL-60 cell clone sensitive to N-(4-hydroxyphenyl) retinamide-mediated clonal growth inhibition. Brigati, C., Ferrari, N., Megna, M., Roncella, S., Cutrona, G., Tosetti, F., Vidali, G. Leuk. Lymphoma (1995) [Pubmed]
  30. Influence of hormones on N-(4-hydroxyphenyl) retinamide inhibition of 7,12-dimethylbenz[alpha]anthracene transformation of mammary cells in organ culture. Chatterjee, M., Banerjee, M.R. Cancer Lett. (1982) [Pubmed]
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