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Chemical Compound Review

NSC-256942     (7S,9R)-7-(4-amino-5-hydroxy- 6-methyl-oxan...

Synonyms: Lipodox, Epirubicin HCl, CCRIS 740, SureCN317302, DOX HCl, ...
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Disease relevance of NCI60_000547

  • The results confirm a role for beta-adrenergics in the management of experimental ADM skin ulceration and suggest that local toxicity is mediated through specific beta-receptors (possibly beta 1) in the mouse skin [1].
  • PATIENTS AND METHODS: Seventy-one patients with stage IV breast cancer were treated with Caelyx at doses of 45 to 60 mg/m2 every 3 to 4 weeks for a maximum of six cycles [2].
  • Radiation improves the distribution and uptake of liposomal doxorubicin (caelyx) in human osteosarcoma xenografts [3].
  • Total cytosolic ACC activity, expressed per g body weight, was increased in both NA and ADR rats by 45% and 39%, respectively (P < 0.05) [4].
  • Phase III data on Caelyx in ovarian cancer [5].

High impact information on NCI60_000547


Chemical compound and disease context of NCI60_000547


Biological context of NCI60_000547

  • Under the same assay conditions, ADR demonstrated much higher IC50 values: 550 microM for TPA and greater than 350 microM for PDBu [15].
  • Amongst the factors governing the response of cells in spheroids to cytotoxic drugs, the responses to ADM and VCR are thought to be largely dictated by cell cycle distribution and limited drug penetrability, whilst for HN2 the response may be determined by the factor of cell cycle distribution [16].
  • Interaction pharmacokinetics of pegylated liposomal doxorubicin (Caelyx) on coadministration with paclitaxel or docetaxel [17].
  • In contrast, X-ray-pretreated VCR-resistant cells (MCF/DXR-10) cells exhibited a distinctive resistance phenotype proving cross-resistant to VLB and VP-16 but not to ADR, and Pgp overexpression was not detectable [18].
  • These preliminary data indicate a difference in biotransformation between ADR and 4'-DOX despite their close structural similarities [19].

Anatomical context of NCI60_000547

  • AM, DEA and verapamil induced an increase in cytotoxicity of Adr, vincristine and etoposide (VP16) in COLO 320 cells, while in the GLC4 and GLC4-Adr cell line no effect was seen [20].
  • The colony-forming unit granulocyte macrophage (CFU-GM) assay showed no increase in cytotoxicity of Adr when AM was added [20].
  • Bone-marrow toxicity was the same as expected from Adr alone in these patients [20].
  • Thus, we conclude that administration of ADR not mixed with lipiodol and given through the hepatic artery is the preferred modality for treating early metastatic liver tumors [21].
  • In groups III and IV, ADR mixed with lipiodol (lipiodolized ADR) 4 mg/kg was given into the hepatic artery or into the portal vein, respectively, 24 h after inoculation [21].

Associations of NCI60_000547 with other chemical compounds

  • Furthermore, an additive growth inhibitory effect occurred when GEO cells were exposed to the AS S-oligos after treatment with different concentrations of either 5-FU, MIT, ADR or CDDP [22].
  • CDDP and ADR, which sensitized DU145 and PC-3 cells to Fas-L- and TNF-mediated killing, inhibited de novo protein synthesis in both cell lines, while VP-16 only inhibited protein synthesis in DU145 cells [23].
  • For POC spheroids, cells in the outer region of spheroids are more sensitive to ADM and VCR than cells in the inner region whilst a reverse trend is seen for the response to CCNU [16].
  • RESULTS: The drugs cis-diamminedichloroplatinum (II) (CDDP), adriamycin (ADR), and etoposide (VP-16) sensitized DU145 and PC-3 cells to Fas killing [23].
  • This effect is discernible at significantly lower levels of AD 143 than of ADR, corresponding to less than LD50 measured by the clonogenic assay [24].

Gene context of NCI60_000547

  • Also consistent with independence of P-170gp mediated MDR and TNF response, the P388/ADM cell line (exhibiting P-170gp mediated MDR) remained as resistant to TNF as the P388 parental line [25].
  • Total FAS activity was increased by 65% and 115% in NA and ADR rats, respectively (P < 0.05) [4].
  • Although K562/ADM was not cross-resistant to 3'-deamino-3'-morpholino-13-deoxo-10-hydroxycarminomycin (MX2), an anthracycline derivative, K562/TPA was cross-resistant to MX2 [26].
  • BACKGROUND: The aim of this study was to determine the activity and safety of pegylated liposomal doxorubicin (PLD; Caelyx) and docetaxel combination as first-line treatment in patients with metastatic breast cancer (MBC) [27].
  • The objective of this multicenter phase II study was to evaluate the safety, tolerance and anti-tumour activity of Caelyx as monotherapy in patients with recurrent SCLC [28].

Analytical, diagnostic and therapeutic context of NCI60_000547


  1. Modulation of experimental doxorubicin skin toxicity by beta-adrenergic compounds. Dorr, R.T., Alberts, D.S. Cancer Res. (1981) [Pubmed]
  2. Treatment of advanced breast cancer with sterically stabilized liposomal doxorubicin: results of a multicenter phase II trial. Ranson, M.R., Carmichael, J., O'Byrne, K., Stewart, S., Smith, D., Howell, A. J. Clin. Oncol. (1997) [Pubmed]
  3. Radiation improves the distribution and uptake of liposomal doxorubicin (caelyx) in human osteosarcoma xenografts. Davies, C.d.e. .L., Lundstrøm, L.M., Frengen, J., Eikenes, L., Bruland S, Ø.S., Kaalhus, O., Hjelstuen, M.H., Brekken, C. Cancer Res. (2004) [Pubmed]
  4. Plasma triglyceride levels are higher in nephrotic than in analbuminemic rats despite a similar increase in hepatic triglyceride secretion. Joles, J.A., Bijleveld, C., van Tol, A., Geelen, M.J., Koomans, H.A. Kidney Int. (1995) [Pubmed]
  5. Phase III data on Caelyx in ovarian cancer. Muggia, F., Hamilton, A. Eur. J. Cancer (2001) [Pubmed]
  6. Small molecules that dramatically alter multidrug resistance phenotype by modulating the substrate specificity of P-glycoprotein. Kondratov, R.V., Komarov, P.G., Becker, Y., Ewenson, A., Gudkov, A.V. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  7. Liposomal doxorubicin and conventionally fractionated radiotherapy in the treatment of locally advanced non-small-cell lung cancer and head and neck cancer. Koukourakis, M.I., Koukouraki, S., Giatromanolaki, A., Archimandritis, S.C., Skarlatos, J., Beroukas, K., Bizakis, J.G., Retalis, G., Karkavitsas, N., Helidonis, E.S. J. Clin. Oncol. (1999) [Pubmed]
  8. Modulation of doxorubicin resistance by valinomycin (NSC 122023) and liposomal valinomycin in Chinese hamster ovary cells. Daoud, S.S., Juliano, R.L. Cancer Res. (1989) [Pubmed]
  9. Interleukin-12 enhances the sensitivity of human osteosarcoma cells to 4-hydroperoxycyclophosphamide by a mechanism involving the Fas/Fas-ligand pathway. Duan, X., Zhou, Z., Jia, S.F., Colvin, M., Lafleur, E.A., Kleinerman, E.S. Clin. Cancer Res. (2004) [Pubmed]
  10. Concurrent administration of Docetaxel and Stealth liposomal doxorubicin with radiotherapy in non-small cell lung cancer : excellent tolerance using subcutaneous amifostine for cytoprotection. Koukourakis, M.I., Romanidis, K., Froudarakis, M., Kyrgias, G., Koukourakis, G.V., Retalis, G., Bahlitzanakis, N. Br. J. Cancer (2002) [Pubmed]
  11. Randomised phase II trial of pegylated liposomal doxorubicin (DOXIL/CAELYX) versus doxorubicin in the treatment of advanced or metastatic soft tissue sarcoma: a study by the EORTC Soft Tissue and Bone Sarcoma Group. Judson, I., Radford, J.A., Harris, M., Blay, J.Y., van Hoesel, Q., le Cesne, A., van Oosterom, A.T., Clemons, M.J., Kamby, C., Hermans, C., Whittaker, J., Donato di Paola, E., Verweij, J., Nielsen, S. Eur. J. Cancer (2001) [Pubmed]
  12. EORTC 10968: a phase I clinical and pharmacokinetic study of polyethylene glycol liposomal doxorubicin (Caelyx, Doxil) at a 6-week interval in patients with metastatic breast cancer. European Organization for Research and Treatment of Cancer. Hamilton, A., Biganzoli, L., Coleman, R., Mauriac, L., Hennebert, P., Awada, A., Nooij, M., Beex, L., Piccart, M., Van Hoorebeeck, I., Bruning, P., de Valeriola, D. Ann. Oncol. (2002) [Pubmed]
  13. Phase II study of pegylated liposomal doxorubicin HCl (Caelyx) in combination with cyclophosphamide and vincristine as second-line treatment of patients with small cell lung cancer. Leighl, N.B., Goss, G.D., Lopez, P.G., Burkes, R.L., Dancey, J.E., Rahim, Y.H., Rudinskas, L.C., Pouliot, J.F., Rodgers, A., Pond, G.R., Shepherd, F.A. Lung Cancer (2006) [Pubmed]
  14. Modulation of multidrug resistance by SDZ PSC 833 in leukemic and solid-tumor-bearing mouse models. Watanabe, T., Naito, M., Oh-hara, T., Itoh, Y., Cohen, D., Tsuruo, T. Jpn. J. Cancer Res. (1996) [Pubmed]
  15. Activation of human leukemia protein kinase C by tumor promoters and its inhibition by N-trifluoroacetyladriamycin-14-valerate (AD 32). Chuang, L.F., Kung, H.F., Israel, M., Chuang, R.Y. Biochem. Pharmacol. (1992) [Pubmed]
  16. Use of a tritiated thymidine suicide technique in the study of the cytotoxic drug response of cells located at different depths within multicellular spheroids. Kwok, T.T., Twentyman, P.R. Br. J. Cancer (1987) [Pubmed]
  17. Interaction pharmacokinetics of pegylated liposomal doxorubicin (Caelyx) on coadministration with paclitaxel or docetaxel. Briasoulis, E., Karavasilis, V., Tzamakou, E., Rammou, D., Soulti, K., Piperidou, C., Pavlidis, N. Cancer Chemother. Pharmacol. (2004) [Pubmed]
  18. Differential expression of steroid receptors, hsp27, and pS2 in a series of drug resistant human breast tumor cell lines derived following exposure to antitumor drugs or to fractionated X-irradiation. Whelan, R.D., Hill, B.T. Breast Cancer Res. Treat. (1993) [Pubmed]
  19. Occurrence of circulating 7-deoxyaglycone metabolites of 4'-deoxydoxorubicin in man. Cummings, J., Kerr, D.J., Kaye, S.B. Cancer Chemother. Pharmacol. (1987) [Pubmed]
  20. In vitro and in vivo modulation of multi-drug resistance with amiodarone. van der Graaf, W.T., de Vries, E.G., Uges, D.R., Nanninga, A.G., Meijer, C., Vellenga, E., Mulder, P.O., Mulder, N.H. Int. J. Cancer (1991) [Pubmed]
  21. A comparative study on effects of doxorubicin alone or mixed with lipiodol given through the hepatic artery or portal vein for liver tumors in rats. Utsunomiya, T., Kanematsu, T., Matsumata, T., Shirabe, K., Yamagata, M., Sugimachi, K. Oncology (1994) [Pubmed]
  22. Anti-sense oligonucleotides directed against EGF-related growth factors enhance anti-proliferative effect of conventional anti-tumor drugs in human colon-cancer cells. De Luca, A., Selvam, M.P., Sandomenico, C., Pepe, S., Bianco, A.R., Ciardiello, F., Salomon, D.S., Normanno, N. Int. J. Cancer (1997) [Pubmed]
  23. Sensitization of immunoresistant prostate carcinoma cell lines to Fas/Fas ligand-mediated killing by cytotoxic lymphocytes: independence of de novo protein synthesis. Frost, P.J., Belldegrun, A., Bonavida, B. Prostate (1999) [Pubmed]
  24. Effects of N-trifluoroacetyladriamycin-14-O-hemiadipate and radiation on L1210 cells. Potmesil, M., Israel, M., Kirschenbaum, S., Bowen, J., Silber, R. Radiat. Res. (1986) [Pubmed]
  25. The relationship between multidrug resistance and tumor necrosis factor resistance in an EL4 cell line model. Ujhazy, P., Chen, Y.F., Fredericks, W., Ho, R.L., Mihich, E., Baker, R.M., Ehrke, M.J. Cancer Commun. (1990) [Pubmed]
  26. Establishment of a human leukemia subline resistant to the growth-inhibitory effect of 12-O-tetradecanoylphorbol 13-acetate (TPA) and showing non-P-glycoprotein-mediated multi-drug resistance. Takeda, Y., Nishio, K., Sugimoto, Y., Kasahara, K., Kubo, S., Fujiwara, Y., Niitani, H., Saijo, N. Int. J. Cancer (1991) [Pubmed]
  27. Phase II study of pegylated liposomal doxorubicin (Caelyx) and docetaxel as first-line treatment in metastatic breast cancer. Alexopoulos, A., Karamouzis, M.V., Stavrinides, H., Ardavanis, A., Kandilis, K., Stavrakakis, J., Georganta, C., Rigatos, G. Ann. Oncol. (2004) [Pubmed]
  28. Phase II study of pegylated liposomal doxorubicin: inactive in recurrent small-cell lung cancer. A Hellenic Cooperative Oncology Group Study. Samantas, E., Kalofonos, H., Linardou, H., Nicolaides, C., Mylonakis, N., Fountzilas, G., Kosmidis, P., Skarlos, D. Ann. Oncol. (2000) [Pubmed]
  29. HER2 overexpression and doxorubicin in adjuvant chemotherapy for resectable breast cancer. Moliterni, A., Ménard, S., Valagussa, P., Biganzoli, E., Boracchi, P., Balsari, A., Casalini, P., Tomasic, G., Marubini, E., Pilotti, S., Bonadonna, G. J. Clin. Oncol. (2003) [Pubmed]
  30. Liposomal doxorubicin in conjunction with reirradiation and local hyperthermia treatment in recurrent breast cancer: a phase I/II trial. Kouloulias, V.E., Dardoufas, C.E., Kouvaris, J.R., Gennatas, C.S., Polyzos, A.K., Gogas, H.J., Sandilos, P.H., Uzunoglu, N.K., Malas, E.G., Vlahos, L.J. Clin. Cancer Res. (2002) [Pubmed]
  31. Phase I study of paclitaxel (taxol) and pegylated liposomal doxorubicin (caelyx) administered every 2 weeks in patients with advanced solid tumors. Mavroudis, D., Kouroussis, C.h., Kakolyris, S., Agelaki, S., Kalbakis, K., Androulakis, N., Souglakos, J., Samonis, G., Georgoulias, V. Oncology (2002) [Pubmed]
  32. Phase II study of pegylated liposomal doxorubicin (Caelyx) as induction chemotherapy for patients with squamous cell cancer of the head and neck. Harrington, K.J., Lewanski, C., Northcote, A.D., Whittaker, J., Peters, A.M., Vile, R.G., Stewart, J.S. Eur. J. Cancer (2001) [Pubmed]
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