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Chemical Compound Review

Diaziquona     ethyl N-[2,5-bis(aziridin-1-yl)-4...

Synonyms: diaziquone, Diaziquonum, Prestwick_54, CHEMBL36016, CI-904, ...
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Disease relevance of CI 904


High impact information on CI 904

  • The 60 patients underwent 72 autologous transplants after three high-dose chemotherapy regimens: 30 received high-dose carmustine in combination, five received high-dose busulfan and cyclophosphamide, and 37 received high-dose aziridinylbenzoquinone [5].
  • The lack of significant nonhematologic toxicity and the activity in patients with relapsed ANLL render diaziquone of interest as second-line therapy or consolidation therapy in first remission for patients with ANLL [2].
  • Intensification included one cycle of high-dose cytarabine (HDAC) followed by etoposide/cyclophosphamide and mitoxantrone/diaziquone (group I), three HDAC cycles (group II), four intermediate-dose cytarabine (IDAC) or HDAC cycles (group III), or one HDAC/etoposide cycle and autologous stem-cell transplantation (ASCT; group IV) [6].
  • The order was the same for human E. coli DTD with one exception; diaziquone was reduced slightly faster than mitomycin A [7].
  • High-density growth-arrested wild-type BALB/c 3T3 cells exhibited a greater sensitivity to growth inhibition by the antitumor quinone diaziquone [1,4-cyclohexadiene-1,4- dicarbamic acid, 2,5-bis(1-aziridinyl)-3,6-dioxo-, diethyl ether], which is metabolically activated by DT-diaphorase, than do low-cell-density, growth-arrested cells [8].

Chemical compound and disease context of CI 904


Biological context of CI 904


Anatomical context of CI 904


Associations of CI 904 with other chemical compounds


Gene context of CI 904


Analytical, diagnostic and therapeutic context of CI 904


  1. Myeloablation with diaziquone: in vitro assessment. Kushner, B.H., Siena, S., Castro-Malaspina, H. Blood (1987) [Pubmed]
  2. Diaziquone given as a continuous infusion is an active agent for relapsed adult acute nonlymphocytic leukemia. Lee, E.J., Van Echo, D.A., Egorin, M.J., Nayar, M.S., Shulman, P., Schiffer, C.A. Blood (1986) [Pubmed]
  3. Granulocyte-colony stimulating factor (filgrastim) accelerates granulocyte recovery after intensive postremission chemotherapy for acute myeloid leukemia with aziridinyl benzoquinone and mitoxantrone: Cancer and Leukemia Group B study 9022. Moore, J.O., Dodge, R.K., Amrein, P.C., Kolitz, J., Lee, E.J., Powell, B., Godfrey, S., Robert, F., Schiffer, C.A. Blood (1997) [Pubmed]
  4. Phase II and pharmacokinetic study of aziridinylbenzoquinone [2,5-diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone, diaziquone, NSC 182986] in high-grade gliomas. Curt, G.A., Kelley, J.A., Kufta, C.V., Smith, B.H., Kornblith, P.L., Young, R.C., Collins, J.M. Cancer Res. (1983) [Pubmed]
  5. Autologous bone marrow transplantation using unfractionated cells cryopreserved in dimethylsulfoxide and hydroxyethyl starch without controlled-rate freezing. Stiff, P.J., Koester, A.R., Weidner, M.K., Dvorak, K., Fisher, R.I. Blood (1987) [Pubmed]
  6. Outcome of induction and postremission therapy in younger adults with acute myeloid leukemia with normal karyotype: a cancer and leukemia group B study. Farag, S.S., Ruppert, A.S., Mrózek, K., Mayer, R.J., Stone, R.M., Carroll, A.J., Powell, B.L., Moore, J.O., Pettenati, M.J., Koduru, P.R., Stamberg, J., Baer, M.R., Block, A.W., Vardiman, J.W., Kolitz, J.E., Schiffer, C.A., Larson, R.A., Bloomfield, C.D. J. Clin. Oncol. (2005) [Pubmed]
  7. Metabolism of bioreductive antitumor compounds by purified rat and human DT-diaphorases. Beall, H.D., Mulcahy, R.T., Siegel, D., Traver, R.D., Gibson, N.W., Ross, D. Cancer Res. (1994) [Pubmed]
  8. Increased NAD(P)H:(quinone-acceptor)oxidoreductase activity is associated with density-dependent growth inhibition of normal but not transformed cells. Schlager, J.J., Hoerl, B.J., Riebow, J., Scott, D.P., Gasdaska, P., Scott, R.E., Powis, G. Cancer Res. (1993) [Pubmed]
  9. Treatment of human glioma and medulloblastoma tumor lines in athymic mice with diaziquone and diaziquone-based drug combinations. Schold, S.C., Friedman, H.S., Bjornsson, T.D., Bigner, D.D. Cancer Res. (1984) [Pubmed]
  10. Photosensitization of leukemia L1210 cells with diaziquone. Kessel, D., Thompson, P. Cancer Res. (1986) [Pubmed]
  11. An evaluation of combinations of diaziquone, etoposide and mitoxantrone in the treatment of adults with relapsed or refractory acute myeloid leukemia: results of 8722, a randomized phase II study conducted by Cancer and Leukemia Group B. Lee, E.J., George, S.L., Amrein, P.C., Paciucci, P.A., Allen, S.L., Schiffer, C.A. Leukemia (1998) [Pubmed]
  12. Inhibition of cellular thioredoxin reductase by diaziquone and doxorubicin. Relationship to the inhibition of cell proliferation and decreased ribonucleotide reductase activity. Mau, B.L., Powis, G. Biochem. Pharmacol. (1992) [Pubmed]
  13. Combination of aziridinylbenzoquinone and cis-platinum with radiation therapy in the 9L rat brain tumor model. Kimler, B.F., Liu, C., Evans, R.G., Morantz, R.A. Int. J. Radiat. Oncol. Biol. Phys. (1993) [Pubmed]
  14. Phase I evaluation and pharmacokinetics of aziridinylbenzoquinone using a weekly intravenous schedule. Schilcher, R.B., Young, J.D., Leichman, L.P., Haas, C.D., Baker, L.H. Cancer Res. (1983) [Pubmed]
  15. Phase I study of aziridinylbenzoquinone (AZQ, NSC 182986) in children with cancer. Tan, C.T., Hancock, C.H., Mondora, A., Hoffman, N.W. Cancer Res. (1984) [Pubmed]
  16. Sister chromatid exchange induction by diaziquone in human and mouse lymphocytes following both in vivo and in vitro exposures. Kligerman, A.D., Erexson, G.L., Bryant, M.F. Cancer Res. (1988) [Pubmed]
  17. Metabolism of diaziquone by NAD(P)H:(quinone acceptor) oxidoreductase (DT-diaphorase): role in diaziquone-induced DNA damage and cytotoxicity in human colon carcinoma cells. Siegel, D., Gibson, N.W., Preusch, P.C., Ross, D. Cancer Res. (1990) [Pubmed]
  18. Diaziquone, 2,5-diaziridinyl-3,6-biscarboethoxyamino-1,4-benzoquinone, plasma and cerebrospinal fluid kinetics. Bachur, N.R., Collins, J.M., Kelley, J.A., Van Echo, D.A., Kaplan, R.S., Whitacre, M. Clin. Pharmacol. Ther. (1982) [Pubmed]
  19. Cellular pharmacology in murine and human leukemic cell lines of diaziquone (NSC 182986). Egorin, M.J., Fox, B.M., Spiegel, J.F., Gutierrez, P.L., Friedman, R.D., Bachur, N.R. Cancer Res. (1985) [Pubmed]
  20. Cerebrospinal fluid pharmacokinetics of intraventricular and intravenous aziridinylbenzoquinone. Zimm, S., Collins, J.M., Curt, G.A., O'Neill, D., Poplack, D.G. Cancer Res. (1984) [Pubmed]
  21. Modulation of trenimon-induced cytotoxicity by DT-diaphorase in isolated rat hepatocytes under aerobic versus hypoxic conditions. Silva, J.M., Rao, D.N., O'Brien, P.J. Cancer Res. (1992) [Pubmed]
  22. Diaziquone-induced cytotoxicity in isolated rat hepatocytes. Silva, J.M., O'Brien, P.J. Cancer Res. (1989) [Pubmed]
  23. Toxicity of intrathecally administered cytotoxic drugs and their antitumor activity against an intrathecal Walker 256 carcinosarcoma model for meningeal carcinomatosis in the rat. Kooistra, K.L., Rodriguez, M., Powis, G. Cancer Res. (1989) [Pubmed]
  24. Free radicals in quinone-containing antitumor agents. Electrochemical reduction of diaziquone (2,5-diaziridine-3,6-bis(carboethoxyamino)-1,4 -benzoquinone) and two analogues. Gutierrez, P.L., Fox, B.M., Mossoba, M.M., Bachur, N.R. Mol. Pharmacol. (1984) [Pubmed]
  25. Preclinical phase II studies in human tumor xenografts: a European multicenter follow-up study. Langdon, S.P., Hendriks, H.R., Braakhuis, B.J., Pratesi, G., Berger, D.P., Fodstad, O., Fiebig, H.H., Boven, E. Ann. Oncol. (1994) [Pubmed]
  26. Comparison of in vitro activity of epipodophyllotoxins with other chemotherapeutic agents in human medulloblastomas. Tomlinson, F.H., Lihou, M.G., Smith, P.J. Br. J. Cancer (1991) [Pubmed]
  27. Survival and cell cycle kinetics responses of Chinese hamster ovary cells, and clones of human adenocarcinoma of the stomach and astrocytoma to diaziquone (AZQ) in vitro. Barranco, S.C., Schechter, G.A., Boerwinkle, W.R., Howell, K.A., Rubin, N.H. Investigational new drugs. (1983) [Pubmed]
  28. Role of p53 in aziridinylbenzoquinone-induced p21waf1 expression. Wu, R.C., Hohenstein, A., Park, J.M., Qiu, X., Mueller, S., Cadenas, E., Schönthal, A.H. Oncogene (1998) [Pubmed]
  29. Quinone reductases multitasking in the metabolic world. Ross, D. Drug Metab. Rev. (2004) [Pubmed]
  30. In vitro multidrug resistance of P388 murine leukemia selected for resistance to diaziquone. Gutierrez, P.L., Wilder, P.J., Biswal, N. Cancer Commun. (1989) [Pubmed]
  31. Phase I/II trial and pharmacokinetics of intrathecal diaziquone in refractory meningeal malignancies. Berg, S.L., Balis, F.M., Zimm, S., Murphy, R.F., Holcenberg, J., Sato, J., Reaman, G., Steinherz, P., Gillespie, A., Doherty, K. J. Clin. Oncol. (1992) [Pubmed]
  32. A phase I trial of high-dose diaziquone and autologous bone marrow transplantation: an Illinois Cancer Council study. Stiff, P.J., McKenzie, R.S., Potempa, L.D., Albain, K., Koch, D., Braud, E., Bansal, V.K., Weidner, M.K., Lanzotti, V.J., Chun, H.G. J. Clin. Oncol. (1991) [Pubmed]
  33. Responsiveness of retinoblastoma to local diaziquone. Studies in a xenograft model. White, L. Invest. Ophthalmol. Vis. Sci. (1990) [Pubmed]
  34. Pharmacokinetics of 2,5-diaziridinyl-3,6-bis(2-hydroxyethylamino)-1,4-benzoquinone (BZG, NSC 224070) during a phase I clinical trial. Betteridge, R.F., Bosanquet, A.G., Gilby, E.D. Eur. J. Cancer (1990) [Pubmed]
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