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Chemical Compound Review

AC1L9PSK     1-(2-chloroethyl)-1-nitroso- 3-[(2R,3R,4R...

Synonyms: NSC178248, C19170
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Disease relevance of CHLOROZOTOCIN


High impact information on CHLOROZOTOCIN


Chemical compound and disease context of CHLOROZOTOCIN


Biological context of CHLOROZOTOCIN


Anatomical context of CHLOROZOTOCIN


Associations of CHLOROZOTOCIN with other chemical compounds

  • ACNU has in vitro alkylating activy 40% less than that of 2-[3-(2-chloroethyl)-3-nitrosoureido]-D-glucopyranose (chlorozotocin) but shares the property of negligible carbamoylating activity with the latter compounds [20].
  • The yields to 2-chloroethanol from CNU, BCNU, and chlorozotocin were shown to be the same, indicating that these agents generate the same yield of alkylating intermediate at 37 degrees C and pH 7.4 [21].
  • Three human colon tumor (HCT) cell lines, designated C, Moser and 116, exhibiting a gradation of resistance to chlorozotocin, a glucose-linked chloroethylnitrosourea (1-, 2.9-, and 5.8-fold respectively) were examined to assess the determinants of drug sensitivity [19].
  • Single-dose BCNU or chlorozotocin (CLZ) treatment of EMT6 mammary carcinoma tumors of the BALB/c mouse has only a transient effect on tumor growth, after which tumors follow control growth patterns [22].
  • Administration of methyl-CCNU or chlorozotocin IP to CF1 mice produced a dose-dependent inhibition of calmodulin activity in the small intestine [23].

Gene context of CHLOROZOTOCIN

  • Inhibition of glutathione reductase activity by TCNU demonstrated that in carbamoylating activity the drug was intermediate between chlorozotocin and 1,(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU) in both A427 and A549 cells [24].
  • Streptozotocin and the haloethyl nitrosoureas, chlorozotocin and bis-chloroethylnitrosourea were less efficient in inducing HPRT-deficient mutants and a smaller degree of protection was afforded by the transfected genes [25].
  • Phase II study of cisplatin, maytansine, and chlorozotocin in small cell lung carcinoma (EST 2578) [26].

Analytical, diagnostic and therapeutic context of CHLOROZOTOCIN


  1. Streptozocin-doxorubicin, streptozocin-fluorouracil or chlorozotocin in the treatment of advanced islet-cell carcinoma. Moertel, C.G., Lefkopoulo, M., Lipsitz, S., Hahn, R.G., Klaassen, D. N. Engl. J. Med. (1992) [Pubmed]
  2. Chlorozotocin. Mechanism of reduced bone marrow toxicity in mice. Panasci, L.C., Green, D., Schein, P.S. J. Clin. Invest. (1979) [Pubmed]
  3. Enhanced cloning efficiency of murine rhabdomyosarcoma cells after chlorozotocin treatment: relationship with enhanced lung metastasis. Pauwels, C., Rebischung, J.L., Jasmin, C., Poupon, M.F. J. Natl. Cancer Inst. (1985) [Pubmed]
  4. Repair of DNA alkylation induced in L1210 leukemia and murine bone marrow by three chloroethylnitrosoureas. Ahlgren, J.D., Green, D.C., Tew, K.D., Schein, P.S. Cancer Res. (1982) [Pubmed]
  5. Chlorozotocin, 2-(3-(2-chloroethyl)-3-nitrosoureido)-D-glucopyranose, an antitumor agent with modified bone marrow toxicity. Anderson, T., McMenamin, M.G., Schein, P.S. Cancer Res. (1975) [Pubmed]
  6. Cellular and molecular mechanisms of the bone marrow sparing effects of the glucose chloroethylnitrosourea chlorozotocin. Byrne, P., Tew, K., Jemionek, J., MacVittie, T., Erickson, L., Schein, P. Blood (1984) [Pubmed]
  7. Chemical structure of carbamoylating groups and their relationship to bone marrow toxicity and antiglioma activity of bifunctionally alkylating and carbamoylating nitrosoureas. Ali-Osman, F., Giblin, J., Berger, M., Murphy, M.J., Rosenblum, M.L. Cancer Res. (1985) [Pubmed]
  8. Diabetogenic effect of pentamidine. In vitro and in vivo studies in a patient with malignant insulinoma. Osei, K., Falko, J.M., Nelson, K.P., Stephens, R. Am. J. Med. (1984) [Pubmed]
  9. Comparison of the transport of chlorozotocin and CCNU in L1210 leukemia and murine bone marrow cells in vitro. Lazarus, P., Germina, J.S., Dufour, M., Palmer, G., Wallace, D., Panasci, L.C. Cancer Chemother. Pharmacol. (1983) [Pubmed]
  10. Effects of three new nitrosourea analogs (CNCC, RFCNU and chlorozotocin) on in vivo destruction of L 1210 leukemia cells and on the immune response. Andrade Mena, C.E., Orbach-Arbouys, S., Cosmatopoulos, K., Mathé, G. Chemotherapy. (1986) [Pubmed]
  11. Randomized trial of chlorozotocin, neocarzinostatin, or methyl-CCNU in patients with malignant melanoma. Von Hoff, D.D., Amato, D.A., Kaufman, J.H., Falkson, G., Cunningham, T.J. Am. J. Clin. Oncol. (1984) [Pubmed]
  12. DNA damage and repair in the bone marrow of rats treated with four chloroethylnitrosoureas. Bedford, P., Eisenbrand, G. Cancer Res. (1984) [Pubmed]
  13. Differences in transformation of repair-deficient mutants of E. coli with BPDE- or chlorozotocin-modified plasmid DNA. Vadi, H.V. Carcinogenesis (1983) [Pubmed]
  14. A comparative analysis of drug-induced DNA effects in a nitrogen mustard resistant cell line expressing sensitivity to nitrosoureas. Dean, S.W., Johnson, A.B., Tew, K.D. Biochem. Pharmacol. (1986) [Pubmed]
  15. Toxicology studies in mice, beagle dogs and rhesus monkeys given chlorozotocin (NSC 178, 248). Gralla, E.J., Fleischman, R.W., Luthra, Y.K. Toxicology (1979) [Pubmed]
  16. Binding of chlorozotocin and 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea to chromatin and nucleosomal fractions of HeLa cells. Tew, K.D., Sudhakar, S., Schein, P.S., Smulson, M.E. Cancer Res. (1978) [Pubmed]
  17. DNA damage in cultured L1210 cells by 2-haloethyl esters of (methylsulfonyl)methanesulfonic acid. Alexander, J.A., Bowdon, B.J., Wheeler, G.P. Cancer Res. (1986) [Pubmed]
  18. Comparative interactions of streptozotocin and chlorozotocin with DNA of an insulin-secreting cell line (RINr). Mossman, B.T., Ireland, C.M., Filipak, M., LeDoux, S., Wilson, G.L. Diabetologia (1986) [Pubmed]
  19. Formation and disappearance of DNA interstrand cross-links in human colon tumor cell lines with different levels of resistance to chlorozotocin. Srivenugopal, K.S. Biochem. Pharmacol. (1992) [Pubmed]
  20. A comparison of the biological and biochemical properties of 1-(4-amino-2-methylpyrimidin-5-yl)methyl-3-(2-chloroethyl)-3-nitrosourea and 2-[3-(2-chloroethyl)-3-nitrosoureido]-D-glucopyranose. Nagourney, R.A., Fox, P., Schein, P.S. Cancer Res. (1978) [Pubmed]
  21. An analysis of 1-(2-chloroethyl)-1-nitrosourea activity at the cellular level. Weinkam, R.J., Dolan, M.E. J. Med. Chem. (1983) [Pubmed]
  22. Cure rates and tumor resistance in cured mice after nitrosourea treatment of EMT6 ascites tumors. Feola, J.M., Maruyama, Y. Oncology (1986) [Pubmed]
  23. Effect of nitrosoureas on calmodulin activity in vitro and in mouse intestine in vivo. Harrison, S.D., Mann, D.M., Giles, R.C. Cancer Chemother. Pharmacol. (1985) [Pubmed]
  24. The effect of a novel taurine nitrosourea, 1-(2-chloroethyl)-3-[2-(dimethylaminosulfonyl)ethyl]-1-nitrosour ea (TCNU) on cytotoxicity, DNA crosslinking and glutathione reductase in lung carcinoma cell lines. Tew, K.D., Dean, S.W., Gibson, N.W. Cancer Chemother. Pharmacol. (1987) [Pubmed]
  25. Protection of Chinese hamster cells against the cytotoxic and mutagenic effects of alkylating agents by transfection of the Escherichia coli alkyltransferase gene and a truncated derivative. Fox, M., Brennand, J., Margison, G.P. Mutagenesis (1987) [Pubmed]
  26. Phase II study of cisplatin, maytansine, and chlorozotocin in small cell lung carcinoma (EST 2578). Creech, R.H., Stanley, K., Vogl, S.E., Ettinger, D.S., Bonomi, P.D., Salazar, O. Cancer treatment reports. (1982) [Pubmed]
  27. Biological and biochemical properties of 1-(2-chloroethyl)-3-(beta-D-glucopyranosyl)-1-nitrosourea (NSC D 254157), a nitrosourea with reduced bone marrow toxicity. Fox, P.A., Panasci, L.C., Schein, P.S. Cancer Res. (1977) [Pubmed]
  28. Chlorozotocin, an anti-tumour agent lacking bone marrow toxicity at therapeutic doses: effects on lymphocyte subpopulations in mice. Fisher, R.I., Mandell, G.L., Bostick, F., McMenamin, M.G., Anderson, T. Clin. Exp. Immunol. (1980) [Pubmed]
  29. Chlorozotocin treatment of advanced gastrointestinal cancer. Veronesi, A., Magri, M.D., Tirelli, U., Galligioni, E., Figoli, F., Zagonel, V., Tumolo, S., Grigoletto, E. Med. Pediatr. Oncol. (1983) [Pubmed]
  30. A phase I study of chlorozotocin (NSC 178248). Kovach, J.S., Moertel, C.G., Schutt, A.J., Frytak, S., O'Connell, M.J., Rubin, J., Ingle, J.N. Cancer (1979) [Pubmed]
  31. Preclinical and clinical studies on chlorozotocin, a new nitrosourea with decreased bone marrow toxicity. Macdonald, J.S., Hoth, D., Schein, P.S. Recent Results Cancer Res. (1980) [Pubmed]
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