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Chemical Compound Review

semustine     1-(2-chloroethyl)-3-(4- methylcyclohexyl)-1...

Synonyms: Semustina, MeCCNU, Semustinum, Methyl-CCNU, Prestwick_1013, ...
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Disease relevance of Methyl-CCNU


High impact information on Methyl-CCNU


Chemical compound and disease context of Methyl-CCNU


Biological context of Methyl-CCNU

  • From linear extrapolation of the terminal part of the cell survival curve to zero drug dose, it appeared that about 1 in 10(5) (or 0.001%) of tumour cells were resistant to MeCCNU [13].
  • Recombinant interferons have achieved a place in the developmental armamentarium of medical oncology for melanoma--and phase III trials to compare the relative effects of decarbazine or semustine and interferon alpha are under way [14].
  • The effect of treatment dose on the kinetics of MeCCNU resistance development was also studied in a retreatment regimen where the tumours were allowed to regrow and then transplanted into fresh hosts for the next treatment [15].
  • However, the relative toxicological significance of either protein carbamylation or DNA alkylation in mediating MeCCNU-induced nephropathy is not yet understood [16].
  • Three repeated injections of 30 mg/kg (at 10 day intervals) of methyl-CCNU to 15 day-old male mice resulted in inhibition of spermatogenesis without alteration in plasma testosterone [17].

Anatomical context of Methyl-CCNU


Associations of Methyl-CCNU with other chemical compounds


Gene context of Methyl-CCNU

  • We have shown in earlier studies that repeated weekly exposures of a human astrocytoma clone (AST 3-4) to MeCCNU (10 micrograms/ml for 1 h per week) produced a linear decrease in survival over the first 3 weekly treatments [24].
  • The response rates were 6% (3/50) for AHC, 9% (3/34) for DBD, and 14% (7/49) for methyl-CCNU [28].
  • Calmodulin inhibition by methyl-CCNU was dependent on the concentration of calcium in the preincubation mixture [29].
  • In March of 1972, the Southwest Oncology Group initiated a Phase II study, No. 7200, utilizing methyl-CCNU in the treatment of patients with solid tumors and lymphomas [30].
  • Moreover, a dose of 130 mg/mg of MeCCNU with 800 mg/m2/day of ICRF is well tolerated [31].

Analytical, diagnostic and therapeutic context of Methyl-CCNU


  1. Improving adjuvant therapy for rectal cancer by combining protracted-infusion fluorouracil with radiation therapy after curative surgery. O'Connell, M.J., Martenson, J.A., Wieand, H.S., Krook, J.E., Macdonald, J.S., Haller, D.G., Mayer, R.J., Gunderson, L.L., Rich, T.A. N. Engl. J. Med. (1994) [Pubmed]
  2. Leukemia and preleukemia after adjuvant treatment of gastrointestinal cancer with semustine (methyl-CCNU). Boice, J.D., Greene, M.H., Killen, J.Y., Ellenberg, S.S., Keehn, R.J., McFadden, E., Chen, T.T., Fraumeni, J.F. N. Engl. J. Med. (1983) [Pubmed]
  3. Randomized comparisons of radiotherapy and nitrosoureas for the treatment of malignant glioma after surgery. Walker, M.D., Green, S.B., Byar, D.P., Alexander, E., Batzdorf, U., Brooks, W.H., Hunt, W.E., MacCarty, C.S., Mahaley, M.S., Mealey, J., Owens, G., Ransohoff, J., Robertson, J.T., Shapiro, W.R., Smith, K.R., Wilson, C.B., Strike, T.A. N. Engl. J. Med. (1980) [Pubmed]
  4. Phase I trial of semustine plus weekly fluorouracil and high-dose leucovorin calcium in patients with advanced colorectal cancer. Abbruzzese, J.L., Weeks, A., Raber, M.N., Gravel, D., DuBrow, R.A., Levin, B., Grem, J., Chun, H.G. J. Natl. Cancer Inst. (1989) [Pubmed]
  5. Randomized trial of postoperative adjuvant chemotherapy with or without radiotherapy for carcinoma of the rectum: National Surgical Adjuvant Breast and Bowel Project Protocol R-02. Wolmark, N., Wieand, H.S., Hyams, D.M., Colangelo, L., Dimitrov, N.V., Romond, E.H., Wexler, M., Prager, D., Cruz, A.B., Gordon, P.H., Petrelli, N.J., Deutsch, M., Mamounas, E., Wickerham, D.L., Fisher, E.R., Rockette, H., Fisher, B. J. Natl. Cancer Inst. (2000) [Pubmed]
  6. Male sterility in the domestic fowl (Gallus domesticus) after 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitroso-trans-urea (NSC-95441) treatment of chicks. Zimber, Z., Perk, K. J. Natl. Cancer Inst. (1978) [Pubmed]
  7. Impact of T and N stage and treatment on survival and relapse in adjuvant rectal cancer: a pooled analysis. Gunderson, L.L., Sargent, D.J., Tepper, J.E., Wolmark, N., O'Connell, M.J., Begovic, M., Allmer, C., Colangelo, L., Smalley, S.R., Haller, D.G., Martenson, J.A., Mayer, R.J., Rich, T.A., Ajani, J.A., MacDonald, J.S., Willett, C.G., Goldberg, R.M. J. Clin. Oncol. (2004) [Pubmed]
  8. An Eastern Cooperative Oncology Group evaluation of combinations of methyl-CCNU, mitomycin C, Adriamycin, and 5-fluorouracil in advanced measurable gastric cancer (EST 2277). Douglass, H.O., Lavin, P.T., Goudsmit, A., Klaassen, D.J., Paul, A.R. J. Clin. Oncol. (1984) [Pubmed]
  9. The response of hypoxic B16 melanoma cells to in vivo treatment with chemotherapeutic agents. Hill, R.P., Stanley, J.A. Cancer Res. (1975) [Pubmed]
  10. Priming with low doses of methyl-CCNU reduce the toxicity of high doses of methyl-CCNU and melphalan, and increase the lifespan of mice implanted with Lewis lung carcinoma. Zimber, A., Perk, K., Livnat, I. Br. J. Cancer (1988) [Pubmed]
  11. Chemosensitization by chlorpromazine (CPZ) and caffeine (C) in human melanoma xenografts sensitive or resistant to methyl-CCNU (semustine). Osieka, R., Glatte, P., Schmidt, C.G. Strahlentherapie und Onkologie : Organ der Deutschen Röntgengesellschaft ... [et al]. (1989) [Pubmed]
  12. Adjuvant immunochemotherapy in colorectal cancer Dukes C. Sertoli, M.R., Guarneri, D., Rubagotti, A., Porcile, G., Nobile, M.T., Rosso, R. Oncology (1987) [Pubmed]
  13. Identification of a subpopulation of MeCCNU resistant cells in previously untreated Lewis lung tumours. Stephens, T.C., Adams, K., Peacock, J.H. Br. J. Cancer (1984) [Pubmed]
  14. Melanoma: therapeutic options with recombinant interferons. Kirkwood, J.M., Ernstoff, M. Semin. Oncol. (1985) [Pubmed]
  15. Emergence of nitrosourea resistant sublines of Lewis lung tumour following MeCCNU treatment in vivo. Stephens, T.C., Adams, K., Peacock, J.H. Br. J. Cancer (1986) [Pubmed]
  16. Differential distribution and covalent binding of two labeled forms of methyl-CCNU in the Fischer 344 rat. Kramer, R.A., McMenamin, M.G., Boyd, M.R. Cancer Chemother. Pharmacol. (1985) [Pubmed]
  17. The effect of high doses of methyl-CCNU on male and female fertility in SJL/J mice. Yegana, Y., Zimber, A., Perk, K. Anticancer Res. (1988) [Pubmed]
  18. Combined actions of 5-fluorouracil and 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea on human colonic carcinoma cells in vitro. Sutton, J.E., Roos, I.A., Hillcoat, B.L. Cancer Res. (1982) [Pubmed]
  19. Clinical results of autotransplantation after nitrosourea therapy. Weiner, R.S., Richman, C.M., Yankee, R.A., Parker, L. Exp. Hematol. (1979) [Pubmed]
  20. A high pressure liquid chromatographic procedure for monitoring 1-(2-chloroethyl)-3-(4-trans-methylcyclohexyl)-1-nitrosourea levels in body fluids. Caddy, B., Idowu, O.R., Stuart, J.F. Therapeutic drug monitoring. (1982) [Pubmed]
  21. Genotoxic effects of MeCCNU on human peripheral blood lymphocytes. Vyas, R.C., Adhvaryu, S.G., Shah, V.C. Toxicol. Lett. (1988) [Pubmed]
  22. Toxicity of very high dose nitrosourea administration. Breeden, J.H., Vollmer, J.T., Twomey, P.L. Cancer (1982) [Pubmed]
  23. Postoperative adjuvant chemotherapy or radiation therapy for rectal cancer: results from NSABP protocol R-01. Fisher, B., Wolmark, N., Rockette, H., Redmond, C., Deutsch, M., Wickerham, D.L., Fisher, E.R., Caplan, R., Jones, J., Lerner, H. J. Natl. Cancer Inst. (1988) [Pubmed]
  24. Changes in drug sensitivity of a human astrocytoma clone previously treated with 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea in vitro. Barranco, S.C., Townsend, C.M., Jenkins, V.K., Koester, S.K., Ho, B.Y., Reumont, K.J. Investigational new drugs. (1988) [Pubmed]
  25. Chemotherapy of brain metastases from lung carcinoma: a controlled randomized study. Ushio, Y., Arita, N., Hayakawa, T., Mogami, H., Hasegawa, H., Bitoh, S., Oku, Y., Ikeda, H., Kanai, N., Kanoh, M. Neurosurgery (1991) [Pubmed]
  26. Adriamycin and methyl-CCNU combination therapy in hepatocellular carcinoma: clinical and pharmacokinetic aspects. Chlebowski, R.T., Chan, K.K., Tong, M.J., Weiner, J.M., Ryden, V.M., Bateman, J.R. Cancer (1981) [Pubmed]
  27. Selective action of alkylating agents against cells participating in suppression of antibody responses. Paul, R.D., Ghaffar, A., Sigel, M.M. Int. J. Immunopharmacol. (1982) [Pubmed]
  28. Phase II evaluation of dibromodulcitol and actinomycin D, hydroxyurea, and cyclophosphamide in previously untreated patients with malignant melanoma. Amato, D.A., Bruckner, H., Guerry, D., Ash, A., Falkson, G., Borden, E.C., Creech, R.H., Savlov, E.D., Cunningham, T.J. Investigational new drugs. (1987) [Pubmed]
  29. 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]
  30. A phase II study of methyl CCNU in the treatment of solid tumors and lymphomas: a Southwest Oncology Group study. Tranum, B.L., Haut, A., Rivkin, S., Weber, E., Quagliana, J.M., Shaw, M., Tucker, W.G., Smith, F.E., Samson, M., Gottlieb, J. Cancer (1975) [Pubmed]
  31. Phase I trial of ICRF-159 in combination with 1.3 bis-(2-chloroethyl)-1-nitrosourea (MeCCNU). Paul, A.R., Catalano, R.B., Engstrom, P.F. Cancer clinical trials. (1978) [Pubmed]
  32. Leukemia after adjuvant chemotherapy with semustine (methyl-CCNU)--evidence of a dose-response effect. Boice, J.D., Greene, M.H., Killen, J.Y., Ellenberg, S.S., Fraumeni, J.F., Keehn, R.J., McFadden, E., Chen, T.T., Stablein, D. N. Engl. J. Med. (1986) [Pubmed]
  33. The combination of methyl-CCNU and irradiation: cell survival studies on a human tumor xenograft. Bateman, A.E., Fu, K.K., Towse, G.D. Int. J. Radiat. Oncol. Biol. Phys. (1979) [Pubmed]
  34. Current treatment approaches in colorectal cancer. Grem, J.L. Semin. Oncol. (1991) [Pubmed]
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