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Chemical Compound Review

Misonidazole     1-methoxy-3-(2-nitroimidazol- 1-yl)propan-2-ol

Synonyms: Misonidazol, Misonidazolum, CHEMBL42161, SureCN51943, CCRIS 1160, ...
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Disease relevance of Misonidazole


High impact information on Misonidazole

  • The effect of pretreating the C3H/He mouse MBT-2 tumor with diethyl maleate (DEM), buthionine-S R-sulfoximine (BSO), or misonidazole (MISO) before administration of cyclophosphamide (CTX) was studied with the use of tumor volume-doubling time delay as an endpoint [6].
  • The highest number of chromosome aberrations and alterations, including an increase in heteroploidy, was also noticed in the bone marrow cells of the mice whose tumors were treated simultaneously with MIS + delta + X [7].
  • Misonidazole radiosensitized the leg-implanted tumor as measured both by cell survival and regrowth delay [8].
  • Autoradiographs of liver from mice treated with radiolabeled misonidazole demonstrated enhanced binding of adducts within hepatocytes surrounding hepatic veins [3].
  • Misonidazole binding in murine liver tissue: a marker for cellular hypoxia in vivo [3].

Chemical compound and disease context of Misonidazole


Biological context of Misonidazole


Anatomical context of Misonidazole

  • PURPOSE: Long-term follow-up data of a randomized trial that compared hydroxyurea and the hypoxic-cell radiosensitizer to misonidazole as adjuncts to standard radiation therapy in locally advanced carcinoma of the cervix are reported [18].
  • We have investigated the effects of misonidazole on the biosynthesis of prostaglandins (PGs) in a murine mammary adenocarcinoma cell line (No. 4526) under aerobic and hypoxic conditions in attempts to exploit modulation of PG levels under hypoxia as a means of improving therapeutic approaches for the treatment of solid tumors [19].
  • Misonidazole was delivered intravenously (IV) at a dose of 3.5 g/m2 in conjunction with IORT of 1,500 to 2,000 cGy to the pancreas [20].
  • Several interpretations of this result are possible, including the postulate that intermittent blood flow occurs in all 9L tumor capillaries, which results in the majority of the binding of misonidazole occurring during the periods of transient hypoxia [21].
  • The clearance of misonidazole and demethylmisonidazole from the peritoneal fluid was 19.1 and 12.4 ml/min, respectively [22].

Associations of Misonidazole with other chemical compounds


Gene context of Misonidazole


Analytical, diagnostic and therapeutic context of Misonidazole


  1. Addition of misonidazole, etanidazole, or hyperthermia to treatment with fluosol-DA/carbogen/radiation. Teicher, B.A., Herman, T.S., Holden, S.A., Jones, S.M. J. Natl. Cancer Inst. (1989) [Pubmed]
  2. Toxicity, radiation sensitivity modification, and combined drug effects of ascorbic acid with misonidazole in vivo on FSaII murine fibrosarcomas. Okunieff, P., Suit, H.D. J. Natl. Cancer Inst. (1987) [Pubmed]
  3. Misonidazole binding in murine liver tissue: a marker for cellular hypoxia in vivo. Maxwell, A.P., MacManus, M.P., Gardiner, T.A. Gastroenterology (1989) [Pubmed]
  4. Response of aerobic and hypoxic cells in a solid tumor to adriamycin and cyclophosphamide and interaction of the drugs with radiation. Tannock, I. Cancer Res. (1982) [Pubmed]
  5. Misonidazole Neuropathy: a clinical, electrophysiological, and histological study. Melgaard, B., Hansen, H.S., Kamieniecka, Z., Paulson, O.B., Pedersen, A.G., Tang, X., Trojaborg, W. Ann. Neurol. (1982) [Pubmed]
  6. Relationship between thiol depletion and chemosensitization in a transplantable murine bladder tumor. Tomashefsky, P., Astor, M., White, R.D. J. Natl. Cancer Inst. (1985) [Pubmed]
  7. Sister chromatid exchanges and chromosome aberrations induced by radiosensitizing agents in bone marrow cells of treated tumor-bearing mice. Banerjee, R., Goldfeder, A., Mitra, J. J. Natl. Cancer Inst. (1983) [Pubmed]
  8. Response to the RIF-1 tumor in vitro and in C3H/Km mice to X-radiation (cell survival, regrowth delay, and tumor control), chemotherapeutic agents, and activated macrophages. Brown, J.M., Twentyman, P.R., Zamvil, S.S. J. Natl. Cancer Inst. (1980) [Pubmed]
  9. Lung tumorigenic response of strain A mice exposed to hypoxic cell sensitizers alone and in combination with gamma-radiation. Mian, T.A., Theiss, J.C., Grdina, D.J. Cancer Res. (1983) [Pubmed]
  10. Enhancement of the clinical activity of melphalan by the hypoxic cell sensitizer misonidazole. Coleman, C.N., Carlson, R.W., Artim, R.A., Sampson, W.I., Lawrence, H.J., Wong, P., Halsey, J., Kohler, M., Gribble, M., Sikic, B.I. Cancer Res. (1988) [Pubmed]
  11. Enhancement of antitumor activity of alkylating agents by the radiation sensitizer misonidazole. Clement, J.J., Gorman, M.S., Wodinsky, I., Catane, R., Johnson, R.K. Cancer Res. (1980) [Pubmed]
  12. Effect of tumor size on S-2-(3-aminopropylamino)ethylphosphorothioic acid and misonidazole alteration of tumor response to cyclophosphamide. Milas, L., Ito, H., Hunter, N. Cancer Res. (1983) [Pubmed]
  13. Effect of partition coefficient on the ability of nitroimidazoles to enhance the cytotoxicity of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea. Hirst, D.G., Brown, J.M., Hazlehurst, J.L. Cancer Res. (1983) [Pubmed]
  14. Nitroaromatic radiation sensitizers substitute for oxygen in neocarzinostatin-induced DNA damage. Kappen, L.S., Goldberg, I.H. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  15. Cytological effects of 1-(2-nitro-1-imidazolyl)-3-methoxy-2-propanol (misonidazole) on hypoxic mammalian cells in vitro. Geard, C.R., Povlas, S.F., Astor, M.B., Hall, E.J. Cancer Res. (1978) [Pubmed]
  16. Combined effects of misonidazole, microwave hyperthermia, and X-rays on the in vivo sister chromatid exchanges and chromosomal abnormalities of the dbrB tumor and on the survival of its host. Banerjee, R., Goldfeder, A., Mitra, J. Cancer Res. (1983) [Pubmed]
  17. Kinetics of misonidazole enantiomers. Williams, K.M. Clin. Pharmacol. Ther. (1984) [Pubmed]
  18. Hydroxyurea versus misonidazole with radiation in cervical carcinoma: long-term follow-up of a Gynecologic Oncology Group trial. Stehman, F.B., Bundy, B.N., Thomas, G., Keys, H.M., d'Ablaing, G., Fowler, W.C., Mortel, R., Creasman, W.T. J. Clin. Oncol. (1993) [Pubmed]
  19. Modulation of prostaglandin biosynthesis in hypoxic murine mammary adenocarcinoma cells by misonidazole. Shalinsky, D.R., McNamara, D.B., Agrawal, K.C. Cancer Res. (1989) [Pubmed]
  20. The role of misonidazole combined with intraoperative radiation therapy in the treatment of pancreatic carcinoma. Tepper, J.E., Shipley, W.U., Warshaw, A.L., Nardi, G.L., Wood, W.C., Orlow, E.L. J. Clin. Oncol. (1987) [Pubmed]
  21. Distribution of misonidazole adducts in 9L gliosarcoma tumors and spheroids: implications for oxygen distribution. Franko, A.J., Koch, C.J., Boisvert, D.P. Cancer Res. (1992) [Pubmed]
  22. Pharmacokinetics of the hypoxic radiosensitizers misonidazole and demethylmisonidazole after intraperitoneal administration in humans. Gianni, L., Jenkins, J.F., Greene, R.F., Lichter, A.S., Myers, C.E., Collins, J.M. Cancer Res. (1983) [Pubmed]
  23. Mechanism of sensitization of Chinese hamster ovary cells to melphalan by hypoxic treatment with misonidazole. Taylor, Y.C., Evans, J.W., Brown, J.M. Cancer Res. (1983) [Pubmed]
  24. Phase I trial of misonidazole (NSC#261037) plus cyclophosphamide in solid tumors. Davila, E., Klein, L., Vogel, C.L., Johnson, R., Ostroy, F., Browning, S., Gorowski, E., Furner, R.L., Presant, C.A. J. Clin. Oncol. (1985) [Pubmed]
  25. Effect of oxygen on misonidazole chemosensitization and cytotoxicity in vitro. Mulcahy, R.T. Cancer Res. (1984) [Pubmed]
  26. Chemical modifiers of cancer treatment. Coleman, C.N., Bump, E.A., Kramer, R.A. J. Clin. Oncol. (1988) [Pubmed]
  27. Time-dose relationships for simultaneous misonidazole and 1,3-bis(2-chloroethyl)-1-nitrosourea exposures in vitro. Mulcahy, R.T., Dembs, N. Cancer Res. (1983) [Pubmed]
  28. Effect of hypoxic cell radiosensitizers on glutathione level and related enzyme activities in isolated rat hepatocytes. Noguchi, K., Hattori, T., Igarashi, T., Ueno, K., Satoh, T., Kitagawa, H., Hori, H., Shibata, T., Inayama, S. Life Sci. (1985) [Pubmed]
  29. Influence of buthionine sulfoximine and misonidazole on glutathione level and radiosensitivity of human tumor xenografts. Guichard, M., Lespinasse, F., Malaise, E.P. Radiat. Res. (1986) [Pubmed]
  30. Radiosensitizer conjugation to the carcinoma 19-9 monoclonal antibody. Borlinghaus, K.P., Fitzpatrick, D.A., Heindel, N.D., Mattis, J.A., Mease, B.A., Schray, K.J., Shealy, D.J., Walton, H.L., Woo, D.V. Cancer Res. (1987) [Pubmed]
  31. In vivo potentiation of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea by the radiation sensitizer benznidazole. Siemann, D.W., Morrissey, S., Wolf, K. Cancer Res. (1983) [Pubmed]
  32. Regional measurements of [14C]misonidazole distribution and blood flow in subcutaneous RT-9 experimental tumors. Blasberg, R., Horowitz, M., Strong, J., Molnar, P., Patlak, C., Owens, E., Fenstermacher, J. Cancer Res. (1985) [Pubmed]
  33. Treatment of Dunning R3327-AT rat prostate tumors with photodynamic therapy in combination with misonidazole. Gonzalez, S., Arnfield, M.R., Meeker, B.E., Tulip, J., Lakey, W.H., Chapman, J.D., McPhee, M.S. Cancer Res. (1986) [Pubmed]
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