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Chemical Compound Review

Holoxan     N,3-bis(2-chloroethyl)-2-oxo- 1-oxa-3-aza...

Synonyms: ifosfamide, Iphosphamide, Isofosfamide, Isophosphamide, Iso-Endoxan, ...
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Disease relevance of ifosfamide

  • Understanding and control of the urinary toxicity of ifosfamide therapy has allowed greater use and inclusion of ifosfamide in combinations in the treatment of malignant diseases [1].
  • Between April 1987 and July 1988, 44 adults with histologically proven, objectively assessable advanced nonosseous sarcomas were treated with 2.5 g of ifosfamide/m2, 100 mg of etoposide/m2, and 2.5 g of mesna/m2 (500 mg/m2 X 5) daily for 3 consecutive days every 4 weeks [2].
  • Malignant pleural mesothelioma: phase II pilot study of ifosfamide and mesna [3].
  • High-dose ifosfamide-induced exacerbation of peripheral neuropathy [4].
  • Because of the potential CNS effects of ifosfamide, we recommended that elderly patients, persons receiving high doses of opiates, and patients susceptible to the syndrome of vertigo, perspiration, and hypotension (without tachycardia) be hospitalized for treatment [2].

Psychiatry related information on ifosfamide


High impact information on ifosfamide


Chemical compound and disease context of ifosfamide


Biological context of ifosfamide


Anatomical context of ifosfamide


Associations of ifosfamide with other chemical compounds


Gene context of ifosfamide


Analytical, diagnostic and therapeutic context of ifosfamide


  1. Ifosfamide. Zalupski, M., Baker, L.H. J. Natl. Cancer Inst. (1988) [Pubmed]
  2. Phase II study of ifosfamide-etoposide-mesna in adults with advanced nonosseous sarcomas. Edmonson, J.H., Buckner, J.C., Long, H.J., Loprinzi, C.L., Schaid, D.J. J. Natl. Cancer Inst. (1989) [Pubmed]
  3. Malignant pleural mesothelioma: phase II pilot study of ifosfamide and mesna. Alberts, A.S., Falkson, G., Van Zyl, L. J. Natl. Cancer Inst. (1988) [Pubmed]
  4. High-dose ifosfamide-induced exacerbation of peripheral neuropathy. Patel, S.R., Forman, A.D., Benjamin, R.S. J. Natl. Cancer Inst. (1994) [Pubmed]
  5. Ifosfamide causes a diazepam-sensitive encephalopathy. Simonian, N.A., Gilliam, F.G., Chiappa, K.H. Neurology (1993) [Pubmed]
  6. Ambulatory 4-day continuous-infusion schedule of high-dose ifosfamide with mesna uroprotection and granulocyte colony-stimulating factor in advanced solid tumours: a phase I study. Toma, S., Palumbo, R., Comandone, A., Oliva, C., Vincenti, M., Bumma, C., Rosso, R. Ann. Oncol. (1995) [Pubmed]
  7. Phase II trial of ifosfamide and mesna in mixed mesodermal tumors of the uterus (a Gynecologic Oncology Group study). Sutton, G.P., Blessing, J.A., Rosenshein, N., Photopulos, G., DiSaia, P.J. Am. J. Obstet. Gynecol. (1989) [Pubmed]
  8. Hallucinations and ifosfamide-induced neurotoxicity. DiMaggio, J.R., Brown, R., Baile, W.F., Schapira, D. Cancer (1994) [Pubmed]
  9. Radiologist review versus group peer review of claimed responses in a phase II study on high-dose ifosfamide in advanced soft tissue sarcomas of the adult: a study of the EORTC Soft Tissue and Bone Sarcoma Group. Gwyther, S.J., Nielsen, O.S., Judson, I.R., van Glabbeke, M., Verweij, J. Anticancer Drugs (2000) [Pubmed]
  10. A randomized trial comparing preoperative chemotherapy plus surgery with surgery alone in patients with non-small-cell lung cancer. Rosell, R., Gómez-Codina, J., Camps, C., Maestre, J., Padille, J., Cantó, A., Mate, J.L., Li, S., Roig, J., Olazábal, A. N. Engl. J. Med. (1994) [Pubmed]
  11. Influence of doxorubicin dose intensity on response and outcome for patients with osteogenic sarcoma and Ewing's sarcoma. Smith, M.A., Ungerleider, R.S., Horowitz, M.E., Simon, R. J. Natl. Cancer Inst. (1991) [Pubmed]
  12. Combination bleomycin, ifosfamide, and cisplatin chemotherapy in cervical cancer. Buxton, E.J., Meanwell, C.A., Hilton, C., Mould, J.J., Spooner, D., Chetiyawardana, A., Latief, T., Paterson, M., Redman, C.W., Luesley, D.M. J. Natl. Cancer Inst. (1989) [Pubmed]
  13. Microencapsulated cell-mediated treatment of inoperable pancreatic carcinoma. Löhr, M., Hoffmeyer, A., Kröger, J., Freund, M., Hain, J., Holle, A., Karle, P., Knöfel, W.T., Liebe, S., Müller, P., Nizze, H., Renner, M., Saller, R.M., Wagner, T., Hauenstein, K., Günzburg, W.H., Salmons, B. Lancet (2001) [Pubmed]
  14. Risk factors for ifosfamide nephrotoxicity in children. Skinner, R., Pearson, A.D., English, M.W., Price, L., Wyllie, R.A., Coulthard, M.G., Craft, A.W. Lancet (1996) [Pubmed]
  15. Epidermal growth factor receptors and doxorubicin plus ifosfamide/mesna in recurrent breast cancer. Cantwell, B.M., Hennessy, C., Millward, M.J., Lennard, T.W. Lancet (1991) [Pubmed]
  16. Prevention of isophosphamide-induced urothelial toxicity with 2-mercaptoethane sulphonate sodium (mesnum) in patients with advanced carcinoma. Bryant, B.M., Jarman, M., Ford, H.T., Smith, I.E. Lancet (1980) [Pubmed]
  17. Salvage therapy in recurrent germ cell cancer: ifosfamide and cisplatin plus either vinblastine or etoposide. Loehrer, P.J., Lauer, R., Roth, B.J., Williams, S.D., Kalasinski, L.A., Einhorn, L.H. Ann. Intern. Med. (1988) [Pubmed]
  18. IMVP-16: an effective regimen for patients with lymphoma who have relapsed after initial combination chemotherapy. Cabanillas, F., Hagemeister, F.B., Bodey, G.P., Freireich, E.J. Blood (1982) [Pubmed]
  19. Favorable outcome of B-cell acute lymphoblastic leukemia in childhood: a report of three consecutive studies of the BFM group. Reiter, A., Schrappe, M., Ludwig, W.D., Lampert, F., Harbott, J., Henze, G., Niemeyer, C.M., Gadner, H., Müller-Weihrich, S., Ritter, J. Blood (1992) [Pubmed]
  20. Ifosfamide pharmacokinetics and neurotoxicity. Lewis, L.D., Meanwell, C.A. Lancet (1990) [Pubmed]
  21. High-dose ifosfamide with mesna uroprotection: a phase I study. Elias, A.D., Eder, J.P., Shea, T., Begg, C.B., Frei, E., Antman, K.H. J. Clin. Oncol. (1990) [Pubmed]
  22. Pharmacokinetics and metabolism of ifosfamide administered as a continuous infusion in children. Boddy, A.V., Yule, S.M., Wyllie, R., Price, L., Pearson, A.D., Idle, J.R. Cancer Res. (1993) [Pubmed]
  23. In vivo perturbation of human marrow cell cycle progression by ifosfamide. Rentschler, R.E., Barlogie, B., Johnston, D.A., Bodey, G.P. Cancer Res. (1978) [Pubmed]
  24. Ifosfamide-induced nephrotoxicity: mechanism and prevention. Nissim, I., Horyn, O., Daikhin, Y., Nissim, I., Luhovyy, B., Phillips, P.C., Yudkoff, M. Cancer Res. (2006) [Pubmed]
  25. High-dose ifosfamide is associated with severe, reversible cardiac dysfunction. Quezado, Z.M., Wilson, W.H., Cunnion, R.E., Parker, M.M., Reda, D., Bryant, G., Ognibene, F.P. Ann. Intern. Med. (1993) [Pubmed]
  26. Mobilization of peripheral blood progenitor cells by sequential administration of interleukin-3 and granulocyte-macrophage colony-stimulating factor following polychemotherapy with etoposide, ifosfamide, and cisplatin. Brugger, W., Bross, K., Frisch, J., Dern, P., Weber, B., Mertelsmann, R., Kanz, L. Blood (1992) [Pubmed]
  27. Mobilization of tumor cells and hematopoietic progenitor cells into peripheral blood of patients with solid tumors. Brugger, W., Bross, K.J., Glatt, M., Weber, F., Mertelsmann, R., Kanz, L. Blood (1994) [Pubmed]
  28. Differential effects of ifosfamide on the capacity of cytotoxic T lymphocytes and natural killer cells to lyse their target cells correlate with intracellular glutathione levels. Multhoff, G., Meier, T., Botzler, C., Wiesnet, M., Allenbacher, A., Wilmanns, W., Issels, R.D. Blood (1995) [Pubmed]
  29. Age-adjusted International Prognostic Index predicts autologous stem cell transplantation outcome for patients with relapsed or primary refractory diffuse large B-cell lymphoma. Hamlin, P.A., Zelenetz, A.D., Kewalramani, T., Qin, J., Satagopan, J.M., Verbel, D., Noy, A., Portlock, C.S., Straus, D.J., Yahalom, J., Nimer, S.D., Moskowitz, C.H. Blood (2003) [Pubmed]
  30. Ifosfamide impairs the allostimulatory capacity of human dendritic cells by intracellular glutathione depletion. Kuppner, M.C., Scharner, A., Milani, V., Von Hesler, C., Tschop, K.E., Heinz, O., Issels, R.D. Blood (2003) [Pubmed]
  31. Neoadjuvant chemotherapy with high-dose Ifosfamide, high-dose methotrexate, cisplatin, and doxorubicin for patients with localized osteosarcoma of the extremity: a joint study by the Italian and Scandinavian Sarcoma Groups. Ferrari, S., Smeland, S., Mercuri, M., Bertoni, F., Longhi, A., Ruggieri, P., Alvegard, T.A., Picci, P., Capanna, R., Bernini, G., Müller, C., Tienghi, A., Wiebe, T., Comandone, A., Böhling, T., Del Prever, A.B., Brosjö, O., Bacci, G., Saeter, G. J. Clin. Oncol. (2005) [Pubmed]
  32. Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes. Chang, T.K., Weber, G.F., Crespi, C.L., Waxman, D.J. Cancer Res. (1993) [Pubmed]
  33. Enhanced cyclophosphamide and ifosfamide activation in primary human hepatocyte cultures: response to cytochrome P-450 inducers and autoinduction by oxazaphosphorines. Chang, T.K., Yu, L., Maurel, P., Waxman, D.J. Cancer Res. (1997) [Pubmed]
  34. Identification of the polymorphically expressed CYP2C19 and the wild-type CYP2C9-ILE359 allele as low-Km catalysts of cyclophosphamide and ifosfamide activation. Chang, T.K., Yu, L., Goldstein, J.A., Waxman, D.J. Pharmacogenetics (1997) [Pubmed]
  35. Secondary leukemia associated with a conventional dose of etoposide: review of serial germ cell tumor protocols. Nichols, C.R., Breeden, E.S., Loehrer, P.J., Williams, S.D., Einhorn, L.H. J. Natl. Cancer Inst. (1993) [Pubmed]
  36. Increased risk of ifosfamide-induced renal Fanconi's syndrome after unilateral nephrectomy. Rossi, R., Kleinebrand, A., Gödde, A., Rath, B., Jürgens, H. Lancet (1993) [Pubmed]
  37. High-dose induction chemoradiotherapy followed by autologous bone marrow transplantation as consolidation therapy in rhabdomyosarcoma, extraosseous Ewing's sarcoma, and undifferentiated sarcoma. Boulad, F., Kernan, N.A., LaQuaglia, M.P., Heller, G., Lindsley, K.L., Rosenfield, N.S., Abramson, S.J., Gerald, W.L., Small, T.N., Gillio, A.P., Gulati, S.C., O'Reilly, R.J., Ghavimi, F. J. Clin. Oncol. (1998) [Pubmed]
  38. Sequential dose-intensive paclitaxel, ifosfamide, carboplatin, and etoposide salvage therapy for germ cell tumor patients. Motzer, R.J., Mazumdar, M., Sheinfeld, J., Bajorin, D.F., Macapinlac, H.A., Bains, M., Reich, L., Flombaum, C., Mariani, T., Tong, W.P., Bosl, G.J. J. Clin. Oncol. (2000) [Pubmed]
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