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Chemical Compound Review

Merphalan     2-amino-3-[4-[bis(2- chloroethyl)amino]phen...

Synonyms: Medfalan, Mephalan, Merfalan, Levofalan, Sarcolysin, ...
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Disease relevance of Phenylalanine mustard

  • Treatment with the four-drug combination was associated with a significantly increased overall response rate (75 vs. 54 per cent) (P less than 0.05), more complete remissions (33 vs. 16 per cent) and longer median survival (29 vs. 17 months) (P less than 0.02) but more severe toxicity than occurred with melphalan [1].
  • The remaining patients with localized ovarian cancer should receive adjuvant therapy, and with adjuvant melphalan or intraperitoneal 32P should have a five-year disease-free survival of about 80 percent [2].
  • 1-Phenylalanine mustard (L-PAM) in the management of primary breast cancer. A report of early findings [3].
  • Resolution of acquired factor X deficiency and amyloidosis with melphalan and prednisone therapy [4].
  • The four-drug regimen is more effective than melphalan in the management of advanced ovarian adenocarcinoma [1].

Psychiatry related information on Phenylalanine mustard

  • High-dose melphalan appears to be a valuable agent for conditioning therapy in AML [5].
  • Two parameters, temperature and intracellular glutathione (GSH) content, were varied to investigate the role of cellular defense mechanisms in the dye-sensitized photoinactivation of normal murine granulocyte/macrophage progenitors (CFU-GM) and K562, L1210, and melphalan-resistant L1210/L-PAM1 leukemia cells [6].
  • A randomized prospective therapy trial in patients with stage III optimal epithelial carcinoma of the ovary was accomplished by the Gynecologic Oncology Group. Therapy with melphalan or melphalan plus immuno-adjuvant, Corynebacterium parvum (C. parvum), was utilized as adjuvant treatment following surgical therapy [7].
  • Patients with advanced MM received 100 mg/day oral thalidomide escalated weekly up to 600 mg/day (n=23; T group), alone or with 0.20 oral mg/kg/die melphalan administered monthly for four consecutive days (n=27; TM group) [8].

High impact information on Phenylalanine mustard


Chemical compound and disease context of Phenylalanine mustard

  • Eighty patients with advanced ovarian adenocarcinoma were treated in a prospective, randomized trial comparing a four-drug combination--hexamethylmelamine, cyclophosphamide, methotrexate and 5-fluorouracil--with the oral alkylating agent, melphalan [1].
  • Dose-response curves in AKR or CD2F1 mice were obtained for AKR leukemia, L1210 leukemia, and hematopoietic stem cells following in vivo administration of one of the following anticancer agents alone or in combination with amphotericin B (AmB): doxorubicin, lomustine, or melphalan [12].
  • Cisplatin and melphalan given ip exert a synergistic therapeutic effect against ascitic P388 leukemia in mice and have different dose-limiting toxic effects as well as favorable pharmacokinetic characteristics in ip phase I studies [13].
  • Cellular loss of nonprotein thiols by treatment with BSO correlated with enhanced L-PAM toxicity; however, a far greater effect was achieved when this enzymatic inhibitor was used in combination with a hypoxic cell sensitizer [14].
  • The present study deals with the identification of effector-cytotoxic cells that may be developed as a result of chemotherapy-induced tumor regression and their possible potentiation by active, specific immunization with melphalan- and glutaraldehyde-treated MOPC-315 plasmacytoma cells [15].

Biological context of Phenylalanine mustard


Anatomical context of Phenylalanine mustard


Associations of Phenylalanine mustard with other chemical compounds

  • When SR-4233 was administered just before single-dose treatment with CDDP, CPM, BCNU, or L-PAM, however, marked dose enhancement leading to increased cytotoxic effects on tumor cells and on bone marrow cells was observed [22].
  • Radiopharmaceutical therapy of 5T33 murine myeloma by sequential treatment with samarium-153 ethylenediaminetetramethylene phosphonate, melphalan, and bone marrow transplantation [23].
  • Cross-trial analysis suggests that M7 is comparable to melphalan and prednisone or melphalan, prednisone, and vincristine; that the efficacy of ABCM in the Vth trial and VIth MRC trials is comparable; and that ABCM gave better survival than intermittent melphalan regimens in the prognostic groups analysed [24].
  • In the Vth MRC myelomatosis trial, the survival of 314 patients randomised to receive ABCM (adriamycin, BCNU, cyclophosphamide, and melphalan) as first-line treatment was significantly longer than that of 316 patients given intermittent melphalan (M7) (p = 0.0003) [24].
  • Therapeutic recommendations include plateletpheresis for major thrombo-hemorrhagic phenomena, or megakaryocyte suppression with radioactive phosphorus, alkylating agents (such as melphalan), or hydroxyurea; minor symptoms may respond to platelet antiaggregating agents [25].

Gene context of Phenylalanine mustard


Analytical, diagnostic and therapeutic context of Phenylalanine mustard

  • After a median follow-up of more than six years, there were no significant differences between the patients given no chemotherapy and those treated with melphalan with respect to either five-year disease-free survival (91 vs. 98 percent; P = 0.41) or overall survival (94 vs. 98 percent; P = 0.43) [2].
  • In this trial (median follow-up, greater than 6 years) the outcomes for the two treatment groups were similar with respect to five-year disease-free survival (80 percent in both groups) and overall survival (81 percent with melphalan vs. 78 percent with 32P; P = 0.48) [2].
  • Treatment failures occurred in 22 per cent of 108 patients receiving placebo and 9.7 per cent of 103 women given L-PAM (p = 0.01) [3].
  • Prolonged 1-phenylalanine mustard (L-PAM) administration as an adjuvant to mastectomy in the management of patients with primary breast cancer and pathologically positive axillary nodes was evaluated by a prospective, randomized, clinical trial [3].
  • Carcinoma of the breast. Occurence after treatment with melphalan for multiple myeloma [31].


  1. Advanced ovarian adenocarcinoma. A prospective clinical trial of melphalan (L-PAM) versus combination chemotherapy. Young, R.C., Chabner, B.A., Hubbard, S.P., Fisher, R.I., Bender, R.A., Anderson, T., Simon, R.M., Canellos, G.P., DeVita, V.T. N. Engl. J. Med. (1978) [Pubmed]
  2. Adjuvant therapy in stage I and stage II epithelial ovarian cancer. Results of two prospective randomized trials. Young, R.C., Walton, L.A., Ellenberg, S.S., Homesley, H.D., Wilbanks, G.D., Decker, D.G., Miller, A., Park, R., Major, F. N. Engl. J. Med. (1990) [Pubmed]
  3. 1-Phenylalanine mustard (L-PAM) in the management of primary breast cancer. A report of early findings. Fisher, B., Carbone, P., Economou, S.G., Frelick, R., Glass, A., Lerner, H., Redmond, C., Zelen, M., Band, P., Katrych, D.L., Wolmark, N., Fisher, E.R. N. Engl. J. Med. (1975) [Pubmed]
  4. Resolution of acquired factor X deficiency and amyloidosis with melphalan and prednisone therapy. Camoriano, J.K., Greipp, P.R., Bayer, G.K., Bowie, E.J. N. Engl. J. Med. (1987) [Pubmed]
  5. Results of intensive therapy in childhood acute myeloid leukemia, incorporating high-dose melphalan and autologous bone marrow transplantation in first complete remission. Tiedemann, K., Waters, K.D., Tauro, G.P., Tucker, D., Ekert, H. Blood (1993) [Pubmed]
  6. Role of cytoprotective mechanisms in the photochemical purging of autologous bone marrow grafts. Yamazaki, T., Sato, Y., Sieber, F. Exp. Hematol. (1997) [Pubmed]
  7. Therapy of stage III (optimal) epithelial carcinoma of the ovary with melphalan or melphalan plus Corynebacterium parvum (a Gynecologic Oncology Group Study). Gall, S., Bundy, B., Beecham, J., Whitney, C., Homesley, H., Lifshitz, S., Adcock, L.L. Gynecol. Oncol. (1986) [Pubmed]
  8. Thalidomide plus oral melphalan compared with thalidomide alone for advanced multiple myeloma. Offidani, M., Corvatta, L., Marconi, M., Olivieri, A., Catarini, M., Mele, A., Brunori, M., Candela, M., Malerba, L., Capelli, D., Montanari, M., Leoni, P. Hematol. J. (2004) [Pubmed]
  9. Risk of leukemia after chemotherapy and radiation treatment for breast cancer. Curtis, R.E., Boice, J.D., Stovall, M., Bernstein, L., Greenberg, R.S., Flannery, J.T., Schwartz, A.G., Weyer, P., Moloney, W.C., Hoover, R.N. N. Engl. J. Med. (1992) [Pubmed]
  10. Acquired factor X deficiency and amyloidosis treated with melphalan and prednisone. Levin, M., Chokas, W. N. Engl. J. Med. (1987) [Pubmed]
  11. Overexpression of metallothionein confers resistance to anticancer drugs. Kelley, S.L., Basu, A., Teicher, B.A., Hacker, M.P., Hamer, D.H., Lazo, J.S. Science (1988) [Pubmed]
  12. Amphotericin B potentiation of the cytotoxicity of anticancer agents against both normal hematopoietic and leukemia cells in mice. Valeriote, F., Medoff, G., Tolen, S., Dieckman, J. J. Natl. Cancer Inst. (1984) [Pubmed]
  13. Intraperitoneal chemotherapy with cisplatin and melphalan. Piccart, M.J., Abrams, J., Dodion, P.F., Crespeigne, N., Sculier, J.P., Pector, J.C., Finet, C., Nouwijnck, C., Bondue, H., Atassi, G. J. Natl. Cancer Inst. (1988) [Pubmed]
  14. Selective enhancement of hypoxic cell killing by melphalan via thiol depletion: in vitro studies with hypoxic cell sensitizers and buthionine sulfoximine. Roizin-Towle, L. J. Natl. Cancer Inst. (1985) [Pubmed]
  15. Development of resistance to MOPC-315 plasmacytoma after intralesional and intraperitoneal melphalan therapy of tumor-bearing BALB/c mice. II. Enhancement of in vitro cell-mediated cytotoxicity by combined chemotherapy-immunotherapy. Adler, A., Keisari, Y., Ofir, R. J. Natl. Cancer Inst. (1985) [Pubmed]
  16. In vitro evidence for homologous recombinational repair in resistance to melphalan. Wang, Z.M., Chen, Z.P., Xu, Z.Y., Christodoulopoulos, G., Bello, V., Mohr, G., Aloyz, R., Panasci, L.C. J. Natl. Cancer Inst. (2001) [Pubmed]
  17. Biologic effects of prolonged melphalan treatment of murine long-term bone marrow cultures and interleukin 3-dependent hematopoietic progenitor cell lines. Greenberger, J.S., Palaszynski, E.W., Pierce, J.H., Sakakeeny, M.A., Ruscetti, S.K., Ihle, J.N., Daugherty, C. J. Natl. Cancer Inst. (1985) [Pubmed]
  18. Effect of granulocyte colony stimulating factor on neutropenia induced by cytotoxic chemotherapy. Morstyn, G., Campbell, L., Souza, L.M., Alton, N.K., Keech, J., Green, M., Sheridan, W., Metcalf, D., Fox, R. Lancet (1988) [Pubmed]
  19. Clinical applications of TNF-alpha in cancer. Lejeune, F.J., Rüegg, C., Liénard, D. Curr. Opin. Immunol. (1998) [Pubmed]
  20. Differential competition with cytotoxic agents: an approach to selectivity in cancer chemotherapy. Rabinowitz, M., Uehara, Y., Vistica, D.T. Science (1979) [Pubmed]
  21. Aggressive conventional chemotherapy compared with high-dose chemotherapy with autologous haemopoietic stem-cell transplantation for relapsed chemosensitive Hodgkin's disease: a randomised trial. Schmitz, N., Pfistner, B., Sextro, M., Sieber, M., Carella, A.M., Haenel, M., Boissevain, F., Zschaber, R., Müller, P., Kirchner, H., Lohri, A., Decker, S., Koch, B., Hasenclever, D., Goldstone, A.H., Diehl, V. Lancet (2002) [Pubmed]
  22. Enhancement of alkylating agent activity by SR-4233 in the FSaIIC murine fibrosarcoma. Holden, S.A., Teicher, B.A., Ara, G., Herman, T.S., Coleman, C.N. J. Natl. Cancer Inst. (1992) [Pubmed]
  23. Radiopharmaceutical therapy of 5T33 murine myeloma by sequential treatment with samarium-153 ethylenediaminetetramethylene phosphonate, melphalan, and bone marrow transplantation. Turner, J.H., Claringbold, P.G., Manning, L.S., O'Donoghue, H.L., Berger, J.D., Glancy, R.J. J. Natl. Cancer Inst. (1993) [Pubmed]
  24. Combined chemotherapy with ABCM versus melphalan for treatment of myelomatosis. The Medical Research Council Working Party for Leukaemia in Adults. MacLennan, I.C., Chapman, C., Dunn, J., Kelly, K. Lancet (1992) [Pubmed]
  25. Neurologic manifestations of essential thrombocythemia. Jabaily, J., Iland, H.J., Laszlo, J., Massey, E.W., Faguet, G.B., Brière, J., Landaw, S.A., Pisciotta, A.V. Ann. Intern. Med. (1983) [Pubmed]
  26. Involvement of Notch-1 signaling in bone marrow stroma-mediated de novo drug resistance of myeloma and other malignant lymphoid cell lines. Nefedova, Y., Cheng, P., Alsina, M., Dalton, W.S., Gabrilovich, D.I. Blood (2004) [Pubmed]
  27. Cytokine levels and systemic toxicity in patients undergoing isolated limb perfusion with high-dose tumor necrosis factor, interferon gamma, and melphalan. Thom, A.K., Alexander, H.R., Andrich, M.P., Barker, W.C., Rosenberg, S.A., Fraker, D.L. J. Clin. Oncol. (1995) [Pubmed]
  28. A hypoxia-driven vascular endothelial growth factor/Flt1 autocrine loop interacts with hypoxia-inducible factor-1alpha through mitogen-activated protein kinase/extracellular signal-regulated kinase 1/2 pathway in neuroblastoma. Das, B., Yeger, H., Tsuchida, R., Torkin, R., Gee, M.F., Thorner, P.S., Shibuya, M., Malkin, D., Baruchel, S. Cancer Res. (2005) [Pubmed]
  29. Role of multidrug resistance protein 1 (MRP1) and glutathione S-transferase A1-1 in alkylating agent resistance. Kinetics of glutathione conjugate formation and efflux govern differential cellular sensitivity to chlorambucil versus melphalan toxicity. Paumi, C.M., Ledford, B.G., Smitherman, P.K., Townsend, A.J., Morrow, C.S. J. Biol. Chem. (2001) [Pubmed]
  30. Kupffer cell-expressed membrane-bound TNF mediates melphalan hepatotoxicity via activation of both TNF receptors. Kresse, M., Latta, M., Künstle, G., Riehle, H.M., van Rooijen, N., Hentze, H., Tiegs, G., Biburger, M., Lucas, R., Wendel, A. J. Immunol. (2005) [Pubmed]
  31. Carcinoma of the breast. Occurence after treatment with melphalan for multiple myeloma. Bell, R., Sullivan, J.R., Fone, D.J., Hurley, T.H. JAMA (1976) [Pubmed]
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