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Chemical Compound Review

NLPD     amino-[bis(2-chloroethyl) amino]phosphinic...

Synonyms: CHEMBL525, Friedman acid, CCRIS 5127, CHEBI:8163, ASTA 5317, ...
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Disease relevance of Phosphamide mustard


High impact information on Phosphamide mustard

  • Nevertheless, both control and CY-treated AML cells demonstrated similar dose-dependent sensitivity to 100 to 500 mumol/L phosphoramide mustard (PhM), the active alkylating end-product of CY activation in vivo [6].
  • BG had no effect on 4hydroperoxydidechlorocyclophosphamide (which generates acrolein and a nonalkylating form of PM) in CHO cells and CHOMIK cells, but enhancement of toxicity was observed with PM in both these cell lines [1].
  • CHO cells transduced with wild-type human AGT (CHO(AGT)) and pcDNA3 (CHOpcDNA3) were treated with activated cyclophosphamide derivatives, 4-hydroperoxycyclophosphamide (4-HC), 4-hydroperoxydidechlorocyclophosphamide (4-HDC), a progenitor of acrolein, and phosphoramide mustard (PM) [7].
  • The present study demonstrates that AGT plays an important role in protecting against the toxic and mutagenic effect of cyclophosphamide and suggests that acrolein, not PM, is responsible for generating the toxic and mutagenic lesion(s) protected by the AGT protein [7].
  • Plasma 4-(p-nitrobenzyl)pyridine activity was found to correlate the closest with PM profiles, with respect to both standard pharmacokinetic parameters and AUC values [8].

Chemical compound and disease context of Phosphamide mustard


Biological context of Phosphamide mustard


Anatomical context of Phosphamide mustard


Associations of Phosphamide mustard with other chemical compounds


Gene context of Phosphamide mustard

  • Furthermore, two interspecific hybrids derived from UV41, both of which retained the region of human chromosome 16 that harbors the ERCC4 gene, displayed essentially wild-type resistance to 4HC and PM, confirming the importance of ERCC4 for the repair of 4HC-induced DNA damage [25].
  • To confirm the importance of the ERCC1 gene for cellular resistance to 4HC and PM, UV20 cells were transfected with the human ERCC1 gene and subsequently exposed to 4HC and PM [25].
  • RESULTS: The rank ordering of sensitivity to both 4HC and PM, based on the combined survival data, was UV41/UV4/UV20 > > UV61/UV24/UV135/EM9 > or = UV5 approximately AA8 [25].
  • Similarly, the inhibition of proliferation was probably not related to endogenous IL-2 levels: addition of exogenous IL-2 to PM-containing cultures did not result in any restoration of proliferation [26].
  • Thus, concanavalin A-stimulated lymphocytes still acquired IL-2 receptors (Tac antigen) normally in the presence of PM (10(-6) to 10(-9) M) [26].

Analytical, diagnostic and therapeutic context of Phosphamide mustard


  1. Effect of O6-benzylguanine on alkylating agent-induced toxicity and mutagenicity. In Chinese hamster ovary cells expressing wild-type and mutant O6-alkylguanine-DNA alkyltransferases. Cai, Y., Wu, M.H., Xu-Welliver, M., Pegg, A.E., Ludeman, S.M., Dolan, M.E. Cancer Res. (2000) [Pubmed]
  2. The role of DNA damage in the resistance of human chronic myeloid leukemia cells to cyclophosphamide analogues. Andersson, B.S., Mroue, M., Britten, R.A., Murray, D. Cancer Res. (1994) [Pubmed]
  3. Experimental chemotherapy of human medulloblastoma cell lines and transplantable xenografts with bifunctional alkylating agents. Friedman, H.S., Colvin, O.M., Skapek, S.X., Ludeman, S.M., Elion, G.B., Schold, S.C., Jacobsen, P.F., Muhlbaier, L.H., Bigner, D.D. Cancer Res. (1988) [Pubmed]
  4. Nitroaryl phosphoramides as novel prodrugs for E. coli nitroreductase activation in enzyme prodrug therapy. Hu, L., Yu, C., Jiang, Y., Han, J., Li, Z., Browne, P., Race, P.R., Knox, R.J., Searle, P.F., Hyde, E.I. J. Med. Chem. (2003) [Pubmed]
  5. Phosphorus-nitrogen compounds. 24. Phosphoramide mustard carrier derivatives. Cates, L.A., Li, V.S., Powell, D.R., van der Helm, D. J. Med. Chem. (1984) [Pubmed]
  6. Development and characterization of a cyclophosphamide-resistant subline of acute myeloid leukemia in the Lewis x Brown Norway hybrid rat. Koelling, T.M., Yeager, A.M., Hilton, J., Haynie, D.T., Wiley, J.M. Blood (1990) [Pubmed]
  7. Role of O6-alkylguanine-DNA alkyltransferase in protecting against cyclophosphamide-induced toxicity and mutagenicity. Cai, Y., Wu, M.H., Ludeman, S.M., Grdina, D.J., Dolan, M.E. Cancer Res. (1999) [Pubmed]
  8. Clinical pharmacokinetics of cyclophosphamide and metabolites with and without SR-2508. Chan, K.K., Hong, P.S., Tutsch, K., Trump, D.L. Cancer Res. (1994) [Pubmed]
  9. Effect of acrolein on phosphoramide mustard-induced sister chromatid exchanges in cultured human lymphocytes. Wilmer, J.L., Erexson, G.L., Kligerman, A.D. Cancer Res. (1990) [Pubmed]
  10. Comparative studies of total cross-linking, cell survival and cell cycle perturbations in Chinese hamster cells treated with alkylating agents in vitro. Millar, B.C., Tilby, M.J., Ormerod, M.G., Payne, A.W., Jinks, S., Loverock, P.S. Biochem. Pharmacol. (1986) [Pubmed]
  11. Thiazolidinyl- and perhydrothiazinylphosphamidesters: toxicity and preliminary antitumour evaluation. Voelcker, G., Bielicki, L., Hohorst, H.J. J. Cancer Res. Clin. Oncol. (1997) [Pubmed]
  12. Alkylating properties of phosphoramide mustard. Colvin, M., Brundrett, R.B., Kan, M.N., Jardine, I., Fenselau, C. Cancer Res. (1976) [Pubmed]
  13. Phase I trial with pharmacokinetic analyses of high-dose carboplatin, etoposide, and cyclophosphamide with autologous bone marrow transplantation in patients with refractory germ cell tumors. Motzer, R.J., Gulati, S.C., Tong, W.P., Menendez-Botet, C., Lyn, P., Mazumdar, M., Vlamis, V., Lin, S., Bosl, G.J. Cancer Res. (1993) [Pubmed]
  14. Involvement of human glutathione S-transferase isoenzymes in the conjugation of cyclophosphamide metabolites with glutathione. Dirven, H.A., van Ommen, B., van Bladeren, P.J. Cancer Res. (1994) [Pubmed]
  15. Phenotypically deficient urinary elimination of carboxyphosphamide after cyclophosphamide administration to cancer patients. Hadidi, A.H., Coulter, C.E., Idle, J.R. Cancer Res. (1988) [Pubmed]
  16. Restoration of sensitivity to oxazaphosphorines by inhibitors of aldehyde dehydrogenase activity in cultured oxazaphosphorine-resistant L1210 and cross-linking agent-resistant P388 cell lines. Sladek, N.E., Landkamer, G.J. Cancer Res. (1985) [Pubmed]
  17. Enhancement of in vivo and in vitro murine immune responses by the cyclophosphamide metabolite acrolein. Kawabata, T.T., White, K.L. Cancer Res. (1988) [Pubmed]
  18. Cytotoxicity, DNA cross-linking, and single strand breaks induced by activated cyclophosphamide and acrolein in human leukemia cells. Crook, T.R., Souhami, R.L., McLean, A.E. Cancer Res. (1986) [Pubmed]
  19. Rapid development of enhanced clearance after high-dose cyclophosphamide. Moore, M.J., Hardy, R.W., Thiessen, J.J., Soldin, S.J., Erlichman, C. Clin. Pharmacol. Ther. (1988) [Pubmed]
  20. Comparison of sister-chromatid exchange frequencies in mouse T- and B-lymphocytes after exposure to 4-hydroxycyclophosphamide or phosphoramide mustard. Kwanyuen, P., Erexson, G.L., Bryant, M.F., Kligerman, A.D. Mutat. Res. (1990) [Pubmed]
  21. Conversion of 4-hydroperoxycyclophosphamide and 4-hydroxycyclophosphamide to phosphoramide mustard and acrolein mediated by bifunctional catalysis. Low, J.E., Borch, R.F., Sladek, N.E. Cancer Res. (1982) [Pubmed]
  22. DNA cross-linking and single-strand breaks induced by teratogenic concentrations of 4-hydroperoxycyclophosphamide and phosphoramide mustard in postimplantation rat embryos. Little, S.A., Mirkes, P.E. Cancer Res. (1987) [Pubmed]
  23. A cyclophosphamide/DNA phosphoester adduct formed in vitro and in vivo. Maccubbin, A.E., Caballes, L., Riordan, J.M., Huang, D.H., Gurtoo, H.L. Cancer Res. (1991) [Pubmed]
  24. Cyclophosphamide modulates rat hepatic cytochrome P450 2C11 and steroid 5 alpha-reductase activity and messenger RNA levels through the combined action of acrolein and phosphoramide mustard. Chang, T.K., Waxman, D.J. Cancer Res. (1993) [Pubmed]
  25. Nucleotide excision repair genes as determinants of cellular sensitivity to cyclophosphamide analogs. Andersson, B.S., Sadeghi, T., Siciliano, M.J., Legerski, R., Murray, D. Cancer Chemother. Pharmacol. (1996) [Pubmed]
  26. Inhibition of proliferation without affecting the generation of cytotoxicity in the human mixed lymphocyte reaction. Hengst, J.C., Chan, K.K., Mitchell, M.S. Cell. Immunol. (1985) [Pubmed]
  27. The partitioning of phosphoramide mustard and its aziridinium ions among alkylation and P-N bond hydrolysis reactions. Shulman-Roskes, E.M., Noe, D.A., Gamcsik, M.P., Marlow, A.L., Hilton, J., Hausheer, F.H., Colvin, O.M., Ludeman, S.M. J. Med. Chem. (1998) [Pubmed]
  28. Protonation of phosphoramide mustard and other phosphoramides. Gamcsik, M.P., Ludeman, S.M., Shulman-Roskes, E.M., McLennan, I.J., Colvin, M.E., Colvin, O.M. J. Med. Chem. (1993) [Pubmed]
  29. Pharmacology, relative bioavailability, and toxicity of three different oral cyclophosphamide preparations in a randomized, cross-over study. Stewart, D.J., Morgan, L.R., Verma, S., Maroun, J.A., Thibault, M. Investigational new drugs. (1995) [Pubmed]
  30. Aldehyde dehydrogenase involvement in a variant of the brown Norway rat acute myelocytic leukaemia (BNML) that acquired cyclophosphamide resistance in vivo. de Groot, C.J., Martens, A.C., Hagenbeek, A. Eur. J. Cancer (1994) [Pubmed]
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