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Chemical Compound Review

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

Synonyms: Sendoxan, Endoxan, Neosar, Cytophosphan, Cyclophosphane, ...
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Disease relevance of cyclophosphamide


High impact information on cyclophosphamide

  • Unless CP was administered before the adoptive transfer of TIL, therapy with IL-2 and TIL in these B mice was ineffective in the absence of demonstrable T lymphocytes.(ABSTRACT TRUNCATED AT 400 WORDS)[10]
  • Split femurs from rats given cyclophosphamide (CY) and killed at regular intervals condition media that affect DNA synthesis in a fashion similar to that of HSA-HIA in the rats' sera [11].
  • These results suggest that acrolein has a diminished role in mediating the cytogenetic and cytotoxic effects of CP [12].
  • The combination of CY and ABMFPP also showed a synergistic anti-P388 leukemia effect which appeared to be related to the initial reduction of the tumor burden by CY and the marked augmentation of the cytotoxicity of both natural killer cells and macrophages by ABMFPP [13].
  • These results strongly suggest that the antitumor effect of ABMFPP alone or in combination with CY is at least in part mediated through its augmentation of natural killer cell and/or macrophage activities [13].

Chemical compound and disease context of cyclophosphamide


Biological context of cyclophosphamide

  • When MISO was given as a series of small doses by repeat injection over an 8 h period, in order to stimulate human pharmacokinetics, it significantly enhanced the action of Cy in the SA F tumour [19].
  • These results indicate that COX-1 may be involved in modulating the threshold for activating the micturition reflex in the normal rats and also demonstrates that inhibition of COX-2 prevents or reverses the urodynamic changes associated with bladder inflammation induced either by surgery, LPS or CYP treatments [20].
  • D5 exposure did not modulate humoral immunity, while the internal control, CYP, produced the expected suppression of the AFC response [21].
  • CDDP at 10 microM, CPM at 7.5 microM, ADM at 20 microM and VCR at 150 microM caused 80% cell death of HOS cells after 12 h [15].
  • In contrast to their anticlastogenic efficacy neither of the vitamins displayed any significant anti-SCE effect, nor were they active in affecting the inhibition of cell proliferation caused by TR or CP [22].

Anatomical context of cyclophosphamide

  • Overexpression of either class 1 or class 3 aldehyde dehydrogenase (ALDH) has been found in cell lines selected for resistance to the oxazaphosphorine (OAP) alkylating anticancer agent cyclophosphamide (CPA) [23].
  • In the colony assays, BSO increased the anti-cancer effects of the three chemotherapeutic agents, but did not modify the bone marrow suppression by CYM [24].
  • Fos-IR in the spinal cord was not changed in rats receiving chronic CYP treatment (n = 15, 75 mg/kg, i.p., every 3rd day for 2 weeks) [14].
  • Bladder afferent cells in the L6-S1 DRG labeled by Fluorogold (40 microliters) injected into the bladder wall did not exhibit NOS-IR in control animals; however, following chronic CYP administration, a significant percentage of bladder afferent neurons were NOS-IR: L6 (19.8 +/- 4.6%) and S1 (25.3 +/- 2.9%) [14].
  • In control animals and in animals treated acutely with CYP, only small numbers of NOS-IR cells (0.5-0.7 cell profiles/sections) were detected in the L6-S1 dorsal root ganglia (DRG) [14].

Associations of cyclophosphamide with other chemical compounds

  • Functional B1Rs were demonstrated by evoking ATP release and increases in [Ca(2+)](i) in CYP (24 h)-treated cultured rat urothelial cells with a selective B1 receptor agonist (des-Arg(9)-bradykinin) [4].
  • A karyometric and stereologic study of the effects of gonadotrophin and testosterone on the interstitial gland of the testis of intact and endoxan treated rats [16].
  • Reduced ovarian 32P uptake and a significantly decreased level of total gonadotrophin in the pituitary gland and serum were seen when fish were placed either in a drug concentration that had been found to kill half the fish in 96 h or in a safe concentration of Hexadrin and cythion in aquarium water [25].
  • Male Wistar rats were treated with water, cyclophosphamide (CP) 40 mg/kg, and ribavirin 20, 100 and 200 mg/kg (i.p.) for 5 consecutive days at intervals of 24h [26].
  • Since in vitro CY is inactive we have used in our experiments NM, a compound structurally and functionally related to phosphoramide mustard, the natural biologically active metabolite of CY [27].
  • In 12 of 13 patient samples, increased DNA damage (gammaH2AX) was observed with clofarabine and cyclophosphamide compared with cyclophosphamide alone [28].
  • The combination of veliparib with metronomic cyclophosphamide is well tolerated and shows promising activity in a subset of patients with BRCA mutations [29].

Gene context of cyclophosphamide


Analytical, diagnostic and therapeutic context of cyclophosphamide

  • Myeloablative conditioning (MC) was performed with Bu/cyclophosphamide (Cy)/etoposide (Eto) (n=4), Bu/Cy (n=2), and total body irradiation (TBI)/Cy/Eto (n=1) [35].
  • CYP (24 h)-treated rats demonstrated bladder hyperactivity that was significantly reduced by intravesical administration of either B1 (des-Arg(10)-Hoe-140) or B2 (Hoe-140) receptor antagonists [4].
  • Before TBI, conditioning chemotherapy consisted of cyclophosphamide (CY) alone (60 mg/kg per day on 2 successive days) in 24 patients, CY combined with other drugs in 6, and combinations without CY in 6 [36].
  • Injection of CYP (n = 10, 75 mg/kg, i.p.) 2 hours prior to perfusion (acute treatment) of the animals increased Fos-immunoreactivity (IR) in neurons in the dorsal commissure, dorsal horn, and autonomic regions of spinal segments (L1-L2 and L6-S1) which receive afferent inputs from the bladder, urethra, and ureter [14].
  • CY reduces CFU-S numbers, but the fraction synthesizing DNA can be either increased or decreased depending on time after treatment [37].


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  4. Expression and function of bradykinin B1 and B2 receptors in normal and inflamed rat urinary bladder urothelium. Chopra, B., Barrick, S.R., Meyers, S., Beckel, J.M., Zeidel, M.L., Ford, A.P., de Groat, W.C., Birder, L.A. J. Physiol. (Lond.) (2005) [Pubmed]
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  6. Polymorphism of the DNA repair enzyme XRCC1 is associated with treatment prediction in anthracycline and cyclophosphamide/methotrexate/5-fluorouracil-based chemotherapy of patients with primary invasive breast cancer. Jaremko, M., Justenhoven, C., Schroth, W., Abraham, B.K., Fritz, P., Vollmert, C., Illig, T., Simon, W., Schwab, M., Brauch, H. Pharmacogenet. Genomics (2007) [Pubmed]
  7. Induction of remission in active anti-neutrophil cytoplasmic antibody-associated vasculitis with mycophenolate mofetil in patients who cannot be treated with cyclophosphamide. Stassen, P.M., Tervaert, J.W., Stegeman, C.A. Ann. Rheum. Dis. (2007) [Pubmed]
  8. Allogeneic granulocyte macrophage colony-stimulating factor-secreting tumor immunotherapy alone or in sequence with cyclophosphamide for metastatic pancreatic cancer: a pilot study of safety, feasibility, and immune activation. Laheru, D., Lutz, E., Burke, J., Biedrzycki, B., Solt, S., Onners, B., Tartakovsky, I., Nemunaitis, J., Le, D., Sugar, E., Hege, K., Jaffee, E. Clin. Cancer Res. (2008) [Pubmed]
  9. A novel synergistic combination of cyclophosphamide and gene transfer of interleukin-12 eradicates colorectal carcinoma in mice. Malvicini, M., Rizzo, M., Alaniz, L., Piñero, F., García, M., Atorrasagasti, C., Aquino, J.B., Rozados, V., Scharovsky, O.G., Matar, P., Mazzolini, G. Clin. Cancer Res. (2009) [Pubmed]
  10. Synergistic antitumor activity of tumor-infiltrating lymphocytes, interleukin 2, and local tumor irradiation. Studies on the mechanism of action. Cameron, R.B., Spiess, P.J., Rosenberg, S.A. J. Exp. Med. (1990) [Pubmed]
  11. Relationship of the hematopoietic cycle to the combined activities of a stimulator and a short-lived inhibitor. Burke, P.J., Karp, J.E. Blood (1987) [Pubmed]
  12. 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]
  13. Mechanism of antitumor action of pyrimidinones in the treatment of B16 melanoma and P388 leukemia. Li, L.H., Wallace, T.L., Richard, K.A., Tracey, D.E. Cancer Res. (1985) [Pubmed]
  14. Increased expression of neuronal nitric oxide synthase in bladder afferent pathways following chronic bladder irritation. Vizzard, M.A., Erdman, S.L., de Groat, W.C. J. Comp. Neurol. (1996) [Pubmed]
  15. Cisplatin (CDDP) specifically induces apoptosis via sequential activation of caspase-8, -3 and -6 in osteosarcoma. Seki, K., Yoshikawa, H., Shiiki, K., Hamada, Y., Akamatsu, N., Tasaka, K. Cancer Chemother. Pharmacol. (2000) [Pubmed]
  16. A karyometric and stereologic study of the effects of gonadotrophin and testosterone on the interstitial gland of the testis of intact and endoxan treated rats. Fichna, P., Malendowicz, L.K. Cell Tissue Res. (1975) [Pubmed]
  17. Effect of an intensive chemotherapy followed by mediastinal irradiation on pulmonary and cardiac function in advanced Hodgkin's disease. Villani, F., Fede Catania, A., Laffranchi, A., Maffioli, L., Viviani, S., Bonfante, V. Cancer Invest. (2003) [Pubmed]
  18. Inhibition of influenza virus infections in immunosuppressed mice with orally administered peramivir (BCX-1812). Sidwell, R.W., Bailey, K.W., Morrey, J.D., Wong, M.H., Baldwin, T.J., Smee, D.F. Antiviral Res. (2003) [Pubmed]
  19. Enhancement of the action of alkylating agents by single high, or chronic low doses of misonidazole. McNally, N.J., Hinchliffe, M., de Ronde, J. Br. J. Cancer (1983) [Pubmed]
  20. Pharmacological evaluation of the role of cyclooxygenase isoenzymes on the micturition reflex following experimental cystitis in rats. Lecci, A., Birder, L.A., Meini, S., Catalioto, R.M., Tramontana, M., Giuliani, S., Criscuoli, M., Maggi, C.A. Br. J. Pharmacol. (2000) [Pubmed]
  21. Toxicology and humoral immunity assessment of decamethylcyclopentasiloxane (D5) following a 1-month whole body inhalation exposure in Fischer 344 rats. Burns-Naas, L.A., Mast, R.W., Klykken, P.C., McCay, J.A., White, K.L., Mann, P.C., Naas, D.J. Toxicol. Sci. (1998) [Pubmed]
  22. The action of anticlastogens in human lymphocyte cultures and their modification by rat-liver S9 mix. II. Studies with vitamins C and E. Gebhart, E., Wagner, H., Grziwok, K., Behnsen, H. Mutat. Res. (1985) [Pubmed]
  23. Oxazaphosphorine-specific resistance in human MCF-7 breast carcinoma cell lines expressing transfected rat class 3 aldehyde dehydrogenase. Bunting, K.D., Lindahl, R., Townsend, A.J. J. Biol. Chem. (1994) [Pubmed]
  24. Chemosensitization by buthionine sulfoximine in vivo. Tsutsui, K., Komuro, C., Ono, K., Nishidai, T., Shibamoto, Y., Takahashi, M., Abe, M. Int. J. Radiat. Oncol. Biol. Phys. (1986) [Pubmed]
  25. Short-term effect of two pesticides on the survival, ovarian 32P uptake and gonadotrophic potency in a freshwater catfish, Heteropneustes fossilis (Blouch). Singh, H., Singh, T.P. J. Endocrinol. (1980) [Pubmed]
  26. Ribavirin-induced sperm shape abnormalities in Wistar rat. Narayana, K., D'Souza, U.J., Seetharama Rao, K.P. Mutat. Res. (2002) [Pubmed]
  27. The in vivo and in vitro effects of an alkylating agent, mechlorethamine, on IL-6 production in mice and the role of macrophages. Bryniarski, K., Ptak, M., Ptak, W. Immunopharmacology (1996) [Pubmed]
  28. A phase 1 clinical-laboratory study of clofarabine followed by cyclophosphamide for adults with refractory acute leukemias. Karp, J.E., Ricklis, R.M., Balakrishnan, K., Briel, J., Greer, J., Gore, S.D., Smith, B.D., McDevitt, M.A., Carraway, H., Levis, M.J., Gandhi, V. Blood (2007) [Pubmed]
  29. A phase I study of veliparib in combination with metronomic cyclophosphamide in adults with refractory solid tumors and lymphomas. Kummar, S., Ji, J., Morgan, R., Lenz, H.J., Puhalla, S.L., Belani, C.P., Gandara, D.R., Allen, D., Kiesel, B., Beumer, J.H., Newman, E.M., Rubinstein, L., Chen, A., Zhang, Y., Wang, L., Kinders, R.J., Parchment, R.E., Tomaszewski, J.E., Doroshow, J.H. Clin. Cancer Res. (2012) [Pubmed]
  30. O(6)-methylguanine-DNA methyl transferase gene expression and prognosis in breast carcinoma. Cayre, A., Penault-Llorca, F., De Latour, M., Rolhion, C., Feillel, V., Ferrière, J.P., Kwiatkowski, F., Finat-Duclos, F., Verrelle, P. Int. J. Oncol. (2002) [Pubmed]
  31. IL-1beta expression in islet cells of the NOD mouse and its spatial relationship to beta cells and inducible nitric oxide synthase. Reddy, S., Young, M. Ann. N. Y. Acad. Sci. (2002) [Pubmed]
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  34. Genetic polymorphisms of CYP2B6 affect the pharmacokinetics/pharmacodynamics of cyclophosphamide in Japanese cancer patients. Nakajima, M., Komagata, S., Fujiki, Y., Kanada, Y., Ebi, H., Itoh, K., Mukai, H., Yokoi, T., Minami, H. Pharmacogenet. Genomics (2007) [Pubmed]
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