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Chemical Compound Review

WR-2721     2-(3-aminopropylamino) ethylsulfanylphospho...

Synonyms: ETHYOL (TN), AC-6800, AC1L3WIM, KB-162616, LS-172202, ...
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Disease relevance of Gammaphos


Psychiatry related information on Gammaphos


High impact information on Gammaphos


Chemical compound and disease context of Gammaphos


Biological context of Gammaphos

  • Patient diaries demonstrated lower swallowing dysfunction AUC with amifostine (z test P = .025) [14].
  • Fifteen patients experienced nondose-limiting (< 25%), transient decreases in blood pressure after the amifostine infusion [15].
  • Amifostine also synergized with paclitaxel in the arrest of the cell cycle at the G2-M phase and in the induction of apoptosis [16].
  • As expected, lethality and morphologic perturbations were more pronounced earlier in embryogenesis and with higher radiation doses and were partially reversed by amifostine [17].
  • Paclitaxel IC50 value was reduced from 14 to 2 nmol/L with pretreatment of a single dose of 178 micromol/L of amifostine for 72 hours [16].

Anatomical context of Gammaphos


Associations of Gammaphos with other chemical compounds


Gene context of Gammaphos

  • Growth of cells in the free radical scavenger antioxidant, amifostine (WR2721; 4 mM) decreased numbers of adipocytes in Sod2(-/-) BMSCs in both basal (38.0%, p = 0.037) and adipocytogenic (37.5%, p = 0.021) media and reduced to undetectable the levels of expression of PPARgamma and LPL [25].
  • This is the first report showing smad 7 activation by amifostine [26].
  • In amifostine-treated marrows, smad 2/3 and smad4 were not detected in the nucleus but were positive in the cytoplasm of megakaryocytes 10 days after irradiation [26].
  • In conclusion, in none of the MDR positive and negative cell lines did Amifostine modify the toxicity of the anticancer drugs [27].
  • This UVC-induced PLD activity was found to be dependent on the presence of extracellular calcium and was inhibited by catalase as well as amifostine-an intracellular thiol antioxidant [28].

Analytical, diagnostic and therapeutic context of Gammaphos

  • Ex vivo treatment of marrow with amifostine significantly shortens the time to marrow recovery, thereby reducing the risk of myelosuppressive complications in breast cancer patients receiving high-dose chemotherapy and 4-HC-purged ABMS [2].
  • In the nontumorigenic murine myeloid progenitor 32D cells incubated with amifostine, we detected a reduction of the IkappaBalpha cytoplasmic levels by Western blotting and a raising of nuclear NF-kappaB/Rel complexes by electrophoretic mobility shift assay [3].
  • The average number of platelet transfusions (12 v 29; P = .017) and days of antibiotic therapy (28 v 40; P = .012) were significantly less for patients whose marrow was exposed to amifostine + 4-HC, compared with 4-HC alone [2].
  • Subcutaneous administration of amifostine during fractionated radiotherapy: a randomized phase II study [29].
  • The present results suggest that more data from growing immature animal models are needed to analyze the safety of amifostine treatment and its mechanisms of action before wider clinical use of this drug in pediatric cancer patients is recommended [30].


  1. Stimulation of hematopoiesis by amifostine in patients with myelodysplastic syndrome. List, A.F., Brasfield, F., Heaton, R., Glinsmann-Gibson, B., Crook, L., Taetle, R., Capizzi, R. Blood (1997) [Pubmed]
  2. Amifostine (WR-2721) shortens the engraftment period of 4-hydroperoxycyclophosphamide-purged bone marrow in breast cancer patients receiving high-dose chemotherapy with autologous bone marrow support. Shpall, E.J., Stemmer, S.M., Hami, L., Franklin, W.A., Shaw, L., Bonner, H.S., Bearman, S.I., Peters, W.P., Bast, R.C., McCulloch, W. Blood (1994) [Pubmed]
  3. Amifostine inhibits hematopoietic progenitor cell apoptosis by activating NF-kappaB/Rel transcription factors. Romano, M.F., Lamberti, A., Bisogni, R., Garbi, C., Pagnano, A.M., Auletta, P., Tassone, P., Turco, M.C., Venuta, S. Blood (1999) [Pubmed]
  4. Phase III randomized trial of amifostine as a radioprotector in head and neck cancer. Vikram, B. J. Clin. Oncol. (2001) [Pubmed]
  5. Radioprotection, pharmacokinetic and behavioural studies in mouse implanted with biodegradable drug (amifostine) pellets. Srinivasan, V., Pendergrass, J.A., Kumar, K.S., Landauer, M.R., Seed, T.M. Int. J. Radiat. Biol. (2002) [Pubmed]
  6. Choices of methodology in pharmacoeconomics studies. Longo, C.J. Medical care. (1999) [Pubmed]
  7. A randomized trial of amifostine as a cytoprotectant for patients receiving myeloablative therapy for allogeneic hematopoietic stem cell transplantation. Hwang, W.Y., Koh, L.P., Ng, H.J., Tan, P.H., Chuah, C.T., Fook, S.C., Chow, H., Tan, K.W., Wong, C., Tan, C.H., Goh, Y.T. Bone Marrow Transplant. (2004) [Pubmed]
  8. Patients with myelodysplastic syndromes benefit from palliative therapy with amifostine, pentoxifylline, and ciprofloxacin with or without dexamethasone. Raza, A., Qawi, H., Lisak, L., Andric, T., Dar, S., Andrews, C., Venugopal, P., Gezer, S., Gregory, S., Loew, J., Robin, E., Rifkin, S., Hsu, W.T., Huang, R.W. Blood (2000) [Pubmed]
  9. Effect of amifostine on toxicities associated with sequential chemotherapy and radiation therapy for unresectable non-small-cell lung cancer: results of a phase II trial. Tannehill, S.P., Mehta, M.P., Larson, M., Storer, B., Pellet, J., Kinsella, T.J., Schiller, J.H. J. Clin. Oncol. (1997) [Pubmed]
  10. Clinical trial of the effect of S-2-(3-aminopropylamino)-ethylphosphorothioic acid (WR-2721) (NSC 296961) on the toxicity of cyclophosphamide. Woolley, P.V., Ayoob, M.J., Smith, F.P., Dritschilo, A. J. Clin. Oncol. (1983) [Pubmed]
  11. Randomized double-blind trial of combined modality treatment with or without amifostine in unresectable stage III non-small-cell lung cancer. Leong, S.S., Tan, E.H., Fong, K.W., Wilder-Smith, E., Ong, Y.K., Tai, B.C., Chew, L., Lim, S.H., Wee, J., Lee, K.M., Foo, K.F., Ang, P., Ang, P.T. J. Clin. Oncol. (2003) [Pubmed]
  12. WR-1065, the active metabolite of amifostine (Ethyol), does not inhibit the cytotoxic effects of a broad range of standard anticancer drugs against human ovarian and breast cancer cells. Alberts, D.S., Speicher, L.A., Krutzsch, M., Wymer, J., Capizzi, R.L., Conlon, J., Barrett, A., Aickin, M. Eur. J. Cancer (1996) [Pubmed]
  13. Concurrent administration of Docetaxel and Stealth liposomal doxorubicin with radiotherapy in non-small cell lung cancer : excellent tolerance using subcutaneous amifostine for cytoprotection. Koukourakis, M.I., Romanidis, K., Froudarakis, M., Kyrgias, G., Koukourakis, G.V., Retalis, G., Bahlitzanakis, N. Br. J. Cancer (2002) [Pubmed]
  14. Randomized trial of amifostine in locally advanced non-small-cell lung cancer patients receiving chemotherapy and hyperfractionated radiation: radiation therapy oncology group trial 98-01. Movsas, B., Scott, C., Langer, C., Werner-Wasik, M., Nicolaou, N., Komaki, R., Machtay, M., Smith, C., Axelrod, R., Sarna, L., Wasserman, T., Byhardt, R. J. Clin. Oncol. (2005) [Pubmed]
  15. A phase I trial of amifostine (WR-2721) and melphalan in children with refractory cancer. Adamson, P.C., Balis, F.M., Belasco, J.E., Lange, B., Berg, S.L., Blaney, S.M., Craig, C., Poplack, D.G. Cancer Res. (1995) [Pubmed]
  16. A potential synergistic anticancer effect of paclitaxel and amifostine on endometrial cancer. Dai, D., Holmes, A.M., Nguyen, T., Davies, S., Theele, D.P., Verschraegen, C., Leslie, K.K. Cancer Res. (2005) [Pubmed]
  17. Zebrafish as a "biosensor"? Effects of ionizing radiation and amifostine on embryonic viability and development. Geiger, G.A., Parker, S.E., Beothy, A.P., Tucker, J.A., Mullins, M.C., Kao, G.D. Cancer Res. (2006) [Pubmed]
  18. Amifostine improves the antileukemic therapeutic index of mafosfamide: implications for bone marrow purging. Douay, L., Hu, C., Giarratana, M.C., Bouchet, S., Conlon, J., Capizzi, R.L., Gorin, N.C. Blood (1995) [Pubmed]
  19. Salivary gland protection by amifostine in high-dose radioiodine treatment: results of a double-blind placebo-controlled study. Bohuslavizki, K.H., Klutmann, S., Brenner, W., Mester, J., Henze, E., Clausen, M. J. Clin. Oncol. (1998) [Pubmed]
  20. Doxorubicin induces apoptosis in germ line stem cells in the immature rat testis and amifostine cannot protect against this cytotoxicity. Hou, M., Chrysis, D., Nurmio, M., Parvinen, M., Eksborg, S., Söder, O., Jahnukainen, K. Cancer Res. (2005) [Pubmed]
  21. Direct amifostine effect on renal tubule cells in rats. Weichert-Jacobsen, K.J., Bannowski, A., Küppers, F., Loch, T., Stöckle, M. Cancer Res. (1999) [Pubmed]
  22. Preclinical evaluation of WR-151327: an orally active chemotherapy protector. Green, D., Bensely, D., Schein, P. Cancer Res. (1994) [Pubmed]
  23. A comparative study on the protection profile of lidocaine, amifostine, and pilocarpin on the parotid gland during radiotherapy. Hakim, S.G., Kosmehl, H., Lauer, I., Nadrowitz, R., Wedel, T., Sieg, P. Cancer Res. (2005) [Pubmed]
  24. The cytoprotective aminothiol WR1065 activates p21waf-1 and down regulates cell cycle progression through a p53-dependent pathway. North, S., El-Ghissassi, F., Pluquet, O., Verhaegh, G., Hainaut, P. Oncogene (2000) [Pubmed]
  25. Adipocyte differentiation in Sod2(-/-) and Sod2(+/+) murine bone marrow stromal cells is associated with low antioxidant pools. Lechpammer, S., Epperly, M.W., Zhou, S., Nie, S., Glowacki, J., Greenberger, J.S. Exp. Hematol. (2005) [Pubmed]
  26. Amifostine does not prevent activation of TGFbeta1 but induces smad 7 activation in megakaryocytes irradiated in vivo. Segreto, H.R., Ferreira, A.T., Kimura, E.T., Franco, M., Egami, M.I., Silva, M.R., Segreto, R.A. Am. J. Hematol. (2002) [Pubmed]
  27. Amifostine does not inhibit the toxic effects of anthracycline derivates or mitoxantrone on MDR tumor cell lines. Michieli, M., Michelutti, A., Damiani, D., Ermacora, A., Masolini, P., Stocchi, R., Russo, D. Leuk. Lymphoma (2001) [Pubmed]
  28. Involvement of protein kinase C pathway in UVC-stimulated phospholipase D2 activity in Vero 76 cells. Kim, S., Choi, M.S., Choi, M.U. Exp. Mol. Med. (2005) [Pubmed]
  29. Subcutaneous administration of amifostine during fractionated radiotherapy: a randomized phase II study. Koukourakis, M.I., Kyrias, G., Kakolyris, S., Kouroussis, C., Frangiadaki, C., Giatromanolaki, A., Retalis, G., Georgoulias, V. J. Clin. Oncol. (2000) [Pubmed]
  30. Amifostine protects against early but not late toxic effects of doxorubicin in infant rats. Jahnukainen, K., Jahnukainen, T., Salmi, T.T., Svechnikov, K., Eksborg, S., Söder, O. Cancer Res. (2001) [Pubmed]
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