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Troxacitabine

Troxacitabine is a dioxolane derivative and a novel L-configuration deoxycytidine analogue with potent antineoplastic activity. When incorporated into growing chain during DNA replication, troxacitabine stops DNA polymerization due to its unnatural L-configuration, in contrast to the normal nucleotides with D-configuration. As a result, this agent terminates DNA synthesis upon incorporated into DNA molecules, and consequently interrupts tumor cell proliferation. (from NCI's webpage)

Current developer:      SGX Pharmaceuticals, Inc.

1: McNeill DR, Lam W, DeWeese TL, Cheng YC, Wilson DM 3rd. Impairment of APE1 function enhances cellular sensitivity to clinically relevant alkylators and antimetabolites. Mol Cancer Res. 2009 Jun;7(6):897-906. Epub 2009 May 26. PubMed PMID: 19470598; PubMed Central PMCID: PMC2745049.

2: Lin CC, Beeram M, Rowinsky EK, Takimoto CH, Ng CM, Geyer CE Jr, Denis LJ, De Bono JS, Hao D, Tolcher AW, Rha SY, Jolivet J, Patnaik A. Phase I and pharmacokinetic study of cisplatin and troxacitabine administered intravenously every 28 days in patients with advanced solid malignancies. Cancer Chemother Pharmacol. 2009 Dec;65(1):167-75. Epub 2009 May 16. PubMed PMID: 19449006.

3: Lam W, Bussom S, Cheng YC. Effect of hypoxia on the expression of phosphoglycerate kinase and antitumor activity of troxacitabine and gemcitabine in non-small cell lung carcinoma. Mol Cancer Ther. 2009 Feb;8(2):415-23. Epub 2009 Feb 10. PubMed PMID: 19208827.

4: Ewald B, Sampath D, Plunkett W. ATM and the Mre11-Rad50-Nbs1 complex respond to nucleoside analogue-induced stalled replication forks and contribute to drug resistance. Cancer Res. 2008 Oct 1;68(19):7947-55. PubMed PMID: 18829552; PubMed Central PMCID: PMC2631429.

5: Wang Y, Liu X, Matsuda A, Plunkett W. Repair of 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentofuranosylcytosine-induced DNA single-strand breaks by transcription-coupled nucleotide excision repair. Cancer Res. 2008 May 15;68(10):3881-9. PubMed PMID: 18483273.

6: Galmarini CM, Popowycz F, Joseph B. Cytotoxic nucleoside analogues: different strategies to improve their clinical efficacy. Curr Med Chem. 2008;15(11):1072-82. Review. PubMed PMID: 18473803.

7: Faderl S, Gandhi V, Kantarjian HM. Potential role of novel nucleoside analogs in the treatment of acute myeloid leukemia. Curr Opin Hematol. 2008 Mar;15(2):101-7. Review. PubMed PMID: 18300755.

8: Jimeno A, Messersmith WA, Lee CK, Ma WW, Laheru D, Donehower RC, Baker SD, Hidalgo M. Phase I study of troxacitabine administered by continuous infusion in subjects with advanced solid malignancies. Ann Oncol. 2008 Feb;19(2):374-9. PubMed PMID: 18245131.

9: Adema AD, Radi M, Daft J, Narayanasamy J, Hoebe EK, Alexander LE, Chu CK, Peters GJ. Troxacitabine prodrugs for pancreatic cancer. Nucleosides Nucleotides Nucleic Acids. 2007;26(8-9):1073-7. PubMed PMID: 18058539.

10: Sparreboom A, Wolff AC, Mathijssen RH, Chatelut E, Rowinsky EK, Verweij J, Baker SD. Evaluation of alternate size descriptors for dose calculation of anticancer drugs in the obese. J Clin Oncol. 2007 Oct 20;25(30):4707-13. PubMed PMID: 17947717.

11: Damaraju VL, Bouffard DY, Wong CK, Clarke ML, Mackey JR, Leblond L, Cass CE, Grey M, Gourdeau H. Synergistic activity of troxacitabine (Troxatyl) and gemcitabine in pancreatic cancer. BMC Cancer. 2007 Jul 3;7:121. PubMed PMID: 17608948; PubMed Central PMCID: PMC1948004.

12: Swords R, Apostolidou E, Giles F. Troxacitabine in leukemia. Hematology. 2006 Oct;11(5):321-9. Review. PubMed PMID: 17607581.

13: Lam W, Leung CH, Bussom S, Cheng YC. The impact of hypoxic treatment on the expression of phosphoglycerate kinase and the cytotoxicity of troxacitabine and gemcitabine. Mol Pharmacol. 2007 Sep;72(3):536-44. Epub 2007 Jun 12. PubMed PMID: 17565005.

14: Swords R, Giles F. Troxacitabine in acute leukemia. Hematology. 2007 Jun;12(3):219-27. Review. PubMed PMID: 17558697.

15: Radi M, Adema AD, Daft JR, Cho JH, Hoebe EK, Alexander LE, Peters GJ, Chu CK. In vitro optimization of non-small cell lung cancer activity with troxacitabine, L-1,3-dioxolane-cytidine, prodrugs. J Med Chem. 2007 May 3;50(9):2249-53. Epub 2007 Apr 10. PubMed PMID: 17419604.

16: Quintás-Cardama A, Cortes J. Evaluation of the L-stereoisomeric nucleoside analog troxacitabine for the treatment of acute myeloid leukemia. Expert Opin Investig Drugs. 2007 Apr;16(4):547-57. Review. PubMed PMID: 17371201.

17: Vose JM, Panwalkar A, Belanger R, Coiffier B, Baccarani M, Gregory SA, Facon T, Fanin R, Caballero D, Ben-Yehuda D, Giles F. A phase II multicenter study of troxacitabine in relapsed or refractory lymphoproliferative neoplasms or multiple myeloma. Leuk Lymphoma. 2007 Jan;48(1):39-45. PubMed PMID: 17325846.

18: Sabini E, Hazra S, Konrad M, Burley SK, Lavie A. Structural basis for activation of the therapeutic L-nucleoside analogs 3TC and troxacitabine by human deoxycytidine kinase. Nucleic Acids Res. 2007;35(1):186-92. Epub 2006 Dec 7. PubMed PMID: 17158155; PubMed Central PMCID: PMC1802566.

19: Roboz GJ, Giles FJ, Ritchie EK, Allen-Bard S, Curcio TJ, Wilkes MA, Park SL, Kantarjian HM, Faderl S, Ravandi F, Kelner MJ, Feldman EJ. Phase I/II study of continuous-infusion troxacitabine in refractory acute myeloid leukemia. J Clin Oncol. 2007 Jan 1;25(1):10-5. Epub 2006 Dec 4. PubMed PMID: 17146106.

20: Adema AD, Zuurbier L, Floor K, Hubeek I, Kaspers GJ, Albertoni F, Peters GJ. Cellular resistance against troxacitabine in human cell lines and pediatric patient acute myeloid leukemia blast cells. Nucleosides Nucleotides Nucleic Acids. 2006;25(9-11):981-6. PubMed PMID: 17065050.

21: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Jun;28(5):323-43. PubMed PMID: 16845450.

22: Lee CK, Rowinsky EK, Li J, Giles F, Moore MJ, Hidalgo M, Capparelli E, Jolivet J, Baker SD. Population pharmacokinetics of troxacitabine, a novel dioxolane nucleoside analogue. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2158-65. PubMed PMID: 16609029.

23: Lam W, Park SY, Leung CH, Cheng YC. Apurinic/apyrimidinic endonuclease-1 protein level is associated with the cytotoxicity of L-configuration deoxycytidine analogs (troxacitabine and beta-L-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine) but not D-configuration deoxycytidine analogs (gemcitabine and beta-D-arabinofuranosylcytosine). Mol Pharmacol. 2006 May;69(5):1607-14. Epub 2006 Feb 15. PubMed PMID: 16481390.

24: Jordheim LP, Galmarini CM, Dumontet C. Gemcitabine resistance due to deoxycytidine kinase deficiency can be reverted by fruitfly deoxynucleoside kinase, DmdNK, in human uterine sarcoma cells. Cancer Chemother Pharmacol. 2006 Oct;58(4):547-54. Epub 2006 Feb 4. PubMed PMID: 16463058.

25: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Oct;27(8):569-612. PubMed PMID: 16273137.

26: Dent SF, Arnold A, Stewart DJ, Gertler S, Ayoub J, Batist G, Goss G, Nevile A, Soulieres D, Jolivet J, McLntosh L, Seymour L. Phase II study of troxacitabine (BCH-4556) in patients with advanced non-small-cell lung cancer. Lung. 2005 Jul-Aug;183(4):265-72. PubMed PMID: 16211462.

27: Lapointe R, Létourneau R, Steward W, Hawkins RE, Batist G, Vincent M, Whittom R, Eatock M, Jolivet J, Moore M. Phase II study of troxacitabine in chemotherapy-naive patients with advanced cancer of the pancreas: gastrointestinal tumors. Ann Oncol. 2005 Feb;16(2):289-93. PubMed PMID: 15668286.

28: Szafraniec SI, Stachnik KJ, Skierski JS. New nucleoside analogs in the treatment of solid tumors. Acta Pol Pharm. 2004 Jul-Aug;61(4):297-305. Review. PubMed PMID: 15575597.

29: Gourdeau H, Leblond L, Hamelin B, Dong K, Ouellet F, Boudreau C, Custeau D, Richard A, Gilbert MJ, Jolivet J. Species differences in troxacitabine pharmacokinetics and pharmacodynamics: implications for clinical development. Clin Cancer Res. 2004 Nov 15;10(22):7692-702. PubMed PMID: 15570003.

30: Foss FM. Nucleoside analogs and antimetabolite therapies for myelodysplastic syndrome. Best Pract Res Clin Haematol. 2004 Dec;17(4):573-84. Review. PubMed PMID: 15494295.

31: Szafraniec SI, Stachnik KJ, Skierski JS. New nucleoside analogs in the treatment of hematological disorders. Acta Pol Pharm. 2004 May-Jun;61(3):223-32. Review. PubMed PMID: 15481249.

32: Jordheim LP, Cros E, Gouy MH, Galmarini CM, Peyrottes S, Mackey J, Perigaud C, Dumontet C. Characterization of a gemcitabine-resistant murine leukemic cell line: reversion of in vitro resistance by a mononucleotide prodrug. Clin Cancer Res. 2004 Aug 15;10(16):5614-21. PubMed PMID: 15328204.

33: Kim TE, Park SY, Hsu CH, Dutschman GE, Cheng YC. Synergistic antitumor activity of troxacitabine and camptothecin in selected human cancer cell lines. Mol Pharmacol. 2004 Aug;66(2):285-92. PubMed PMID: 15266019.

34: Yoshida C, Melo JV. Biology of chronic myeloid leukemia and possible therapeutic approaches to imatinib-resistant disease. Int J Hematol. 2004 Jun;79(5):420-33. Review. PubMed PMID: 15239391.

35: Gourdeau H, Jolivet J. [Troxacitabine]. Bull Cancer. 2004 Mar;91(3):213-8. Review. French. PubMed PMID: 15171046.

36: Krett NL, Ayres M, Nabhan C, Ma C, Nowak B, Nawrocki S, Rosen ST, Gandhi V. In vitro assessment of nucleoside analogs in multiple myeloma. Cancer Chemother Pharmacol. 2004 Aug;54(2):113-21. Epub 2004 May 4. PubMed PMID: 15133625.

37: Boivin AJ, Gourdeau H, Momparler RL. Action of troxacitabine on cells transduced with human cytidine deaminase cDNA. Cancer Invest. 2004;22(1):25-9. PubMed PMID: 15069761.

38: Orsolic N, Giles FJ, Gourdeau H, Golemovic M, Beran M, Cortes J, Freireich EJ, Kantarjian H, Verstovsek S. Troxacitabine and imatinib mesylate combination therapy of chronic myeloid leukaemia: preclinical evaluation. Br J Haematol. 2004 Mar;124(6):727-38. PubMed PMID: 15009060.

39: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Jan-Feb;26(1):53-84. Review. PubMed PMID: 14988742.

40: Ravandi F, Kantarjian H, Giles F, Cortes J. New agents in acute myeloid leukemia and other myeloid disorders. Cancer. 2004 Feb 1;100(3):441-54. Review. PubMed PMID: 14745859.

41: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Dec;25(10):831-55. PubMed PMID: 14735233.

42: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Nov;25(9):747-71. PubMed PMID: 14685303.

43: Cortes J, Giles F. New agents in chronic myelogenous leukemia. J Natl Compr Canc Netw. 2003 Oct;1(4):501-12. Review. PubMed PMID: 19774741.

44: Bouffard DY, Jolivet J, Leblond L, Hamelin B, Ouellet F, Barbeau S, Richard A, Gourdeau H. Complementary antineoplastic activity of the cytosine nucleoside analogues troxacitabine (Troxatyl) and cytarabine in human leukemia cells. Cancer Chemother Pharmacol. 2003 Dec;52(6):497-506. Epub 2003 Sep 3. PubMed PMID: 12955470.

45: Giles FJ, Feldman EJ, Roboz GJ, Larson RA, Mamus SW, Cortes JE, Verstovsek S, Faderl S, Talpaz M, Beran M, Albitar M, O'Brien SM, Kantarjian HM. Phase II study of troxacitabine, a novel dioxolane nucleoside analog, in patients with untreated or imatinib mesylate-resistant chronic myelogenous leukemia in blastic phase. Leuk Res. 2003 Dec;27(12):1091-6. PubMed PMID: 12921945.

46: Adis International Ltd. Troxacitabine: BCH 4556, SPD 758, Troxatyl. Drugs R D. 2003;4(4):264-8. PubMed PMID: 12848594.

47: Giles FJ, Kantarjian HM, Cortes JE, Garcia-Manero G, Verstovsek S, Faderl S, Thomas DA, Ferrajoli A, O'Brien S, Wathen JK, Xiao LC, Berry DA, Estey EH. Adaptive randomized study of idarubicin and cytarabine versus troxacitabine and cytarabine versus troxacitabine and idarubicin in untreated patients 50 years or older with adverse karyotype acute myeloid leukemia. J Clin Oncol. 2003 May 1;21(9):1722-7. PubMed PMID: 12721247.

48: Townsley CA, Chi K, Ernst DS, Belanger K, Tannock I, Bjarnason GA, Stewart D, Goel R, Ruether JD, Siu LL, Jolivet J, McIntosh L, Seymour L, Moore MJ; National Cancer Institute of Canada-Clinical Trials Group. Phase II study of troxacitabine (BCH-4556) in patients with advanced and/or metastatic renal cell carcinoma: a trial of the National Cancer Institute of Canada-Clinical Trials Group. J Clin Oncol. 2003 Apr 15;21(8):1524-9. PubMed PMID: 12697876.

49: Giles FJ, Faderl S, Thomas DA, Cortes JE, Garcia-Manero G, Douer D, Levine AM, Koller CA, Jeha SS, O'Brien SM, Estey EH, Kantarjian HM. Randomized phase I/II study of troxacitabine combined with cytarabine, idarubicin, or topotecan in patients with refractory myeloid leukemias. J Clin Oncol. 2003 Mar 15;21(6):1050-6. Erratum in: J Clin Oncol. 2004 Apr 1;22(7):1351. Dosage error in published abstract; MEDLINE/PubMed abstract corrected; Dosage error in article text. PubMed PMID: 12637470.

50: Chou KM, Cheng YC. The exonuclease activity of human apurinic/apyrimidinic endonuclease (APE1). Biochemical properties and inhibition by the natural dinucleotide Gp4G. J Biol Chem. 2003 May 16;278(20):18289-96. Epub 2003 Mar 6. PubMed PMID: 12624104.

51: Cortes J, Kantarjian H. Advanced-phase chronic myeloid leukemia. Semin Hematol. 2003 Jan;40(1):79-86. Review. PubMed PMID: 12563614.

52: Baker SD, Verweij J, Rowinsky EK, Donehower RC, Schellens JH, Grochow LB, Sparreboom A. Role of body surface area in dosing of investigational anticancer agents in adults, 1991-2001. J Natl Cancer Inst. 2002 Dec 18;94(24):1883-8. PubMed PMID: 12488482.

53: Gourdeau H, Genne P, Kadhim S, Bibeau L, Duchamp O, Ouellet F, deMuys JM, Bouffard DY, Attardo G. Antitumor activity of troxacitabine (Troxatyl) against anthracycline-resistant human xenografts. Cancer Chemother Pharmacol. 2002 Dec;50(6):490-6. Epub 2002 Oct 16. PubMed PMID: 12451476.

54: Ecker G. Troxacitabine (Shire Pharmaceuticals). Curr Opin Investig Drugs. 2002 Oct;3(10):1533-8. PubMed PMID: 12431032.

55: Giles F, Garcia-Manero G, O'Brien S, Estey E, Kantarjian H. Fatal hepatic veno-occlusive disease in a phase I study of mylotarg and troxatyl in patients with refractory acute myeloid leukemia or myelodysplastic syndrome. Acta Haematol. 2002;108(3):164-7. PubMed PMID: 12373091.

56: Alvarado Y, Kantarjian HM, Cortes JE, Apostolidou E, Bivins C, Giles FJ. Troxacitabine activity in extramedullary myeloid leukemia. Hematology. 2002 Jun;7(3):179-85. PubMed PMID: 12243982.

57: Cheson BD. Hematologic malignancies: new developments and future treatments. Semin Oncol. 2002 Aug;29(4 Suppl 13):33-45. Review. PubMed PMID: 12170431.

58: Giles FJ. New drugs in acute myeloid leukemia. Curr Oncol Rep. 2002 Sep;4(5):369-74. Review. PubMed PMID: 12162909.

59: Karrison T, Ratain M. Troxacitabine in patients with refractory leukemia. J Clin Oncol. 2002 Aug 1;20(15):3356; author reply 3356-7. PubMed PMID: 12149312.

60: Giles FJ. Troxacitabine-based therapy of refractory leukemia. Expert Rev Anticancer Ther. 2002 Jun;2(3):261-6. Review. PubMed PMID: 12113049.

61: Bayes M, Rabasseda X, Prous JR. Gateways to Clinical Trials. Methods Find Exp Clin Pharmacol. 2002 Apr;24(3):159-84. Review. PubMed PMID: 12087878.

62: Bélanger K, Moore M, Baker SD, Dionne J, Maclean M, Jolivet J, Siu L, Soulières D, Wainman N, Seymour L. Phase I and pharmacokinetic study of novel L-nucleoside analog troxacitabine given as a 30-minute infusion every 21 days. J Clin Oncol. 2002 May 15;20(10):2567-74. Erratum in: J Clin Oncol 2002 Aug 1;20(15):3361. PubMed PMID: 12011137.

63: Hui YF, Giles FJ, Cortes JE. Chemotherapy-induced palmar-plantar erythrodysesthesia syndrome--recall following different chemotherapy agents. Invest New Drugs. 2002 Feb;20(1):49-53. PubMed PMID: 12003194.

64: Giles FJ, Garcia-Manero G, Cortes JE, Baker SD, Miller CB, O'Brien SM, Thomas DA, Andreeff M, Bivins C, Jolivet J, Kantarjian HM. Phase II study of troxacitabine, a novel dioxolane nucleoside analog, in patients with refractory leukemia. J Clin Oncol. 2002 Feb 1;20(3):656-64. PubMed PMID: 11821445.

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68: Gourdeau H, Clarke ML, Ouellet F, Mowles D, Selner M, Richard A, Lee N, Mackey JR, Young JD, Jolivet J, Lafrenière RG, Cass CE. Mechanisms of uptake and resistance to troxacitabine, a novel deoxycytidine nucleoside analogue, in human leukemic and solid tumor cell lines. Cancer Res. 2001 Oct 1;61(19):7217-24. PubMed PMID: 11585758.

69: Johnson SA. Nucleoside analogues in the treatment of haematological malignancies. Expert Opin Pharmacother. 2001 Jun;2(6):929-43. Review. PubMed PMID: 11585009.

70: Günzburg WH, Salmons B. Novel clinical strategies for the treatment of pancreatic carcinoma. Trends Mol Med. 2001 Jan;7(1):30-7. Review. PubMed PMID: 11427987.

71: Galmarini CM, Mackey JR, Dumontet C. Nucleoside analogues: mechanisms of drug resistance and reversal strategies. Leukemia. 2001 Jun;15(6):875-90. Review. PubMed PMID: 11417472.

72: Larson RA. New agents for induction and postremission therapy of acute myeloid leukemia. Leukemia. 2001 Apr;15(4):675-6. Review. PubMed PMID: 11368378.

73: Gourdeau H, Bibeau L, Ouellet F, Custeau D, Bernier L, Bowlin T. Comparative study of a novel nucleoside analogue (Troxatyl, troxacitabine, BCH-4556) and AraC against leukemic human tumor xenografts expressing high or low cytidine deaminase activity. Cancer Chemother Pharmacol. 2001 Mar;47(3):236-40. PubMed PMID: 11320667.

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