Eribulin mesilate: Antimitotic drug tubulin polymerization inhibitor oncolytic

Drugs of the Future

Volumn 32, Issue 8, 2007, Pages 681-698

  Wang, Y ^a   Serradell, N ^b   Bolos J ^b   Rosa, E ^b  

^a IBC   (United States)

^b PROUS SCIENCE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT; ANTINEOPLASTIC AGENT; CARBOPLATIN; CISPLATIN; DOCETAXEL; DOXIFLURIDINE; DOXORUBICIN; E 7389; EPIRUBICIN; ER 076349; ER 086526; ERIBULIN MESILATE; GEMCITABINE; HALICHONDRIN B; NAVELBINE; PACLITAXEL; TRASTUZUMAB; UNCLASSIFIED DRUG; VINBLASTINE; VINCRISTINE;

ALOPECIA; ANEMIA; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; AREA UNDER THE CURVE; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CLINICAL TRIAL; COMBINATION CHEMOTHERAPY; DRUG DOSE REGIMEN; DRUG EFFICACY; DRUG HALF LIFE; DRUG MEGADOSE; DRUG METABOLISM; DRUG POTENTIATION; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERABILITY; FATIGUE; FEBRILE NEUTROPENIA; HUMAN; HYPOGLYCEMIA; HYPOPHOSPHATEMIA; IN VITRO STUDY; IN VIVO STUDY; INTERSTITIAL PNEUMONIA; MITOSIS INHIBITION; MONOTHERAPY; MULTIPLE CYCLE TREATMENT; NAUSEA; NEUTROPENIA; NONHUMAN; PERIPHERAL NEUROPATHY; SINGLE DRUG DOSE; TISSUE DISTRIBUTION; TUMOR REGRESSION; TUMOR XENOGRAFT;

EID: 35648961242     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2007.032.08.1127245     Document Type: Article

References (55)

1. Littlefield, B.A., Palme, M.H., Zheng, W., Towle, M.J., Yu, M.J., Seletsky, B.M. (Eisai Co., Ltd.). Macrocyclic analogs and methods of their use and preparation. JP 2002518384, US 6214865, WO 9965894.
2. Zheng, W., Seletsky, B.M., Palme, M.H. et al. Macrocyclic ketone analogues of halichondrin B. Bioorg Med Chem Lett 2004, 14(22): 5551-4.
3. Austad, B., Chase, C.E., Fang, F.G. (Eisai Co., Ltd.). Intermediates for the preparation of halichondrin B. EP 1771431, WO 2005118565.
4. Stamos, D.P., Kishi, Y. Synthetic studies on halichondrins. A practical synthesis of the C.1-C.13 segment. Tetrahedron Lett 1996, 37(48): 8643.
5. Uemura, D., Takahashi, K., Yamamoto, T. et al. Norhalichondrin A: An antitumor polyether macrolide from a marine sponge. J Am Chem Soc 1985, 107: 4796-8.
6. Bai, R., Paul, K.D., Herald, C.L., Malspeis, L., Petti, G.R., Hamel, E. Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. J Biol Chem 1999, 266: 15882-9.
7. Aicher, T.D., Buszek, K.R., Fang, F.G. et al. Total synthesis of halichondrin B and norhalichondrin B. J Am Chem Soc 1992, 114(8): 3162-4.
8. Wang, Y., Habgood, G.J., Christ, W.J., Kishi, Y., Littlefield, B.A., Yu, M.J. Structure-activity relationships of halichondrin B analogues: Modifications at C.30-C.80. Bioorg Med Chem Lett 2000, 10(10): 1029-32.
9. Littlefield, B.A. Novel tubulin targeting opportunities via exploration of marine sponge natural products: Discovery and development of a synthetic halichondrin B analog E7389. 7th Jt Conf Am Assoc Cancer Res Jpn Cancer Assoc (Jan 21-25, Walkoloa) 2007, Abst.
10. Littlefield, B.A., Yu, M.J., Fang, F.G., Lewis, M.D., Silberman, S.L., Kishi, Y. Discovery and development of synthetic halichondrin B analog E7389. 17th AACR-NCI-EORTC Int Conf Mol Targets Cancer Ther (Nov 14-18, Philadelphia) 2005, Abst.
11. Towle, M.J., Wels, B.F., Cheng, H. et al. Halichondrin B macrocyclic ketone analog E7389: Medicinal chemistry repair of lactone ester instability generated during structural simplification to clinical candidate. Proc Am Assoc Cancer Res (AACR) 2002, 43: Abst 5721.
12. Zheng, W., Seletsky, B.M., Palme, M.H. et al. Synthetic macrocyclic ketone analogs of halichondrin B: Structure-activity relationships. Proc Am Assoc Cancer Res (AACR) 2000, 41: Abst 1915.
13. Newman, DJ. Preclinical development of halichondrin B and its derivative Eisai E7389. 17th AACR-NCI-EORTC Int Conf Mol Targets Cancer Ther (Nov 14-18, Philadelphia) 2005, Abst.
14. Yu, M.J. Structurally simplified analogs of halichondrin B: Discovery of E7389, a highly potent anticancer agent. 224th ACS Natl Meet (Aug 18-22, Boston) 2002, Abst MEDI 238.
15. Towle, M.J., Salvato, K.A., Budrow, J. et al. Highly potent in vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogs of halichonrin B. Proc Am Assoc Cancer Res (AACR) 2000, 41: Abst 1370.
16. Towle, M.J., Salvato, K.A., Budrow, J. et al. In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin. Cancer Res 2001, 61(3): 1013-21.
17. Okouneva, T., Wilson, L., Littelfield, B.A., Jordan, M.A. E7389 and ER-076349, synthetic halichondrin B analogs, suppress centromere dynamics in concert with mitotic block. Proc Am Assoc Cancer Res (AACR) 2001, 45: Abst 5436.
18. Jordan, M.A., Kamath, K., Manna, T. et al. The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth. Mol Cancer Ther 2005, 4(7): 1086-95.
19. Kamath, K., Okouneva, T., Miller, H. et al. E7389, a synthetic analog of halichondrin B, suppresses microtubule dynamics in living MCF7 cells by a novel mechanism. Proc Am Assoc Cancer Res (AACR) 2003, 44(2nd Ed.): Abst LB-43.
20. Towle, M.J., Salvato, K.A., Budrow, J. et al. In vivo anticancer activity of synthetic halichondrin B macrocyclic ketone analogs ER-076349 and ER-086526 correlates with ability to induce irreversible mitotic blocks. Proc Am Assoc Cancer Res (AACR) 2001, 42: Abst 1976.
21. Kuznetsov, G., Towle, M.J., Cheng, H. et al. Induction of morphological and biochemical apoptosis following prolonged mitotic blockage by halichondrin B macrocyclic ketone analog E7389. Cancer Res 2004, 64(16): 5760-6.
22. Budman, D.R., Calabro, A., Littlefield, B.A. Synergistic combinations of E7389 (halichondrin B analogue) with conventional agents: In vitro median effect analysis in cell lines with potential clinical implications. 27th Annu San Antonio Breast Cancer Symp (Dec 8-11, San Antonio) 2004, Abst 6055.
23. Towle, M.J., Agoulnik, S., Kuznetsov, G. et al. In vivo efficacy of E7389, a synthetic analog of the marine sponge antitubulin agent halichondrin B, against human tumor xenografts under monotherapy and combination therapy conditions. Proc Am Assoc Cancer Res (AACR) 2003, 44(2nd Ed.): Abst 2749.
24. Alley, M.C., Smith, A.C., Donohue, S.J., Schweikart, K.M., Newman, D.J., Tomaszewski, J.E. Comparison of the relative efficacies and toxicities of halichondrin B analogues. 17th AACR-NCI-EORTC Int Conf Mol Targets Cancer Ther (Nov 14-18, Philadelphia) 2005, Abst C230.
25. Rhie, J.K., Lin, T-H., Johnson, J.D. et al. Preclinical pharmacokinetics of halichondrin macrocyclic ketone analog E7389 (NSC-707389) in rats and dogs. Proc Am Assoc Cancer Res (AACR) 2002, 43: Abst 1066.
26. Synold, T.W., Morgan, R.J., Newman, E.M et al. A phase I pharmacokinetic and target validation study of the novel anti-tubulin agent E7389: A California Cancer Consortium trial. 41st Annu Meet Am Soc Clin Oncol (ASCO) (May 13-17, Orlando), 2005, Abst 3036.
27. Synold, T.W., Lawrence, J., Xi, B., Colevas, A.D., Lewis, M.D., Doroshow, J.H. Human pharmacokinetics of E7389 (halichondrin B analog), a novel antimicrotubule agent undergoing phase I investigation in the California Cancer Consortium (CCC). Proc Am Soc Clin Oncol (ASCO) 2003, 22: Abst 575.
28. Wong, N., Desjardins, C., Silberman, S., Lewis, M. Pharmacokinetics (PK) of E7389, a halichondrin B analog with novel anti-tubulin activity: Results of two phase I studies with different schedules of administration. 41st Annu Meet Am Soc Clin Oncol (ASCO) (May 13-17, Orlando) 2005, Abst 2013.
29. Rubin, E.H., Rosen, L., Rajeev, V., Wiggins, L., Sicam, J., Silberman, S., Shapiro, G. Phase I study of E7389 administered by 1 hour infusion every 21 days. 41st Annu Meet Am Soc Clin Oncol (ASCO) (May 13-17, Orlando) 2005, Abst 2054.
30. Tosca, P., Bollinger, L.H., Merrill, J.W., Ryan, M.J., Turner, N.A., Smith, A.C., Lewis, M. Preclinical toxicology studies for halichondrin B macrocylic ketone analog E7389 (NSC-707389) in beagle dogs and rats. Proc Am Assoc Cancer Res (AACR) 2002, 43: Abst 5422.
31. Desai, K.K., Goel, S., Mita, A. et al. Dose escalation and pharmacokinetic (pk) study of E 7389, a microtubule-binding drug in patients (pts) with advanced solid tumors. 41st Annu Meet Am Soc Clin Oncol (ASCO) (May 13-17, Orlando) 2005, Abst 3090.
32. Blum, J., Forero, L., Heiskala, M.K. et al. E7389, a novel anti-tubulin, in patients with refractory breast cancer. 42nd Annu Meet Am Soc Clin Oncol (ASCO) (June 3-6, Atlanta) 2006, Abst 653.
33. Blum, J.L., Pruitt, B., Fabian, J. et al. Phase II study of eribulin mesylate (E7389) halichondrin B analog in patients with refractory breast cancer. J Clin Oncol [43rd Annu Meet Am Soc Clin Oncol (ASCO) (June 1-5, Chicago) 2007] 2007, 25(18, Suppl.): Abst 1034.
34. Silberman, S.L., O'Shaughnessy, J., Vahdat, L. et al. E7389, a novel anti-tubulin, is safe and effective in patients with refractory breast cancer. 28th Annu San Antonio Breast Cancer Symp (Dec 8-11, San Antonio) 2005, Abst 1063.
35. Das, A., Spira, A., Iannotti, N. et al. A phase II study of a novel anti-tubulin, E7389, in patients with advanced non-small cell lung cancer (NSCLC). 42nd Annu Meet Am Soc Clin Oncol (ASCO) (June 3-6, Atlanta) 2006, Abst 7106.
36. Spira, A.I., Iannotti, N.O., Savin, M.A. et al. Phase II study of eribulin mesylate (E7389), a mechanistically novel inhibitor of microtubule dynamics, in patients with advanced non-small lung cancer (NSCLC). J Clin Oncol [43rd Annu Meet Am Soc Clin Oncol (ASCO) (June 1-5, Chicago) 2007] 2007, 25(18, Suppl.): Abst 7546.
37. A dose-finding study of E7389 in combination with carboplatin in patients with solid tumors (NCT00268905). ClinicalTrials.gov Web site, August 10, 2007.
38. E7389 and gemcitabine in treating patients with metastatic solid tumors or solid tumors that cannot be removed by surgery (NCT00410553). ClinicalTrials.gov Web site, August 10, 2007.
39. E7389 in treating patients with locally advanced or metastatic cancer of the urothelium and kidney dysfunction (NCT00365157). ClinicalTrials.gov Web site, August 10, 2007.
40. E7389 in hormone refractory prostate cancer with advanced and/or metastatic disease stratified by prior chemotherapy (NCT00278993). ClinicalTrials.gov Web site, August 10, 2007.
41. E7389 in treating patients with metastatic prostate cancer that did not respond to hormone therapy (NCT00337077). ClinicalTrials.gov Web site, August 10, 2007.
42. E7389 in treating patients with recurrent ovarian epithelial, primary peritoneal cavity, or fallopian tube cancer (NCT00334893). ClinicalTrials.gov Web site, August 10, 2007.
43. E7389 as second-line therapy in treating patients with locally advanced, unresectable, or metastatic pancreatic cancer (NCT00383760). ClinicalTrials.gov Web site, August 10, 2007.
44. E7389 in treating patients with metastatic or recurrent head and neck cancer (NCT00337129). ClincalTrials.gov Web site, August 10, 2007.
45. E7389 in treating patients with recurrent or progressive stage IHB or stage IV non-small cell lung cancer (NCT00400829). ClinicalTrials.gov Web site, August 10, 2007.
46. E7389 administered as an IV bolus infusion day 1 and day 8 every 3 weeks in pre-treated patients with advanced and/or metastatic soft tissue sarcoma (NCT00413192). ClinicalTrials.gov Web site, August 10, 2007.
47. A multi center study of E7389 versus treatment of physician's choice in locally recurrent or metastatic breast cancer (NCT00388726). ClinicalTrials.gov Web site, August 10, 2007.
48. E7389 versus capecitabine in patients with locally advanced or metastatic breast cancer previously treated with anthracyclines and taxanes and refractory to the most recent chemotherapy (NCT00337013). ClinicalTrials.gov Web site, August 10, 2007.
49. Verdier-Pinard, P., Bai, R., Yu, MJ., Littlefield, B.A., Hamel, E. Interaction of ER-086526, anew synthetic halichondrin B analog, with tubulin. Mol Biol Cell 2000, 11 (Suppl.): 188a.
50. Kuznetsov, G., Towle, M.J., Cheng, T. et al. Induction of morphological and biochemical apoptosis following prolonged mitotic blockage by E7389, a macrocyclic ketone analog of halichondrin B. Proc Am Assoc Cancer Res (AACR) 2002, 43: Abst 1318.
51. Zhang, W., Seletsky, B.M., Palme, M.H. et al. Structure-activity relationships of synthetic halichondrin B analog E7389: In vitro susceptibility to PgP-mediated drug efflux. Proc Am Assoc Cancer Res (AACR) 2003, 44(2nd Ed.): Abst 2751.
52. Agoulnik, S., Kuznetsov, G., Tendyke, K. et al. Sensitivity to halichondrin analog E7389 and hemisterlin analog E7974 correlates with βIII tubulin isotype expression in human breast cancer cell lines. 41st Annu Meet Am Soc Clin Oncol (ASCO) (May 13-17, Orlando) 2005, Abst 2012.
53. Dabydeen, D.A., Burnett, J.C., Bai, R. et al. Comparison of the activities of the truncated halichondrin B analog NSC 707389 (E7389) with those of the parent compound and a proposed binding site on tubulin. Mol Pharmacol 2006, 70(6): 1866-75.
54. Dabydeen, D.A., Littlefield, B.A., Hamel, E. Comparative analysis of the effects of halichondrin B and its simplified, synthetic analog NSC 707389 (E7389) on endothelial cell growth, microtubule morphology, and gene expression. Proc Am Assoc Cancer Res (AACR) 2002, 43: Abst 5741.
55. Zhang, Z.-Y., King, B.M., Pelletier, R.D., Wong, Y.N. Characterization of in vitro metabolism of an anticancer agent E7389: Prediction of the potential risk of clinical drug-drug interactions. Drug Metab Rev 2003, 35(Suppl. 2): Abst 367.