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Ixabepilone

Ixabepilone (INN; also known as azaepothilone B, codenamed BMS-247550) is an epothilone B analog[1] developed by Bristol-Myers Squibb as a cancer drug. It is produced by Sorangium cellulosum. On October 16, 2007, the U.S. Food and Drug Administration approved ixabepilone for the treatment of aggressive metastatic or locally advanced breast cancer no longer responding to currently available chemotherapies. In November 2008, the EMEA has refused a marketing authorisation for Ixabepilone. Ixabepilone is administered through injection, and is marketed under the trade name Ixempra.

IXEMPRA (ixabepilone) is a microtubule inhibitor belonging to a class of antineoplastic agents, the epothilones and their analogs. The epothilones are isolated from the myxobacterium Sorangium cellulosum. Ixabepilone is a semisynthetic analog of epothilone B, a 16-membered polyketide macrolide, with a chemically modified lactam substitution for the naturally existing lactone.

Ixabepilone is a semi-synthetic analog of epothilone B. Ixabepilone binds directly to β-tubulin subunits on microtubules, leading to suppression of microtubule dynamics. Ixabepilone suppresses the dynamic instability of αβ-II and αβ-III microtubules. Ixabepilone possesses low in vitro susceptibility to multiple tumor resistance mechanisms including efflux transporters, such as MRP-1 and P-glycoprotein (P-gp). Ixabepilone blocks cells in the mitotic phase of the cell division cycle, leading to cell death.

In cancer patients, ixabepilone has a plasma concentration-dependent effect on tubulin dynamics in peripheral blood mononuclear cells that is observed as the formation of microtubule bundles. Ixabepilone has antitumor activity in vivo against multiple human tumor xenografts, including drug-resistant types that overexpress P-gp, MRP-1, and βIII tubulin isoforms, or harbor tubulin mutations. Ixabepilone is active in xenografts that are resistant to multiple agents including taxanes, anthracyclines, and vinca alkaloids. Ixabepilone demonstrated synergistic antitumor activity in combination with capecitabine in vivo. In addition to direct antitumor activity, ixabepilone has antiangiogenic activity.

Current developer:  Bristol-Myers Squibb

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4: Peereboom DM, Supko JG, Carson KA, Batchelor T, Phuphanich S, Lesser G, Mikkelson T, Fisher J, Desideri S, He X, Grossman SA; The New Approaches to Brain Tumor Therapy (NABTT) Consortium. A phase I/II trial and pharmacokinetic study of ixabepilone in adult patients with recurrent high-grade gliomas. J Neurooncol. 2010 May 7. [Epub ahead of print] PubMed PMID: 20449631.

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6: Chuang E, Wiener N, Christos P, Kessler R, Cobham M, Donovan D, Goldberg GL, Caputo T, Doyle A, Vahdat L, Sparano JA. Phase I trial of ixabepilone plus pegylated liposomal doxorubicin in patients with adenocarcinoma of breast or ovary. Ann Oncol. 2010 Mar 31. [Epub ahead of print] PubMed PMID: 20357034.

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14: Yardley DA. Visceral disease in patients with metastatic breast cancer: efficacy and safety of treatment with ixabepilone and other chemotherapeutic agents. Clin Breast Cancer. 2010 Feb;10(1):64-73. Review. PubMed PMID: 20133261.

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17: Bourdeanu L, Wong SF. Supporting Asian patients with metastatic breast cancer during ixabepilone therapy. Expert Opin Drug Saf. 2010 May;9(3):383-96. PubMed PMID: 20105113.

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23: Cömezoğlu SN, Ly VT, Zhang D, Humphreys WG, Bonacorsi SJ, Everett DW, Cohen MB, Gan J, Beumer JH, Beijnen JH, Schellens HM, Lappin G. Biotransformation profiling of [(14)C]ixabepilone in human plasma, urine and feces samples using accelerator mass spectrometry (AMS). Drug Metab Pharmacokinet. 2009;24(6):511-22. PubMed PMID: 20045986.

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33: Bosch-Barrera J, Espinós J, Gómez-Ibáñez A, Gállego Pérez-Larraya J, Iriarte J. Sensory-motor axonal peripheral neuropathy in an advanced breast cancer patient treated with ixabepilone. Clin Transl Oncol. 2009 Nov;11(11):765-7. PubMed PMID: 19917541.

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50: Murphy CG, Seidman AD. Evolving approaches to metastatic breast cancer previously treated with anthracyclines and taxanes. Clin Breast Cancer. 2009 Jun;9 Suppl 2:S58-65. Review. PubMed PMID: 19596644.

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54: Dizon DS, Blessing JA, McMeekin DS, Sharma SK, Disilvestro P, Alvarez RD. Phase II trial of ixabepilone as second-line treatment in advanced endometrial cancer: gynecologic oncology group trial 129-P. J Clin Oncol. 2009 Jul 1;27(19):3104-8. Epub 2009 May 18. PubMed PMID: 19451430; PubMed Central PMCID: PMC2716935.

55: Yardley DA. Proactive management of adverse events maintains the clinical benefit of ixabepilone. Oncologist. 2009 May;14(5):448-55. Epub 2009 May 1. Review. PubMed PMID: 19411315.

56: Kurebayashi J. Possible treatment strategies for triple-negative breast cancer on the basis of molecular characteristics. Breast Cancer. 2009;16(4):275-80. Epub 2009 May 1. PubMed PMID: 19408071.

57: Morris PG, Fornier MN. Ixabepilone and other epothilones: microtubule-targeting agents for metastatic breast cancer. Clin Adv Hematol Oncol. 2009 Feb;7(2):115-22. PubMed PMID: 19367253.

58: Rosenberg JE, Ryan CJ, Weinberg VK, Smith DC, Hussain M, Beer TM, Ryan CW, Mathew P, Pagliaro LC, Harzstark AL, Sharib J, Small EJ. Phase I study of ixabepilone, mitoxantrone, and prednisone in patients with metastatic castration-resistant prostate cancer previously treated with docetaxel-based therapy: a study of the department of defense prostate cancer clinical trials consortium. J Clin Oncol. 2009 Jun 10;27(17):2772-8. Epub 2009 Apr 6. PubMed PMID: 19349545; PubMed Central PMCID: PMC2698016.

59: Reed SD, Li Y, Anstrom KJ, Schulman KA. Cost effectiveness of ixabepilone plus capecitabine for metastatic breast cancer progressing after anthracycline and taxane treatment. J Clin Oncol. 2009 May 1;27(13):2185-91. Epub 2009 Mar 30. PubMed PMID: 19332722.

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62: Gupta D, Mani S. The efficacy and safety of ixabepilone monotherapy in the treatment of breast and gynecologic malignancies. Expert Opin Drug Saf. 2009 Jan;8(1):81-8. Review. PubMed PMID: 19236220.

63: Cigler T, Vahdat L. Integrating epothilones into the treatment of patients with metastatic breast cancer: clinical perspectives on incorporating recent data in the practice setting. Clin Breast Cancer. 2008 Dec;8 Suppl 4:S166-70. Review. PubMed PMID: 19158037.

64: Hunt JT. Discovery of ixabepilone. Mol Cancer Ther. 2009 Feb;8(2):275-81. Epub 2009 Jan 27. Review. PubMed PMID: 19174552.

65: Boehnke Michaud L. The optimal therapeutic use of ixabepilone in patients with locally advanced or metastatic breast cancer. J Oncol Pharm Pract. 2009 Jun;15(2):95-106. Epub 2009 Jan 26. Review. PubMed PMID: 19171553.

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73: Weimer LH, Sachdev N. Update on medication-induced peripheral neuropathy. Curr Neurol Neurosci Rep. 2009 Jan;9(1):69-75. Review. PubMed PMID: 19080756.

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84: Halterman PA. Lapatinib and ixabepilone for the treatment of metastatic breast cancer. Pharmacotherapy. 2008 Oct;28(10):1255-66. Review. PubMed PMID: 18823221.

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93: Buzdar AU. Clinical experience with epothilones in patients with breast cancer. Clin Breast Cancer. 2008 Mar;8 Suppl 2:S71-8. Review. PubMed PMID: 18637402.

94: Andreopoulou E, Muggia F. Pharmacodynamics of tubulin and tubulin-binding agents: extending their potential beyond taxanes. Clin Breast Cancer. 2008 Mar;8 Suppl 2:S54-60. Review. PubMed PMID: 18637400.

95: Lechleider RJ, Kaminskas E, Jiang X, Aziz R, Bullock J, Kasliwal R, Harapanhalli R, Pope S, Sridhara R, Leighton J, Booth B, Dagher R, Justice R, Pazdur R. Ixabepilone in combination with capecitabine and as monotherapy for treatment of advanced breast cancer refractory to previous chemotherapies. Clin Cancer Res. 2008 Jul 15;14(14):4378-84. PubMed PMID: 18628451.

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97: Hussar DA. New drugs08, part 2. Nursing. 2008 Jul;38(7):41-8; quiz 49. PubMed PMID: 18580663.

98: Swain SM, Arezzo JC. Neuropathy associated with microtubule inhibitors: diagnosis, incidence, and management. Clin Adv Hematol Oncol. 2008 Jun;6(6):455-67. Review. PubMed PMID: 18567992.

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100: Moulder SL. Ixabepilone for the treatment of taxane-refractory breast cancer. Future Oncol. 2008 Jun;4(3):333-40. Review. PubMed PMID: 18518758.

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