1. Cell Cycle/DNA Damage
    Cytoskeleton
  2. Microtubule/Tubulin

Ixabepilone (Synonyms: Azaepothilone B; BMS 247550; BMS 247550-1)

Cat. No.: HY-10222 Purity: >95.0%
Data Sheet SDS Handling Instructions

Ixabepilone is an orally bioavailable microtubule inhibitor, which binds to tubulin and promotes tubulin polymerization and microtubule stabilization, thereby arrests cells in the G2-M phase of the cell cycle and induces tumor cell apoptosis.

For research use only. We do not sell to patients.
Ixabepilone Chemical Structure

Ixabepilone Chemical Structure

CAS No. : 219989-84-1

Size Price Stock Quantity
10 mM * 1 mL in DMSO $279 In-stock
5 mg $250 In-stock
10 mg $440 In-stock
50 mg $1500 In-stock
100 mg   Get quote  
200 mg   Get quote  

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Description

Ixabepilone is an orally bioavailable microtubule inhibitor, which binds to tubulin and promotes tubulin polymerization and microtubule stabilization, thereby arrests cells in the G2-M phase of the cell cycle and induces tumor cell apoptosis.

In Vitro

BMS-247550 is a highly potent cytotoxic agent capable of killing cancer cells at low nanomolar concentrations and retains its antineoplastic activity against human cancers that are naturally insensitive to paclitaxel or that have developed resistance to paclitaxel[1].

In Vivo

BMS-247550 demonstrates antitumor activity that is superior to paclitaxel in both paclitaxel-resistant and -sensitive tumors. BMS-247550 is more efficacious than paclitaxel in all five paclitaxel-resistant tumors evaluated in this study (four human and one murine): the clinically derived paclitaxel resistant Pat-7 ovarian carcinoma, the A2780Tax ovarian carcinoma that is resistant to paclitaxel because of tubulin mutations, the HCT116/VM46 MDR colon carcinoma, the clinically derived paclitaxel-resistant Pat-21 breast carcinoma, and the murine fibrosarcoma M5076. Against three paclitaxel-sensitive human tumor xenografts, BMS-247550 produces antitumor activity equivalent to paclitaxel: A2780 human ovarian carcinoma, HCT116, and LS174T human colon carcinoma[1].

Clinical Trial
NCT Number Sponsor Condition Start Date Phase
NCT03093155 Yale University|R-Pharm US, Inc. Epithelial Ovarian Cancer|Fallopian Tube Cancer|Primary Peritoneal Cancer April 3, 2017 Phase 2
NCT01018966 R-Pharm Solid Tumors April 2004 Phase 1
NCT00683904 R-Pharm Non-small Cell Lung Cancer (NSCLC) June 2008 Phase 1
NCT01818999 University of Texas Southwestern Medical Center METASTATIC BREAST CANCER August 2013 Phase 2
NCT01012362 Masonic Cancer Center, University of Minnesota|GlaxoSmithKline Breast Cancer|Lung Cancer|Colon Cancer|Pancreatic Cancer|Head and Neck Cancer|Kidney Cancer|Sarcoma|Hepatocellular Cancer December 2009 Phase 1
NCT00633464 R-Pharm Triple Negative Locally Advanced Non-resectable Breast Cancer|Metastatic Breast Cancer June 2008 Phase 2
NCT01027208 R-Pharm Metastatic Breast Cancer December 2006 Phase 2
NCT00924066 National Cancer Institute (NCI)|National Institutes of Health Clinical Center (CC) Cervical Carcinoma|Cervical Adenocarcinoma|Cervical Adenosquamous Carcinoma|Cervical Carcinoma, Non-SquamousType November 2008 Phase 2
NCT00983801 R-Pharm Stomach Neoplasms November 2009 Phase 2
NCT01057212 Providence Health & Services|Genentech, Inc.|Bristol-Myers Squibb Non-squamous Non-small Cell Lung Cancer February 2010 Phase 2
NCT00924352 Accelerated Community Oncology Research Network|Bristol-Myers Squibb Metastatic Breast Cancer June 2009 Phase 1|Phase 2
NCT00331643 National Cancer Institute (NCI) Adult Rhabdomyosarcoma|Adult Synovial Sarcoma|Alveolar Childhood Rhabdomyosarcoma|Childhood Synovial Sarcoma|Embryonal Childhood Rhabdomyosarcoma|Previously Treated Childhood Rhabdomyosarcoma|Recurrent Adult Soft Tissue Sarcoma|Recurrent Childhood Rhabdomyosarcoma|Recurrent Childhood Soft Tissue Sarcoma|Recurrent Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor|Recurrent Neuroblastoma|Recurrent Osteosarcoma|Recurrent Wilms Tumor and Other Childhood Kidney Tumors April 2006 Phase 2
NCT00672009 Cedars-Sinai Medical Center|Bristol-Myers Squibb Prostatic Diseases|Genital Neoplasms, Male|Urogenital Neoplasms|Genital Diseases, Male|Adenocarcinoma|Prostatic Neoplasms|Neoplasms, Glandular and Epithelial|Carcinoma April 2008 Phase 2
NCT00095979 National Cancer Institute (NCI) Endometrial Adenocarcinoma|Recurrent Endometrial Carcinoma|Stage IV Endometrial Carcinoma May 2005 Phase 2
NCT00751868 Consorzio Oncotech Breast Cancer September 2008 Phase 2
NCT00877500 M.D. Anderson Cancer Center|Bristol-Myers Squibb Breast Cancer April 2009 Phase 2
NCT00593827 R-Pharm|US Oncology Research Metastatic Breast Cancer May 2008 Phase 2
NCT01019577 R-Pharm Metastatic Breast Cancer October 2005 Phase 2
NCT00309049 R-Pharm Cancer April 2006 Phase 1|Phase 2
NCT01220609 National Cancer Institute (NCI) Recurrent Uterine Corpus Sarcoma|Uterine Corpus Leiomyosarcoma November 2010 Phase 2
NCT00568022 R-Pharm Breast Cancer February 2008 Phase 1
NCT00362830 Bristol-Myers Squibb Cancer August 2006 Phase 1
NCT01075100 US Oncology Research|Bristol-Myers Squibb Metastatic Breast Cancer January 2010 Phase 2
NCT00207090 R-Pharm Advanced Solid Tumors|Neoplasms September 2005 Phase 1
NCT00717704 Washington Hospital Center|Bristol-Myers Squibb Solid Tumor July 2008 Phase 1
NCT00825734 SCRI Development Innovations, LLC|Bayer|Bristol-Myers Squibb Metastatic Breast Cancer March 2009 Phase 1|Phase 2
NCT01168232 National Cancer Institute (NCI) Recurrent Uterine Sarcoma|Uterine Carcinosarcoma September 2010 Phase 2
NCT00058019 National Cancer Institute (NCI) Anaplastic Large Cell Lymphoma|Recurrent Adult Burkitt Lymphoma|Recurrent Adult Diffuse Large Cell Lymphoma|Recurrent Adult Diffuse Mixed Cell Lymphoma|Recurrent Grade 3 Follicular Lymphoma|Recurrent Mantle Cell Lymphoma February 2003 Phase 2
NCT00828308 Brown University|Rhode Island Hospital|The Miriam Hospital Prostate Cancer February 2009 Phase 2
NCT01375829 National Cancer Institute (NCI) Adult Solid Neoplasm June 27, 2011 Phase 1
NCT00021099 National Cancer Institute (NCI) Distal Urethral Cancer|Metastatic Transitional Cell Cancer of the Renal Pelvis and Ureter|Proximal Urethral Cancer|Recurrent Bladder Cancer|Recurrent Transitional Cell Cancer of the Renal Pelvis and Ureter|Recurrent Urethral Cancer|Regional Transitional Cell Cancer of the Renal Pelvis and Ureter|Stage III Bladder Cancer|Stage IV Bladder Cancer|Transitional Cell Carcinoma of the Bladder|Urethral Cancer Associated With Invasive Bladder Cancer June 2001 Phase 2
NCT00632424 R-Pharm Advanced Solid Tumors May 2008 Phase 1
NCT00804310 University of California, Davis|National Cancer Institute (NCI)|Genentech, Inc.|Bristol-Myers Squibb Unspecified Adult Solid Tumor, Protocol Specific August 2009 Phase 1
NCT00821886 SCRI Development Innovations, LLC|Bristol-Myers Squibb|Genentech, Inc. Breast Cancer February 2009 Phase 2
NCT00025155 National Cancer Institute (NCI) Primary Peritoneal Cavity Cancer|Recurrent Ovarian Epithelial Cancer July 2002 Phase 2
NCT00627978 Weill Medical College of Cornell University|Bristol-Myers Squibb Metastatic Breast Cancer November 2007 Phase 2
NCT00884676 Jaime Merchan|Bristol-Myers Squibb|Pfizer|University of Miami Unspecified Adult Solid Tumor, Protocol Specific November 2008 Phase 1
NCT00923130 National Cancer Institute (NCI)|National Institutes of Health Clinical Center (CC) Renal Cell Carcinoma December 2008 Phase 2
NCT00866905 SCRI Development Innovations, LLC|Bristol-Myers Squibb Breast Cancer April 2009 Phase 2
NCT00383149 R-Pharm Metastatic Pancreatic Cancer January 2007 Phase 2
NCT00182767 National Cancer Institute (NCI) Fallopian Tube Cancer|Female Reproductive Cancer|Recurrent Breast Cancer|Recurrent Ovarian Epithelial Cancer|Stage III Ovarian Epithelial Cancer|Stage IV Breast Cancer|Stage IV Ovarian Epithelial Cancer January 2006 Phase 1|Phase 2
NCT01170871 University of Southern California Advanced Solid Tumors Phase 1
NCT00033618 National Cancer Institute (NCI) Metastatic Squamous Neck Cancer With Occult Primary Squamous Cell Carcinoma|Recurrent Metastatic Squamous Neck Cancer With Occult Primary|Recurrent Salivary Gland Cancer|Recurrent Squamous Cell Carcinoma of the Hypopharynx|Recurrent Squamous Cell Carcinoma of the Larynx|Recurrent Squamous Cell Carcinoma of the Lip and Oral Cavity|Recurrent Squamous Cell Carcinoma of the Oropharynx|Recurrent Squamous Cell Carcinoma of the Paranasal Sinus and Nasal Cavity|Recurrent Verrucous Carcinoma of the Laryn November 2002 Phase 2
NCT00546364 R-Pharm Breast Neoplasms February 2008 Phase 2
NCT00182702 National Cancer Institute (NCI) Clear Cell Renal Cell Carcinoma|Recurrent Renal Cell Cancer|Stage III Renal Cell Cancer|Stage IV Renal Cell Cancer July 2005 Phase 2
NCT00087139 National Cancer Institute (NCI) Adenocarcinoma of the Prostate|Recurrent Prostate Cancer|Stage IV Prostate Cancer September 2004 Phase 2
NCT00028561 National Cancer Institute (NCI) Unspecified Adult Solid Tumor, Protocol Specific October 2001 Phase 1
NCT01097642 Jenny C. Chang, MD|Bristol-Myers Squibb|The Methodist Hospital System Breast Cancer October 2008 Phase 2
NCT00634088 R-Pharm|GlaxoSmithKline Locally Advanced or Metastatic Breast Cancer June 2008 Phase 1
NCT00832117 R-Pharm Non Small Cell Lung Cancer May 2009 Phase 1
NCT00370552 R-Pharm Metastatic Breast Cancer March 2007 Phase 2
NCT00022542 National Cancer Institute (NCI) Recurrent Adult Soft Tissue Sarcoma|Stage III Adult Soft Tissue Sarcoma|Stage IV Adult Soft Tissue Sarcoma June 2001 Phase 2
NCT00331344 National Cancer Institute (NCI) Adenocarcinoma of the Prostate|Recurrent Prostate Cancer|Stage IV Prostate Cancer April 2006 Phase 1|Phase 2
NCT00096317 Albert Einstein College of Medicine, Inc.|National Cancer Institute (NCI) Unspecified Adult Solid Tumor, Protocol Specific March 2003 Phase 1|Phase 2
NCT00079326 National Cancer Institute (NCI) HER2-positive Breast Cancer|Recurrent Breast Cancer|Stage IV Breast Cancer January 2004 Phase 2
NCT00490646 R-Pharm Metastatic Breast Cancer February 2008 Phase 2
NCT00723957 R-Pharm Advanced/Metastatic Non-Small Cell Lung Cancer December 2008 Phase 2
NCT00883116 R-Pharm Endometrial Cancer August 2009 Phase 3
NCT00030108 National Institutes of Health Clinical Center (CC)|National Cancer Institute (NCI) Brain and Central Nervous System Tumors|Childhood Germ Cell Tumor|Extragonadal Germ Cell Tumor|Kidney Cancer|Leukemia|Liver Cancer|Neuroblastoma|Ovarian Cancer|Sarcoma|Unspecified Childhood Solid Tumor, Protocol Specific November 2001 Phase 1
NCT00741988 SCRI Development Innovations, LLC|Bristol-Myers Squibb|Genentech, Inc. Non-Small Cell Lung Cancer September 2008 Phase 2
NCT00077376 National Cancer Institute (NCI) HER2-positive Breast Cancer|Male Breast Cancer|Recurrent Breast Cancer|Stage IV Breast Cancer March 2005 Phase 2
NCT00162136 R-Pharm Solid Malignancies September 2005 Phase 1
NCT00765765 University of Medicine and Dentistry of New Jersey|National Cancer Institute (NCI)|Rutgers, The State University of New Jersey Breast Cancer February 2009 Phase 1|Phase 2
NCT00023946 National Cancer Institute (NCI) Adult Primary Cholangiocellular Carcinoma|Adult Primary Hepatocellular Carcinoma|Advanced Adult Primary Liver Cancer|Cholangiocarcinoma of the Extrahepatic Bile Duct|Cholangiocarcinoma of the Gallbladder|Localized Extrahepatic Bile Duct Cancer|Localized Gallbladder Cancer|Localized Resectable Adult Primary Liver Cancer|Localized Unresectable Adult Primary Liver Cancer|Recurrent Adult Primary Liver Cancer|Recurrent Extrahepatic Bile Duct Cancer|Recurrent Gallbladder Cancer|Unresectable Extrahepat August 2001 Phase 2
NCT00790894 Hellenic Cooperative Oncology Group Metastatic Breast Cancer November 2008 Phase 2
NCT00082433 R-Pharm Cancer|Breast Cancer November 2003 Phase 3
NCT00422097 R-Pharm Cancer January 2007 Phase 1
NCT00207129 R-Pharm Advanced Solid Tumors|Neoplasms October 2004 Phase 1
NCT00045097 National Cancer Institute (NCI) Breast Cancer May 2002 Phase 2
NCT00080262 R-Pharm Breast Cancer|Metastases February 2004 Phase 2
NCT00998101 UNC Lineberger Comprehensive Cancer Center|National Cancer Institute (NCI) Lung Cancer July 2009 Phase 2
NCT00322374 R-Pharm Metastatic Breast Cancer August 2006 Phase 1
NCT01084057 City of Hope Medical Center Male Breast Cancer|Recurrent Breast Cancer|Stage IV Breast Cancer May 17, 2010 Phase 1
NCT00879086 Eisai Inc. Breast Cancer March 2009 Phase 2
NCT00455533 Bristol-Myers Squibb Breast Cancer October 2007 Phase 2
NCT00998738 Mayo Clinic|National Cancer Institute (NCI) Neuropathy|Pain|Recurrent Breast Carcinoma|Stage IV Breast Cancer November 2009 Phase 3
NCT00058084 National Cancer Institute (NCI) Adenocarcinoma of the Prostate|Recurrent Prostate Cancer|Stage IV Prostate Cancer March 2003 Phase 2
NCT00070096 Memorial Sloan Kettering Cancer Center|National Cancer Institute (NCI) Brain and Central Nervous System Tumors|Extragonadal Germ Cell Tumor|Ovarian Cancer|Testicular Germ Cell Tumor August 2003 Phase 2
NCT00030706 Albert Einstein College of Medicine, Inc.|National Cancer Institute (NCI) Ovarian Cancer|Peritoneal Cavity Cancer November 2004 Phase 2
NCT00052572 Memorial Sloan Kettering Cancer Center|National Cancer Institute (NCI) Leukemia|Lymphoma October 2002 Phase 2
NCT00785291 National Cancer Institute (NCI) Estrogen Receptor Negative|Estrogen Receptor Positive|HER2/Neu Negative|HER2/Neu Positive|Male Breast Carcinoma|Progesterone Receptor Negative|Progesterone Receptor Positive|Recurrent Breast Carcinoma|Stage IIIC Breast Cancer AJCC v6|Stage IV Breast Cancer October 2008 Phase 3
NCT00006221 National Cancer Institute (NCI) Lymphoma|Small Intestine Cancer|Unspecified Adult Solid Tumor, Protocol Specific November 2000 Phase 1
NCT00045708 National Cancer Institute (NCI) Adult Anaplastic Astrocytoma|Adult Giant Cell Glioblastoma|Adult Gliosarcoma|Recurrent Adult Brain Tumor October 2002 Phase 1|Phase 2
NCT00789581 SCRI Development Innovations, LLC|Bristol-Myers Squibb Breast Cancer December 2008 Phase 3
NCT00977574 National Cancer Institute (NCI) Endometrial Adenocarcinoma|Endometrial Adenosquamous Carcinoma|Endometrial Clear Cell Adenocarcinoma|Endometrial Serous Adenocarcinoma|Recurrent Uterine Corpus Carcinoma|Stage IIIA Uterine Corpus Cancer|Stage IIIB Uterine Corpus Cancer|Stage IIIC Uterine Corpus Cancer|Stage IVA Uterine Corpus Cancer|Stage IVB Uterine Corpus Cancer September 2009 Phase 2
NCT00033306 University of Alabama at Birmingham|National Cancer Institute (NCI) Colorectal Cancer February 2002 Phase 2
NCT01079793 Simmons Cancer Center|National Cancer Institute (NCI) Prostate Cancer May 2010 Phase 1|Phase 2
NCT00025194 Memorial Sloan Kettering Cancer Center|National Cancer Institute (NCI) Prostate Cancer July 2001 Phase 1|Phase 2
NCT00036764 National Cancer Institute (NCI) Recurrent Melanoma|Stage IV Melanoma February 2002 Phase 2
NCT00630032 UNICANCER Breast Cancer September 2007 Phase 3
NCT00057850 National Cancer Institute (NCI) Head and Neck Cancer January 2002 Phase 1|Phase 2
NCT00020904 Memorial Sloan Kettering Cancer Center|National Cancer Institute (NCI) Breast Cancer February 2001 Phase 2
NCT00016965 Southwest Oncology Group|National Cancer Institute (NCI) Pancreatic Cancer July 2001 Phase 2
NCT00004927 R-Pharm|National Cancer Institute (NCI)|Memorial Sloan Kettering Cancer Center Unspecified Adult Solid Tumor, Protocol Specific July 1999 Phase 1
NCT00017043 Bristol-Myers Squibb|National Cancer Institute (NCI) Esophageal Cancer|Gastric Cancer February 2001 Phase 2
NCT00016393 Southwest Oncology Group|National Cancer Institute (NCI) Prostate Cancer June 2001 Phase 2
NCT00005807 Albert Einstein College of Medicine, Inc.|National Cancer Institute (NCI) Breast Cancer|Ovarian Cancer|Unspecified Adult Solid Tumor, Protocol Specific July 2000 Phase 1
NCT00017056 Memorial Sloan Kettering Cancer Center|National Cancer Institute (NCI) Esophageal Cancer|Gastric Cancer February 2001 Phase 2
NCT01349088 Sidney Kimmel Cancer Center at Thomas Jefferson University|Susan G. Komen Breast Cancer Foundation|Amgen|Thomas Jefferson University Breast Cancer|Metastatic Breast Cancer|Stage IV Breast Cancer December 2013 Phase 1|Phase 2
NCT00080301 R-Pharm Breast Cancer|Metastases September 2003 Phase 3
NCT00043095 Memorial Sloan Kettering Cancer Center|National Cancer Institute (NCI) Unspecified Adult Solid Tumor, Protocol Specific June 2002 Phase 1
NCT00049244 R-Pharm|National Cancer Institute (NCI) Breast Cancer September 2002 Phase 1
NCT01416389 Eli Lilly and Company Metastatic Breast Cancer August 2011 Phase 2
NCT00637897 Wake Forest University Health Sciences|National Cancer Institute (NCI) Breast Cancer March 2008 Phase 1
NCT00798252 Bristol-Myers Squibb Advanced Cancer March 2009 Phase 1
NCT01446016 Jenny C. Chang, MD|The Methodist Hospital System Breast Neoplasms|Breast Cancer September 2011 Phase 2
NCT02915744 Nektar Therapeutics Metastasis|Breast Cancer November 2016 Phase 3
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References
Preparing Stock Solutions
Concentration Volume (DMSO) Mass 1 mg 5 mg 10 mg
1 mM 1.9736 mL 9.8678 mL 19.7355 mL
5 mM 0.3947 mL 1.9736 mL 3.9471 mL
10 mM 0.1974 mL 0.9868 mL 1.9736 mL
Kinase Assay
[1]

The potency with which BMS-247550 and paclitaxel polymerize tubulin isolated from calf brain is evaluated by Published techniques. Briefly, different concentrations of paclitaxel or BMS-247550 in polymerization buffer [0.1 M mes, 1 mM EGTA, 0.5 mM MgCl2 (pH 6.6)] are added to tubulin in polymerization buffer at 37°C in microcuvette wells of a Beckman. Model DU 7400 UV spectrophotometer. A final microtubule protein concentration of 1.0 mg/mL and compound concentrations of generally 2.5, 5.0, and 10 μM are used. Initial slopes of absorbance (A280 nM) change, measured every 10 s, are calculated by the software program accompanying the instrument.

Cell Assay
[1]

BMS-247550 is dissolved in 100% DMSO.

HCT116 cells from cultures are collected by trypsinization after 1, 2, 4, 8, 16, and 24 h exposure to 7.5 nm of BMS-247550. Cells are pelleted and fixed in 80% ethanol at −20°C. After an overnight storage at −20°C, cells are rehydrated with PBS buffer and DNA stain by incubation with propidium iodide (5 μg/mL) in 0.1% RNase for 15-30 min. Fluorescence-activated cell sorter acquisition is performed using the FACS Calibur instrument and analysis is done using Cellquest and Modfit software.

References
M.Wt

506.7

Formula

C₂₇H₄₂N₂O₅S

CAS No.

219989-84-1

Storage
Powder -20°C 3 years
  4°C 2 years
In solvent -80°C 6 months
  -20°C 1 month
Shipping

Room temperature in continental US; may vary elsewhere

Solvent & Solubility

10 mM in DMSO

* "<1 mg/mL" means slightly soluble or insoluble. "≥" means soluble, but saturation unknown.

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Ixabepilone
Cat. No.:
HY-10222
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