IxabepiloneEpothilone B analog;microtubule-stabilizing agent CAS# 219989-84-1 |
Quality Control & MSDS
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| Cas No. | 219989-84-1 | SDF | Download SDF |
| PubChem ID | 6445540 | Appearance | Powder |
| Formula | C27H42N2O5S | M.Wt | 506.7 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Azaepothilone B; BMS 247550; BMS 247550-1 | ||
| Solubility | DMSO : 83.33 mg/mL (164.46 mM; Need ultrasonic) | ||
| Chemical Name | (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione | ||
| SMILES | CC1CCCC2(C(O2)CC(NC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C)C | ||
| Standard InChIKey | FABUFPQFXZVHFB-PVYNADRNSA-N | ||
| Standard InChI | InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| 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]. References: | |||||
Ixabepilone Dilution Calculator
Ixabepilone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.9736 mL | 9.8678 mL | 19.7355 mL | 39.4711 mL | 49.3389 mL |
| 5 mM | 0.3947 mL | 1.9736 mL | 3.9471 mL | 7.8942 mL | 9.8678 mL |
| 10 mM | 0.1974 mL | 0.9868 mL | 1.9736 mL | 3.9471 mL | 4.9339 mL |
| 50 mM | 0.0395 mL | 0.1974 mL | 0.3947 mL | 0.7894 mL | 0.9868 mL |
| 100 mM | 0.0197 mL | 0.0987 mL | 0.1974 mL | 0.3947 mL | 0.4934 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Ixabepilone (Azaepothilone B; BMS 247550; BMS 247550-1; Ixempra) is an epothilone B analog and nontaxane microtubule-stabilizing compound with clinical activity in a range of solid tumors.
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Systematic review of ixabepilone for treating metastatic breast cancer.[Pubmed:27491426]
Breast Cancer. 2017 Mar;24(2):171-179.
BACKGROUND: Ixabepilone is now a Food and Drug Administration-approved therapeutic option for patients with metastatic breast cancer (MBC) whose disease has progressed despite prior anthracycline and taxane therapy. We conducted a systematic review and meta-analysis to systematically evaluate the efficacy and safety of Ixabepilone for treating metastatic breast cancer. METHODS: A systematic review and meta-analysis were conducted. Randomized controlled studies applying Ixabepilone for treating MBC were included. The primary outcome was Overall Survival (OS). The authors of primary articles were contacted and methodological quality was evaluated. Subgroups were drawn based on intervention measures; heterogeneity and bias were discussed. RESULTS: Eight studies with 5247 patients were included. Compared with a weekly schedule, a triweekly schedule of Ixabepilone was better at improving overall response rate (ORR), while there were no differences in improving OS and progression-free survival (PFS). Ixabepilone plus capecitabine was superior to capecitabine monotherapy in improving OS, PFS and ORR. Paclitaxel was more effective than Ixabepilone in terms of OS and PFS. There was no difference in the improvement of ORR, clinical benefit rate (CBR) and disease control rate (DCR) between Ixabepilone and eribulin. CONCLUSIONS: Current evidence suggests that a triweekly schedule of Ixabepilone is more effective than weekly dosing in improving ORR. Use of Ixabepilone in combination with capecitabine possesses superior clinical efficacy to the use of capecitabine alone. Paclitaxel was more effective than Ixabepilone in terms of OS and PFS. The efficacy and safety between Ixabepilone and eribulin were identical.
Chemotherapy reaction induced by ixabepilone, a microtubule stabilizing agent, mimicking extramammary Paget's disease in a patient with breast carcinoma.[Pubmed:27686876]
J Cutan Pathol. 2016 Dec;43(12):1215-1219.
The histopathologic characteristics of reactions caused by the many novel anticancer agents are under-recognized. We report a case of a 67-year-old female with locally advanced metastatic breast cancer, who initially presented with an extensive reticulated erythematous patch on the trunk caused by intravascular metastases confirmed by a skin biopsy. Owing to disease progression, she was started on Ixabepilone, a mitotic inhibitor. While receiving Ixabepilone, another skin biopsy was obtained and initially interpreted as extramammary Paget's disease. However, the biopsy showed metaphase arrest of numerous keratinocytes in the basilar and suprabasilar epidermis. Atypical epithelial cells were only present in the intravascular spaces similar to the initial biopsy. Given the temporal association between the initiation of Ixabepilone therapy and the epidermal mitotic arrest, a diagnosis of chemotherapy reaction to Ixabepilone was rendered. Ixabepilone is an analog of epothilone, a microtubule stabilizer causing mitotic arrest of the cell cycle approved for the treatment of metastatic and locally advanced treatment-resistant breast cancer. The demonstration of epidermal mitotic arrest caused by Ixabepilone is without precedent. The case emphasizes the importance of considering a chemotherapy reaction in the histologic differential diagnosis of epidermal mitotic arrest in a cancer patient receiving chemotherapy.
Ixabepilone for the treatment of endometrial cancer.[Pubmed:26949829]
Expert Opin Investig Drugs. 2016;25(5):613-8.
INTRODUCTION: Endometrial cancer (EC) is the most common gynaecological cancer. Despite significant progress in the multimodality treatment approach, the prognosis remains poor for patients with advanced disease. Thus, there is the necessity of more effective strategies. The microtubule-stabilizing agent Ixabepilone is the first drug in this new class of agents that has been approved for metastatic breast cancer treatment. Based on empiric data and on the clinical efficacy demonstrated in breast cancer, several clinical trials were proposed to define its role in EC. The aim of this review is to determine whether Ixabepilone improved the clinical outcome in patients with locally advanced, recurrent or metastatic EC. AREAS COVERED: Preclinical and clinical studies of Ixabepilone in endometrial cancer were analyzed and discussed. Data were obtained by searching for English peer-reviewed articles on PubMed, phase I and II studies registered on clincaltrials.gov, and related abstracts recently presented at major international congresses. EXPERT OPINION: Advanced or recurrent EC still represents a challenge and an unmet need in the panorama of gynaecological malignancies. Ixabepilone's future therapeutic role in EC remains ill defined. Nevertheless, despite its limited efficacy in EC, clinicians treating gynaecological tumours should be aware of its main aspects.
A phase II evaluation of ixabepilone in the treatment of recurrent/persistent carcinosarcoma of the uterus, an NRG Oncology/Gynecologic Oncology Group study.[Pubmed:28029447]
Gynecol Oncol. 2017 Jan;144(1):101-106.
BACKGROUND: The primary objectives were to determine the objective response rate (ORR) and safety profile of Ixabepilone in women with recurrent or persistent uterine carcinosarcoma (UCS). Secondary objectives included progression-free survival (PFS) and overall survival (OS). Exploratory translational objectives included characterization of class III beta tubulin expression and its association with response, PFS, and OS. METHODS: Patients had measurable disease; up to two prior chemotherapeutic regimens were allowed, but must have included a taxane. Women received Ixabepilone 40mg/m(2) as a 3hour IV infusion on day 1 of a 21daycycle. Treatment was continued until disease progression or unacceptable toxicity occurred. RESULTS: Forty-two women were enrolled, with 34 eligible and evaluable. Median age was 68years. ECOG performance status was 0 in 56% of women, 38% had received radiation, and 15% had received 2 lines of chemotherapy. Overall ORR was 11.8% (4/34, 90% CI 4.2-25.1%); all were partial responses. Stable disease for at least 8weeks was achieved in 8 patients (23.5%). Median PFS and OS were 1.7mo and 7.7mo, respectively, with a median follow-up of 37mo. Six month PFS was 20.6%. Major grade>/=3 toxicities were neutropenia (47%), fatigue (15%), dehydration (15%), hypertension (15%), and hyponatremia (15%); grade 2 peripheral neuropathy was reported in 18%. In this small sample size, class III beta tubulin expression in the primary tumor was not associated with the response to Ixabepilone, PFS, or OS. CONCLUSION: In this cohort of women, single agent Ixabepilone showed modest but insufficient clinical activity.
