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1. Azaepothilone B
2. Bms 247550
3. Bms-247550
4. Bms247550
1. Azaepothilone B
2. 219989-84-1
3. Ixempra
4. Bms-247550
5. Ixempra Kit
6. Aza-epothilone B
7. Bms 247550-1
8. Bms 247550-01
9. Nsc-747973
10. Chebi:63605
11. Bms-247550-01
12. K27005np0a
13. Nsc747973
14. Bms 247550
15. 17-oxa-4-azabicyclo(14.1.0)heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (1s,3s,7s,10r,11s,12s,16r)-
16. 1s,3s,7s,10r,11s,12s,16r)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((1e)-1-methyl-2-(2-methylthiazol-4-yl)ethenyl)-17-oxa-4-azabicyclo(14.1.0)heptadecane-5,9-dione
17. Ixabepilone [inn]
18. (1~{s},3~{s},7~{s},10~{r},11~{s},12~{s},16~{r})-8,8,10,12,16-pentamethyl-3-[(~{e})-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-7,11-bis(oxidanyl)-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
19. Ixempra (tn)
20. (1r,5s,6s,7r,10s,14s,16s)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-((e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl)-17-oxa-13-azabicyclo(14.1.0)heptadecane-8,12-dione
21. (1r,5s,6s,7r,10s,14s,16s)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-[(e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-13-azabicyclo[14.1.0]heptadecane-8,12-dione
22. Ixempra (tm)
23. 16-aza-epothilone B
24. Ixabepilone [mi]
25. Ixabepilone [jan]
26. Ixabepilone [hsdb]
27. Ixabepilone [usan]
28. Ixabepilone [vandf]
29. Schembl8386
30. Ixabepilone [mart.]
31. Ixabepilone [usp-rs]
32. Ixabepilone [who-dd]
33. Unii-k27005np0a
34. Ixabepilone (jan/usan/inn)
35. Ixabepilone [usan:inn:jan]
36. Gtpl6824
37. Schembl1890345
38. Ixabepilone (bms-247550)
39. Chembl1201752
40. Chebi:95095
41. Hsdb 7738
42. Dtxsid70870252
43. Ixabepilone [orange Book]
44. Ixabepilone [usp Monograph]
45. Ex-a1245
46. Zinc3993846
47. Bdbm50564768
48. Mfcd04307791
49. S7930
50. Akos025401600
51. Ccg-269752
52. Cs-0551
53. Db04845
54. Nsc 747973
55. Nsc-710428
56. Bms 247550 (epothilone B Analogue)
57. Ncgc00378665-02
58. Ac-22618
59. Hy-10222
60. D04645
61. Ab01273979-01
62. 989i841
63. Azaepothilone B;bms 247550;bms 247550-1
64. Sr-01000941577
65. J-014409
66. Sr-01000941577-1
67. Q11711607
68. (1r,5s,6s,7r,10s,14s,16s)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-[[e]-1-(2-methyl-1,3-thiazol-4-yl]prop-1-en-2-yl)-17-oxa-13-azabicyclo(14,1,0)heptadecane-8,12-dione
69. (1s,3s,7s,10r,11s,12s,16r)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
70. 7-oxa-4-azabicyclo[14.1.0]heptadecane -5, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (1s,3s,7s,10r,11s,12s,16r)-
71. Gzx
| Molecular Weight | 506.7 g/mol |
|---|---|
| Molecular Formula | C27H42N2O5S |
| XLogP3 | 3.6 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 2 |
| Exact Mass | 506.28144362 g/mol |
| Monoisotopic Mass | 506.28144362 g/mol |
| Topological Polar Surface Area | 140 Ų |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Complexity | 817 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 2 | |
|---|---|
| Drug Name | Ixempra kit |
| Active Ingredient | Ixabepilone |
| Dosage Form | Injectable |
| Route | Iv (infusion) |
| Strength | 45mg/vial; 15mg/vial |
| Market Status | Prescription |
| Company | Bristol Myers Squibb |
| 2 of 2 | |
|---|---|
| Drug Name | Ixempra kit |
| Active Ingredient | Ixabepilone |
| Dosage Form | Injectable |
| Route | Iv (infusion) |
| Strength | 45mg/vial; 15mg/vial |
| Market Status | Prescription |
| Company | Bristol Myers Squibb |
Ixabepilone is used in combination with oral capecitabine for the treatment of metastatic or locally advanced breast cancer in patients whose disease is resistant to treatment with an anthracycline and a taxane or in patients whose cancer is taxane-resistant and for whom further anthracycline therapy is contraindicated. Anthracycline resistance is defined as progression during therapy or within 6 months in the adjuvant setting or 3 months in the metastatic setting. Taxane resistance is defined as progression during therapy or within 12 months in the adjuvant setting or 4 months in the metastatic setting. /Included in US product label/
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1136
Ixabepilone is used as monotherapy for the treatment of metastatic or locally advanced breast cancer in patients whose tumors are resistant or refractory to anthracyclines, taxanes, and capecitabine. /Included in US product label/
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1136
Chemotherapy efficacy in patients with solid tumors is influenced by primary and acquired multidrug resistance (MDR). Epothilones represent a novel class of microtubule inhibitors with lower susceptibility to drug resistance and efficacy in taxane-resistant tumors. While other epothilones are currently under investigation, ixabepilone is the first epothilone B analogue approved by the U.S. Food and Drug Administration. Ixabepilone has been shown to have preclinical activity in chemotherapy-sensitive and chemotherapy-resistant tumor models, and synergistic antitumor activity with other chemotherapeutic and targeted agents. Single-agent ixabepilone has demonstrated clinical activity in multiple solid tumors including advanced breast, lung, prostate, pancreatic, renal cell, and ovarian cancers. Most notably, efficacy has been demonstrated in patients with metastatic breast cancer (MBC) progressing after treatment with anthracyclines and taxanes. A phase III trial in anthracycline- and taxane-resistant MBC showed superior disease control with ixabepilone plus capecitabine versus capecitabine monotherapy, resulting in its approval. Ixabepilone is also active in chemotherapy-naive and taxane-resistant hormone-refractory prostate cancer and platinum-resistant non-small cell lung cancer. Neutropenia and peripheral sensory neuropathy are the most common adverse events associated with treatment. ...
PMID:19088324 Rivera E et al; Oncologist 13 (12): 1207-23 (2008).
Myelosuppression is one of the major and dose-limiting adverse effects of ixabepilone and is primarily manifested as neutropenia. In clinical studies, grade 4 neutropenia (less than 500 cells/cu mm) occurred in 36% of patients treated with ixabepilone plus capecitabine and 23% of patients treated with ixabepilone monotherapy. Febrile neutropenia and infection with neutropenia were reported in 5 and 6%, respectively, of patients treated with ixabepilone plus capecitabine, and 3 and 5%, respectively, of patients treated with ixabepilone monotherapy. Neutropenia-related death occurred in 1.9% of patients with normal hepatic function or mild hepatic impairment treated with ixabepilone plus capecitabine. The incidence of neutropenia-related death was higher (29%) in patients with serum AST or ALT concentrations exceeding 2.5 times the upper limit of normal or serum bilirubin concentrations exceeding 1.5 times the upper limit of normal. Neutropenia-related death occurred in 0.4% of patients receiving ixabepilone monotherapy. No neutropenia-related deaths were reported in patients with serum AST or ALT concentrations exceeding 2.5 times the upper limit of normal or serum bilirubin concentrations exceeding 1.5 times the upper limit of normal treated with ixabepilone monotherapy.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1137
Patients with baseline AST or ALT >2.5 x ULN or bilirubin >1.5 x ULN experienced greater toxicity than patients with baseline AST or ALT = 2.5 x ULN or bilirubin =1.5 x ULN when treated with Ixempra at 40 mg/sq m in combination with capecitabine or as monotherapy in breast cancer studies. In combination with capecitabine, the overall frequency of grade 3/4 adverse reactions, febrile neutropenia, serious adverse reactions, and toxicity related deaths was greater. With monotherapy, grade 4 neutropenia, febrile neutropenia, and serious adverse reactions were more frequent. The safety and pharmacokinetics of Ixempra as monotherapy were evaluated in a dose escalation study in 56 patients with varying degrees of hepatic impairment. Exposure was increased in patients with elevated AST or bilirubin.
Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 917
Ixempra in combination with capecitabine is contraindicated in patients with AST or ALT >2.5 x /Upper Limit of Normal/ (ULN) or bilirubin >1 x ULN due to increased risk of toxicity and neutropenia-related death. Patients who are treated with Ixempra as monotherapy should receive a reduced dose depending on the degree of hepatic impairment. Use in patients with AST or ALT >10 x ULN or bilirubin >3 x ULN is not recommended. Limited data are available for patients with AST or ALT >5 x ULN. Caution should be used when treating these patients.
Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 917
Peripheral neuropathy, mostly sensory in nature but also motor neuropathy, occurs commonly in ixabepilone-treated patients and was reported in over 60% of patients receiving the drug in controlled studies. Although generally mild to moderate in severity, grade 3 or 4 neuropathy was reported in 14 and 23% of patients receiving ixabepilone monotherapy and ixabepilone combined with capecitabine, respectively, in controlled trials. Neuropathy generally develops early during treatment, with approximately 75% of new-onset or worsening neuropathy occurring during the first 3 cycles. Peripheral neuropathy was often characterized as paresthesia or dysesthesia and manifested as a symmetrical, stocking-and-glove distribution with more pronounced effects in the lower extremities.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1137
For more Drug Warnings (Complete) data for Ixabepilone (19 total), please visit the HSDB record page.
Investigated for use/treatment in breast cancer, head and neck cancer, melanoma, lung cancer, lymphoma (non-hodgkin's), prostate cancer, renal cell carcinoma, and cancer/tumors (unspecified).
L - Antineoplastic and immunomodulating agents
L01 - Antineoplastic agents
L01D - Cytotoxic antibiotics and related substances
L01DC - Other cytotoxic antibiotics
L01DC04 - Ixabepilone
Route of Elimination
Mostly fecal and some renal.
Following IV administration of a single dose of radiolabeled drug, approximately 86% of the dose was eliminated within 7 days, 65% in feces and 21% in urine. Unchanged ixabepilone accounted for less than 2 and 6% of the dose in feces and urine, respectively. The drug has a terminal elimination half-life of approximately 52 hours (range: 20-72 hours). No accumulation in plasma is expected when the drug is administered once every 3 weeks.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1138-9
Not known whether ixabepilone is distributed into human milk; however, in lactating rats given radiolabeled ixabepilone, concentrations of radioactivity in milk were comparable to those in plasma and declined in parallel with plasma concentrations of the drug.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1138
The mean volume of distribution of 40 mg/sq m ixabepilone at steady-state was in excess of 1000 L. In vitro, the binding of ixabepilone to human serum proteins ranged from 67 to 77%, and the blood-to-plasma concentration ratios in human blood ranged from 0.65 to 0.85 over a concentration range of 50 to 5000 ng/mL.
Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 919
Following administration of a single 40 mg/sq m dose of Ixempra in patients with cancer, the mean Cmax was 252 ng/mL (coefficient of variation, CV 56%) and the mean AUC was 2143 ng*hr/mL (CV 48%).Typically Cmax occurred at the end of the 3 hour infusion. In cancer patients, the pharmacokinetics of ixabepilone were linear at doses of 15 to 57 mg/sq m.
Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 919
Ixabepilone is extensively metabolized in the liver, principally by oxidative metabolism via the cytochrome P-450 (CYP) isoenzyme 3A4. The drug is eliminated primarily as metabolized drug, with more than 30 inactive metabolites eliminated in urine and feces. No single metabolite accounted for more than 6% of the administered dose.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1138
52 hours
The drug has a terminal elimination half-life of approximately 52 hours (range: 20-72 hours).
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1139
Binding of Ixabepilone to beta-tubulins (e.g. beta-III tubulin) stabilizes microtubules. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing. Like taxol, Ixabepilone binds to the -tubulin heterodimer subunit. Once bound, the rate of -tubulin dissociation decreases, thus stabilizing the microtubules.
Ixabepilone is a microtubule inhibitor belonging to the epothilone class of antineoplastic agents. Epothilones are naturally occurring products of fermentation from the myxobacterium Sorangium cellulosum. Ixabepilone is a semisynthetic derivative of epothilone B, a 16-membered polyketide macrolide, with a chemically modified lactam substitution for the naturally existing lactone. Ixabepilone binds to beta-tubulin subunits on microtubules and stabilizes and suppresses microtubule activity resulting in mitotic arrest and apoptosis. Although ixabepilone appears to share a similar antimicrotubule mechanism of action with taxanes, the drug differs structurally from taxanes and does not appear to be affected by common mechanisms of taxane resistance.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1138
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