Ixabepilone
 | |
|---|---|
| Systematic (IUPAC) name | |
| (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 | |
| Clinical data | |
| Trade names | Ixempra |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a608042 |
| Licence data | US FDA:link |
| Pregnancy cat. | D (US) |
| Legal status | ℞-only (US) |
| Routes | Intravenous infusion |
| Pharmacokinetic data | |
| Bioavailability | N/A |
| Protein binding | 67 to 77% |
| Metabolism | Extensive, hepatic, CYP3A4-mediated |
| Half-life | 52 hours |
| Excretion | Fecal (mostly) and renal |
| Identifiers | |
| CAS number | 219989-84-1  |
| ATC code | L01DC04 |
| PubChem | CID 6445540 |
| DrugBank | DB04845 |
| ChemSpider | 20145579  |
| UNII | K27005NP0A |
| KEGG | D04645 |
| ChEMBL | CHEMBL1201752 |
| Synonyms | Azaepothilone B |
| Chemical data | |
| Formula | C27H42N2O5S |
| Mol. mass | 506.698 g/mol |
| SMILES
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| (what is this?) (verify) | |
Ixabepilone (INN; also known as azaepothilone B, codenamed BMS-247550) is an epothilone B analog[1] developed by Bristol-Myers Squibb as a chemotherapeutic medication for cancer.[2]
It is produced by Sorangium cellulosum.[3]
Pharmacology
It acts to stabilize microtubules.[4][5] It is highly potent agent, capable of damaging cancer cells in very low concentrations, and retains activity in cases where tumor cells are insensitive to paclitaxel.[6]
Approval
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.[7] In November 2008, the EMEA has refused a marketing authorisation for Ixabepilone.[8]
Ixabepilone is administered through injection, and is marketed under the trade name Ixempra.
Clinical uses
Ixabepilone, in combination with capecitabine, has demonstrated effectiveness in the treatment of metastatic or locally advanced breast cancer in patients after failure of an anthracycline and a taxane.[9]
It has been investigated for use in treatment of non-Hodgkin's lymphoma.[10] In pancreatic cancer phase two trial it showed some promising results (used alone). Combination therapy trials are ongoing.[6]
References
- ↑ Goodin S (May 2008). "Novel cytotoxic agents: epothilones". Am J Health Syst Pharm 65 (10 Suppl 3): S10–5. doi:10.2146/ajhp080089. PMID 18463327.
- ↑ http://www.cancer.org/Treatment/TreatmentsandSideEffects/GuidetoCancerDrugs/Ixabepilone
- ↑ Lee FY, Borzilleri R, Fairchild CR, et al (December 2008). "Preclinical discovery of ixabepilone, a highly active antineoplastic agent". Cancer Chemother. Pharmacol. 63 (1): 157–66. doi:10.1007/s00280-008-0724-8. PMID 18347795.
- ↑ Denduluri N, Swain SM (March 2008). "Ixabepilone for the treatment of solid tumors: a review of clinical data". Expert Opin Investig Drugs 17 (3): 423–35. doi:10.1517/13543784.17.3.423. PMID 18321240.
- ↑ Goodin S (November 2008). "Ixabepilone: a novel microtubule-stabilizing agent for the treatment of metastatic breast cancer". Am J Health Syst Pharm 65 (21): 2017–26. doi:10.2146/ajhp070628. PMID 18945860.
- ↑ 6.0 6.1 M. Vulfovich et al; Rocha-Lima, C (2008). "Novel advances in pancreatic cancer treatment". Expert Rev Anticancer Ther 8 (6): 993–1002. doi:10.1586/14737140.8.6.993. PMID 18533808.
- ↑ Medical News Today
- ↑ London, 20 November 2008 Doc. Ref. EMEA/602569/2008
- ↑ Thomas ES, Gomez HL, Li RK, et al (November 2007). "Ixabepilone plus capecitabine for metastatic breast cancer progressing after anthracycline and taxane treatment". J. Clin. Oncol. 25 (33): 5210–7. doi:10.1200/JCO.2007.12.6557. PMID 17968020.
- ↑ Aghajanian C, Burris HA, Jones S, et al (March 2007). "Phase I study of the novel epothilone analog ixabepilone (BMS-247550) in patients with advanced solid tumors and lymphomas". J. Clin. Oncol. 25 (9): 1082–8. doi:10.1200/JCO.2006.08.7304. PMID 17261851.