Ixabepilone
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| 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 |
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| 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 |
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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]
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Pharmacology [edit]
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 [edit]
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 [edit]
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 [edit]
- ^ 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.
- ^ a b M. Vulfovich et al (2008). "Novel advances in pancreatic cancer treatment". Expert Rev Anticancer Ther 8 (6): 993–1002.
- ^ 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.
External links [edit]
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