Ixabepilone
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| Systematic (IUPAC) name | |
|---|---|
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(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 category |
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| Legal status |
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| Routes of administration |
Intravenous infusion |
| Pharmacokinetic data | |
| Bioavailability | N/A |
| Protein binding | 67 to 77% |
| Metabolism | Extensive, hepatic, CYP3A4-mediated |
| Biological half-life | 52 hours |
| Excretion | Fecal (mostly) and renal |
| Identifiers | |
| CAS Number | 219989-84-1  |
| ATC code | L01DC04 (WHO) |
| PubChem | CID: 6445540 |
| IUPHAR/BPS | 6824 |
| DrugBank | DB04845  |
| ChemSpider | 20145579 |
| UNII | K27005NP0A |
| KEGG | D04645 |
| ChEMBL | CHEMBL1201752 |
| Synonyms | Azaepothilone B |
| Chemical data | |
| Formula | C27H42N2O5S |
| Molecular 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]
Pharmacology
It acts to stabilize microtubules.[4][5][6] 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.[7]
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.[8] In November 2008, the EMEA has refused a marketing authorisation for Ixabepilone.[9]
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.[10]
It has been investigated for use in treatment of non-Hodgkin's lymphoma.[11] In pancreatic cancer phase two trial it showed some promising results (used alone). Combination therapy trials are ongoing.[7]
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ http://www.cancer.org/Treatment/TreatmentsandSideEffects/GuidetoCancerDrugs/Ixabepilone
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 7.0 7.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Medical News Today
- ↑ London, 20 November 2008 Doc. Ref. EMEA/602569/2008
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
