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Ixabepilone

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Ixabepilone
250px
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
  • US: D (Evidence of risk)
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
219989-84-1 7pxN
L01DC04
PubChem CID 6445540
DrugBank DB04845 7pxY
ChemSpider 20145579 7pxY
UNII K27005NP0A 7pxY
KEGG D04645 7pxY
ChEMBL CHEMBL1201752 7pxN
Synonyms Azaepothilone B
Chemical data
Formula C27H42N2O5S
506.698 g/mol
 14pxN (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

  1. ^ Goodin S (May 2008). "Novel cytotoxic agents: epothilones". Am J Health Syst Pharm 65 (10 Suppl 3): S10–5. PMID 18463327. doi:10.2146/ajhp080089. 
  2. ^ http://www.cancer.org/Treatment/TreatmentsandSideEffects/GuidetoCancerDrugs/Ixabepilone
  3. ^ 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. PMID 18347795. doi:10.1007/s00280-008-0724-8. 
  4. ^ 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. PMID 18321240. doi:10.1517/13543784.17.3.423. 
  5. ^ 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. PMID 18945860. doi:10.2146/ajhp070628. 
  6. ^ a b M. Vulfovich; Rocha-Lima, C et al. (2008). "Novel advances in pancreatic cancer treatment". Expert Rev Anticancer Ther 8 (6): 993–1002. PMID 18533808. doi:10.1586/14737140.8.6.993. 
  7. ^ Medical News Today
  8. ^ London, 20 November 2008 Doc. Ref. EMEA/602569/2008
  9. ^ 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. PMID 17968020. doi:10.1200/JCO.2007.12.6557. 
  10. ^ 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. PMID 17261851. doi:10.1200/JCO.2006.08.7304. 

External links