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Ixabepilone: Wikis

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Ixabepilone
Systematic (IUPAC) name
(1R,5S,6S,7R,10 S,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
Identifiers
CAS number 219989-84-1
ATC code L01DC04
PubChem 6445540
Chemical data
Formula C 27H42N2O5S 
Mol. mass 506.698 g/mol
SMILES eMolecules & PubChem
Synonyms Azaepothilone B
Pharmacokinetic data
Bioavailability N/A
Protein binding 67 to 77%
Metabolism Extensive, hepatic, CYP3A4-mediated
Half life 52 hours
Excretion Fecal (mostly) and renal
Therapeutic considerations
Pregnancy cat. D(US)
Legal status -only (US)
Routes Intravenous infusion

Ixabepilone (INN; also known as azaepothilone B, codenamed BMS-247550) is an epothilone B analog[1] developed by Bristol-Myers Squibb as a cancer drug.

It is produced by Sorangium cellulosum.[2]

Contents

Pharmacology

It acts to stabilize microtubules.[3][4]

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.[5] In November 2008, the EMEA has refused a marketing authorisation for Ixabepilone.[6]

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.[7]

It has been investigated for use in treatment of non-Hodgkin's lymphoma.[8]

References

  1. ^ 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.ajhp.org/cgi/pmidlookup?view=long&pmid=18463327.  
  2. ^ 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.  
  3. ^ 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. http://www.expertopin.com/doi/abs/10.1517/13543784.17.3.423.  
  4. ^ 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. http://www.ajhp.org/cgi/pmidlookup?view=long&pmid=18945860.  
  5. ^ Medical News Today
  6. ^ London, 20 November 2008 Doc. Ref. EMEA/602569/2008
  7. ^ 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. http://www.jco.org/cgi/pmidlookup?view=long&pmid=17968020.  
  8. ^ 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. http://www.jco.org/cgi/pmidlookup?view=long&pmid=17261851.  

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