Ixabepilone

Source: Wikipedia, the free encyclopedia.
Ixabepilone
Clinical data
Trade namesIxempra
Other namesAzaepothilone B
AHFS/Drugs.comMonograph
MedlinePlusa608042
License data
Routes of
administration		Intravenous infusion
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityN/A
Protein binding67 to 77%
MetabolismExtensive, hepatic, CYP3A4-mediated
Elimination half-life52 hours
ExcretionFecal (mostly) and renal
Identifiers
  • (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
JSmol)
  • Cc3nc(/C=C(\C)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1)cs3
  • InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1 checkY
  • Key:FABUFPQFXZVHFB-PVYNADRNSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ixabepilone (

Bristol-Myers Squibb as a chemotherapeutic medication for cancer.[2]

History

Ixabepilone is a

metabolic stability and pharmacokinetics.[4] Ixabepilone was designed through medicinal chemistry to improve upon these properties.[4]

Pharmacology

Much like

Taxol, Ixabepilone acts to stabilize microtubules.[5][6][7]
It is highly potent, capable of damaging cancer cells in very low concentrations, and retains activity in cases where tumor cells are insensitive to taxane type drugs.[8]

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.[9] In November 2008, the EMEA has refused a marketing authorisation for Ixabepilone.[10]

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.[11]

It has been investigated for use in treatment of

non-Hodgkin's lymphoma.[12]
In pancreatic cancer phase two trial it showed some promising results (used alone). Combination therapy trials are ongoing.[8]

References

  1. FDA
    . Retrieved 22 Oct 2023.
  2. ^ "More information on cancer drugs". www.cancer.org.
  3. PMID 18463327
    .
  4. ^
    PMID 18347795
    .
  5. S2CID 1842156
    .
  6. S2CID 71169099
    .
  7. PMID 18945860
    .
  8. ^
    S2CID 20049942
    .
  9. ^ "FDA Approves IXEMPRA(TM) (ixabepilone), A Semi-Synthetic Analog Of Epothilone B, For The Treatment Of Advanced Breast Cancer". Medical News Today.
  10. ^ "Questions and answers on recommendation for the refusal of the marketing authorisation for Ixempra" (PDF). European Medicines Agency. London. 20 November 2008. Doc. Ref. EMEA/602569/2008.
  11. PMID 17968020
    .
  12. PMID 17261851
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Ixabepilone&oldid=1197486566"