Ixabepilone Contents History Pharmacology Approval Clinical uses References External links Navigation menuMonographa608042IxabepiloneWHO219989-84-164455406824DB0484520145579K27005NP0AD04645ChEMBL1201752100.158.736Interactive image(verify)"Novel cytotoxic agents: epothilones"10.2146/ajhp0800891846332710.1007/s00280-008-0724-81834779510.1007/s00280-015-2863-z26416565"Ixabepilone for the treatment of solid tumors: a review of clinical data"10.1517/13543784.17.3.42318321240"Ixabepilone: a novel microtubule-stabilizing agent for the treatment of metastatic breast cancer"10.2146/ajhp0706281894586010.1586/14737140.8.6.99318533808Medical News Today"Ixabepilone plus capecitabine for metastatic breast cancer progressing after anthracycline and taxane treatment"10.1200/JCO.2007.12.655717968020"Phase I study of the novel epothilone analog ixabepilone (BMS-247550) in patients with advanced solid tumors and lymphomas"10.1200/JCO.2006.08.730417261851Ixempra product websiteIxempra prescribing informatione

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Bristol-Myers SquibbMitotic inhibitorsThiazolesEpoxidesLactams


INNBristol-Myers Squibbchemotherapeuticsemi-syntheticanalogepothilonemetabolic stabilitypharmacokineticsmedicinal chemistryTaxolmicrotubulesFood and Drug Administrationmetastaticbreast cancerEMEAcapecitabineanthracyclinetaxanenon-Hodgkin's lymphoma
























































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




Contents





  • 1 History


  • 2 Pharmacology


  • 3 Approval


  • 4 Clinical uses


  • 5 References


  • 6 External links




History


Ixabepilone is a semi-synthetic analog of epothilone B, a natural chemical compound produced by Sorangium cellulosum.[2] Epothilone B itself could not be developed as a pharmaceutical drug because of poor metabolic stability and pharmacokinetics.[3] Ixabepilone was designed through medicinal chemistry to improve upon these properties.[3]



Pharmacology


Much like Taxol, Ixabepilone acts to stabilize microtubules.[4][5][6]
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.[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




  1. ^ http://www.cancer.org/Treatment/TreatmentsandSideEffects/GuidetoCancerDrugs/Ixabepilone


  2. ^ 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..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em


  3. ^ ab 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.


  4. ^ Lopus, M; Smiyun, G; Miller, H; Oroudjev, E; Wilson, L; Jordan, MA (2015). "Mechanism of action of ixabepilone and its interactions with the βIII-tubulin isotype". Cancer Chemother Pharmacol. 76: 1013–24. doi:10.1007/s00280-015-2863-z. PMID 26416565.


  5. ^ 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.


  6. ^ 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.


  7. ^ ab M. Vulfovich; Rocha-Lima, C; et al. (2008). "Novel advances in pancreatic cancer treatment". Expert Rev Anticancer Ther. 8 (6): 993–1002. doi:10.1586/14737140.8.6.993. PMID 18533808.


  8. ^ Medical News Today


  9. ^ London, 20 November 2008 Doc. Ref. EMEA/602569/2008


  10. ^ 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.


  11. ^ 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


  • Ixempra product website

  • Ixempra prescribing information

Ixabepilone
Ixabepilone.svg
Clinical data
Trade namesIxempra
SynonymsAzaepothilone B

AHFS/Drugs.com
Monograph
MedlinePlusa608042
License data


  • US FDA: Ixabepilone

Pregnancy
category


  • US: D (Evidence of risk)

Routes of
administration		Intravenous infusion
ATC code

  • L01DC04 (WHO)
Legal status
Legal status


  • US: ℞-only


Pharmacokinetic data
BioavailabilityN/A
Protein binding67 to 77%
MetabolismExtensive, hepatic, CYP3A4-mediated
Elimination half-life
52 hours
ExcretionFecal (mostly) and renal
Identifiers
CAS Number

  • 219989-84-1 ☒N

PubChem CID
  • 6445540
IUPHAR/BPS
  • 6824
DrugBank

  • DB04845 ☑Y
ChemSpider

  • 20145579 ☑Y
UNII
  • K27005NP0A
KEGG

  • D04645 ☑Y
ChEMBL

  • ChEMBL1201752 ☒N
ECHA InfoCard
100.158.736 Edit this at Wikidata
Chemical and physical data
Formula
C27H42N2O5S
Molar mass506.698 g/mol g·mol−1
3D model (JSmol)
  • Interactive image

.mw-parser-output .noboldfont-weight:normal
 ☒N☑Y (what is this?)
  (verify)














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