Eribulin

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Eribulin
Eribulin.svg
Systematic (IUPAC) name
2-(3-Amino-2-hydroxypropyl)hexacosahydro-3-methoxy- 26-methyl-20,27-bis(methylene)11,15-18,21-24,28-triepoxy- 7,9-ethano-12,15-methano-9H,15H-furo(3,2-i)furo(2',3'-5,6) pyrano(4,3-b)(1,4)dioxacyclopentacosin-5-(4H)-one
Clinical data
Trade names Halaven
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a611007
Licence data US FDA:link
Pregnancy
category
  • US: D (Evidence of risk)
Legal status
Routes of
administration		 Intravenous
Identifiers
CAS Number 253128-41-5 N
ATC code L01XX41 (WHO)
PubChem CID: 17755248
ChemSpider 21396142 YesY
UNII LR24G6354G YesY
ChEMBL CHEMBL1237028 N
Chemical data
Formula C40H59NO11
Molecular mass 729.90 g/mol
  • NC[C@@H](O)C[C@H]5O[C@H]4C[C@H]9O[C@@H](CC[C@@H]1O[C@H](CC1=C)CC[C@@]32O[C@@H]6[C@@H]8O[C@H](C2)[C@H](O3)[C@@H]8O[C@H]7CC[C@H](CC(=O)O[C@@H]4[C@H]5OC)O[C@H]67)C[C@@H](C)C9=C
  • InChI=1S/C39H57NO12/c1-18-11-22-5-7-25-19(2)12-24(44-25)9-10-39-16-30-35(51-39)36-37(49-30)38(52-39)33-26(48-36)8-6-23(46-33)14-31(42)50-34-29(15-27(45-22)20(18)3)47-28(32(34)43-4)13-21(41)17-40/h18,21-30,32-38,41H,2-3,5-17,40H2,1,4H3/t18-,21+,22+,23-,24+,25+,26+,27-,28-,29+,30-,32+,33+,34+,35+,36+,37-,38+,39+/m1/s1 YesY
  • Key:VEPHOPLDBFLPDL-KVWSPMLQSA-N YesY
 NYesY (what is this?)  (verify)

Eribulin is an anticancer drug marketed by Eisai Co. under the trade name Halaven. Eribulin is also known as E7389 and ER-086526, and also carries the US NCI designation NSC-707389. It is used to treat certain patients with breast cancer and liposarcoma.

Approvals and indications

Breast cancer

The mesylate salt was approved by the U.S. Food and Drug Administration on November 15, 2010, to treat patients with metastatic breast cancer who have received at least two prior chemotherapy regimens for late-stage disease, including both anthracycline- and taxane-based chemotherapies.[1] It was approved by Health Canada on December 14, 2011, for treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic disease.[2]

Liposarcoma

In January 2016 the US FDA approved Halaven for the treatment of inoperable liposarcoma in patients who received prior chemotherapy that contained an anthracycline drug.[3] A phase III trial reported: With Halaven the median overall survival for patients with liposarcoma was 15.6 months, compared to 8.4 months for patients treated with dacarbazine.[3]

Clinical trials

Eribulin is also being investigated by Eisai Co. for use in a variety of other solid tumors, including non-small cell lung cancer, prostate cancer and sarcoma.[4]

Structure and mechanism

Eribulin is a fully synthetic macrocyclic analogue of the marine natural product halichondrin B,[5][6] the parent molecule being a potent naturally occurring mitotic inhibitor with a unique mechanism of action found in the Halichondria genus of sponges.[7][8]

Eribulin is a mechanistically unique inhibitor of microtubule dynamics,[9][10] binding predominantly to a small number of high affinity sites at the plus ends of existing microtubules.[11][12] Eribulin exerts its anticancer effects by triggering apoptosis of cancer cells following prolonged and irreversible mitotic blockade.[13][14]

A new synthetic route to the drug was published in 2009.[15]

References

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External links

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Notice of Decision for HALAVEN
  3. ↑ 3.0 3.1 FDA approves first drug to show survival benefit in liposarcoma. Jan 2016
  4. ↑ http://www.clinicaltrials.gov/ct2/results?term=eribulin+OR+E7389
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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