Eribulin

Eribulin
Clinical data

Trade names	Halaven
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a611007
License data	US FDA: Eribulin
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Intravenous
ATC code	L01XX41 (WHO)
Legal status
Legal status	US: ℞-only
Identifiers
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
CAS Number	253128-41-5^N
PubChem CID	17755248
ChemSpider	21396142^Y
UNII	LR24G6354G
ChEMBL	CHEMBL1237028^N
ECHA InfoCard	100.230.372
Chemical and physical data
Formula	C₄₀H₅₉NO₁₁
Molar mass	729.90 g/mol
3D model (Jmol)	Interactive image
SMILES 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 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^Y Key:VEPHOPLDBFLPDL-KVWSPMLQSA-N^Y
^NY (what is this?)

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.

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. 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.

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. 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.

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.

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

...
Wikipedia