eribulin   Click here for help

GtoPdb Ligand ID: 6813

Synonyms: E7389 | ER 086526 | Halaven® | NSC-707389
Approved drug PDB Ligand
eribulin is an approved drug (FDA (2010), EMA (2011))
Compound class: Synthetic organic
Comment: A pan tubulin inhibitor which is a fully synthetic macrocyclic ketone analogue of the marine sponge natural product halichondrin B (a mitosis inhibitor). Marketed formulations may contain eribulin mesylate (PubChem CID 17755248).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: eribulin

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 12
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 146.39
Molecular weight 729.41
XLogP 0.56
No. Lipinski's rules broken 1
Click here for help
Isomeric SMILES NC[C@H](C[C@H]1O[C@@H]2[C@@H]([C@H]1OC)CC(=O)C[C@H]1CC[C@H]3[C@H](O1)[C@@H]1O[C@]4(CC[C@@H]5O[C@@H](CC[C@@H]6O[C@H](C2)C(=C)[C@@H](C6)C)C(=C)C5)O[C@@H]2[C@H](O3)[C@H]1O[C@@H]2C4)O
InChI InChI=1S/C40H59NO11/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
No information available.
Summary of Clinical Use Click here for help
An anticancer drug approved 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.
Following FDA orphan drug designation and priority review, the FDA expanded approval to include treatment of patients with unresectable or metastatic liposarcoma who have received a prior anthracycline-containing regimen in January 2016.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
A microtubule inhibitor isolated from the marine sponge Halichondria okadai.
External links Click here for help