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Details

Stereochemistry ABSOLUTE
Molecular Formula C40H59NO11
Molecular Weight 729.8966
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERIBULIN

SMILES

CO[C@H]1[C@@H](C[C@H](O)CN)O[C@H]2C[C@H]3O[C@H](C[C@@H](C)C3=C)CC[C@@H]4O[C@H](CC4=C)CC[C@@]56C[C@H]7O[C@@H]8[C@@H](O[C@H]9CC[C@H](CC(=O)C[C@H]12)O[C@@H]9[C@@H]8O5)[C@H]7O6

InChI

InChIKey=UFNVPOGXISZXJD-JBQZKEIOSA-N
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

HIDE SMILES / InChI

Description

ERIBULIN MESYLATE (HALAVEN®) is a microtubule dynamics inhibitor. It is a synthetic analog of halichondrin B, a product isolated from the marine sponge Halichondria okadai. ERIBULIN MESYLATE (HALAVEN®) inhibits the growth phase of microtubules without affecting the shortening phase and sequesters tubulin into nonproductive aggregates. It exerts its effects via a tubulin-based antimitotic mechanism leading to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after the prolonged mitotic blockage. ERIBULIN MESYLATE (HALAVEN®) is indicated for the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic disease. It is also indicated for the treatment of patients with unresectable or metastatic liposarcoma who have received a prior anthracycline-containing regimen.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HALAVEN
PubMed

PubMed

TitleDatePubMed
Novel second generation analogs of eribulin. Part III: Blood-brain barrier permeability and in vivo activity in a brain tumor model.
2011 Mar 15

Sample Use Guides

In Vivo Use Guide
Administer HALAVEN® 1.4 mg/m2 intravenously over 2 to 5 minutes on Days 1 and 8 of a 21-day cycle.
Route of Administration: Intravenous
Name Type Language
ERIBULIN
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
ERIBULIN [VANDF]
Common Name English
ER-086526
Code English
ERIBULIN [INN]
Common Name English
ERIBULIN [WHO-DD]
Common Name English
ERIBULIN [MI]
Common Name English
ERIBULIN [MART.]
Common Name English
Classification Tree Code System Code
LIVERTOX 364
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
NDF-RT N0000175592
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
NCI_THESAURUS C67422
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
WHO-ATC L01XX41
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
WHO-VATC QL01XX41
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
EMA ASSESSMENT REPORTS HALAVEN (AUTHORIZED: BREAST NEOLPLASMA)
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
Code System Code Type Description
WIKIPEDIA
ERIBULIN
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
IUPHAR
6813
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
PUBCHEM
11354606
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
RXCUI
1045453
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL1683590
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
INN
8854
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
CAS
253128-41-5
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
EVMPD
SUB31134
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
MESH
C490954
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
MERCK INDEX
M4993
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C96748
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY
DRUG BANK
DB08871
Created by admin on Mon Oct 21 21:29:23 UTC 2019 , Edited by admin on Mon Oct 21 21:29:23 UTC 2019
PRIMARY