Eribulin mesylateProduct ingredient for Eribulin

Name
Eribulin mesylate
Drug Entry
Eribulin

Eribulin is a microtubule inhibitor 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. Eribulin was isolated from the marine sponge Halichondria okadai. Eribulin is also being investigated for use in the treatment of advanced solid tumors 2.

Accession Number
DBSALT002427
Structure
Synonyms
Eribulin mesilate / Eribulin monomethanesulfonate
External IDs
E-7389 / E7389
UNII
AV9U0660CW
CAS Number
441045-17-6
Weight
Average: 826.01
Monoisotopic: 825.396926887
Chemical Formula
C41H63NO14S
InChI Key
QAMYWGZHLCQOOJ-WRNBYXCMSA-N
InChI
InChI=1S/C40H59NO11.CH4O3S/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;1-5(2,3)4/h19,23-39,43H,2-3,5-18,41H2,1,4H3;1H3,(H,2,3,4)/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+;/m1./s1
IUPAC Name
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33S,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1^{3,32}.1^{3,33}.1^{6,9}.1^{12,16}.0^{18,22}.0^{29,36}.0^{31,35}]hentetracontan-24-one; methanesulfonic acid
SMILES
CS(O)(=O)=O.[H][C@@]12CC(=C)[C@]([H])(CC[C@@]3([H])C[C@@H](C)C(=C)[C@@]([H])(C[C@]4([H])O[C@H](C[C@H](O)CN)[C@H](OC)[C@@]4([H])CC(=O)C[C@@]4([H])CC[C@]5([H])O[C@@]6([H])[C@H]7O[C@@]8(C[C@]7([H])O[C@@]6([H])[C@@]([H])(O8)[C@@]5([H])O4)CC1)O3)O2
ChemSpider
26386066
ChEBI
70710
ChEMBL
CHEMBL1683544
Wikipedia
Eribulin
Predicted Properties
PropertyValueSource
Water Solubility0.0798 mg/mLALOGPS
logP1.26ALOGPS
logP2.31Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)14.82Chemaxon
pKa (Strongest Basic)9.56Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area146.39 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity186 m3·mol-1Chemaxon
Polarizability82.15 Å3Chemaxon
Number of Rings9Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon