eribulin mesylate (CHEBI:70710)

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CHEBI:70710 - eribulin mesylate

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ChEBI ID	CHEBI:70710
ChEBI Name	eribulin mesylate
Stars
Definition	A methanesulfonate salt obtained by reaction of eribulin with one equivalent of methanesulfonic acid. A fully synthetic macrocyclic ketone analogue of marine sponge natural products. Inhibits growth phase of microtubules via tubulin-based antimitotic mechanism, which leads to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage.
Last Modified	19 October 2012
Submitter	Steve
Downloads	Molfile

Formula	C40H59NO11.CH4O3S
Net Charge	0
Average Mass	826.015
Monoisotopic Mass	825.39693
SMILES	CS(=O)(=O)O.[H][C@@]12CC[C@]3([H])O[C@@]4([H])[C@H]5O[C@]6(CC[C@@]7([H])CC(=C)[C@]([H])(CC[C@@]8([H])C[C@@H](C)C(=C)[C@@]([H])(C[C@]9([H])O[C@H](C[C@H](O)CN)[C@H](OC)[C@@]9([H])CC(=O)C1)O8)O7)C[C@@]5([H])O[C@@]4([H])[C@@]([H])(O6)[C@@]3([H])O2
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
InChIKey	QAMYWGZHLCQOOJ-WRNBYXCMSA-N

Roles Classification

Biological Role:	microtubule-destabilising agent Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	eribulin mesylate (CHEBI:70710) has part eribulin(1+) (CHEBI:70711)
	eribulin mesylate (CHEBI:70710) has role antineoplastic agent (CHEBI:35610)
	eribulin mesylate (CHEBI:70710) has role microtubule-destabilising agent (CHEBI:61951)
	eribulin mesylate (CHEBI:70710) is a methanesulfonate salt (CHEBI:38037)

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 methanesulfonate

Synonyms	Source
Eribulin mesilate	KEGG DRUG
E7389	ChemIDplus
E 7389	ChemIDplus

Brand Name	Source
Halaven	KEGG DRUG

Manual Xrefs	Databases
D08914	KEGG DRUG

Registry Numbers	Sources
Reaxys:11271529	Reaxys
CAS:441045-17-6	KEGG DRUG
CAS:441045-17-6	ChemIDplus

Citations