Term: | eribulin mesylate |
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Accession: | CHEBI:70710
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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. |
Synonyms: | exact_synonym: | 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 |
| related_synonym: | E 7389; E7389; Eribulin mesilate; Formula=C41H63NO14S; Halaven; 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; SMILES=CS(O)(=O)=O.[H][C@@]12CC[C@]3([H])O[C@@]([H])(CC[C@@]45C[C@]6([H])O[C@]7([H])[C@@]([H])(O[C@@]8([H])CC[C@]([H])(CC(=O)C[C@]9([H])[C@@H](OC)[C@@H](C[C@H](O)CN)O[C@@]9([H])C[C@@]([H])(O1)C(=C)[C@H](C)C2)O[C@]8([H])[C@]7([H])O4)[C@H]6O5)CC3=C |
| xref: | CAS:441045-17-6; KEGG:D08914; PMID:21375468; PMID:21526355; PMID:21550727; PMID:21862415; PMID:21887501; PMID:21903605; PMID:21935916; PMID:21989327; PMID:22162924; PMID:22198425; PMID:22216781; PMID:22282463; PMID:22291464; PMID:22514495; PMID:22517020; PMID:22555773; PMID:22593439; PMID:22619477; PMID:22694309; PMID:22739019; PMID:22803519; PMID:22829199; PMID:22953094; PMID:23010853; Reaxys:11271529 |
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