eribulin

CHEBI:CHEBI_63587

Definition

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

Chemical Information

Molecular Formula: C40H59NO11
Molecular Mass: 729.89660
Charge: 0
SMILES: [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
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
InChIKey: UFNVPOGXISZXJD-JBQZKEIOSA-N

Alternative Names

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
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-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

Treatment Applications

spermatogenic failure 27
DOID:0111928

View Disease →

Drug Classification

cyclic ketone
CHEBI:3992

View Class →
polyether
CHEBI:46774

View Class →
primary amino compound
CHEBI:50994

View Class →
cyclic ketal
CHEBI:59779

View Class →
macrocycle
CHEBI:51026

View Class →
polycyclic ether
CHEBI:36468

View Class →
t262065
t262193
t262233

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

Always consult with a healthcare professional before starting, stopping, or modifying any medication.
Side effects may vary and this list may not be comprehensive.
Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000: 1045453
oboInOwl#hasDbXref: Wikipedia:Eribulin
core#notation: CHEBI:63587

Additional References

Wikipedia:Eribulin

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

oboInOwl#hasOBONamespace: chebi_ontology
DRON_00010000: 1045453
oboInOwl#hasDbXref: Wikipedia:Eribulin
oboInOwl#id: CHEBI:63587
core#notation: CHEBI:63587
RO_0000087: http://purl.obolibrary.org/obo/CHEBI_61951
oboInOwl#inSubset: http://purl.obolibrary.org/obo/chebi#3_STAR
chebi#is_conjugate_base_of: http://purl.obolibrary.org/obo/CHEBI_70711
22-rdf-syntax-ns#type: http://www.w3.org/2002/07/owl#Class
has_treatment: http://purl.obolibrary.org/obo/DOID_5701
rdf-schema#range: https://w3id.org/def/predibionto#has_drug_106436
rdf-schema#domain: https://w3id.org/def/predibionto#has_side_effect30460
chebi#is_conjugate_acid_of: http://purl.obolibrary.org/obo/CHEBI_70711
owl#annotatedSource: t262303
owl#someValuesFrom: t3000454