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Eribulin (mesylate)

CAT: 0804-HY-13442A-01Size: 500 µgDry Ice: YesHazardous: No
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CAT#:0804-HY-13442A-01Size:500 µg
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Description
Eribulin (E7389) mesylate is a microtubule targeting agent that is used for the research of metastatic breast cancer. Eribulin mesylate inhibits the proliferation of cancer cells by binding microtubule proteins and microtubules.
CAS Number
441045-17-6
Product Name Alternative
B1939 (mesylate) ; E7389 (mesylate) ; ER-086526 (mesylate)
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Microtubule/Tubulin
Type
Reference compound
Related Pathways
Apoptosis; Cell Cycle/DNA Damage; Cytoskeleton
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/eribulin-mesylate.html
Purity
99.91
Solubility
DMSO : ≥ 100 mg/mL
Smiles
C=C1C[C@@](CC[C@@]2(C[C@@]3([H])O4)O[C@]([C@](O[C@](C5)([H])CC6)([H])[C@@]6([H])O7)([H])[C@@]4([H])[C@]7([H])[C@@]3([H])O2)([H])O[C@@]1([H])CC[C@](C[C@@H](C)C8=C)([H])O[C@]8([H])C[C@@](O[C@H](C[C@H](O)CN)[C@@H]9OC)([H])[C@]9([H])CC5=O.CS(=O)(O)=O
Molecular Formula
C41H63NO14S
Molecular Weight
826.00
Precautions
H302, H315, H319, H335
References & Citations
[1]Okouneva, T., et al., Inhibition of centromere dynamics by eribulin (E7389) during mitotic metaphase. Mol Cancer Ther, 2008. 7 (7) : p. 2003-11.|[2]Smith, J.A., et al., Eribulin binds at microtubule ends to a single site on tubulin to suppress dynamic instability. Biochemistry, 2010. 49 (6) : p. 1331-7.|[3]Towle, M.J., et al., Eribulin induces irreversible mitotic blockade: implications of cell-based pharmacodynamics for in vivo efficacy under intermittent dosing conditions. Cancer Res, 2011. 71 (2) : p. 496-505.|[4]Watanabe K, et, al. Low-dose eribulin reduces lung metastasis of osteosarcoma in vitro and in vivo. Oncotarget. 2019 Jan 4; 10 (2) : 161-174.
Shipping Conditions
Dry Ice
Storage Conditions
-80°C, protect from light, stored under nitrogen
Scientific Category
Reference compound1
Clinical Information
Launched
Citation 01
Cell Rep Med. 2025 Apr 2:102053.|mBio. 2025 Aug 15:e0048425.|Molecules. 2025 Feb 14;30 (4) :895.|Dev Cell. 2025 Mar 25:S1534-5807 (25) 00151-0.|iScience. 2022 Sep 6;25 (10) :105081.|J Control Release. 2025 Oct 14;388 (Pt 1) :114325.|NPJ Breast Cancer. 2025 Feb 17;11 (1) :17.|Res Sq. 2024 Sep 17.

Chemical Information

Eribulin Mesylate

Eribulin mesylate is 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. It has a role as an antineoplastic agent and a microtubule-destabilising agent. It contains an eribulin(1+).

CAS Number441045-17-6
PubChem CID17755248
IUPAC Name(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one;methanesulfonic acid
Molecular FormulaC41H63NO14S
Molecular Weight826.0
Topological Polar Surface Area209
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count15
Rotatable Bond Count4
Heavy Atom Count57
Formal Charge0
Complexity1470
SMILES
C[C@@H]1C[C@@H]2CC[C@H]3C(=C)C[C@@H](O3)CC[C@]45C[C@@H]6[C@H](O4)[C@H]7[C@@H](O6)[C@@H](O5)[C@@H]8[C@@H](O7)CC[C@@H](O8)CC(=O)C[C@H]9[C@H](C[C@H](C1=C)O2)O[C@@H]([C@@H]9OC)C[C@@H](CN)O.CS(=O)(=O)O
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
Chemical Structure
2D Structure
2D structure of Eribulin Mesylate
CAS: 441045-17-6
CID: 17755248
Formula: C41H63NO14S
MW: 826.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight826.0
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count15
Rotatable Bond Count4
Exact Mass825.39692686
Monoisotopic Mass825.39692686
Topological Polar Surface Area209 Ų
Heavy Atom Count57
Formal Charge0
Complexity1470
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
C13775-1mgEribulin Mesylate
C21657-5mgEribulin Mesylate (E7389)
A12804-100Eribulin Mesylate 100mg
A12804-25Eribulin Mesylate 25mg
A12804-10Eribulin Mesylate 10mg
A12804-5Eribulin Mesylate 5mg
A12804-50Eribulin Mesylate 50mg
A12804-1Eribulin Mesylate 1mg
RM-E180202-01Eribulin Mesylate Impurity 2
RM-E180210-01Eribulin Mesylate Impurity 10

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