Eribulin

Modify Date: 2024-01-03 10:29:20

Eribulin structure	Common Name	Eribulin
	CAS Number	253128-41-5	Molecular Weight	729.897
	Density	1.29±0.1 g/cm3	Boiling Point	N/A
	Molecular Formula	C₄₀H₅₉NO₁₁	Melting Point	N/A
	MSDS	N/A	Flash Point	N/A

Use of Eribulin

Eribulin (E7389; ER-086526), a synthetic analogue of halichondrin B in phase III clinical trials for breast cancer, binds to tubulin and microtubules.Target: Microtubule/TubulinEribulin suppressed centromere dynamics at concentrations that arrest mitosis. At 60 nmol/L eribulin (2 x mitotic IC(50)), the relaxation rate was suppressed 21%, the time spent paused increased 67%, and dynamicity decreased 35% (but without reduction in mean centromere separation), indicating that eribulin decreased normal microtubule-dependent spindle tension at the kinetochores, preventing the signal for mitotic checkpoint passage [1]. [(3)H]eribulin binds soluble tubulin at a single site; however, this binding is complex with an overall K(d) of 46 microM, but also showing a real or apparent very high affinity (K(d) = 0.4 microM) for a subset of 25% of the tubulin. Eribulin also binds microtubules with a maximum stoichiometry of 14.7 +/- 1.3 molecules per microtubule (K(d) = 3.5 microM), strongly suggesting the presence of a relatively high-affinity binding site at microtubule ends. At 100 nM, the concentration that inhibits microtubule plus end growth by 50%, we found that one molecule of eribulin is bound per two microtubules, indicating that the binding of a single eribulin molecule at a microtubule end can potently inhibit its growth. Eribulin does not suppress dynamic instability at microtubule minus ends [2]. Eribulin's in vivo superiority derives from its ability to induce irreversible mitotic blockade, which appears related to persistent drug retention and sustained Bcl-2 phosphorylation [3].

Name	eribulin
Synonym	More Synonyms

Description	Eribulin (E7389; ER-086526), a synthetic analogue of halichondrin B in phase III clinical trials for breast cancer, binds to tubulin and microtubules.Target: Microtubule/TubulinEribulin suppressed centromere dynamics at concentrations that arrest mitosis. At 60 nmol/L eribulin (2 x mitotic IC(50)), the relaxation rate was suppressed 21%, the time spent paused increased 67%, and dynamicity decreased 35% (but without reduction in mean centromere separation), indicating that eribulin decreased normal microtubule-dependent spindle tension at the kinetochores, preventing the signal for mitotic checkpoint passage [1]. [(3)H]eribulin binds soluble tubulin at a single site; however, this binding is complex with an overall K(d) of 46 microM, but also showing a real or apparent very high affinity (K(d) = 0.4 microM) for a subset of 25% of the tubulin. Eribulin also binds microtubules with a maximum stoichiometry of 14.7 +/- 1.3 molecules per microtubule (K(d) = 3.5 microM), strongly suggesting the presence of a relatively high-affinity binding site at microtubule ends. At 100 nM, the concentration that inhibits microtubule plus end growth by 50%, we found that one molecule of eribulin is bound per two microtubules, indicating that the binding of a single eribulin molecule at a microtubule end can potently inhibit its growth. Eribulin does not suppress dynamic instability at microtubule minus ends [2]. Eribulin's in vivo superiority derives from its ability to induce irreversible mitotic blockade, which appears related to persistent drug retention and sustained Bcl-2 phosphorylation [3].
Related Catalog	Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Research Areas >> Cancer
References	[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.

Description

Related Catalog

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

Research Areas >> Cancer

References

[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.

Density	1.29±0.1 g/cm3
Molecular Formula	C₄₀H₅₉NO₁₁
Molecular Weight	729.897
Exact Mass	729.408813
PSA	146.39000
LogP	3.88
Index of Refraction	1.584
Storage condition	2-8℃
Water Solubility	Practically insoluble (0.015 g/L) (25 ºC)

Cyclopentanecarboxylicacid,3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-,methyl ester,(1S,3S,4R)

Eribulin

(1S,3S,4R)-3-tert-butoxycarbonylamino-4-hydroxycyclopentanecarboxylic acid methyl ester

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

NSC-707389

Methyl(1S,3S,4R)NBOC3amino4hydroxycyclopentanecarboxylate

Halaven

(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-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1. 1.1.1.0.0.0]hentetracontan-24-one

ER-086526

(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-bis(methylene)-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

DC Chemicals Limited
China
Product Name: Eribulin
Price: $2000.0/10mg $3000.0/25mg $5500.0/100mg
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Zhejiang Hangyu API Co., Ltd
China
Product Name: Eribulin
Price: ￥Inquiry/1kg
Purity: 99.5%
Stocking Period: Inquiry
Contact: Vinnie

Henan Tianfu Chemical Co., Ltd.
China
Product Name: Eribulin
Price: $Inquiry/1kg $Inquiry/25kg $Inquiry/1000kg $Inquiry/10ton
Purity: 99.0%
Stocking Period: Inquiry
Contact: Anson

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Eribulin

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