Name: Eribulin Mesylate
Brand: BOC Sciences
Price: 1099 USD
Availability: MadeToOrder

Synonyms

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, 2-[(2S)-3-amino-2-hydroxypropyl]hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)-, (2R,3R,3aS,7R,8aS,9S,10aR,11S,12R,13aR,13bS,15S,18S,21S,24S,26R,28R,29aS)-, methanesulfonate (1:1); 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, 2-[(2S)-3-amino-2-hydroxypropyl]hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)-, (2R,3R,3aS,7R,8aS,9S,10aR,11S,12R,13aR,13bS,15S,18S,21S,24S,26R,28R,29aS)-, methanesulfonate (salt); E 7389 methanesulfonate; Halaven; Eribulin monomethanesulfonate

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

Canonical SMILES

CC1CC2CCC3C(=C)CC(O3)CCC45CC6C(O4)C7C(O6)C(O5)C8C(O7)CCC(O8)CC(=O)CC9C(CC(C1=C)O2)OC(C9OC)CC(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

Solubility

Soluble in DMSO

Appearance

Powder

Quality Standard

Current Developer

Eisai

NCT Number	Title	Condition Or Disease	Phase	Start Date	Sponsor	Status
NCT00047034	E7389 in Treating Patients With Advanced Solid Tumors	Unspecified Adult Solid Tumor, Protocol Specific	Phase 1	August 2002	National Cancer Institute (NCI)	Completed
NCT00334893	Eribulin Mesylate in Treating Patients With Recurrent Ovarian Epithelial, Primary Peritoneal Cavity, or Fallopian Tube Cancer	Fallopian Tube Cancer	Phase 2	April 2006	National Cancer Institute (NCI)	Completed
NCT00337077	Eribulin Mesylate in Treating Patients With Metastatic Prostate Cancer That Did Not Respond to Hormone Therapy	Adenocarcinoma of the Prostate	Phase 2	November 2006	National Cancer Institute (NCI)	Completed
NCT00337103	E7389 Versus Capecitabine in Patients With Locally Advanced or Metastatic Breast Cancer Previously Treated With Anthracyclines and Taxanes	Metastatic Breast Cancer	Phase 3	June 15, 2006	Eisai Inc.	Completed
NCT00337129	S0618 E7389 in Treating Patients With Metastatic or Recurrent Head and Neck Cancer	Head and Neck Cancer	Phase 2	May 2006	National Cancer Institute (NCI)	Completed

Eribulin Mesylate is a synthetic analog of halichondrin B and a potent ADC cytotoxin explored as an ADC payload in antibody-drug conjugates. It functions as a microtubule dynamics inhibitor, binding to the plus ends of microtubules and preventing their elongation, which leads to mitotic arrest and subsequent apoptosis. Its unique mechanism of action makes it an effective cytotoxic agent for targeted cancer therapies.

Within antibody-drug conjugates, Eribulin Mesylate can be conjugated to monoclonal antibodies using cleavable or non-cleavable linker strategies. These linkers ensure that the payload remains inactive in systemic circulation and is only released within tumor cells after internalization and enzymatic processing. This targeted release enhances the antitumor efficacy of ADCs while minimizing systemic toxicity, making Eribulin Mesylate a reliable payload for precision oncology applications.

Applications of Eribulin Mesylate include its integration into experimental ADCs targeting both solid tumors and hematologic malignancies, such as breast cancer, lung cancer, and sarcomas. Its high cytotoxic potency allows effective antitumor activity even at low drug-to-antibody ratios (DARs). Additionally, Eribulin Mesylate’s structural features support conjugation with diverse linker chemistries, optimizing stability, intracellular release, and overall performance in next-generation ADC development programs.

1.Phase II clinical study of eribulin monotherapy in Japanese patients with metastatic breast cancer who had well-defined taxane resistance.

Inoue K1, Saito T2, Okubo K3, Kimizuka K4, Yamada H5, Sakurai T6, Ishizuna K7, Hata S8, Kai T9, Kurosumi M10. Breast Cancer Res Treat. 2016 Apr 28. [Epub ahead of print]

No clinical evidence on the efficacy and safety of eribulin monotherapy has been obtained by a prospective clinical study in patients with metastatic breast cancer (MBC) who had well-defined taxane resistance. The present Phase II, multicenter, single-arm, open-label study aimed to obtain the evidence. Japanese female patients, aged 33-74 years who had the metastasis of taxane-resistant and histopathologically confirmed breast cancer, received eribulin mesylate 1.4 mg/m2 (equivalent to eribulin 1.23 mg/m2 [expressed as free base]) as a 2- to 5-min intravenous infusion on days 1 and 8 of each 21-day cycle. The primary endpoint was the clinical benefit rate (CBR) [complete response (CR), partial response (PR), and long-term stable disease (LSD) ≥24 weeks]. A total of 51 patients underwent chemotherapy cycles (median 4; range 1-42 cycles). The CBR was 39.2 % (CR 2.0 %; PR 23.5 %; and LSD 13.7 %), and the rate of progressive disease was 49.0 %.

2.Phase II clinical study of eribulin monotherapy in Japanese patients with metastatic breast cancer who had well-defined taxane resistance.

Inoue K1, Saito T2, Okubo K3, Kimizuka K4, Yamada H5, Sakurai T6, Ishizuna K7, Hata S8, Kai T9, Kurosumi M10. Breast Cancer Res Treat. 2016 Apr 28. [Epub ahead of print]

3.Antimitotic and Non-mitotic Effects of Eribulin Mesilate in Soft Tissue Sarcoma.

Kawano S1, Asano M1, Adachi Y1, Matsui J2. Anticancer Res. 2016 Apr;36(4):1553-61.

BACKGROUND: Eribulin mesilate (eribulin), a first-in-class halichondrin B-based microtubule dynamics inhibitor, has been shown to promote vascular remodeling and reversal of epithelial-mesenchymal transition (EMT) apart from its antimitotic activity in breast cancer models.

4.Results of the Belgian expanded access program of eribulin in the treatment of metastatic breast cancer closely mirror those of the pivotal phase III trial.

Aftimos P1, Polastro L2, Ameye L3, Jungels C2, Vakili J2, Paesmans M3, van den Eerenbeemt J2, Buttice A2, Gombos A2, de Valeriola D2, Gil T2, Piccart-Gebhart M2, Awada A2. Eur J Cancer. 2016 Apr 20;60:117-124. doi: 10.1016/j.ejca.2016.03.010. [Epub ahead of print]

BACKGROUND: Eribulin is a non-taxane microtubule dynamics inhibitor that showed a survival benefit versus treatment of physician's choice in a phase III trial enrolling patients with metastatic breast cancer (MBC).

Catalog	Product Name	CAS
BADC-00660	VCP-Eribulin	2130869-17-7
BADC-00860	Mal-PEG2-VCP-Eribulin	2130869-18-8
BADC-01611	Farletuzumab ecteribulin	2407465-18-1
BADC-01379	Eribulin	253128-41-5

What is Eribulin Mesylate?

Eribulin Mesylate is a synthetic microtubule dynamics inhibitor derived from halichondrin B. It interferes with tubulin polymerization, leading to mitotic blockage and apoptosis, and is utilized as a potent payload in ADC research for selective cytotoxic delivery.

2/7/2018

We would like to know how Eribulin Mesylate is used in ADC development.

Eribulin Mesylate serves as a cytotoxic payload in ADCs. It is conjugated to monoclonal antibodies targeting specific antigens, ensuring selective uptake by target cells and induction of apoptosis, while reducing systemic toxicity.

17/2/2018

Dear BOC Sciences, which linkers are suitable for Eribulin Mesylate ADCs?

Eribulin Mesylate can be coupled using cleavable linkers for intracellular release upon target cell internalization, or non-cleavable linkers to enhance stability in circulation. Linker selection affects pharmacokinetics and payload delivery efficiency.

28/8/2019

Dear Sir, may I ask what laboratory precautions are necessary when handling Eribulin Mesylate?

Due to its high cytotoxicity, Eribulin Mesylate must be handled with PPE, biosafety cabinets, and adherence to institutional safety guidelines. Proper waste disposal and containment are required to prevent accidental exposure during conjugation or experiments.

1/3/2019

Good morning! What advantages do Eribulin Mesylate ADCs provide in research applications?

Eribulin Mesylate ADCs allow targeted delivery of cytotoxic agents to cells expressing specific antigens. This improves therapeutic index, supports precision oncology research, and facilitates evaluation of novel ADC constructs in preclinical studies.

10/12/2022

— Dr. Jason Carter, Senior Scientist (USA)

Eribulin Mesylate from BOC Sciences showed high purity and excellent batch reproducibility.

28/8/2019

— Dr. Andrew Collins, Pharmaceutical Researcher (UK)

Eribulin Mesylate from BOC Sciences arrived on time and in excellent condition. It demonstrated consistent performance in our preclinical conjugation trials, reflecting reliable sourcing standards.

10/12/2022

— Dr. Markus Klein, Medicinal Chemist (Germany)

Fast delivery and detailed QC documentation for Eribulin Mesylate met all expectations.

1/3/2019

— Dr. Rebecca Shaw, Oncology Researcher (USA)

Our lab has tested Eribulin Mesylate from various vendors, but BOC Sciences provided the most reliable batch. Its solubility and purity supported efficient conjugation work with minimal troubleshooting.

2/7/2018

— Dr. William Adams, Lead Scientist (USA)

High-quality Eribulin Mesylate and responsive support. Perfect for our pipeline.

— Dr. Peter Hughes, Senior Chemist (UK)

Eribulin Mesylate from BOC Sciences was exceptionally consistent between batches. The compound’s stability allowed us to run prolonged conjugation studies without performance drift.

17/2/2018