Eribulin mesylate
[CAS# 441045-17-6]

Identification

• Classification: API >> Antineoplastic agents
• Name: Eribulin mesylate
• Synonyms: Halaven
• Molecular Formula: C₄₀H₅₉NO₁₁.CH₄O₃S
• Molecular Weight: 826.00
• CAS Registry Number: 441045-17-6
• EC Number: 813-106-4
• 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

Safety Data

• Hazard Symbols: GHS08;GHS09 Warning
• Risk Statements: H341-H361-H410
• Safety Statements: P203-P273-P280-P318-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Germ cell mutagenicity	Muta.	2	H341
Reproductive toxicity	Repr.	2	H361
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovery and Applications

Eribulin mesylate, a synthetic derivative of halichondrin B, was discovered in the early 1980s from a marine sponge called Halichondria okadai. Scientists isolated halichondrin B due to its remarkable antitumor properties. Subsequent research led to the development of eribulin mesylate, a synthetic analog designed to enhance stability and pharmacological properties while retaining the potent anticancer activity of the natural compound. Eisai Co., Ltd., played a pivotal role in the development and refinement of eribulin mesylate, culminating in its approval by the FDA in 2010 for the treatment of metastatic breast cancer.

Eribulin mesylate represents a significant advancement in the treatment of metastatic breast cancer, particularly in patients who have previously received anthracycline- and taxane-based therapies. As a microtubule inhibitor, eribulin disrupts mitotic spindle formation, leading to cell cycle arrest and apoptosis in cancer cells. Eribulin mesylate has also shown promise in the treatment of advanced or metastatic soft tissue sarcomas (STS) in patients who have received prior chemotherapy. Studies have demonstrated its ability to improve overall survival in patients with STS, leading to its approval by regulatory agencies for this indication. Its mechanism of action, which includes inhibition of tumor cell migration and angiogenesis, contributes to its efficacy in this setting.Ongoing research is exploring the potential of eribulin mesylate in other cancer types, including advanced non-small cell lung cancer (NSCLC) and ovarian cancer. Preclinical studies have shown promising results, suggesting that eribulin may have a role in the treatment of these malignancies. Eribulin mesylate's unique mechanism of action distinguishes it from other chemotherapy agents. By binding to tubulin and inhibiting microtubule dynamics, eribulin disrupts mitotic spindle formation, leading to mitotic catastrophe and ultimately cell death. This mechanism, coupled with its low incidence of neuropathy compared to other microtubule inhibitors, makes eribulin mesylate an attractive option in the treatment of metastatic breast cancer and other solid tumors.

References

2005. The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth. Molecular Cancer Therapeutics, 4(7).
DOI: 10.1158/1535-7163.mct-04-0345

2024. Real-world treatment patterns and clinical outcomes in patients treated with eribulin after prior phosphoinositide 3-Kinase inhibitor treatment for metastatic breast cancer. Breast Cancer Research and Treatment, 204(1).
DOI: 10.1007/s10549-023-07080-1

2024. Alteration of DNA Methyltransferases by Eribulin Elicits Broad DNA Methylation Changes with Potential Therapeutic Implications for Triple-Negative Breast Cancer. Epigenomics, 16(4).
DOI: 10.2217/epi-2023-0339