Eribulin

Base Information

• Chemical Name: Eribulin
• CAS No.: 253128-41-5
• Deprecated CAS: 441045-16-5
• Molecular Formula: C40H59NO11
• Molecular Weight: 729.909
• UNII: LR24G6354G
• ChEMBL ID: CHEMBL1683590
• DSSTox Substance ID: DTXSID101009321
• Metabolomics Workbench ID: 62856
• NCI Thesaurus Code: C96748
• Pharos Ligand ID: 1BJVJWPGGFZ6
• RXCUI: 1045453
• Wikidata: Q408717
• Wikipedia: Eribulin
• Mol file: 253128-41-5.mol

Synonyms: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;B 1793;B 1939;B-1793;B-1939;E 7389;E-7389;ER 086526;ER-086526;ER-86526;ER086526;eribulin;eribulin (as mesylate);eribulin mesilate;eribulin mesylate;eribulin monomethanesulfonate;Halaven;NSC 707389;NSC-707389;NSC707389

Chemical Property of Eribulin

Chemical Property:

• PKA: 12.56±0.35(Predicted)
• PSA: 146.39000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 4.13830
• Solubility.: Soluble in DMSO
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 729.40881170
• Heavy Atom Count: 52
• Complexity: 1380

Purity/Quality:

97% ^*data from raw suppliers

Eribulin >99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• 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
• Isomeric 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
• Recent ClinicalTrials: Study of E7389 Liposomal Formulation in Participants With Solid Tumor
• Recent EU Clinical Trials: Can Eribulin enhance the effect of subsequent endocrine therapy?- a phase 2 study for patients with ER positive HER2 normal metastatic breast cancer
• Recent NIPH Clinical Trials: A phase II study of eribulin monotherapy for advanced extramammary Paget's disease
• Description: The U.S. FDA approved eribulin mesylate (also referred to as E7389) in November 2010 for the treatment of metastatic breast cancer (MBC) for patients who previously received at least two chemotherapeutic regimens for late-stage disease. Eribulin is a synthetic analog of the marine natural product halichondrin B, which is isolated from the sea sponge Halichondria okadai. Eribulin retains most of the structural elements that constitute the right hand side of halichondrin B; structure–activity relationship (SAR) studies suggested that the antitumor activity of halichondrin B resides in that part of the molecule . Eribulin is a microtubule inhibitor that binds close to the vinca-binding site of tubulin. Unlike most tubulin inhibitors like taxanes, epothilones, and vinca alkaloids that inhibit microtubule dynamic instability by changing tubulin addition and loss parameters, eribulin’s effects on dynamic instability are novel in that eribulin inhibits the growth phase of microtubules without affecting the shortening phase by binding to microtubule plus ends.
• Uses: Eribulin is a anticancer drug and also is a fully synthetic macrocyclic ketone analogue of the marine natural product halichondrin B. It derived from a marine sponge (Lissodendoryx sp.) with antineoplastic activity.
• Clinical Use: Antineoplastic agent:Treatment of metastatic breast cancer
• Drug interactions: Potentially hazardous interactions with other drugs Antipsychotics: avoid concomitant use with clozapine (increased risk of agranulocytosis).

Technology Process of Eribulin

There total 23 articles about Eribulin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

C40H61NO12 → (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 (253128-41-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 30 ℃; for 16h;

Reference yield: 88.0%

C45H67NO13 → (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 (253128-41-5)

Guidance literature:

C₄₅H₆₇NO₁₃; With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 2.5h;

With potassium carbonate; In methanol; at 20 ℃; for 2h;

Reference yield: 87.0%

(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-azido-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylidene)-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 (253128-40-4) → (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 (253128-41-5)

Guidance literature:

With trimethylphosphane; In tetrahydrofuran; water; at 20 ℃; for 22h;

upstream raw materials:

C₄₁H₆₀O₁₄S

(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-2,3-Dihydroxypropyl]-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

(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-azido-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylidene)-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

ER-809681

Downstream raw materials:

C₄₈H₆₃NO₁₃