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MedKoo Cat#: 413983 | Name: Eribulin free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eribulin is a synthetic analog of halichondrin B and acts as a microtubule dynamics inhibitor with potent antineoplastic activity. Its primary mechanism is irreversible binding to the plus ends of microtubules, thereby suppressing microtubule polymerization without affecting depolymerization, leading to G2/M cell cycle arrest and apoptosis. In vitro, eribulin exhibits nanomolar potency against a wide range of cancer cell lines, with IC₅₀ values typically ranging from 0.1 to 10 nM (e.g., IC₅₀ = 0.3 nM in MDA-MB-231 breast cancer cells). In vivo, eribulin shows significant tumor growth inhibition in xenograft models of breast, lung, and prostate cancers.

Chemical Structure

Eribulin free base
Eribulin free base
CAS#253128-41-5 (free base)

Theoretical Analysis

MedKoo Cat#: 413983

Name: Eribulin free base

CAS#: 253128-41-5 (free base)

Chemical Formula: C40H59NO11

Exact Mass: 729.4088

Molecular Weight: 729.91

Elemental Analysis: C, 65.82; H, 8.15; N, 1.92; O, 24.11

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
5mg USD 950.00 2 Weeks
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Related CAS #
253128-41-5 (free base) 441045-17-6 (mesylate)
Synonym
Eribulin Free Base; E7389; E-7389; E 7389; B1939; B 1939; B-1939; ER 086526; ER086526; ER-086526;
IUPAC/Chemical Name
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
InChi Key
UFNVPOGXISZXJD-JBQZKEIOSA-N
InChi Code
InChI=1S/C40H59NO11/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/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
SMILES Code
CO[C@H]1[C@H](O[C@H]2C[C@H]3O[C@H](C[C@H](C3=C)C)CC[C@@H]4O[C@H](CC4=C)CC[C@@]56C[C@H]7O[C@@H]8[C@H]([C@H]7O6)O[C@H]9CC[C@@H](O[C@@H]9[C@@H]8O5)CC(C[C@H]12)=O)C[C@@H](CN)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 729.91 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Perez-Garcia JM, Cortes J. The safety of eribulin for the treatment of metastatic breast cancer. Expert Opin Drug Saf. 2019 May;18(5):347-355. doi: 10.1080/14740338.2019.1608946. Epub 2019 May 20. PMID: 31107111. 2: Cortes J, O'Shaughnessy J, Loesch D, Blum JL, Vahdat LT, Petrakova K, Chollet P, Manikas A, Diéras V, Delozier T, Vladimirov V, Cardoso F, Koh H, Bougnoux P, Dutcus CE, Seegobin S, Mir D, Meneses N, Wanders J, Twelves C; EMBRACE (Eisai Metastatic Breast Cancer Study Assessing Physician's Choice Versus E7389) investigators. Eribulin monotherapy versus treatment of physician's choice in patients with metastatic breast cancer (EMBRACE): a phase 3 open-label randomised study. Lancet. 2011 Mar 12;377(9769):914-23. doi: 10.1016/S0140-6736(11)60070-6. Epub 2011 Mar 2. PMID: 21376385. 3: Schöffski P, Chawla S, Maki RG, Italiano A, Gelderblom H, Choy E, Grignani G, Camargo V, Bauer S, Rha SY, Blay JY, Hohenberger P, D'Adamo D, Guo M, Chmielowski B, Le Cesne A, Demetri GD, Patel SR. Eribulin versus dacarbazine in previously treated patients with advanced liposarcoma or leiomyosarcoma: a randomised, open-label, multicentre, phase 3 trial. Lancet. 2016 Apr 16;387(10028):1629-37. doi: 10.1016/S0140-6736(15)01283-0. Epub 2016 Feb 10. PMID: 26874885. 4: Yuan P, Hu X, Sun T, Li W, Zhang Q, Cui S, Cheng Y, Ouyang Q, Wang X, Chen Z, Hiraiwa M, Saito K, Funasaka S, Xu B. Eribulin mesilate versus vinorelbine in women with locally recurrent or metastatic breast cancer: A randomised clinical trial. Eur J Cancer. 2019 May;112:57-65. doi: 10.1016/j.ejca.2019.02.002. Epub 2019 Mar 29. PMID: 30928806. 5: Perry CM. Eribulin. Drugs. 2011 Jul 9;71(10):1321-31. doi: 10.2165/11207520-000000000-00000. PMID: 21770478. 6: Kaufman PA, Awada A, Twelves C, Yelle L, Perez EA, Velikova G, Olivo MS, He Y, Dutcus CE, Cortes J. Phase III open-label randomized study of eribulin mesylate versus capecitabine in patients with locally advanced or metastatic breast cancer previously treated with an anthracycline and a taxane. J Clin Oncol. 2015 Feb 20;33(6):594-601. doi: 10.1200/JCO.2013.52.4892. Epub 2015 Jan 20. PMID: 25605862; PMCID: PMC4463422. 7: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Eribulin. 2018 Feb 20. PMID: 31643639. 8: Setola E, Noujaim J, Benson C, Chawla S, Palmerini E, Jones RL. Eribulin in advanced liposarcoma and leiomyosarcoma. Expert Rev Anticancer Ther. 2017 Aug;17(8):717-723. doi: 10.1080/14737140.2017.1344098. Epub 2017 Jun 28. PMID: 28621163. 9: Jain S, Vahdat LT. Eribulin mesylate. Clin Cancer Res. 2011 Nov 1;17(21):6615-22. doi: 10.1158/1078-0432.CCR-11-1807. Epub 2011 Aug 22. PMID: 21859830. 10: Tolaney SM, Barroso-Sousa R, Keenan T, Li T, Trippa L, Vaz-Luis I, Wulf G, Spring L, Sinclair NF, Andrews C, Pittenger J, Richardson ET 3rd, Dillon D, Lin NU, Overmoyer B, Partridge AH, Van Allen E, Mittendorf EA, Winer EP, Krop IE. Effect of Eribulin With or Without Pembrolizumab on Progression-Free Survival for Patients With Hormone Receptor-Positive, ERBB2-Negative Metastatic Breast Cancer: A Randomized Clinical Trial. JAMA Oncol. 2020 Oct 1;6(10):1598-1605. doi: 10.1001/jamaoncol.2020.3524. PMID: 32880602; PMCID: PMC7489368.