Eribulin Mesylate - CAS 441045-17-6
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Eribulin Mesylate - CAS 441045-17-6 Catalog number: BADC-01399

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Eribulin Mesylate is an antitumor drug that can be used to treat patients with metastatic breast cancer. It inhibits the proliferation of cancer cells by binding tubulin and microtubules. Eribulin Mesylate can inhibit experimental metastasis of breast cancer cells by reversing phenotype from epithelial-mesenchymal transition (EMT) to mesenchymal-epithelial transition (MET) states.

Category
ADCs Cytotoxin
Product Name
Eribulin Mesylate
CAS
441045-17-6
Catalog Number
BADC-01399
Molecular Formula
C41H63NO14S
Molecular Weight
826.01
Purity
≥95%
Eribulin Mesylate

Ordering Information

Catalog Number Size Price Quantity
BADC-01399 1 mg $1099 Inquiry

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Description
Eribulin Mesylate is an antitumor drug that can be used to treat patients with metastatic breast cancer. It inhibits the proliferation of cancer cells by binding tubulin and microtubules. Eribulin Mesylate can inhibit experimental metastasis of breast cancer cells by reversing phenotype from epithelial-mesenchymal transition (EMT) to mesenchymal-epithelial transition (MET) states.
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 NumberTitleCondition Or DiseasePhaseStart DateSponsorStatus
NCT00047034E7389 in Treating Patients With Advanced Solid TumorsUnspecified Adult Solid Tumor, Protocol SpecificPhase 1August 2002National Cancer Institute (NCI)Completed
NCT00334893Eribulin Mesylate in Treating Patients With Recurrent Ovarian Epithelial, Primary Peritoneal Cavity, or Fallopian Tube CancerFallopian Tube CancerPhase 2April 2006National Cancer Institute (NCI)Completed
NCT00337077Eribulin Mesylate in Treating Patients With Metastatic Prostate Cancer That Did Not Respond to Hormone TherapyAdenocarcinoma of the ProstatePhase 2November 2006National Cancer Institute (NCI)Completed
NCT00337103E7389 Versus Capecitabine in Patients With Locally Advanced or Metastatic Breast Cancer Previously Treated With Anthracyclines and TaxanesMetastatic Breast CancerPhase 3June 15, 2006Eisai Inc.Completed
NCT00337129S0618 E7389 in Treating Patients With Metastatic or Recurrent Head and Neck CancerHead and Neck CancerPhase 2May 2006National Cancer Institute (NCI)Completed
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]
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 %.
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).
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