Eribulin
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Also known as B-1939E-7389 FREE BASEER-086526EribulinaEribuline
Summary
Eribulin (CHEMBL1683590) is an approved small-molecule antineoplastic agent (ATC L01XX41) targeting TUBB; indicated across 15 conditions including neoplasm and breast carcinoma; with CIViC clinical evidence for 1 variant-indication association (e.g. CDK2 CYTOPLASMIC EXPRESSION in triple-receptor negative breast cancer).
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: L01XX41
- Targets: 1 (TUBB)
- Indications: 15 conditions
- Clinical trials: 107
- Precision-oncology evidence (CIViC): 1 variant–indication association
- Chemistry: 729.9 Da · C40H59NO11
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1683590 |
| Name | Eribulin |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 11354606 |
| ChEBI | CHEBI:63587 |
| ATC | L01XX41 |
| Molecular formula | C40H59NO11 |
| Molecular weight | 729.9 |
| InChIKey | UFNVPOGXISZXJD-JBQZKEIOSA-N |
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
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
ChEBI definition: A fully synthetic macrocyclic ketone analogue of marine sponge natural products. Inhibits growth phase of microtubules via tubulin-based antimitotic mechanism, which leads to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage
Pharmacological roles (ChEBI): antineoplastic agent, microtubule-destabilising agent.
Also known as: B-1939, E-7389 FREE BASE, ER-086526, Eribulin, Eribulina, Eribuline, eribulin, ERIBULIN
Parent form; salt/anhydrous children: CHEMBL1683544, CHEMBL3526882
Patent coverage: 2,319 distinct patent families (5,581 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| TUBB | tubulin beta class I | Inhibition | 8.23 | P07437 |
Bioactivity
No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).
Target pathways
Aggregated over 1 target gene(s): TUBB.
Top Reactome pathways
24 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Cell Cycle | 1 | TUBB |
| Disease | 1 | TUBB |
| Innate Immune System | 1 | TUBB |
| Immune System | 1 | TUBB |
| Organelle biogenesis and maintenance | 1 | TUBB |
| Regulation of PLK1 Activity at G2/M Transition | 1 | TUBB |
| Loss of Nlp from mitotic centrosomes | 1 | TUBB |
| Recruitment of mitotic centrosome proteins and complexes | 1 | TUBB |
| Loss of proteins required for interphase microtubule organization from the centrosome | 1 | TUBB |
| Centrosome maturation | 1 | TUBB |
| Recruitment of NuMA to mitotic centrosomes | 1 | TUBB |
| Mitotic G2-G2/M phases | 1 | TUBB |
| Cilium Assembly | 1 | TUBB |
| Anchoring of the basal body to the plasma membrane | 1 | TUBB |
| Infectious disease | 1 | TUBB |
| Neutrophil degranulation | 1 | TUBB |
| Mitotic Prometaphase | 1 | TUBB |
| M Phase | 1 | TUBB |
| G2/M Transition | 1 | TUBB |
| Cell Cycle, Mitotic | 1 | TUBB |
| AURKA Activation by TPX2 | 1 | TUBB |
| Potential therapeutics for SARS | 1 | TUBB |
| SARS-CoV Infections | 1 | TUBB |
| Viral Infection Pathways | 1 | TUBB |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| microtubule cytoskeleton organization | 1 |
| mitotic cell cycle | 1 |
| microtubule-based process | 1 |
| cytoskeleton-dependent intracellular transport | 1 |
| natural killer cell mediated cytotoxicity | 1 |
| regulation of synapse organization | 1 |
| spindle assembly | 1 |
| cell division | 1 |
| odontoblast differentiation | 1 |
| cytoskeleton organization | 1 |
Indications & clinical
Indications
15 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| neoplasm | 4 | MONDO:0005070 | EFO:0000616 |
| breast carcinoma | 3 | MONDO:0004989 | EFO:0000305 |
| non-small cell lung carcinoma | 3 | MONDO:0005233 | EFO:0003060 |
| sarcoma | 3 | MONDO:0005089 | EFO:0000691 |
| breast neoplasm | 3 | MONDO:0021100 | MONDO:0007254 |
| triple-negative breast carcinoma | 3 | MONDO:0005494 | EFO:0005537 |
| angiosarcoma | 2 | MONDO:0016982 | EFO:0003968 |
| inflammatory breast carcinoma | 2 | MONDO:0006804 | EFO:1000984 |
| hereditary breast ovarian cancer syndrome | 2 | MONDO:0003582 | Orphanet:145 |
| epithelioid hemangioendothelioma | 2 | MONDO:0015523 | MONDO:0015523 |
| solitary fibrous tumor | 2 | MONDO:0016238 | MONDO:0016238 |
| ovarian carcinoma | 1 | MONDO:0005140 | EFO:0001075 |
| metastatic melanoma | 1 | MONDO:0005191 | EFO:0002617 |
| fallopian tube carcinoma | 1 | MONDO:0006206 | EFO:1000251 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 107.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 51 |
| PHASE3 | 28 |
| PHASE1 | 11 |
| PHASE1/PHASE2 | 10 |
| Not specified | 6 |
| EARLY_PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT02344472 | PHASE3 | ACTIVE_NOT_RECRUITING | Detect V / CHEVENDO (Chemo vs. Endo) |
| NCT03734029 | PHASE3 | ACTIVE_NOT_RECRUITING | Trastuzumab Deruxtecan (DS-8201a) Versus Investigator’s Choice for HER2-low Breast Cancer That Has Spread or Cannot be Surgically Removed [DESTINY-Breast04] |
| NCT05063786 | PHASE3 | ACTIVE_NOT_RECRUITING | Trastuzumab + Alpelisib +/- Fulvestrant vs Trastuzumab + CT in Patients With PIK3CA Mutated Previously Treated HER2+ Advanced BrEasT Cancer (ALPHABET) |
| NCT05104866 | PHASE3 | ACTIVE_NOT_RECRUITING | A Phase-3, Open-Label, Randomized Study of Dato-DXd Versus Investigator’s Choice of Chemotherapy (ICC) in Participants With Inoperable or Metastatic HR-Positive, HER2-Negative Breast Cancer Who Have Been Treated With One or Two Prior Lines of Systemic Chemotherapy (TROPION-Breast01) |
| NCT05814354 | PHASE3 | RECRUITING | SHR-A1811 Versus Investigator’s Chemotherapy in Recurrent/Metastatic Breast Cancer Clinical Trial |
| NCT06081959 | PHASE3 | RECRUITING | Study of SKB264 for Locally Advanced, Recurrent or Metastatic HR+/HER2- Breast Cancer |
| NCT06263231 | PHASE3 | ACTIVE_NOT_RECRUITING | A Study to Investigate Efficacy & Safety of Intratumoral INT230-6 Compared to US Standard of Care in Adults With Soft Tissue Sarcomas (INVINCIBLE-3) |
| NCT06268652 | PHASE3 | RECRUITING | Patient Derived Organoid-guided Personalized Treatment Versus Treatment of Physician’s Choice in Breast Cancer |
| NCT06279364 | PHASE3 | RECRUITING | A Study of SKB264 Versus Investigator’s Choice Chemotherapy in Patients With Unresectable Recurrent or Metastatic Triple-Negative Breast Cancer |
| NCT06343948 | PHASE3 | ACTIVE_NOT_RECRUITING | A Study Comparing BL-B01D1 With Chemotherapy of Physician’s Choice in Patients With Unresectable Locally Advanced, Recurrent, or Metastatic HR+HER2- Breast Cancer(PANKU-Breast01) |
| NCT06382142 | PHASE3 | ACTIVE_NOT_RECRUITING | A Study Comparing BL-B01D1 With Chemotherapy of Physician’s Choice in Patients With Unresectable Locally Advanced or Metastatic Triple-Negative Breast Cancer(PANKU-Breast02) |
| NCT06383767 | PHASE3 | RECRUITING | A Phase III Study of ESG401 for Locally Advanced or Metastatic HR+/HER2- Breast Cancer |
| NCT06435429 | PHASE3 | RECRUITING | A Study Comparing the Efficacy and Safety of Zanidatamab to Trastuzumab, Each in Combination With Physician’s Choice Chemotherapy, for the Treatment of Participants With Metastatic HER2-positive Breast Cancer |
| NCT06519370 | PHASE3 | ACTIVE_NOT_RECRUITING | FDA018-ADC vs Investigator’s Choice Chemotherapy to Treat Locally Advanced, Recurrent or Metastatic Triple-negative Breast Cancer |
| NCT06889688 | PHASE3 | RECRUITING | Phase III Trial of Camrelizumab+Apatinib+Eribulin vs. Physician’s Choice Chemotherapy in Advanced Triple-Negative Breast Cancer |
| NCT06957886 | PHASE3 | RECRUITING | A Study of BL-M07D1 Versus Investigator’s Choice of Chemotherapy in Patients With HER2-low Recurrent/Metastatic Breast Cancer |
| NCT07088263 | PHASE3 | RECRUITING | Adaptive Chemotherapy for the Treatment of Advanced Breast Cancer |
| NCT07173751 | PHASE3 | RECRUITING | ROSETTA Breast-01: The Effects and Safety of Pumitamig in Patients With Triple-Negative Breast Cancer |
| NCT07461454 | PHASE3 | RECRUITING | YL202 Versus Treatment of Physician’s Choice in Patients With HR+/HER2- Breast Cancer |
| NCT01454934 | PHASE3 | COMPLETED | A Randomized, Open-label, Multicenter, Phase 3 Study to Compare the Efficacy and Safety of Eribulin With Treatment of Physician’s Choice in Subjects With Advanced Non-Small Cell Lung Cancer |
| NCT02514681 | PHASE3 | COMPLETED | A Phase III Trial of Pertuzumab Retreatment in Previously Pertuzumab Treated Her2-Positive Advanced Breast Cancer |
| NCT02555657 | PHASE3 | COMPLETED | Study of Single Agent Pembrolizumab (MK-3475) Versus Single Agent Chemotherapy for Metastatic Triple Negative Breast Cancer (MK-3475-119/KEYNOTE-119) |
| NCT02574455 | PHASE3 | COMPLETED | Trial of Sacituzumab Govitecan in Participants With Refractory/Relapsed Metastatic Triple-Negative Breast Cancer (TNBC) |
| NCT02915744 | PHASE3 | COMPLETED | A Study of Etirinotecan Pegol (NKTR-102) Versus Treatment of Physician’s Choice (TPC) in Patients With Metastatic Breast Cancer Who Have Stable Brain Metastases and Have Been Previously Treated With an Anthracycline, a Taxane, and Capecitabine |
| NCT03264547 | PHASE3 | COMPLETED | A Study to Compare Eribulin Mesylate + Pertuzumab + Trastuzumab With Paclitaxel or Docetaxel + Pertuzumab + Trastuzumab |
| NCT03786094 | PHASE3 | TERMINATED | Pivotal Study in HER2 Negative, Locally Recurrent or Metastatic Breast Cancer |
| NCT03901339 | PHASE3 | COMPLETED | Study of Sacituzumab Govitecan-hziy Versus Treatment of Physician’s Choice in Participants With HR+/HER2- Metastatic Breast Cancer |
| NCT05134194 | PHASE3 | TERMINATED | A Study of Camrelizumab in Combination With Chemotherapy Regimen Comparative Chemotherapy Regimen for Metastatic Triple-negative Breast Cancer |
| NCT02299999 | PHASE2 | ACTIVE_NOT_RECRUITING | SAFIR02_Breast - Efficacy of Genome Analysis as a Therapeutic Decision Tool for Patients With Metastatic Breast Cancer |
| NCT02623972 | PHASE2 | ACTIVE_NOT_RECRUITING | A Phase 2 Study of Eribulin Followed by AC as Preoperative Therapy for HER2-negative Inflammatory Breast Cancer |
| NCT03202316 | PHASE2 | ACTIVE_NOT_RECRUITING | Atezolizumab, Cobimetinib, and Eribulin in Treating Patients With Chemotherapy Resistant Metastatic Inflammatory Breast Cancer |
| NCT03331250 | PHASE2 | ACTIVE_NOT_RECRUITING | Eribulin in Angiosarcoma and Epithelioid Hemangioendothelioma (EHE) |
| NCT04986579 | PHASE2 | RECRUITING | Scalp Cooling in MBC |
| NCT05458674 | PHASE2 | RECRUITING | Tucatinib+Trastuzumab+Eribulin in HER2+ MBC |
| NCT05570253 | PHASE2 | RECRUITING | A Study of SDX-7320 in Combination With Eribulin for People With Breast Cancer |
| NCT05810870 | PHASE2 | ACTIVE_NOT_RECRUITING | PIK3CA/PTEN-altered Advanced Breast Cancer Treated With MEN1611 Monotherapy or in Combination With Eribulin |
| NCT05824975 | PHASE1/PHASE2 | RECRUITING | A Study to Evaluate the Safety and Therapeutic Activity of GI-102 As a Single Agent and in Combination with Conventional Anti-cancer Drugs, Pembrolizumab or Trastuzumab Deruxtecan(T-DXd) in Patients with Advanced Solid Tumors (KEYNOTE-G08) |
| NCT06102824 | PHASE2 | RECRUITING | Organoid-based Functional Precision Therapy for Advanced Breast Cancer |
| NCT06202313 | PHASE2 | NOT_YET_RECRUITING | Study of Cadonilimab (AK104) Plus Eribulin vs. Eribulin Monotherapy for Recurrent or Metastatic Triple-negative Breast Cancer |
| NCT06308939 | PHASE2 | NOT_YET_RECRUITING | Eribulin Combined With Sintilimab as First-line Treatment for Unresectable Locally Advanced or Metastatic HER2-negative Breast Cancer:A Multicenter, Single-arm,Phase II Clinical Trial |
Clinical evidence (CIViC)
Variant × indication × effect (1 predictive associations from 1 curated evidence items):
| Variant | Indication | Effect | Therapy | Level | CIViC |
|---|---|---|---|---|---|
| CDK2 CYTOPLASMIC EXPRESSION | Triple-receptor Negative Breast Cancer | Sensitivity/Response | Eribulin + Carboplatin | CIViC B | EID2969 |
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
18 molecules share ≥1 primary target. Top 18 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| PODOFILOX | ChEMBL + PubChem | Phase 4 (approved) | TUBB |
| VINBLASTINE | ChEMBL + PubChem | Phase 4 (approved) | TUBB |
| COLCHICINE | ChEMBL | Phase 4 (approved) | TUBB |
| DOCETAXEL | ChEMBL | Phase 4 (approved) | TUBB |
| LEVOFLOXACIN | ChEMBL | Phase 4 (approved) | TUBB |
| NOSCAPINE | ChEMBL | Phase 4 (approved) | TUBB |
| PACLITAXEL | ChEMBL | Phase 4 (approved) | TUBB |
| TIRBANIBULIN | ChEMBL | Phase 4 (approved) | TUBB |
| VINCRISTINE | ChEMBL | Phase 4 (approved) | TUBB |
| VINORELBINE | ChEMBL | Phase 4 (approved) | TUBB |
| PATUPILONE | ChEMBL | Phase 3 | TUBB |
| ABT-751 | ChEMBL | Phase 2 | TUBB |
| DOLASTATIN-10 | ChEMBL | Phase 2 | TUBB |
| INDIBULIN | ChEMBL | Phase 2 | TUBB |
| MAYTANSINE | ChEMBL | Phase 2 | TUBB |
| MOLIBRESIB | ChEMBL | Phase 2 | TUBB |
| NOCODAZOLE | ChEMBL | Phase 2 | TUBB |
| PARBENDAZOLE | ChEMBL | Phase 2 | TUBB |