Eribulin
Highest phase reached
Approved
Drug type
Small molecule
First approval year
2010
- First approval year
- 2010
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Eribulin
- Molecular weight
- 729.91
- Structure (SMILES)
- C=C1C[C@@H]2CC[C@@]34C[C@H]5O[C@H]6[C@@H](O3)[C@H]3O[C@H](CC[C@@H]3O[C@H]6[C@H]5O4)CC(=O)C[C@@H]3[C@@H](OC)[C@@H](C[C@H](O)CN)O[C@H]3C[C@H]3O[C@@H](CC[C@@H]1O2)C[C@@H](C)C3=C
- b 1939
- B-1939
- e 7389 free base
- E-7389 FREE BASE
- er 086526
- ER-086526
- eribulin
- Eribulin
- eribulin [INN]
- ERIBULIN [MART.]
- ERIBULIN [MI]
- ERIBULIN [VANDF]
- Eribulin [WHO-DD]
- eribulin inn
- eribulin mart
- eribulin mi
- eribulin vandf
- eribulin who dd
- eribulina
- Eribulina
- eribuline
- Eribuline
- ATC classification codes
- L01XX41
Sources for recorded values
- CAS registry numbers
- 253128-41-5
- ChEMBL ID
- CHEMBL1683590
- InChIKey
- UFNVPOGXISZXJD-JBQZKEIOSA-N
- PubChem compound IDs
- 11354606
- FDA ingredient codes (UNII)
- LR24G6354G
- 1045452
- 1045453
- Applicant
- EISAI INC
- Approval date
- 15 Nov 2010
- Application number
- NDA201532
- Status
- Authorised
- Status date
- 17 Mar 2011
- Authorisation date
- 17 Mar 2011
- Approved indications
- Halaven monotherapy is indicated for the treatment of patients with locally advanced or metastatic breast cancer who have progressed after at least one chemotherapeutic regimens for advanced disease (see section 5.1). Prior therapy should have included an anthracycline and a taxane unless patients were not suitable for these treatments. Halaven is indicated for the treatment of adult patients with unresectable liposarcoma who have received prior anthracycline containing therapy (unless unsuitable) for advanced or metastatic disease (see section 5.1).
- Product number
- EMEA/H/C/002084
- Authorisation holder
- Eisai GmbH
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 2
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- No
- Exceptional circumstances
- No
Therapeutic areas
- Breast Neoplasms
- Liposarcoma
European medicines record
- First in class
- No
- Orphan designation
- No
- Availability
- Prescription only
- Pharmacology name
- eribulin
- Type
- Synthetic organic
- Drug name stem
- -bulin
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Parenteral
Mechanisms of action
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- tubulin beta class I
- Gene symbol
- TUBB
- Protein identifier
- P07437
- Median affinity
- 8.23
- Affinity units
- pIC50
- Primary target
- Yes
Open Targets mechanisms
- Mechanism
- Tubulin inhibitor
- Action type
- Inhibitor
- Target
- Tubulin
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- TUBB|TUBB1|TUBB2A|TUBB2B|TUBB3|TUBB4A|TUBB4B|TUBB6|TUBB8
- Protein identifier
- P07437|Q9H4B7|Q13885|Q9BVA1|Q13509|P04350|P68371|Q9BUF5|Q3ZCM7
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000305
- Subject identifier
- D001943
- Condition
- Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Sarcoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000691
- Subject identifier
- D012509
- Condition
- Ovarian Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:0001075
- Subject identifier
- D010051
- Condition
- Melanoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0002617
- Subject identifier
- D008545
- Condition
- Carcinoma, Non-Small-Cell Lung
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003060
- Subject identifier
- D002289
- Condition
- Hemangiosarcoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003968
- Subject identifier
- D006394
- Condition
- Triple Negative Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0005537
- Subject identifier
- D064726
- Condition
- Fallopian Tube Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:1000251
- Subject identifier
- D005185
- Condition
- Inflammatory Breast Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:1000984
- Subject identifier
- D058922
- Condition
- Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- MONDO:0004992
- Subject identifier
- D009369
- Condition
- Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0007254
- Subject identifier
- D001943
- Condition
- Hemangioendothelioma, Epithelioid
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0015523
- Subject identifier
- D018323
- Condition
- Solitary Fibrous Tumors
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0016238
- Subject identifier
- D054364
- Condition
- Hereditary Breast and Ovarian Cancer Syndrome
- Highest recorded phase
- 2
- Condition identifier
- Orphanet:145
- Subject identifier
- D061325
- Condition identifier
- EFO_0000569
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000691
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003869
- Condition identifier
- EFO_0003968
- Highest recorded phase
- 2
- Condition identifier
- EFO_0005537
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0001056
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0002142
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0002158
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0004669
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0004971
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0004989
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0004992
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005058
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005060
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005062
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0005070
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005089
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0005105
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0005140
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005154
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005233
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005494
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0006244
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0006804
- Highest recorded phase
- 2
And 15 more, listed on the interactive page.
- Event
- acute lymphocytic leukaemia
- Reports
- 8
- Reporting signal score
- 22.0564
- Event
- alanine aminotransferase increased
- Reports
- 21
- Reporting signal score
- 12.3431
- Event
- anaemia
- Reports
- 44
- Reporting signal score
- 19.9823
- Event
- aphonia
- Reports
- 7
- Reporting signal score
- 12.5948
- Event
- aspartate aminotransferase increased
- Reports
- 19
- Reporting signal score
- 11.4066
- Event
- bile duct stenosis
- Reports
- 11
- Reporting signal score
- 41.1638
- Event
- bone marrow toxicity
- Reports
- 6
- Reporting signal score
- 16.1265
- Event
- bone pain
- Reports
- 17
- Reporting signal score
- 14.8033
- Event
- breast cancer
- Reports
- 43
- Reporting signal score
- 87.365
- Event
- breast cancer metastatic
- Reports
- 56
- Reporting signal score
- 221.576
- Event
- breast cancer recurrent
- Reports
- 17
- Reporting signal score
- 59.0648
- Event
- central nervous system lesion
- Reports
- 12
- Reporting signal score
- 22.5119
- Event
- disease progression
- Reports
- 86
- Reporting signal score
- 148.378
- Event
- dizziness
- Reports
- 5
- Reporting signal score
- 12.3743
- Event
- drug hypersensitivity
- Reports
- 1
- Reporting signal score
- 12.6486
- Event
- ejection fraction abnormal
- Reports
- 4
- Reporting signal score
- 12.5554
- Event
- endometriosis
- Reports
- 9
- Reporting signal score
- 25.4738
- Event
- febrile neutropenia
- Reports
- 119
- Reporting signal score
- 270.149
- Event
- general physical health deterioration
- Reports
- 20
- Reporting signal score
- 13.1273
- Event
- genital abscess
- Reports
- 4
- Reporting signal score
- 17.33
- Event
- haematotoxicity
- Reports
- 27
- Reporting signal score
- 70.4545
- Event
- hormone receptor positive breast cancer
- Reports
- 6
- Reporting signal score
- 33.0037
- Event
- hyperglycaemia
- Reports
- 15
- Reporting signal score
- 14.893
- Event
- hypersensitivity vasculitis
- Reports
- 6
- Reporting signal score
- 11.3706
- Event
- immobile
- Reports
- 8
- Reporting signal score
- 20.0392
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And 49 more, listed on the interactive page.
- Dose
- 1.4 mg/m2
- Route
- Intravenous
- How often
- Days 1 and 8 of a 21-day cycle
Conditions of use
- Administer over 2 to 5 minutes
- Hydrogen bond acceptors
- 12
- Hydrogen bond donors
- 2
- Polar surface area
- 146.39
- Calculated partition coefficient (ALogP)
- 3.44
- Calculated partition coefficient (XLogP)
- 1.1
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 52
- Molecular formula
- C40H59NO11
- Monoisotopic mass
- 729.40881170
- Natural product
- Yes
- Recorded assays
- 75
- Active assays
- 34
- Confirmatory
- Other
Oral bioavailability
- Median
- 3.2
- Mean
- 3.2
- Minimum
- 3.2
- Maximum
- 3.2
- Unit
- %
- Assays
- 1
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- F
Related records
Trials (115)
- 1303GCC: Trastuzmab & Pertuzumab With Hormonal Therapy or Chemotherapy in Women Aged 60 and Over.
- A Multicenter, Single-Arm, Phase II Exploratory Study of Eribulin in Combination With Anlotinib for HER2-Negative Recurrent/Metastatic Breast Cancer Previously Treated With Antibody-Drug Conjugates
- A Multicenter, Single-arm, Prospective Phase II Clinical Study of Epalrotokewali Combined With Eribulin, Anlotinib, and Radiotherapy for the Treatment of Patients With Advanced Soft Tissue Sarcoma.
- A Phase 2 Study of Eribulin Followed by AC as Preoperative Therapy for HER2-negative Inflammatory Breast Cancer
- A Phase I Dose Escalation Study of Eribulin Plus Weekly Carboplatin for Metastatic Breast Patients
- A Phase Ib Trial of Eribulin in Combination With Irinotecan and Temozolamide in Children With Relapsed or Refractory Solid Tumors
- A Phase II Study of Eribulin and Pembrolizumab in Soft Tissue Sarcomas
- A Phase II Trial of Camrelizumab in Combination With Apatinib and Eribulin in Patients With Advanced TNBC
- A Phase III Study of ESG401 for Locally Advanced or Metastatic HR+/HER2- Breast Cancer
- A Phase III Study of JSKN016 Versus Treatment of Physician's Choice in Patients With Triple-Negative Breast Cancer Who Have Failed Standard of Care
- A Phase III Trial of Pertuzumab Retreatment in Previously Pertuzumab Treated Her2-Positive Advanced Breast Cancer
- 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)
- 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
- 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)
- 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)
- 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
- A Study of BL-M07D1 Versus Investigator's Choice of Chemotherapy in Patients With HER2-low Recurrent/Metastatic Breast Cancer
- A Study of Camrelizumab in Combination With Chemotherapy Regimen Comparative Chemotherapy Regimen for Metastatic Triple-negative Breast Cancer
- A Study of Eribulin in Combination With Oral Irinotecan for Adolescent and Young Adult Patients With Relapsed or Refractory Solid Tumors
- A Study of Eribulin With Gemcitabine in Patients With Advanced Liposarcoma or Leiomyosarcoma
Approved for (2)
- Cancer
- Neoplasm
In development for (13)
- Angiosarcoma Phase 2
- Breast cancer Phase 3
- Breast carcinoma Phase 3
- Epithelioid hemangioendothelioma Phase 2
- Fallopian tube carcinoma Phase 1
- Hereditary breast ovarian cancer syndrome Phase 2
- Inflammatory breast carcinoma Phase 2
- Metastatic melanoma Phase 1
- Non-small cell lung carcinoma Phase 3
- Ovarian carcinoma Phase 1
- Sarcoma Phase 3
- Solitary fibrous tumor Phase 2
- Triple-negative breast carcinoma Phase 3
Other linked conditions (2)
Targets (15)
- TUBA1A Tubulin inhibitor
- TUBA1B Tubulin inhibitor
- TUBA1C Tubulin inhibitor
- TUBA3C Tubulin inhibitor
- TUBA3E Tubulin inhibitor
- TUBA4A Tubulin inhibitor
- TUBB Tubulin inhibitor
- TUBB1 Tubulin inhibitor
- TUBB2A Tubulin inhibitor
- TUBB2B Tubulin inhibitor
- TUBB3 Tubulin inhibitor
- TUBB4A Tubulin inhibitor
- TUBB4B Tubulin inhibitor
- TUBB6 Tubulin inhibitor
- TUBB8 Tubulin inhibitor