Eribulin
PubChem CID
11354606
Structure
Primary Hazards
Molecular Formula
Synonyms
- Eribulin
- 253128-41-5
- eribuline
- Eribulina
- E-7389 free base
Molecular Weight
729.9 g/mol
Computed by PubChem 2.2 (PubChem release 2025.04.14)
Dates
- Create:2006-10-26
- Modify:2026-04-04
Description
Eribulin is 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. It has a role as an antineoplastic agent and a microtubule-destabilising agent. It is a polycyclic ether, a cyclic ketone, a polyether, a primary amino compound, a macrocycle and a cyclic ketal. It is a conjugate base of an eribulin(1+).
Eribulin is a microtubule inhibitor indicated for the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic disease. Eribulin was isolated from the marine sponge Halichondria okadai. Eribulin is also being investigated for use in the treatment of advanced solid tumors.
Eribulin is a Microtubule Inhibitor. The physiologic effect of eribulin is by means of Microtubule Inhibition.
See also: 
Eribulin Mesylate (active moiety of).
Eribulin Mesylate (active moiety of).Chemical Structure Depiction
Conformer generation is disallowed since too many atoms
(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
Computed by Lexichem TK 2.7.0 (PubChem release 2025.04.14)
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
Computed by InChI 1.07.2 (PubChem release 2025.04.14)
UFNVPOGXISZXJD-JBQZKEIOSA-N
Computed by InChI 1.07.2 (PubChem release 2025.04.14)
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
Computed by OEChem 2.3.0 (PubChem release 2025.04.14)
C40H59NO11
Computed by PubChem 2.2 (PubChem release 2025.04.14)
441045-16-5
ERIBULIN
- eribulin
- 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
- Eribulin
- 253128-41-5
- eribuline
- Eribulina
- E-7389 free base
- ER 086526
- LR24G6354G
- 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
- CHEBI:63587
- B-1939
- DTXSID101009321
- NSC-707389
- eribulinum
- RefChem:56930
- L01XX41
- DTXCID701436148
- ER-86526
- ER086526
- Eribulin [INN]
- (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
- ER-086526
- (2R,3R,3aS,7R,8aS,9S,10aR,11S,12R,13aR,13bS,15S,18S,21S,24S,26R,28R,29aS)-2-[(2S)-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
- (1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,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[24.9.2.1(3,32).1(3,33).1(6,9).1(12,16).0(18,22).0(29,36).0(31,35)]hentetracontan-24-one
- Eribulin free
- UNII-LR24G6354G
- (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[24.9.2.1~3,32~.1~3,33~.1~6,9~.1~12,16~.0~18,22~.0~29,36~.0~31,35~]hentetracontan-24-One (Non-Preferred Name)
- ERIBULIN [MI]
- ERIBULIN [VANDF]
- ERIBULIN [MART.]
- ERIBULIN [WHO-DD]
- B 1939
- e7389-lf
- GTPL6813
- orb1707961
- CHEMBL1683590
- SCHEMBL15783821
- EX-A4873D
- UFNVPOGXISZXJD-JBQZKEIOSA-N
- C40H59NO11
- GLXC-10730
- MFCD23160037
- AKOS040740784
- AT36513
- DB08871
- NCGC00510497-02
- BP-29357
- DA-52974
- HY-13442
- MS-31267
- Q408717
- 2-[4-[[(2R)-2-Aminobutyl]amino]-2-quinazolinyl]-4-chloro-phenol
- (1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-amino-2-hydroxy-propyl]-21-methoxy-14-methyl-8,15-dimethylene-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
- (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[24.9.2.1~3,32~.1~3,33~.1~6,9~.1~12,16~.0~18,22~.0~29,36~.0~31,35~]hentetracontan-24-one
- (2S,5S,8S,11S,13R,15R,16aS,18R,19R,19aS,23R,24aS,25S,26aR,27S,28R,29aR,29bS)-18-((S)-3-amino-2-hydroxypropyl)-19-methoxy-13-methyl-7,14-dimethylenehexacosahydro-25H-2,27:5,8:11,15-triepoxy-23,25-ethano-2,28-methanofuro[3,2-i]furo[2',3':5,6]pyrano[4,3-b][1,4]dioxacyclopentacosin-21(3H)-one
- 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)-
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
729.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2025.04.14)
Property Name
XLogP3-AA
Property Value
1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2025.04.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Property Name
Exact Mass
Property Value
729.40881170 Da
Reference
Computed by PubChem 2.2 (PubChem release 2025.04.14)
Property Name
Monoisotopic Mass
Property Value
729.40881170 Da
Reference
Computed by PubChem 2.2 (PubChem release 2025.04.14)
Property Name
Topological Polar Surface Area
Property Value
146 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Property Name
Heavy Atom Count
Property Value
52
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1380
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
19
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2025.04.14)
Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Antimitotic Agents
EMA approved medicines: Human medicine
Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see the neighbor discontinuation help page for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Eribulin Mesylate (active moiety of)PubMed Count
Provider
Information
PubChem SID: 516459505
Purchasable Chemical: orb1707961
PubChem SID: 505918859
Purchasable Chemical: API253128415
PubChem SID: 481553321
Purchasable Chemical: AKOS040740784
PubChem SID: 522883386
Purchasable Chemical: RM-E180200
PubChem SID: 513529263
Purchasable Chemical: 253128-41-5
PubChem SID: 495944099
Purchasable Chemical: GLXC-10730
PubChem SID: 493547453
Purchasable Chemical: MCULE-4288647093
PubChem SID: 492744602
Purchasable Chemical: MCULE-9805132778
PubChem SID: 383007456
Purchasable Chemical: MolPort-046-418-101
PubChem SID: 476036767
Purchasable Chemical: 2023-03-14B3133
PubChem SID: 508644319
Purchasable Chemical: MidasPharma-235
PubChem SID: 350095222
Purchasable Chemical: ENKE253128415
PubChem SID: 470540545
Purchasable Chemical: CQ_253128-41-5
MeSH Heading
EFO Term
Max Phase
MeSH Heading
EFO Term
Max Phase
Phase 2
Page of 3
For the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic cancer.
Eribulin mesylate is an inhibitor of microtubule function and is used as an antineoplastic agent for refractory, metastatic breast cancer and liposarcoma. Despite its cytotoxic activity against cancer cells, eribulin has rarely been implicated in causing clinically apparent acute liver injury.
Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Antimitotic Agents
Antineoplastic Agents
- ROSETTA Breast-01: The Effects and Safety of Pumitamig in Patients With Triple-Negative Breast CancerCTID: NCT07173751Phase: Phase 3Status: RecruitingDate: 2026-03-25
- A Cancer Vaccine (STEMVAC) in Combination With Chemotherapy for the Treatment of PD-L1 Negative Metastatic Triple-Negative Breast CancerCTID: NCT07078604Phase: Phase 2Status: RecruitingDate: 2026-03-12
- YL202 Versus Treatment of Physician's Choice in Patients With HR+/HER2- Breast CancerCTID: NCT07461454Phase: Phase 3Status: Not yet recruitingDate: 2026-03-10
- PIK3CA/PTEN-altered Advanced Breast Cancer Treated With MEN1611 Monotherapy or in Combination With EribulinCTID: NCT05810870Phase: Phase 2Status: Active, not recruitingDate: 2026-03-10
- Study of E7389 Liposomal Formulation in Participants With Solid TumorCTID: NCT03207672Phase: Phase 1Status: Active, not recruitingDate: 2026-03-03
Page of 20
- Can Eribulin enhance the effect of subsequent endocrine therapy?- a phase 2 study for patients with ER positive HER2 normal metastatic breast cancerEudraCT: 2020-004909-32Phase: Phase 2Status: CompletedDate: 2021-02-16
- AIRE: – ASSESSING IMMUNORESPONSE POST ERIBULIN: ERIBULIN AND IMMUNOGENICITY IN ADVANCED BREAST CANCER – A PROSPECTIVELY RANDOMIZED PHASE IV STUDYEudraCT: 2020-001938-35Phase: Phase 4Status: Prematurely EndedDate: 2020-10-02
- An International, Phase 3, Multicenter, Randomized, Open-Label Trial Comparing Balixafortide in combination with Eribulin versus Eribulin alone in Patients with HER2 negative, Locally Recurrent or Metastatic Breast CancerEudraCT: 2018-004211-42Phase: Phase 3Status: Prematurely Ended, GB - no longer in EU/EEADate: 2020-03-06
- A Phase I/II, open label, non-randomized study to evaluate safety, tolerability, pharmacokinetics and clinical activity of S64315 in patients with locally advanced or metastatic breast cancer in combination with various standard treatments including hormonal and cytotoxic agentsEudraCT: 2019-000998-23Phase: Phase 1, Phase 2Status: Prematurely EndedDate: 2019-09-19
- Phase 3 Study of Sacituzumab Govitecan (IMMU-132) Versus Treatment of Physician's Choice (TPC) in subjects with Hormonal Receptor-Positive (HR+) Human Epidermal Growth Factor Receptor 2 (HER2) Negative Metastatic Breast Cancer (MBC) who have failed at least two prior chemotherapy regimensEudraCT: 2018-004201-33Phase: Phase 3Status: Completed, GB - no longer in EU/EEA, OngoingDate: 2019-08-16
Page of 8
- Whole brain radiotherapy with concomitant Eribulin for advanced breast cancer brain metastasisCTID: jRCT1031250065Status: RecruitingDate: 2025-04-28
- A phase II study of eribulin monotherapy for advanced extramammary Paget's diseaseCTID: jRCT2011220022Status: RecruitingDate: 2022-10-28
- JCOG1802: A randomized phase II trial of 2nd line treatment for advanced soft tissue sarcoma comparing trabectedin, eribulin and pazopanibCTID: jRCTs031190152Status: Not RecruitingDate: 2019-12-05
- Trastuzumab Deruxtecan (DS-8201a) Versus Investigator's Choice for HER2-low Breast Cancer That Has Spread or Cannot be Surgically Removed [DESTINY-Breast04]CTID: jRCT2080224162Status: completedDate: 2018-11-26
Page of 7
- Category/Dataset: Human medicineActive Substance: Eribulin mesylateStatus: AuthorisedTherapeutic Use: Breast Neoplasms;LiposarcomaCondition/Indication: Eribulin Baxter is indicated for the treatment of adult patients with locally advanced or metastatic breast cancer who have progressed after at least one chemotherapeutic regimen for advanced disease. Prior therapy should have included an anthracycline and a taxane in either the adjuvant or metastatic setting unless patients were not suitable for these treatments. Eribulin Baxter is indicated for the treatment of adult patients with unresectable liposarcoma who have received prior anthracycline containing therapy (unless unsuitable) for advanced or metastatic diseasePublish Date: 2024-06-27Update Date: 2026-02-24
- Category/Dataset: Human medicineProduct/no.: Mevlyq (EMA Product Number: EMEA/H/C/006134)Active Substance: Eribulin mesylateStatus: AuthorisedTherapeutic Use: Breast Neoplasms;LiposarcomaCondition/Indication: Mevlyq is indicated for the treatment of adult patients with locally advanced or metastatic breast cancer who have progressed after at least one chemotherapeutic regimen for advanced disease. Prior therapy should have included an anthracycline and a taxane in either the adjuvant or metastatic setting unless patients were not suitable for these treatments. Mevlyq 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.Publish Date: 2024-02-09Update Date: 2024-10-16
- Category/Dataset: Human medicineProduct/no.: Halaven (EMA Product Number: EMEA/H/C/002084)Active Substance: EribulinStatus: AuthorisedTherapeutic Use: Breast Neoplasms;LiposarcomaCondition/Indication: 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).Publish Date: 2011-03-17Update Date: 2024-10-11
- Category/Dataset: Paediatric investigation plans (PIP)Active Substance: EribulinStatus: PIP decision type: PM: decision on the application for modification of an agreed PIPPharmaceutical Form: Solution for injectionAdministration Route: Intravenous useTherapeutic Use: OncologyCondition/Indication: Treatment of soft tissue sarcomaPublish Date: 2021-12-06Update Date: 2023-03-16
- Category/Dataset: EMA Article 57Product/no.: EribulinActive Substance: EribulinStatus: Product authorisation country: Croatia; Latvia; Estonia; Lithuania; Sweden; FinlandAdministration Route: Intravenous Use
Page of 7
Max Phase
Approved
First Approval
2010
Availability Type
Prescription Only
Route of Administration
Parenteral
Structure
Gene
Protein
Open Targets Target ID
Mechanism of Action
Structure
Gene
Protein
Open Targets Target ID
Mechanism of Action
Tubulin inhibitor
Structure
Gene
Protein
Open Targets Target ID
Mechanism of Action
Tubulin inhibitor
Structure
Gene
Protein
Open Targets Target ID
Mechanism of Action
Tubulin inhibitor
Structure
Gene
Protein
Open Targets Target ID
Mechanism of Action
Tubulin inhibitor
Structure
Gene
Protein
Open Targets Target ID
Mechanism of Action
Tubulin inhibitor
Page of 2
Linear
FDA UNII
LR24G6354G
Active Moiety
ERIBULIN
Pharmacological Classes
Physiologic Effects [PE] - Microtubule Inhibition
Pharmacological Classes
Established Pharmacologic Class [EPC] - Microtubule Inhibitor
FDA Pharmacology Summary
Eribulin is a Microtubule Inhibitor. The physiologic effect of eribulin is by means of Microtubule Inhibition.
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (2021) DOI:10.1021/acsenvironau.1c00008. List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
L - Antineoplastic and immunomodulating agents
L01 - Antineoplastic agents
L01X - Other antineoplastic agents
L01XX - Other antineoplastic agents
L01XX41 - Eribulin
ATCvet Code
Route of Elimination
Eribulin is eliminated primarily in feces unchanged.
Volume of Distribution
43 L/m2 to 114 L/m2
Clearance
1.16 L/hr/m2 to 2.42 L/hr/m2 (dose range of 0.25 mg/m2 to 4.0 mg/m2). [FDA]
49 to 65%.
There are no major human metabolites of eribulin, CYP3A4 negligibly metabolizes eribulin in vitro.
about 40 hours
Eribulin inhibits the growth phase of microtubules without affecting the shortening phase and sequesters tubulin into nonproductive aggregates. Eribulin exerts its effects via a tubulin-based antimitotic mechanism leading to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage. [FDA]
Pictogram(s)
Signal
Danger
GHS Hazard Statements
H301+H311+H331 (95%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
H301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]
H311 (97.5%): Toxic in contact with skin [Danger Acute toxicity, dermal]
H331 (97.5%): Toxic if inhaled [Danger Acute toxicity, inhalation]
H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
H351 (97.5%): Suspected of causing cancer [Warning Carcinogenicity]
H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
Precautionary Statement Codes
ECHA C&L Notifications Summary
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Acute Tox. 3 (97.5%)
Acute Tox. 3 (97.5%)
Acute Tox. 3 (97.5%)
Muta. 2 (100%)
Carc. 2 (97.5%)
Repr. 2 (100%)
Eribulin is a cytotoxic chemotherapeutic agent and serum aminotransferase and alkaline phosphatase elevations are common during cyclic therapy of breast cancer and liposarcoma. The reported rates of ALT elevations have ranged from 8% to 83% with values above 5 times the upper limit or normal (ULN) in 2% to 5%. Isolated mention of “toxic hepatitis” have been made in reports of clinical trials of eribulin but no details of the onset, clinical features and course have been published and the role of eribulin in these outcomes is uncertain. Nevertheless, despite high rates of serum enzyme elevations during treatment, cases of clinically apparent liver injury have not been reported in detail and must be rare.
Likelihood score: E* (unproven but suspected cause of liver injury).
◉ Summary of Use during Lactation
No information is available on the clinical use of eribulin during breastfeeding. The manufacturer recommends that breastfeeding be discontinued during eribulin therapy and for 2 weeks after the last dose.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
Source Disease
Data Source
Page of 3
- Publication Name: The Journal of clinical investigationPublication Date: 2025-07-01
- Publication Name: Asian Pacific journal of cancer prevention : APJCPPublication Date: 2025-05-01
- Publication Name: In vivo (Athens, Greece)Publication Date: 2025-04-28
- Publication Name: International Journal of CancerPublication Date: 2025-04-15PMID: 40232157DOI: 10.1002/ijc.35446
Page of 135
Publication Date: 2015Publication Name: Handbook of Anticancer Drugs from Marine Origin- Publication Date: 2024Publication Name: BJC Reports
- Publication Date: 2023Publication Name: Cancer Nanotechnology
Page of 2
- Publication Date: 2018Publication Name: Synthesis
- Publication Date: 2016Publication Name: Synthesis
- Publication Date: 2013Publication Name: Synlett
- Publication Date: 2013Publication Name: Synlett
- Publication Date: 2013Publication Name: Synlett
Chemical
Selected evidence
Chemical
Selected evidence
656 articles
View All- Eribulin Mesylate for the Treatment of Patients with Refractory Metastatic Breast Cancer: Use of a “Physician's Choice” Control Arm in a Randomized Approval TrialPMID 22282463; DOI 10.1158/1078-0432.ccr-11-2149; Clinical cancer research : an official journal of the American Association for Cancer Research 2012-03-14Name matches: eribulin mesylate eribulin
- Antitumor and anticancer stem cell activities of eribulin mesylate and antiestrogens in breast cancer cellsPMID 25552385; DOI 10.1007/s12282-014-0580-9; Breast cancer (Tokyo, Japan) 2015-01-01Name matches: eribulin mesylate eribulin
- Mesenchymal–epithelial Transition and Tumor Vascular Remodeling in Eribulin Chemotherapy for Breast CancerPMID 29277801; DOI 10.21873/anticanres.12236; Anticancer Research 2018-01-02Name matches: eribulin mesylate eribulin
Chemical
![(1S,3S,6S,9S,12S,14R,16R,18S,20R,21S,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,23,30,34,37,39,40,41-nonaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one.png](data:image/webp;base64,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)
Selected evidence
78 articles
View All- Phase I Study of Eribulin Mesylate Administered Once Every 21 Days in Patients with Advanced Solid TumorsPMID 19509146; DOI 10.1158/1078-0432.ccr-09-0360; Clinical cancer research : an official journal of the American Association for Cancer Research 2009-06-15
- Interactions between the chemotherapeutic agent eribulin mesylate (E7389) and P-glycoprotein in CF-1 abcb1a-deficient mice and Caco-2 cellsPMID 21162698; DOI 10.3109/00498254.2010.542256; Xenobiotica; the fate of foreign compounds in biological systems 2010-12-17
- Eribulin approved for advanced breast cancerPMID 21164057; DOI 10.2146/news100085; American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 2011-01-01
Chemical
Selected evidence
126 articles
View All- Phase II clinical study of eribulin monotherapy in Japanese patients with metastatic breast cancer who had well-defined taxane resistancePMID 27125669; DOI 10.1007/s10549-016-3808-x; Breast Cancer Research and Treatment 2016-04-28Name matches: taxane eribulin
- Eribulin mesylate in the treatment of metastatic breast cancerPMID 22291464; DOI 10.2147/btt.s19811; Biologics: Targets and Therapy 2012-01-01Name matches: taxane eribulin
- [Efficacy, safety and cost of eribulin in patients with metastatic breast cancer]PMID 26022285; DOI 10.1016/j.bulcan.2015.03.021; Bulletin du cancer 2015-09-01Name matches: taxane eribulin
Gene/Protein/Enzyme
Selected evidence
Gene/Protein/Enzyme
Selected evidence
10 articles
View All- Phase II clinical study of eribulin monotherapy in Japanese patients with metastatic breast cancer who had well-defined taxane resistancePMID 27125669; DOI 10.1007/s10549-016-3808-x; Breast Cancer Research and Treatment 2016-04-28
- Significant Association Between Low Baseline Neutrophil-to-Lymphocyte Ratio and Improved Progression-free Survival of Patients With Locally Advanced or Metastatic Breast Cancer Treated With Eribulin But Not With Nab-PaclitaxelPMID 29605174; DOI 10.1016/j.clbc.2018.03.002; Clinical Breast Cancer 2018-10-01
- Quality of life outcomes including neuropathy-associated scale from a phase II, multicenter, randomized trial of eribulin plus gemcitabine versus paclitaxel plus gemcitabine as first-line chemotherapy for HER2-negative metastatic breast cancer: Korean Cancer Study Group Trial (KCSG BR13-11)PMID 31138332; DOI 10.1186/s40880-019-0375-7; Cancer communications (London, England) 2019-05-28
Gene/Protein/Enzyme
Selected evidence
4 articles
View All- Clinical usefulness of eribulin as first- or second-line chemotherapy for recurrent HER2-negative breast cancer: a randomized phase II study (JBCRG-19)PMID 33891194; DOI 10.1007/s10147-021-01920-0; International Journal of Clinical Oncology 2021-04-23
- Quality of life outcomes including neuropathy-associated scale from a phase II, multicenter, randomized trial of eribulin plus gemcitabine versus paclitaxel plus gemcitabine as first-line chemotherapy for HER2-negative metastatic breast cancer: Korean Cancer Study Group Trial (KCSG BR13-11)PMID 31138332; DOI 10.1186/s40880-019-0375-7; Cancer communications (London, England) 2019-05-28
- Evolution of overall survival and receipt of new therapies by subtype among 20 446 metastatic breast cancer patients in the 2008-2017 ESME cohortPMID 33895695; DOI 10.1016/j.esmoop.2021.100114; ESMO Open 2021-06-01
Gene/Protein/Enzyme
Selected evidence
1 article
View All- Identifying Therapies to Combat Epithelial Mesenchymal Plasticity-Associated Chemoresistance to Conventional Breast Cancer Therapies Using An shRNA Library ScreenPMID 32365878; DOI 10.3390/cancers12051123; Cancers 2020-04-30Name matches: ccdc80 eribulin
Disease
Selected evidence
Disease
Selected evidence
23 articles
View All- Phase II clinical study of eribulin monotherapy in Japanese patients with metastatic breast cancer who had well-defined taxane resistancePMID 27125669; DOI 10.1007/s10549-016-3808-x; Breast Cancer Research and Treatment 2016-04-28Name matches: breast cancer eribulin
- Clinical usefulness of eribulin as first- or second-line chemotherapy for recurrent HER2-negative breast cancer: a randomized phase II study (JBCRG-19)PMID 33891194; DOI 10.1007/s10147-021-01920-0; International Journal of Clinical Oncology 2021-04-23Name matches: bc; breast cancer; her2-negative eribulin
- Significant Association Between Low Baseline Neutrophil-to-Lymphocyte Ratio and Improved Progression-free Survival of Patients With Locally Advanced or Metastatic Breast Cancer Treated With Eribulin But Not With Nab-PaclitaxelPMID 29605174; DOI 10.1016/j.clbc.2018.03.002; Clinical Breast Cancer 2018-10-01Name matches: breast cancer eribulin
Disease
Selected evidence
20 articles
View All- Phase II clinical study of eribulin monotherapy in Japanese patients with metastatic breast cancer who had well-defined taxane resistancePMID 27125669; DOI 10.1007/s10549-016-3808-x; Breast Cancer Research and Treatment 2016-04-28Name matches: metastasis; metastatic eribulin
- [Maintenance of Long-Term Stable Disease(SD)in Metastatic Breast Cancer with Eribulin - A Case Report of Long-Term SD in Japan]PMID 28028262; Gan to kagaku ryoho. Cancer & chemotherapy 2016-12-01 (Review Article)Name matches: metastatic eribulin
- [Efficacy, safety and cost of eribulin in patients with metastatic breast cancer]PMID 26022285; DOI 10.1016/j.bulcan.2015.03.021; Bulletin du cancer 2015-09-01Name matches: metastatic eribulin
Disease
Selected evidence
19 articles
View All- A Single Low Dose of Eribulin Regressed a Highly Aggressive Triple-negative Breast Cancer in a Patient-derived Orthotopic Xenograft ModelPMID 32366392; DOI 10.21873/anticanres.14218; Anticancer Research 2020-05-01Name matches: tumor; tumors eribulin
- In vivo imaging of eribulin-induced reoxygenation in advanced breast cancer patients: a comparison to bevacizumabPMID 27140309; DOI 10.1038/bjc.2016.122; British Journal of Cancer 2016-05-03Name matches: tumour eribulin
- Costs associated with Eribulin treatment for patients with metastatic breast cancer in a comprehensive cancer center in FrancePMID 27639032; DOI 10.1016/j.breast.2016.08.015; Breast (Edinburgh, Scotland) 2016-12-01Name matches: cancer eribulin
Organism
Selected evidence
Organism
Selected evidence
1 article
View All- Evolution of overall survival and receipt of new therapies by subtype among 20 446 metastatic breast cancer patients in the 2008-2017 ESME cohortPMID 33895695; DOI 10.1016/j.esmoop.2021.100114; ESMO Open 2021-06-01Name matches: esme eribulin
Organism
Selected evidence
12 articles
View All- Characterization of a New Small Bowel Adenocarcinoma Cell Line and Screening of Anti-Cancer Drug against Small Bowel AdenocarcinomaPMID 25478808; DOI 10.1016/j.ajpath.2014.10.006; The American Journal of Pathology 2015-02-01
- Induction of Morphological and Biochemical Apoptosis following Prolonged Mitotic Blockage by Halichondrin B Macrocyclic Ketone Analog E7389PMID 15313917; DOI 10.1158/0008-5472.can-04-1169; Cancer Research 2004-08-15
- Comparison of the Activities of the Truncated Halichondrin B Analog NSC 707389 (E7389) with Those of the Parent Compound and a Proposed Binding Site on TubulinPMID 16940412; DOI 10.1124/mol.106.026641; Molecular Pharmacology 2006-12-01
Organism
Selected evidence
2 articles
View All- A Single Low Dose of Eribulin Regressed a Highly Aggressive Triple-negative Breast Cancer in a Patient-derived Orthotopic Xenograft ModelPMID 32366392; DOI 10.21873/anticanres.14218; Anticancer Research 2020-05-01Name matches: mice eribulin
- Interactions between the chemotherapeutic agent eribulin mesylate (E7389) and P-glycoprotein in CF-1 abcb1a-deficient mice and Caco-2 cellsPMID 21162698; DOI 10.3109/00498254.2010.542256; Xenobiotica; the fate of foreign compounds in biological systems 2010-12-17Name matches: mice eribulin
- Publication Number: CN-119746092-APriority Date: 2025-01-07
- Publication Number: CN-119371542-BPriority Date: 2024-12-27Grant Date: 2025-04-04
- Publication Number: CN-119524152-APriority Date: 2024-12-06
- Publication Number: CN-119488484-APriority Date: 2024-11-26
Page of 1,323
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=UFNVPOGXISZXJD-JBQZKEIOSA-N
Chemical
Selected evidence
Chemical
Selected evidence
26 patents from 19 patent families
View All- Use of eribulin and lenvatinib as combination therapy for treatment of cancerUS-9549922-B2; Grant Date: 2017-01-24
- Methods and uses for predicting response to eribulinEP-2686441-B1; Grant Date: 2019-05-08
- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
Chemical
Selected evidence
30 patents from 17 patent families
View All- Compounds useful in the synthesis of halichondrin B analogsUS-8203010-B2; Grant Date: 2012-06-19
- Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin BJP-6625533-B2; Grant Date: 2019-12-25
- Synthetic process for preparing macrocyclic C1-keto analogues of halichondrin B and useful intermediates thereforJP-6531911-B2; Grant Date: 2019-06-19
Chemical
Selected evidence
30 patents from 17 patent families
View All- Compounds useful in the synthesis of halichondrin B analogsUS-8203010-B2; Grant Date: 2012-06-19
- Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin BJP-6625533-B2; Grant Date: 2019-12-25
- Methods and uses for predicting response to eribulinEP-2686441-B1; Grant Date: 2019-05-08
Disease
Selected evidence
Disease
Selected evidence
103 patents from 63 patent families
View All- Methods and uses for predicting response to eribulinEP-2686441-B1; Grant Date: 2019-05-08
- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
- Use of eribulin in the treatment of breast cancerJP-6466339-B2; Grant Date: 2019-02-06
Disease
Selected evidence
11 patents from 9 patent families
View All- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
- Methods and compositions for predicting response to eribulinJP-6612280-B2; Grant Date: 2019-11-27
- Use of eribulin in the treatment of breast cancerJP-6678783-B2; Grant Date: 2020-04-08
Disease
Selected evidence
113 patents from 73 patent families
View All- Use of eribulin and lenvatinib as combination therapy for treatment of cancerUS-9549922-B2; Grant Date: 2017-01-24
- Methods and uses for predicting response to eribulinEP-2686441-B1; Grant Date: 2019-05-08
- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
Gene
Selected evidence
Gene
Selected evidence
1 patent from 1 patent family
View All- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
Gene
Selected evidence
20 patents from 14 patent families
View All- Use of eribulin and lenvatinib as combination therapy for treatment of cancerUS-9549922-B2; Grant Date: 2017-01-24
- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
- Synthetic process for preparing macrocyclic C1-keto analogues of halichondrin B and useful intermediates thereforJP-6531911-B2; Grant Date: 2019-06-19
Gene
Selected evidence
2 patents from 1 patent family
View All- Methods and compositions for predicting response to eribulinJP-6612280-B2; Grant Date: 2019-11-27
Organism
Selected evidence
Organism
Selected evidence
18 patents from 12 patent families
View All- Use of eribulin and lenvatinib as combination therapy for treatment of cancerUS-9549922-B2; Grant Date: 2017-01-24
- Methods and uses for predicting response to eribulinEP-2686441-B1; Grant Date: 2019-05-08
- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
Organism
Selected evidence
12 patents from 7 patent families
View All- Use of eribulin and lenvatinib as combination therapy for treatment of cancerUS-9549922-B2; Grant Date: 2017-01-24
- Methods and uses for predicting response to eribulinEP-2686441-B1; Grant Date: 2019-05-08
- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
Organism
Selected evidence
12 patents from 7 patent families
View All- Use of eribulin and lenvatinib as combination therapy for treatment of cancerUS-9549922-B2; Grant Date: 2017-01-24
- Methods and uses for predicting response to eribulinEP-2686441-B1; Grant Date: 2019-05-08
- Use of eribulin in the treatment of cancerEP-3148526-B1; Grant Date: 2021-01-06
Protein
Gene
Taxonomy
Action
Evidence
Data Source
Protein
Gene
Taxonomy
Action
INHIBITOR
Evidence
Data Source
Protein
Gene
Taxonomy
Action
INHIBITOR
Evidence
Data Source
Protein
Gene
Taxonomy
Action
Inhibitor
Evidence
Data Source
Protein
Gene
Taxonomy
Action
Inhibition
Evidence
Data Source
Protein
Gene
Taxonomy
Action
INHIBITOR
Evidence
Data Source
Page of 3
- BioAssay AID: 1963824Target Name: SYK - spleen associated tyrosine kinase (human)
- BioAssay AID: 1963824Target Name: Tyrosine-protein kinase SYK (human)
- BioAssay AID: 1963823Target Name: Tyrosine-protein kinase SYK (human)
- BioAssay AID: 1963823Target Name: SYK - spleen associated tyrosine kinase (human)
- BioAssay AID: 2202234
Page of 15
- An analogue of halichondrin B, a substance derived from a marine sponge (Lissodendoryx sp.) with antineoplastic activity. Eribulin binds to the vinca domain of tubulin and inhibits the polymerization of tubulin and the assembly of microtubules, resulting in inhibition of mitotic spindle assembly, induction of cell cycle arrest at G2/M phase, and, potentially, tumor regression.
- 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
- Microtubule Inhibitor [EPC]
- Microtubule Inhibition [PE]
- Antineoplastic Agents
- CTDComparative Toxicogenomics Database - CTD selects and organizes gene, sequence, chemical, reference, and taxonomic data about gene-chemical interactions. It is hosted at North Carolina State University (NCSU).
- ChEBIChemical Entities of Biological Interest - Dictionary of molecular entities focused on "small" chemical compounds. ChEBI is part of the EMBL-European Bioinformatics Institute.
- ClinicalTrials.govClinicalTrials.gov - ClinicalTrials.gov offers up-to-date information for locating federally and privately supported clinical trials for a wide range of diseases and conditions
- DailyMedDailyMed - Information about marketed drugs including FDA approved labels (package inserts)
Page of 5
- Tubulins are a family of intracellular proteins most commonly associated with microtubules, part of the cytoskeleton. They are exploited for therapeutic gain in cancer chemotherapy as targets for agents derived from a variety of natural products: taxanes, colchicine and vinca alkaloids. These are thought to act primarily through β-tubulin, thereby interfering with the normal processes of tubulin polymer formation and disassembly.
- H301: Toxic if swallowed [Danger: Acute toxicity, oral]
- H301+H311+H331: Toxic if swallowed, in contact with skin or if inhaled [Danger: Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
- H311: Toxic in contact with skin [Danger: Acute toxicity, dermal]
- H331: Toxic if inhaled [Danger: Acute toxicity, inhalation]
- H341: Suspected of causing genetic defects [Warning: Germ cell mutagenicity]
Page of 7
- Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (2021) DOI:10.1021/acsenvironau.1c00008. List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
- SOLUTIONSMLOS contains the chemicals used for modelling in the SOLUTIONS project (www.solutions-project.eu/), provided by Jaroslav Slobodnik (EI). Dataset DOI:10.5281/zenodo.2653022
- A list of chemicals associated with neurotoxicity compiled through systematic literature mining of PubMed using MeSH terms, compiled by Nancy Baker, Antony Williams (US EPA) and Emma Schymanski (LCSB), details in Schymanski et al. 2019, DOI:10.1039/C9EM00068B. Dataset DOI:10.5281/zenodo.2653214
- A comprehensive list of 7074 endocrine disruptors compiled by PARC T4.2., integrating assessments by EU and national regulators, contributions from entities like the European Chemicals Agency (ECHA) and complemented by other potential endocrine disruptors (hormones, bisphenols, etc.). The list also includes potentially active endocrine disruptors screened from all substances in the NORMAN SusDat database (https://www.norman-network.com/nds/susdat/) using VEGA (QSAR) EDC prediction models (https://www.vegahub.eu/about-qsar), in vitro assay data and machine learning predictions from ToxCast. Dataset DOI:10.5281/zenodo.10944198
- Short_Description: CPDat Structure lists are versioned iteratively and this panel navigates between the various versions
- Short_Description: Chemicals associated with neurotoxicity via PubMed Literature Mining
- Short_Description: Pharmaceuticals marketed in Luxembourg
- Short_Description: List containing the 6462 chemicals used for modelling in the SOLUTIONS project.
- Short_Description: Wikipedia includes data for thousands of chemicals. ChemBoxes and DrugBoxes includes data such as CAS Registry Numbers, SMILES and InChIs.
Page of 3
- alkyl primary amines
- alkyl primary amines
- acetals
- pyranose derivativesChEBI: 79986
- macrocyclic ring systemsCompounds that contain a ring system with more than 11 atoms in the ring.
Page of 4
- Drug and substance information from paediatric investigation plans
- Human drug and substance information from the public assessment reports
- Drug and substance list from EMA Article 57 database
- A primary or metastatic malignant neoplasm affecting the head and neck. Representative examples include oral cavity squamous cell carcinoma, laryngeal squamous cell carcinoma, and salivary gland carcinoma.
- A malignant neoplasm involving the male breast.
- A group of at least three distinct histological types of lung cancer, including non-small cell squamous cell carcinoma, adenocarcinoma, and large cell carcinoma. Non-small cell lung carcinomas have a poor response to conventional chemotherapy.
- An invasive breast carcinoma which is negative for expression of estrogen receptor (ER), progesterone receptor (PR), and human epidermal growth factor receptor 2 (HER2).
- A carcinoma that arises from epithelial cells of the breast
Page of 7
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/chemidplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_use
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- European Chemicals Agency (ECHA)LICENSEUse of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.https://echa.europa.eu/web/guest/legal-noticeEribulin (EC: 803-583-7)https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/236937
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ChEBIChEBI Ontologyhttps://www.ebi.ac.uk/chebi/
- FDA Pharm ClassesLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingFDA Pharmacological Classificationhttps://www.fda.gov/industry/structured-product-labeling-resources/pharmacologic-class
- LiverTox
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licenceDisease Classificationhttps://www.opentargets.org/
- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- DrugCentral
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)https://www.guidetopharmacology.org/about.jsp#licenseGuide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Drugs and Lactation Database (LactMed)
- European Medicines Agency (EMA)LICENSEInformation on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.https://www.ema.europa.eu/en/about-us/about-website/legal-noticeEribulin Baxterhttps://www.ema.europa.eu/en/medicines
- EU Clinical Trials Register
- Japan Chemical Substance Dictionary (Nikkaji)
- Metabolomics Workbench
- NIPH Clinical Trials Search of Japan
- NLM RxNorm TerminologyLICENSEThe RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- WHO Anatomical Therapeutic Chemical (ATC) ClassificationLICENSEUse of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.https://www.whocc.no/copyright_disclaimer/ATC Classificationhttps://atcddd.fhi.no/atc_ddd_index/
- WHO ATCvet - Classification of Veterinary MedicinesLICENSEUse of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.https://atcddd.fhi.no/copyright_disclaimer/ATCvet Classificationhttps://atcddd.fhi.no/atcvet/atcvet/
- PharmGKBLICENSEPharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).https://www.pharmgkb.org/page/policies
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/about
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.https://www.rcsb.org/pages/policies
- Springer Nature
- Therapeutic Target Database (TTD)
- Thieme ChemistryLICENSEThe Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc-nd/4.0/
- Wikidata
- Wikipedia
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.html
- PubChem
- GHS Classification (UNECE)GHS Classificationhttps://unece.org/about-ghs
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 393759455https://pubchem.ncbi.nlm.nih.gov/substance/393759455
- NCBI
CONTENTS