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Compound Detail

CHEMBL1683590

ERIBULIN
💊 Approved Drug
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💊 Approved Drug
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
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1683590
Name ERIBULIN
Phase Approved
Structure Type MOL
InChI Key UFNVPOGXISZXJD-JBQZKEIOSA-N
Therapeutic ✓ Yes

Known Names

B-1939 E-7389 FREE BASE ER-086526 Eribulin Eribulina Eribuline
3
Targets
9
Activities
1
Assay Types
5
PK Parameters
11
Publications
6
Known Names
15
Indications

Molecular Properties

729.9
MW (Da)
3.44
ALogP
12
HBA
2
HBD
146.4
PSA (Ų)
0.41
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2010
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -bulin
USAN Year 2006

Extended Properties

Molecular Formula C40H59NO11
MW 729.91
Aromatic Rings 0
Heavy Atoms 52
NP-Likeness 1.84

Indications

Neoplasms Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma, Non-Small-Cell Lung Sarcoma Triple Negative Breast Neoplasms Hemangioendothelioma, Epithelioid Hemangiosarcoma Hereditary Breast and Ovarian Cancer Syndrome Inflammatory Breast Neoplasms Solitary Fibrous Tumors Fallopian Tube Neoplasms Melanoma Ovarian Neoplasms

ATC Classification

L01XX41
eribulin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 9 meas. best 8.78

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.78 7.145 1.7 4
DLD-1
CHEMBL614285
 IC50 7.89 7.7633 13.0 3
HCT-15
CHEMBL612263
 IC50 6.69 6.69 204.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 161.0 ng.hr.mL-1 Mus musculus
CL 19.83 mL.min-1.kg-1 Mus musculus
F 3.2 % Mus musculus
T1/2 15.4 hr Mus musculus
Tmax 0.08333 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 1.66 nM 8.78 Antiproliferative activity against human MES-SA cells assessed as growth inhibit... 21324686
NON-PROTEIN TARGET IC50 = 1.66 nM 8.78 Cytotoxicity against human MES-SA cells 21324692
DLD-1 IC50 = 13.0 nM 7.89 Antiproliferative activity against human DLD-1 cells assessed as inhibition of c... 39068862
DLD-1 IC50 = 20.0 nM 7.7 Antiproliferative activity against human DLD1 cells assessed as growth inhibitio... 21324686
DLD-1 IC50 = 20.0 nM 7.7 Cytotoxicity against human DLD1 cells 21324692
HCT-15 IC50 = 204.0 nM 6.69 Antiproliferative activity against human HCT15 cells assessed as growth inhibiti... 21324686
HCT-15 IC50 = 204.0 nM 6.69 Cytotoxicity against human HCT15 cells 21324692
NON-PROTEIN TARGET IC50 = 3058.0 nM 5.51 Antiproliferative activity against P-gp overexpressing human MES-SA/Dx5-Rx1 cell... 21324686
NON-PROTEIN TARGET IC50 = 3058.0 nM 5.51 Cytotoxicity against human MES-SA/Dx5-Rx1 cells 21324692

Literature References

PubMed DOI Target Context # Activities
21324692 10.1016/j.bmcl.2011.01.097 Mus musculus 6
21324686 10.1016/j.bmcl.2011.01.111 NON-PROTEIN TARGET 4
25455639 10.1016/j.ejmech.2014.10.062 Homo sapiens 3
21324692 10.1016/j.bmcl.2011.01.097 NON-PROTEIN TARGET 2
21324686 10.1016/j.bmcl.2011.01.111 DLD-1 1
21324686 10.1016/j.bmcl.2011.01.111 HCT-15 1
21324686 10.1016/j.bmcl.2011.01.111 ADMET 1
21324692 10.1016/j.bmcl.2011.01.097 DLD-1 1
21324692 10.1016/j.bmcl.2011.01.097 HCT-15 1
21324692 10.1016/j.bmcl.2011.01.097 MES-SA 1
39068862 10.1016/j.ejmech.2024.116709 DLD-1 1

Data from ChEMBL 36 via Core Engine