Compound Detail
CHEMBL1683544
ERIBULIN MESYLATE 💊 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.CS(=O)(=O)O
Basic Information
| ChEMBL ID | CHEMBL1683544 |
| Name | ERIBULIN MESYLATE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | QAMYWGZHLCQOOJ-WRNBYXCMSA-N |
| Therapeutic | ✓ Yes |
| Parent Compound | CHEMBL1683590 |
| Active Moiety | CHEMBL1683590 |
3
Targets
6
Activities
1
Assay Types
11
PK Parameters
11
Publications
10
Known Names
20
Indications
1
Mechanisms
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 |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Tubulin inhibitor | INHIBITOR | Tubulin | ✓ | ✓ |
Indications
Breast Neoplasms Breast Neoplasms Breast Neoplasms Liposarcoma Sarcoma Triple Negative Breast Neoplasms Breast Neoplasms, Male Carcinoma, Non-Small-Cell Lung Head and Neck Neoplasms Osteosarcoma Pancreatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Retroviridae Infections Salivary Gland Neoplasms Uterine Cervical Neoplasms Lymphoma Neoplasms Neoplasms Urinary Bladder Neoplasms
Activity Summary
IC50 6 meas. best 8.78
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| NON-PROTEIN TARGET CHEMBL3879801 | IC50 | 8.78 | 7.1425 | 1.7 | 4 |
| U-251 CHEMBL615022 | IC50 | 8.23 | 8.23 | 5.9 | 1 |
| SF-295 CHEMBL614908 | IC50 | 7.55 | 7.55 | 27.9 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 435.0 | ng.hr/g | Mus musculus |
| AUC | 627.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 681.0 | ng.hr.mL-1 | Homo sapiens |
| CL | 3.93 | L/hr | Homo sapiens |
| CL | 0.3 | L/hr | Homo sapiens |
| Cmax | 608.29 | nM | Homo sapiens |
| Fu | - | - | Mus musculus |
| T1/2 | 46.0 | hr | Mus musculus |
| T1/2 | 45.6 | hr | Homo sapiens |
| T1/2 | 36.0 | hr | Homo sapiens |
| Tmax | 0.5 | 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 | 21324687 |
| NON-PROTEIN TARGET | IC50 | = | 1.7 | nM | 8.77 | Cytotoxicity against human MES-SA cells | 23141916 |
| U-251 | IC50 | = | 5.87 | nM | 8.23 | Antiproliferative activity against human U251 cells | 21324687 |
| SF-295 | IC50 | = | 27.85 | nM | 7.55 | Antiproliferative activity against human SF295 cells | 21324687 |
| NON-PROTEIN TARGET | IC50 | = | 3058.0 | nM | 5.51 | Antiproliferative activity against human doxorubicin-resistant MES-SA/Dx5-Rx1 ce... | 21324687 |
| NON-PROTEIN TARGET | IC50 | = | 3100.0 | nM | 5.51 | Cytotoxicity against human MES-SA/Dx5-Rx1 cells | 23141916 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 22041109 | 10.1124/dmd.111.042762 | Homo sapiens | 13 |
| 21324687 | 10.1016/j.bmcl.2011.01.096 | Mus musculus | 3 |
| 21324687 | 10.1016/j.bmcl.2011.01.096 | NON-PROTEIN TARGET | 2 |
| 23141916 | 10.1016/j.bmcl.2012.10.077 | NON-PROTEIN TARGET | 2 |
| 22041109 | 10.1124/dmd.111.042762 | ADMET | 2 |
| 21324687 | 10.1016/j.bmcl.2011.01.096 | MES-SA | 1 |
| 21324687 | 10.1016/j.bmcl.2011.01.096 | U-251 | 1 |
| 21324687 | 10.1016/j.bmcl.2011.01.096 | SF-295 | 1 |
| 21324687 | 10.1016/j.bmcl.2011.01.096 | ADMET | 1 |
| 21324687 | 10.1016/j.bmcl.2011.01.096 | Brain | 1 |
| 23141916 | 10.1016/j.bmcl.2012.10.077 | MES-SA | 1 |
Data from ChEMBL 36 via Core Engine