Compound Detail
CHEMBL1201752
IXABEPILONE 💊 Approved Drug
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💊 Approved Drug
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1
Basic Information
| ChEMBL ID | CHEMBL1201752 |
| Name | IXABEPILONE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | FABUFPQFXZVHFB-PVYNADRNSA-N |
| Therapeutic | ✓ Yes |
6
Targets
8
Activities
2
Assay Types
3
PK Parameters
20
Publications
9
Known Names
20
Indications
1
Mechanisms
Molecular Properties
506.7
MW (Da)
4.05
ALogP
7
HBA
3
HBD
112.0
PSA (Ų)
0.52
QED
1
Ro5 Violations
2
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 2007 |
| 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 Neoplasms Neoplasms Endometrial Neoplasms Bile Duct Neoplasms Breast Neoplasms, Male Burkitt Lymphoma Carcinoma, Non-Small-Cell Lung Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Verrucous Cholangiocarcinoma Colorectal Neoplasms Gallbladder Neoplasms Hypopharyngeal Neoplasms Leukemia Liver Neoplasms Lung Neoplasms
ATC Classification
L01DC04
ixabepilone
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS
Drug Warnings
Black Box Warning
General Warning
Activity Summary
IC50 7 meas. best 8.59
Kd 1 meas. best 6.47
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| HCT-116 CHEMBL394 | IC50 | 8.59 | 8.59 | 2.6 | 1 |
| CCRF-CEM CHEMBL382 | IC50 | 8.52 | 8.52 | 3.0 | 1 |
| 1A9 CHEMBL614075 | IC50 | 8.18 | 8.18 | 6.7 | 1 |
| KB CHEMBL398 | IC50 | 8.1 | 8.1 | 8.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 7.46 | 6.9967 | 35.0 | 3 |
| Apoptosis regulator Bcl-2 CHEMBL4860 | Kd | 6.47 | 6.47 | 337.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 10.0 | mL.min-1.kg-1 | Homo sapiens |
| MRT | 18.0 | hr | Homo sapiens |
| T1/2 | 17.0 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| HCT-116 | IC50 | = | 2.6 | nM | 8.59 | Cytotoxicity against human HCT116 cells | 29251920 |
| CCRF-CEM | IC50 | = | 3.0 | nM | 8.52 | Antiproliferative activity against human CCRF-CEM cells assessed as reduction in... | 31419740 |
| 1A9 | IC50 | = | 6.65 | nM | 8.18 | Cytotoxicity against human 1A9 cells | 28850227 |
| KB | IC50 | = | 8.0 | nM | 8.1 | Antiproliferative activity against human KB cells assessed as reduction in cell ... | 31419740 |
| Unchecked | IC50 | = | 35.0 | nM | 7.46 | Antiproliferative activity against human KBtax cells assessed as reduction in ce... | 31419740 |
| Unchecked | IC50 | = | 150.0 | nM | 6.82 | Antiproliferative activity against human CCRF-CEM/VBL cells assessed as reductio... | 31419740 |
| Unchecked | IC50 | = | 193.0 | nM | 6.71 | Antiproliferative activity against human KB/VCR cells assessed as reduction in c... | 31419740 |
| Apoptosis regulator Bcl-2 | Kd | = | 337.0 | nM | 6.47 | Binding affinity to human recombinant Bcl-2 expressed in Escherichia coli by Sur... | 32428794 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 32428794 | 10.1016/j.ejmech.2020.112421 | Apoptosis regulator Bcl-2 | 21 |
| 32428794 | 10.1016/j.ejmech.2020.112421 | BT-549 | 19 |
| 32428794 | 10.1016/j.ejmech.2020.112421 | MDA-MB-231 | 12 |
| 31419740 | 10.1016/j.ejmech.2019.111584 | Unchecked | 6 |
| 18426954 | 10.1124/dmd.108.020479 | ADMET | 4 |
| 20014752 | 10.1021/tx900326k | Hepatotoxicity | 3 |
| 25455639 | 10.1016/j.ejmech.2014.10.062 | Homo sapiens | 3 |
| 32428794 | 10.1016/j.ejmech.2020.112421 | U-251 | 3 |
| 32428794 | 10.1016/j.ejmech.2020.112421 | HepG2 | 3 |
| 32428794 | 10.1016/j.ejmech.2020.112421 | MCF7 | 3 |
| - | 10.6019/CHEMBL4808148 | Histone deacetylase 6 | 2 |
| 32428794 | 10.1016/j.ejmech.2020.112421 | Unchecked | 2 |
| - | 10.6019/CHEMBL4495565 | SARS-CoV-2 | 2 |
| 26948801 | 10.1016/j.drudis.2016.02.015 | Homo sapiens | 2 |
| - | 10.6019/CHEMBL4495564 | Replicase polyprotein 1ab | 1 |
| 31419740 | 10.1016/j.ejmech.2019.111584 | KB | 1 |
| 31419740 | 10.1016/j.ejmech.2019.111584 | CCRF-CEM | 1 |
| - | 10.1101/2020.04.21.054387 | SARS-CoV-2 | 1 |
| - | 10.21203/rs.3.rs-23951/v1 | SARS-CoV-2 | 1 |
| 29251920 | 10.1021/acs.jmedchem.7b01457 | HCT-116 | 1 |
Data from ChEMBL 36 via Core Engine