Compound Detail
CHEMBL1096885
VALRUBICIN 💊 Approved Drug
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💊 Approved Drug
CCCCC(=O)OCC(=O)[C@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O2)C1)C(=O)c1c(OC)cccc1C3=O
Basic Information
| ChEMBL ID | CHEMBL1096885 |
| Name | VALRUBICIN |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | ZOCKGBMQLCSHFP-KQRAQHLDSA-N |
| Therapeutic | ✓ Yes |
4
Targets
4
Activities
1
Assay Types
1
PK Parameters
13
Publications
8
Known Names
5
Indications
2
Mechanisms
Molecular Properties
723.6
MW (Da)
2.46
ALogP
13
HBA
5
HBD
215.2
PSA (Ų)
0.15
QED
2
Ro5 Violations
10
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1998 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| DNA topoisomerase II alpha inhibitor | INHIBITOR | DNA topoisomerase 2-alpha | ✓ | ✓ |
| DNA inhibitor | INHIBITOR | DNA | ✓ | ✓ |
Indications
Carcinoma Neoplasms Carcinoma in Situ Urinary Bladder Neoplasms Urinary Bladder Neoplasms
ATC Classification
L01DB09
valrubicin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS
Activity Summary
IC50 4 meas. best 4.62
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Bile salt export pump CHEMBL6020 | IC50 | 4.62 | 4.62 | 24100.0 | 1 |
| ATP-binding cassette sub-family C member 4 CHEMBL1743128 | IC50 | 4.43 | 4.43 | 36800.0 | 1 |
| ATP-binding cassette sub-family C member 2 CHEMBL5748 | IC50 | 4.19 | 4.19 | 64000.0 | 1 |
| ATP-binding cassette sub-family C member 3 CHEMBL5918 | IC50 | 4.12 | 4.12 | 76300.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 570.24 | ng.hr.mL-1 | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Bile salt export pump | IC50 | = | 24100.0 | nM | 4.62 | Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... | 23956101 |
| ATP-binding cassette sub-family C member 4 | IC50 | = | 36800.0 | nM | 4.43 | Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... | 23956101 |
| ATP-binding cassette sub-family C member 2 | IC50 | = | 64000.0 | nM | 4.19 | Inhibition of human MRP2 overexpressed in Sf9 cell membrane vesicles assessed as... | 23956101 |
| ATP-binding cassette sub-family C member 3 | IC50 | = | 76300.0 | nM | 4.12 | Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... | 23956101 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 22194678 | 10.1371/journal.pcbi.1002310 | Hepatotoxicity | 14 |
| 23956101 | 10.1093/toxsci/kft176 | Unchecked | 4 |
| 23956101 | 10.1093/toxsci/kft176 | Homo sapiens | 2 |
| - | 10.6019/CHEMBL4495565 | SARS-CoV-2 | 2 |
| - | 10.6019/CHEMBL4808148 | Histone deacetylase 6 | 2 |
| 20106561 | 10.1016/j.ejmech.2009.12.043 | No relevant target | 1 |
| 23956101 | 10.1093/toxsci/kft176 | Bile salt export pump | 1 |
| 23956101 | 10.1093/toxsci/kft176 | ATP-binding cassette sub-family C member 2 | 1 |
| 23956101 | 10.1093/toxsci/kft176 | ATP-binding cassette sub-family C member 3 | 1 |
| 23956101 | 10.1093/toxsci/kft176 | ATP-binding cassette sub-family C member 4 | 1 |
| - | 10.21203/rs.3.rs-23951/v1 | SARS-CoV-2 | 1 |
| - | 10.1101/2020.04.21.054387 | SARS-CoV-2 | 1 |
| - | 10.6019/CHEMBL4495564 | Replicase polyprotein 1ab | 1 |
Data from ChEMBL 36 via Core Engine