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Compound Detail

CHEMBL77305

RUBITECAN
🧪 Phase III
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🧪 Phase III
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c([N+](=O)[O-])cccc3nc2-1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL77305
Name RUBITECAN
Phase Phase III
Structure Type MOL
InChI Key VHXNKPBCCMUMSW-FQEVSTJZSA-N

Known Names

9-nc 9-nitro-20(s)-camptothecin 9-nitro-20-(s)-camptothecin 9-nitrocamptothecin RFS 2000 RFS-2000 RFS2000 Rubitecan
8
Targets
8
Activities
1
Assay Types
0
PK Parameters
20
Publications
8
Known Names
12
Indications
1
Mechanisms

Molecular Properties

393.4
MW (Da)
1.99
ALogP
8
HBA
1
HBD
124.6
PSA (Ų)
0.31
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -tecan
USAN Year 1999

Extended Properties

Molecular Formula C20H15N3O6
MW 393.36
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness 0.56

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA topoisomerase I inhibitor INHIBITOR DNA topoisomerase 1 ✓ ✓

Indications

Pancreatic Neoplasms Breast Neoplasms Central Nervous System Neoplasms Colorectal Neoplasms Endometrial Neoplasms Lung Neoplasms Melanoma Ovarian Neoplasms Peritoneal Neoplasms Urethral Neoplasms Urinary Bladder Neoplasms Neoplasms

Activity Summary

IC50 8 meas. best 6.95

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.95 6.95 112.0 1
Jurkat
CHEMBL397
 IC50 6.89 6.89 128.0 1
A-375
CHEMBL613859
 IC50 6.86 6.86 138.0 1
HeLa
CHEMBL399
 IC50 6.46 6.46 343.0 1
MDA-MB-231
CHEMBL400
 IC50 6.32 6.32 479.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 5.29 5.29 5100.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
 IC50 4.99 4.99 10200.0 1
ATP-binding cassette sub-family C member 2
CHEMBL5748
 IC50 4.22 4.22 60500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 112.0 nM 6.95 Cytotoxicity against human Caco2 cells after 24 hrs by MTT assay 24980118
Jurkat IC50 = 128.0 nM 6.89 Cytotoxicity against human Jurkat cells after 24 hrs by MTT assay 24980118
A-375 IC50 = 138.0 nM 6.86 Cytotoxicity against human A375 cells after 24 hrs by MTT assay 24980118
HeLa IC50 = 343.0 nM 6.46 Cytotoxicity against human HeLa cells after 24 hrs by MTT assay 24980118
MDA-MB-231 IC50 = 479.0 nM 6.32 Cytotoxicity against human MDA-MB-231 cells after 24 hrs by MTT assay 24980118
ATP-binding cassette sub-family C member 4 IC50 = 5100.0 nM 5.29 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
ATP-binding cassette sub-family C member 3 IC50 = 10200.0 nM 4.99 Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... 23956101
ATP-binding cassette sub-family C member 2 IC50 = 60500.0 nM 4.22 Inhibition of human MRP2 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
24980118 10.1016/j.ejmech.2014.06.050 Caco-2 19
9438019 10.1021/jm9607562 Mus musculus 5
3783593 10.1021/jm00161a035 P338 5
9438019 10.1021/jm9607562 ADMET 5
24980118 10.1016/j.ejmech.2014.06.050 HeLa 4
24980118 10.1016/j.ejmech.2014.06.050 A-375 4
24980118 10.1016/j.ejmech.2014.06.050 MDA-MB-231 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL4513161 Pseudomonas aeruginosa 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 4 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 2 1
23956101 10.1093/toxsci/kft176 Bile salt export pump 1

Data from ChEMBL 36 via Core Engine