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Compound Detail

CHEMBL73822

APAZIQUONE
🧪 Phase III
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🧪 Phase III
Cn1c(/C=C/CO)c(CO)c2c1C(=O)C=C(N1CC1)C2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL73822
Name APAZIQUONE
Phase Phase III
Structure Type MOL
InChI Key MXPOCMVWFLDDLZ-NSCUHMNNSA-N

Known Names

Apazicuona Apaziquone EO-9 EO9 Eoquin NOR-701 NSC-382456 NSC-382459 Qapzola
4
Targets
5
Activities
1
Assay Types
0
PK Parameters
10
Publications
9
Known Names
2
Indications
1
Mechanisms

Molecular Properties

288.3
MW (Da)
0.10
ALogP
6
HBA
2
HBD
82.5
PSA (Ų)
0.77
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Year 2002

Extended Properties

Molecular Formula C15H16N2O4
MW 288.30
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 0.84

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Urinary Bladder Neoplasms Urinary Bladder Neoplasms

Activity Summary

IC50 5 meas. best 8.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NCI-H460
CHEMBL396
 IC50 8.23 8.23 5.9 1
A549
CHEMBL392
 IC50 7.23 7.23 59.0 1
HT-29
CHEMBL384
 IC50 6.91 6.91 124.0 1
BE
CHEMBL614798
 IC50 6.22 6.06 600.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NCI-H460 IC50 = 5.9 nM 8.23 Cytotoxicity against high NQO1 protein expressing human H460 cells by MTT assay 17643990
A549 IC50 = 59.0 nM 7.23 Chemosensitivity against DT-diaphorase rich A549 cell lines 10514277
HT-29 IC50 = 124.0 nM 6.91 Chemosensitivity against DT-diaphorase rich H29 cell lines 10514277
BE IC50 = 600.0 nM 6.22 Cytotoxicity against low NQO1 protein expressing human BE cells by MTT assay 17643990
BE IC50 = 1250.0 nM 5.9 Chemosensitivity against DT-diaphorase deficient BEcell lines 10514277

Literature References

PubMed DOI Target Context # Activities
10514277 10.1021/jm991063z NAD(P)H dehydrogenase [quinone] 1 3
10514277 10.1021/jm991063z Unchecked 3
9240349 10.1021/jm9608422 V79 3
17643990 10.1016/j.bmc.2007.06.062 BE 2
10514277 10.1021/jm991063z A549 1
10514277 10.1021/jm991063z HT-29 1
10514277 10.1021/jm991063z BE 1
10514277 10.1021/jm991063z NON-PROTEIN TARGET 1
17643990 10.1016/j.bmc.2007.06.062 NCI-H460 1
17643990 10.1016/j.bmc.2007.06.062 NAD(P)H dehydrogenase [quinone] 1 1

Data from ChEMBL 36 via Core Engine