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Compound Detail

CHEMBL23330

TRETAZICAR
🧪 Phase II
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🧪 Phase II
NC(=O)c1cc(N2CC2)c([N+](=O)[O-])cc1[N+](=O)[O-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL23330
Name TRETAZICAR
Phase Phase II
Structure Type MOL
InChI Key WOCXQMCIOTUMJV-UHFFFAOYSA-N

Known Names

CB-1954 NSC-115829 Tretazicar
14
Targets
60
Activities
3
Assay Types
1
PK Parameters
20
Publications
3
Known Names
1
Indications

Molecular Properties

252.2
MW (Da)
0.42
ALogP
6
HBA
1
HBD
132.4
PSA (Ų)
0.47
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C9H8N4O5
MW 252.19
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -1.41

Indications

Carcinoma, Hepatocellular

Activity Summary

IC50 56 meas. best 8.75
EC50 3 meas. best 6.27
Ki 1 meas. best 5.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
PC-3
CHEMBL390
 IC50 8.75 8.75 1.8 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.52 6.7075 30.0 4
ADMET
CHEMBL612558
 IC50 7.44 6.2933 36.0 3
V79
CHEMBL614074
 IC50 7.44 6.7775 36.0 4
EMT6
CHEMBL614294
 IC50 7.01 5.5625 98.0 4
RT-112
CHEMBL614145
 IC50 6.82 5.435 150.0 2
Trypanosoma brucei
CHEMBL612849
 EC50 6.27 5.4533 540.0 3
Trypanosoma cruzi
CHEMBL368
 IC50 6.24 6.24 570.0 1
SK-OV-3
CHEMBL614925
 IC50 6.19 5.4038 640.0 8
Modulator of drug activity A
CHEMBL5502
 IC50 6.05 6.05 890.0 1
WiDr-NTR
CHEMBL612808
 IC50 5.94 5.94 1140.0 1
WiDr
CHEMBL614647
 IC50 5.94 4.685 1140.0 4
Danio rerio
CHEMBL613963
 IC50 5.92 5.92 1200.0 1
Trypanosoma brucei
CHEMBL612849
 IC50 5.53 5.53 2970.0 1
Putative nitroreductase
CHEMBL4523956
 Ki 5.22 5.22 5960.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.08333 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
PC-3 IC50 = 1.792 nM 8.75 Cytotoxicity against human PC3 cells expressing Staphylococcus saprophyticus nit... 31841727
PC-3 IC50 = 1.792 nM 8.75 Cytotoxicity against human PC3 cells assessed as reduction in cell viability mea... 30928710
NON-PROTEIN TARGET IC50 = 30.0 nM 7.52 Cytotoxicity against Chinese hamster T116 cells expressing Escherichia coli Nitr... 27876476
ADMET IC50 = 36.0 nM 7.44 Inhibitory activity against V79 (chinese hamster fibroblast) cell line with Esch... 14584930
V79 IC50 = 36.0 nM 7.44 Antiproliferative activity against NTR expressing chinese hamster V79 cells afte... 16821793
NON-PROTEIN TARGET IC50 = 50.0 nM 7.3 Cytotoxicity against Chinese hamster 186/6 cells expressing rat NQO1 assessed as... 27876476
EMT6 IC50 = 98.0 nM 7.01 Growth inhibitory potency against NTR-Transfected (nitroreductase) mouse mammary... 15163209
EMT6 IC50 = 98.0 nM 7.01 Antiproliferative activity against mouse EMT6 NTRpuro cells after 18 hrs 17326614
RT-112 IC50 = 150.0 nM 6.82 Cytotoxicity against NQO2 expressing human RT112 cells in presence of NRH cofact... 17643990
V79 IC50 = 260.0 nM 6.58 Growth inhibitory potency against NTR-Transfected (nitroreductase) chinese hamst... 15163209
V79 IC50 = 260.0 nM 6.58 Antiproliferative activity against chinese hamster V79 NTRpuro cells after 18 hr... 17326614
V79 IC50 = 310.0 nM 6.51 Antiproliferative activity against NTR expressing chinese hamster V79 cells afte... 16821793
ADMET IC50 = 310.0 nM 6.51 Inhibitory activity against V79 (chinese hamster fibroblast) cell line with Esch... 14584930
Trypanosoma brucei EC50 = 540.0 nM 6.27 Antimicrobial activity against Trypanosoma brucei 20439607
Trypanosoma cruzi IC50 = 570.0 nM 6.24 Antitrypanosomal activity against Trypanosoma cruzi clone Cl-Brener infected in ... 20679506
SK-OV-3 IC50 = 640.0 nM 6.19 Growth inhibitory potency against NTR-Transfected (nitroreductase) human ovarian... 15163209
NON-PROTEIN TARGET IC50 = 640.0 nM 6.19 Antiproliferative activity against human Skov3 NTRneo cells after 18 hrs 17326614
SK-OV-3 IC50 = 760.0 nM 6.12 In vitro for cytotoxicity against SKOV-3 cells in the presence of 1 mM NADH co-f... 10617083
Modulator of drug activity A IC50 = 890.0 nM 6.05 Cytotoxicity in T79-A3 (NR-positive) cell lines 9111301
SK-OV-3 IC50 = 1010.0 nM 6.0 In vitro for cytotoxicity against SKOV-3 cells in the presence of 1 mM NADH co-f... 10617083

Literature References

PubMed DOI Target Context # Activities
22546205 10.1016/j.bmc.2012.04.004 ADMET 24
16821793 10.1021/jm051246n SK-OV-3 9
17326614 10.1021/jm061062o V79 7
14584930 10.1021/jm034133h ADMET 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
16821793 10.1021/jm051246n V79 6
17326614 10.1021/jm061062o WiDr 5
31841727 10.1016/j.ejmech.2019.111937 Putative nitroreductase 5
20439607 10.1128/aac.00332-10 Trypanosoma brucei 5
14584930 10.1021/jm034133h SK-OV-3 4
17326614 10.1021/jm061062o EMT6 4
10617083 10.1016/s0960-894x(99)00627-7 NON-PROTEIN TARGET 4
31841727 10.1016/j.ejmech.2019.111937 Oxygen-insensitive NAD(P)H nitroreductase 4
31841727 10.1016/j.ejmech.2019.111937 Unchecked 4
27876476 10.1016/j.bmcl.2016.11.024 NON-PROTEIN TARGET 4
14584930 10.1021/jm034133h Unchecked 4
30928710 10.1016/j.ejmech.2019.03.035 Putative nitroreductase 4
31841727 10.1016/j.ejmech.2019.111937 PC-3 4
15163209 10.1021/jm0498699 V79 4
1507207 10.1021/jm00095a018 ADMET 4

Data from ChEMBL 36 via Core Engine