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Compound Detail

CHEMBL1454910

NITROXOLINE
💊 Approved Drug
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💊 Approved Drug
O=[N+]([O-])c1ccc(O)c2ncccc12

Basic Information

ChEMBL ID CHEMBL1454910
Name NITROXOLINE
Phase Approved
Structure Type MOL
InChI Key RJIWZDNTCBHXAL-UHFFFAOYSA-N

Known Names

A-82 Nitroxolina Nitroxoline NSC-74947
20
Targets
56
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

190.2
MW (Da)
1.85
ALogP
4
HBA
1
HBD
76.3
PSA (Ų)
0.55
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C9H6N2O3
MW 190.16
Aromatic Rings 2
Heavy Atoms 14
NP-Likeness -1.02

Indications

Bacterial Infections

ATC Classification

J01XX07
nitroxoline
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Drug Warnings

Withdrawn
occular toxicity
cataracts have developed in rats in prolonged dosage studies
Country: Ireland   Year: 1973

Activity Summary

IC50 32 meas. best 7.26
EC50 17 meas. best 6.79
Ki 7 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Methionine aminopeptidase 2
CHEMBL3922
IC50 7.26 7.26 55.0 2
Unchecked
CHEMBL612545
IC50 7.22 5.8928 60.0 18
Unchecked
CHEMBL612545
EC50 6.79 5.378 161.0 5
ATP-dependent molecular chaperone HSP82
CHEMBL1293251
EC50 6.17 6.17 681.0 1
Bromodomain-containing protein 4
CHEMBL1163125
IC50 6.01 6.01 980.0 3
Prostaglandin G/H synthase 2
CHEMBL230
Ki 6.0 6.0 1000.0 1
Candida albicans
CHEMBL366
IC50 6.0 6.0 1000.0 3
HUVEC
CHEMBL613979
IC50 5.72 5.72 1900.0 1
Acinetobacter baumannii
CHEMBL614425
EC50 5.6 5.6 2500.0 1
Klebsiella pneumoniae
CHEMBL350
EC50 5.55 5.55 2800.0 1
Escherichia coli
CHEMBL354
EC50 5.4 5.4 4000.0 1
MV4-11
CHEMBL613835
IC50 5.31 5.31 4900.0 1
Cystathionine gamma-lyase
CHEMBL4295745
IC50 5.22 5.0967 6000.0 3
Enterobacter cloacae
CHEMBL349
EC50 5.18 5.18 6600.0 1
BJ
CHEMBL614358
EC50 5.03 4.7833 9441.0 3
Staphylococcus aureus
CHEMBL352
EC50 5.02 5.02 9500.0 1
Protein RecA
CHEMBL1741171
EC50 4.84 4.84 14400.0 1
Enterococcus faecium
CHEMBL357
EC50 4.75 4.75 18000.0 1
Catechol O-methyltransferase
CHEMBL2372
IC50 4.7 4.7 19952.6 1
Cathepsin B
CHEMBL4072
Ki 4.4 4.4 39500.0 2
Pseudomonas aeruginosa
CHEMBL348
EC50 4.0 4.0 99000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Methionine aminopeptidase 2 IC50 = 55.0 nM 7.26 Inhibition of human methionine aminopeptidase 2 24376907
Methionine aminopeptidase 2 IC50 = 55.0 nM 7.26 Inhibition of recombinant human N-terminal His-tagged MetAP2 expressed in baculo... 30939017
Unchecked IC50 = 60.0 nM 7.22 Inhibition of Burkholderia pseudomallei recombinant methionine aminopeptidase 1 ... 24376907
Unchecked EC50 = 161.0 nM 6.79 PUBCHEM_BIOASSAY: Fluorescence Cell-Based Retest of Candida albicans Growth in t... -
Unchecked IC50 = 295.2 nM 6.53 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -
Unchecked IC50 = 375.09 nM 6.43 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 604.58 nM 6.22 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
ATP-dependent molecular chaperone HSP82 EC50 = 681.0 nM 6.17 PUBCHEM_BIOASSAY: Fluorescence Cell-Based Secondary Assay to Identify Inhibitors... -
Unchecked IC50 = 683.66 nM 6.17 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Unchecked IC50 = 710.08 nM 6.15 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 790.0 nM 6.1 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Unchecked IC50 = 920.57 nM 6.04 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 960.0 nM 6.02 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Bromodomain-containing protein 4 IC50 = 980.0 nM 6.01 Inhibition of BRD4 BD1 (unknown origin) using N-C:SGRG-K(Ac)-GG K(Ac)-GLG-K(Ac)-... 38278080
Bromodomain-containing protein 4 IC50 = 980.0 nM 6.01 Inhibition of BRD4 BD1 (unknown origin) using biotin labelled NeC: SGRG-K(Ac)-GG... 30529546
Bromodomain-containing protein 4 IC50 = 980.0 nM 6.01 Inhibition of BRD4 in human MV4-11 cells using biotin labelled N-C:SGRG-K(Ac)-GG... 30529546
Candida albicans IC50 = 1000.0 nM 6.0 Antibiofilm activity against Candida albicans SC5314 after 48 hrs by Alamar blue... 28051303
Candida albicans IC50 = 1000.0 nM 6.0 Antibiofilm activity against Candida albicans CAF2-1 after 48 hrs by Alamar blue... 28051303
Prostaglandin G/H synthase 2 Ki = 1000.0 nM 6.0 Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate assesse... 24088053
Candida albicans IC50 = 1000.0 nM 6.0 Antibiofilm activity against fluconazole-resistant Candida albicans 29E clinical... 28051303

Literature References

PubMed DOI Target Context # Activities
34865870 10.1016/j.ejmech.2021.113975 Unchecked 9
23252745 10.1021/jm301544x Cathepsin B 5
29503024 10.1016/j.bmcl.2018.02.042 Cathepsin B 5
30562026 10.1021/acs.jmedchem.8b01720 Cystathionine gamma-lyase 5
401891 10.1021/jm00211a019 No relevant target 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
30562026 10.1021/acs.jmedchem.8b01720 Unchecked 4
28051303 10.1021/acs.jmedchem.6b01203 Candida albicans 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
30529546 10.1016/j.ejmech.2018.11.018 Bromodomain-containing protein 4 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
24376907 10.1021/ml400034m Burkholderia thailandensis 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
34655985 10.1016/j.ejmech.2021.113865 Cathepsin B 2
23252745 10.1021/jm301544x Unchecked 2

Data from ChEMBL 36 via Core Engine