Nitroxoline

Summary

Nitroxoline (CHEMBL1454910) is an approved small-molecule antimicrobial agent (ATC J01XX07) targeting METAP2; indicated across 1 condition including bacterial infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01XX07
• Targets: 1 (METAP2)
• Indications: 1 condition
• Chemistry: 190.16 Da · C9H6N2O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1454910
Name	Nitroxoline
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	19910
ChEBI	CHEBI:67121
ATC	J01XX07
Molecular formula	C9H6N2O3
Molecular weight	190.16
InChIKey	RJIWZDNTCBHXAL-UHFFFAOYSA-N

SMILES: C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]

IUPAC name: 5-nitroquinolin-8-ol

ChEBI definition: A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5.

Pharmacological roles (ChEBI): antimicrobial agent, antifungal agent, renal agent, antiinfective agent.

Also known as: A-82, Nitroxolina, Nitroxoline, NSC-74947, SID11532939, SID29216358, SID56423111, SID144205522, SID170466124, NITROXOLINE, nitroxoline

Parent form; salt/anhydrous children: CHEMBL3251404

Patent coverage: 692 distinct patent families (1,860 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 1,684 (91%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
METAP2	Methionyl aminopeptidase 2	Inhibition	7.26	68.1%	P50579

Broader ChEMBL bioactivity targets: 35 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Bromodomain-containing protein 4, Microtubule-associated protein tau, Lysine-specific demethylase 4E, Nuclear receptor ROR-gamma, Survival motor neuron protein, Fructose-bisphosphate aldolase, Prelamin-A/C, NPC intracellular cholesterol transporter 1, Ras-related protein Rab-9A.

Bioactivity

ChEMBL activities: 36 potent at pChembl ≥ 5 of 49 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
METAP2	7.26	IC50	55	nM	CHEMBL_ACT_13387338
METAP2	7.26	IC50	55	nM	CHEMBL_ACT_19230423
P51450	6.55	Potency	281.8	nM	CHEMBL_ACT_4758679
TDP1	6.4	Potency	398.1	nM	CHEMBL_ACT_3928792
P51450	6.35	Potency	446.7	nM	CHEMBL_ACT_4087069
P51450	6.25	Potency	562.3	nM	CHEMBL_ACT_4095427
P51450	6.15	Potency	707.9	nM	CHEMBL_ACT_4761661
LMNA	6.05	Potency	891.3	nM	CHEMBL_ACT_3638891
BRD4	6.01	IC50	980	nM	CHEMBL_ACT_18951340
BRD4	6.01	IC50	980	nM	CHEMBL_ACT_18951579
BRD4	6.01	IC50	980	nM	CHEMBL_ACT_25872589
PTGS2	6	Ki	1000	nM	CHEMBL_ACT_13830399
HSP90AA1	6	AC50	996	nM	CHEMBL_ACT_7446715
KDM4E	5.55	Potency	2818	nM	CHEMBL_ACT_3717494
PDE4D	5.5	AC50	3200	nM	CHEMBL_ACT_25185856
HTT	5.45	Potency	3548	nM	CHEMBL_ACT_3748165
HTT	5.45	Potency	3548	nM	CHEMBL_ACT_4855697
HRH1	5.31	AC50	4900	nM	CHEMBL_ACT_25213039
HTR2C	5.26	AC50	5500	nM	CHEMBL_ACT_25132312
OPRD1	5.24	AC50	5700	nM	CHEMBL_ACT_25154583
DRD3	5.24	AC50	5800	nM	CHEMBL_ACT_25194042
CTH	5.22	IC50	6000	nM	CHEMBL_ACT_22426754
RAB9A	5.2	Potency	6310	nM	CHEMBL_ACT_3860231
NPC1	5.2	Potency	6310	nM	CHEMBL_ACT_4700680
DRD2	5.19	AC50	6400	nM	CHEMBL_ACT_25140859
HTR3A	5.18	AC50	6600	nM	CHEMBL_ACT_25149635
P9WMR3	5.18	AC50	6604	nM	CHEMBL_ACT_7253472
ADRA2C	5.15	AC50	7100	nM	CHEMBL_ACT_25148406
CHRM3	5.12	AC50	7600	nM	CHEMBL_ACT_25137193
CTH	5.1	IC50	8000	nM	CHEMBL_ACT_22426790

Target pathways

Aggregated over 1 target gene(s): METAP2.

Top Reactome pathways

4 total, by targets touching each:

Pathway	Targets	Genes
Visual phototransduction	1	METAP2
The phototransduction cascade	1	METAP2
Inactivation, recovery and regulation of the phototransduction cascade	1	METAP2
Sensory Perception	1	METAP2

Dominant GO biological processes

GO term	Targets
regulation of translational initiation	1
protein processing	1
proteolysis	1

Indications & clinical

Indications

1 indication (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
bacterial infectious disease	4	MONDO:0005113	EFO:0000771

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

14 molecules share ≥1 primary target. Top 14 by shared-target count:

Molecule	Source	Status	Shared targets
CLIOQUINOL	ChEMBL	Phase 4 (approved)	METAP2
THIABENDAZOLE	ChEMBL	Phase 4 (approved)	METAP2
BELORANIB	ChEMBL	Phase 3	METAP2
EBSELEN	ChEMBL	Phase 3	METAP2
BENZOXIQUINE	ChEMBL	Phase 2	METAP2
CLOXYQUIN	ChEMBL	Phase 2	METAP2
FUMAGILLIN	ChEMBL	Phase 2	METAP2
O-CHLOROACETYLCARBAMOYLFUMAGILLOL	ChEMBL	Phase 2	METAP2
Albendazole	PubChem	Approved	METAP2
Anthralin	PubChem	Approved	METAP2
Fenbendazole	PubChem	Approved	METAP2
Fosfomycin	PubChem	Approved	METAP2
Mebendazole	PubChem	Approved	METAP2
oxyquinoline	PubChem	Approved	METAP2