Nitroxoline

Summary

Nitroxoline (CHEMBL1454910) is a small-molecule antimicrobial agent (ATC J01XX07) targeting METAP2; approved for 1 indication (bacterial infectious disease).

At a glance

• Status: Not FDA-approved (reached ChEMBL max clinical phase 4)
• Modality: Small molecule
• ATC class: J01XX07
• Targets: 1 (METAP2) (top 5% of drugs corpus-wide)
• Indications: 1 condition
• Chemistry: 190.16 Da · C9H6N2O3
• Target biology: 1 curated target implicated as cohort gene in 1 disease corpus-wide; indicated or in trials for 1 (0 on both)
• Competitive landscape: target METAP2 is also targeted by 1 other curated drug in the corpus

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: 696 distinct patent families (1,882 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 1,703 (90%) 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 screening hits — not curated targets; per-target potencies are in the ChEMBL bioactivities table below).

Bioactivity

ChEMBL activities: 36 potent at pChembl ≥ 5 of 49 total. Top 31 distinct by potency (10 = 0.1 nM, 6 = 1 µM):

Protein	UniProt	Gene	pChembl	Type	Value	Activity ID
Methionine aminopeptidase 2	P50579	METAP2	7.26	IC50	55 nM	CHEMBL_ACT_13387338
Nuclear receptor ROR-gamma (house mouse)	P51450		6.55	Potency	281.8 nM	CHEMBL_ACT_4758679
Tyrosyl-DNA phosphodiesterase 1	Q9NUW8	TDP1	6.4	Potency	398.1 nM	CHEMBL_ACT_3928792
Nuclear receptor ROR-gamma (house mouse)	P51450		6.35	Potency	446.7 nM	CHEMBL_ACT_4087069
Nuclear receptor ROR-gamma (house mouse)	P51450		6.25	Potency	562.3 nM	CHEMBL_ACT_4095427
Nuclear receptor ROR-gamma (house mouse)	P51450		6.15	Potency	707.9 nM	CHEMBL_ACT_4761661
Prelamin-A/C	P02545	LMNA	6.05	Potency	891.3 nM	CHEMBL_ACT_3638891
Bromodomain-containing protein 4	O60885	BRD4	6.01	IC50	980 nM	CHEMBL_ACT_18951340
Prostaglandin G/H synthase 2	P35354	PTGS2	6	Ki	1000 nM	CHEMBL_ACT_13830399
Heat shock protein HSP 90-alpha	P07900	HSP90AA1	6	AC50	996 nM	CHEMBL_ACT_7446715
Lysine-specific demethylase 4E	B2RXH2	KDM4E	5.55	Potency	2818 nM	CHEMBL_ACT_3717494
3’,5’-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D	5.5	AC50	3200 nM	CHEMBL_ACT_25185856
Huntingtin	P42858	HTT	5.45	Potency	3548 nM	CHEMBL_ACT_3748165
Histamine H1 receptor	P35367	HRH1	5.31	AC50	4900 nM	CHEMBL_ACT_25213039
5-hydroxytryptamine receptor 2C	P28335	HTR2C	5.26	AC50	5500 nM	CHEMBL_ACT_25132312
Delta-type opioid receptor	P41143	OPRD1	5.24	AC50	5700 nM	CHEMBL_ACT_25154583
D(3) dopamine receptor	P35462	DRD3	5.24	AC50	5800 nM	CHEMBL_ACT_25194042
Cystathionine gamma-lyase	P32929	CTH	5.22	IC50	6000 nM	CHEMBL_ACT_22426754
Ras-related protein Rab-9A	P51151	RAB9A	5.2	Potency	6310 nM	CHEMBL_ACT_3860231
NPC intracellular cholesterol transporter 1	O15118	NPC1	5.2	Potency	6310 nM	CHEMBL_ACT_4700680
D(2) dopamine receptor	P14416	DRD2	5.19	AC50	6400 nM	CHEMBL_ACT_25140859
5-hydroxytryptamine receptor 3A	P46098	HTR3A	5.18	AC50	6600 nM	CHEMBL_ACT_25149635
Replicative DNA helicase DnaB (Mycobacterium tuberculosis H37Rv)	P9WMR3		5.18	AC50	6604 nM	CHEMBL_ACT_7253472
Alpha-2C adrenergic receptor	P18825	ADRA2C	5.15	AC50	7100 nM	CHEMBL_ACT_25148406
Muscarinic acetylcholine receptor M3	P20309	CHRM3	5.12	AC50	7600 nM	CHEMBL_ACT_25137193
Cystathionine gamma-lyase	P32929	CTH	5.1	IC50	8000 nM	CHEMBL_ACT_22426790
Muscarinic acetylcholine receptor M1	P11229	CHRM1	5.07	AC50	8500 nM	CHEMBL_ACT_25135987
Alpha-2B adrenergic receptor	P18089	ADRA2B	5.06	AC50	8800 nM	CHEMBL_ACT_25144213
Microtubule-associated protein tau	P10636	MAPT	5.05	Potency	8912 nM	CHEMBL_ACT_4047784
Kappa-type opioid receptor	P41145	OPRK1	5.03	AC50	9300 nM	CHEMBL_ACT_25129907
Replicative DNA helicase DnaB (Mycobacterium tuberculosis H37Rv)	P9WMR3		5	AC50	9951 nM	CHEMBL_ACT_6592113

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

Predicted targets — Sugi Predict

This molecule is SureChEMBL compound SCHEMBL29363027 — see its predicted protein targets + similar patent compounds on Sugi Predict.

Indications & clinical

Indications

1 approved indication. FDA phase 4.

Indication	Phase	MONDO	EFO
bacterial infectious disease	4	MONDO:0005113	EFO:0000771

Regulatory approval & mechanism (DrugCentral)

No agency approval flag recorded in DrugCentral.

DrugCentral (CC BY-SA): authoritative regulatory-approval status + curated mechanism. The drug’s full target set is in Targets above.

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

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

Pharmacology

MeSH pharmacological classification

Pharmacological action: Anti-Infective Agents, Urinary; Antifungal Agents.

Broader MeSH heading: Nitroquinolines.

MeSH supplementary concept C005308 “nitroxoline” — exact-name match.

Pharmacogenomics

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

Adverse-event reports (FAERS)

45 reports across 1 FAERS drug-name record; 34 distinct MedDRA reactions.

openFDA FAERS — spontaneous post-marketing reports. Co-occurrence, not causation: reports are voluntary, unverified, and confounded by indication and reporting bias (the drug’s own indication often appears as a ‘reaction’). PRR is a disproportionality heuristic (reaction rate for this drug vs the FAERS background), NOT a risk estimate. Counts are pooled across the drug’s name records.

Most-reported events

Serious = reports flagged serious (death / life-threatening / hospitalisation / disability / other medically important).

34 reactions by report volume:

Reaction (MedDRA PT)	Reports	Serious	PRR
headache	9	9 (100%)	6.7×
urinary tract infection	9	7 (78%)	24.6×
flank pain	8	8 (100%)	398.0×
general physical health deterioration	8	8 (100%)	32.4×
infection	8	8 (100%)	25.9×
diarrhoea	6	6 (100%)	4.3×
off label use	5	5 (100%)	2.7×
tachycardia	5	5 (100%)	26.2×
urinary incontinence	5	5 (100%)	78.7×
abdominal pain	4	2 (50%)	8.0×
acute kidney injury	3	3 (100%)	9.2×
covid-19	3	1 (33%)	7.9×
electrocardiogram qt prolonged	3	3 (100%)	38.8×
overdose	3	3 (100%)	6.5×
anaemia	2	2 (100%)	4.9×
asthenia	2	2 (100%)	2.5×
blood pressure decreased	2	2 (100%)	14.1×
cardiomyopathy	2	2 (100%)	63.0×
death	2	2 (100%)	1.1×
disturbance in attention	2	2 (100%)	17.2×
drug ineffective for unapproved indication	2	2 (100%)	16.7×
drug interaction	2	2 (100%)	5.9×
epilepsy	2	2 (100%)	30.5×
gastric haemorrhage	2	2 (100%)	80.4×
hypertension	2	2 (100%)	4.4×
hypokalaemia	2	2 (100%)	20.3×
hyponatraemia	2	2 (100%)	16.6×
intentional product use issue	2	2 (100%)	10.6×
neutrophil count decreased	2	2 (100%)	23.0×
oral herpes	2	0 (0%)	47.9×
pulmonary embolism	2	2 (100%)	9.8×
renal failure	2	2 (100%)	7.0×
thrombocytopenia	2	2 (100%)	8.4×
vomiting	2	2 (100%)	2.0×

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