Norfloxacin

Summary

Norfloxacin (CHEMBL9) is an approved small-molecule antibacterial drug (ATC J01MA06); indicated across 8 conditions including bacterial infectious disease and eye infectious disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01MA06 (+1 more)
• Indications: 8 conditions
• Clinical trials: 19
• Chemistry: 319.33 Da · C16H18FN3O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL9
Name	Norfloxacin
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	4539
ChEBI	CHEBI:100246
ATC	J01MA06, S01AE02
Molecular formula	C16H18FN3O3
Molecular weight	319.33
InChIKey	OGJPXUAPXNRGGI-UHFFFAOYSA-N

SMILES: CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCNCC3)F)C(=O)O

IUPAC name: 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid

ChEBI definition: A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.

Pharmacological roles (ChEBI): antibacterial drug, DNA synthesis inhibitor.

Other ChEBI roles (chemical / environmental): xenobiotic, environmental contaminant.

Also known as: Baccidal, Chibroxin, MK-366, Norfloxacin, Norfloxacine, Norfloxacino, Noroxin, NSC-757250, Quinabic, Utinor, norfloxacin, SID11112831

Parent form; salt/anhydrous children: CHEMBL4635810

Patent coverage: 15,081 distinct patent families (46,757 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 15 (assay-derived). Sample: Bromodomain-containing protein 4, Lysine-specific demethylase 4E, Prelamin-A/C, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Multidrug resistance protein MdtK, GABA-A receptor; anion channel, Thyrotropin receptor, DNA gyrase, Topoisomerase IV, Cytochrome P450 2J2.

Bioactivity

ChEMBL activities: 12 potent at pChembl ≥ 5 of 24 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
O09028	7.7	IC50	20	nM	CHEMBL_ACT_601762
P0AES4	6.22	IC50	600	nM	CHEMBL_ACT_1667320
BRD4	6.01	IC50	980	nM	CHEMBL_ACT_25007370
KDM4E	5.9	Potency	1259	nM	CHEMBL_ACT_3728479
CYP2J2	5.59	IC50	2560	nM	CHEMBL_ACT_15461596
HPGD	5.55	Potency	2818	nM	CHEMBL_ACT_4788238
P0C1U9	5.46	IC50	3500	nM	CHEMBL_ACT_1667325
HTT	5.45	Potency	3548	nM	CHEMBL_ACT_3772360
NPSR1	5.3	Potency	5012	nM	CHEMBL_ACT_4897503
LMNA	5.1	Potency	7943	nM	CHEMBL_ACT_3646952
ALDH1A1	5.05	Potency	8912	nM	CHEMBL_ACT_4185953
ALDH1A1	5	Potency	10000	nM	CHEMBL_ACT_4139900

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

8 indications (2 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
eye infectious disorder	4	MONDO:0043885	EFO:1001888
cirrhosis of liver	3	MONDO:0005155	EFO:0001422
infectious peritonitis	3	MONDO:0004522	EFO:0008588
esophageal varices	3	MONDO:0001221	EFO:0009545
cystitis	3	MONDO:0006032	EFO:1000025
Hermansky-Pudlak syndrome	2	MONDO:0019312	MONDO:0019312
osteomyelitis	0	MONDO:0005246	EFO:0003102

Clinical trials

Total trials: 19.

Phase distribution

Phase	Trials
PHASE3	9
PHASE4	5
Not specified	3
PHASE2/PHASE3	1
PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00359853	PHASE4	COMPLETED	Norfloxacin In The Primary Prophylaxis Of Spontaneous Bacterial Peritonitis
NCT01039545	PHASE4	TERMINATED	Symptomatic Therapy of Uncomplicated Lower Urinary Tract Infections in the Ambulatory Setting.
NCT01542801	PHASE4	COMPLETED	Norfloxacin Versus Ciprofloxacin for Spontaneous Bacterial Peritonitis (SBP) Prevention
NCT03506256	PHASE4	UNKNOWN	Noroxin Efficacy and Safety Trial
NCT06827756	PHASE4	COMPLETED	Comparative Study of Secondary Prophylaxis for SBP
NCT04161768	PHASE3	RECRUITING	Norfloxacin With Itopride Versus Norfloxacin in Secondary Prophylaxis of Spontaneous Bacterial Peritonitis
NCT00678613	PHASE2/PHASE3	UNKNOWN	Role of Probiotics in the Prevention of Spontaneous Bacterial Peritonitis in Cirrhotic Patients: A Randomized Placebo Control Trial
NCT00947336	PHASE3	COMPLETED	Evaluation of Safety & Efficacy of Synbiotic on the Incidence and Recurrence of Spontaneous Bacterial Peritonitis (SBP) in Cirrhotics
NCT01037959	PHASE3	TERMINATED	Norfloxacin Therapy for Patients With Cirrhosis and Severe Liver Failure
NCT01134692	PHASE3	UNKNOWN	Probiotics for Portal Hypertension
NCT01527019	PHASE3	WITHDRAWN	Comparison in the Treatment of Acute Cystitis Using Cephalosporin and Norfloxacin (CECI)
NCT02120196	PHASE3	UNKNOWN	Comparative Study of Rifaximin Versus Norfloxacin in the Secondary Prophylaxis of Spontaneous Bacterial Peritonitis
NCT03695705	PHASE3	COMPLETED	Rifaximin and Norfloxacin for Prevention of SBP in Adults With Decompensated Cirrhosis
NCT04159870	PHASE3	UNKNOWN	Rifaximin Versus Norfloxacin in Spontaneous Bacterial Peritonitis
NCT04746937	PHASE3	UNKNOWN	Nitazoxanide in Prevention of Secondary Spontaneous Peritonitis
NCT00362752	PHASE2	COMPLETED	A Pilot Study of Norfloxacin for Hepatopulmonary Syndrome
NCT00163982	Not specified	UNKNOWN	Vasoactive Peptides in Portal Pressure
NCT03702426	Not specified	COMPLETED	Comparison of the Efficacy of Granulocyte-Macrophage Colony Stimulating Factor (GM-CSF) and Norfloxacin in Secondary Prophylaxis for Spontaneous Bacterial Peritonitis
NCT06199843	Not specified	UNKNOWN	Efficacy of Rifaximin vs Norfloxacin for Secondary Prophylaxis of SBP (NORRIF Trial)

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPIC Guideline for aminosalicylic acid, chloramphenicol,	CPIC	G6PD

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).