Nalidixic Acid

Summary

Nalidixic Acid (CHEMBL5) is an approved small-molecule antibacterial drug (ATC J01MB02); indicated across 2 conditions including bacterial infectious disease and osteomyelitis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01MB02
• Indications: 2 conditions
• Chemistry: 232.23 Da · C12H12N2O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL5
Name	Nalidixic Acid
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	4421
ChEBI	CHEBI:100147
ATC	J01MB02
Molecular formula	C12H12N2O3
Molecular weight	232.23
InChIKey	MHWLWQUZZRMNGJ-UHFFFAOYSA-N

SMILES: CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O

IUPAC name: 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid

ChEBI definition: A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively. An orally administered antibacterial, it is used in the treatment of lower urinary-tract infections due to Gram-negative bacteria, including the majority of E. coli, Enterobacter, Klebsiella, and Proteus species.

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

Also known as: Acide nalidixique, Acido nalidixico, Mictral, Nalidixane, Nalidixate, Nalidixic acid, Nalix, Neggram, Negram, NSC-82174, Neg gram, Uriben

Parent form; salt/anhydrous children: CHEMBL1255939, CHEMBL1741367

Patent coverage: 9,359 distinct patent families (30,727 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 30,563 (99%) 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

Broader ChEMBL bioactivity targets: 7 (assay-derived). Sample: Pyruvate kinase PKM, Nuclear receptor ROR-gamma, Prelamin-A/C, ATP-binding cassette sub-family C member 4, Menin/Histone-lysine N-methyltransferase MLL, DNA gyrase, Prostaglandin G/H synthase 1.

Bioactivity

ChEMBL activities: 4 potent at pChembl ≥ 5 of 9 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
LMNA	6.9	Potency	125.9	nM	CHEMBL_ACT_3663264
MEN1	5.55	Potency	2818	nM	CHEMBL_ACT_4559782
P51450	5.55	Potency	2818	nM	CHEMBL_ACT_5004408
PTGS1	5.14	AC50	7268	nM	CHEMBL_ACT_25205364

Target pathways

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

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	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

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

PharmGKB also curates 0 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

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