nalidixic acid   Click here for help

GtoPdb Ligand ID: 12773

Synonyms: NegGram® | Win 18,320
Approved drug PDB Ligand
nalidixic acid is an approved drug (FDA (1964), EMA)
Compound class: Synthetic organic
Comment: Nalidixic acid is a 1,8-naphthyridine derivative belonging to the quinolone class of antibacterial compounds, with activity against Gram-negative bacteria [3].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 69.97
Molecular weight 232.24
XLogP 1
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCN1C=C(C(=O)C2=CC=C(C)N=C21)C(=O)O
Isomeric SMILES CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
InChI InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)
InChI Key MHWLWQUZZRMNGJ-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Nalidixic acid was approved by a number individual national regulatory agencies but was withdrawn from use in European jurisdictions in 2018 following the EMA's recommendation on the use of quinolone antibacterials [2]. The drug also had US FDA approval but is now discontinued.
Nalidixic acid was introduced clinically in the 1960s and was used to treat urinary tract infections caused by susceptible Gram-negative bacteria, including Enterobacter species, Escherichia coli, Klebsiella pneumoniae, Morganella morganii, Proteus mirabilis, Proteus vulgaris, and Providencia rettgeri.