Nalidixic acid

Class: Quinolone

Spectrum of activity:	Gram-negative
Details of activity:	Binds to type II topoisomerases, gyrase and topoisomerase IV and thus, inhibits DNA cleavage and ligation reactions. It kills bacterial cells by increasing the concentration of enzyme–DNA cleavage complexes, thereby inhibiting cell replication.
Description:	Synthetic naphthyridone. Progenitor of the quinolone antibitics. Renal elimination and little absorption after oral application.
Year first mentioned:	1962
Development status:	Approved, off-patent, not available in most countries

Chemical structure(s):
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
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/4421

External links:
Guide to Pharmacology:	nalidixic acid
Main Source:	https://pubs.acs.org/doi/abs/10.1021/jm01240a021
Citation:	https://www.pnas.org/doi/10.1073/pnas.74.11.4767