Compound ID | 2023

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Nalidixic acid

Class: Quinolone

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: DNA synthesis inhibitor. Binds to type II topoisomerases, gyrase and topoisomerase IV to inhibitor DNA cleavage and ligation reactions; bacterial topoisomerase inhibitor
Description: Synthetic naphthyridone. Progenitor of the quinolone antibitics. Renal elimination and little absorption after oral application.
Year first mentioned: 1962
Highest development stage: Approved by FDA in 1964
Development status: Withdrawn
Reason dropped: Obsolete (other alternatives exist); resistance development issues
Chemical structure(s):
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Molecular weight: 232.24
Iso. SMILES: CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
InChI Key: MHWLWQUZZRMNGJ-UHFFFAOYSA-N
Can. SMILES: CCN1C=C(C(=O)C2=CC=C(C)N=C21)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)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/4421
Guide to Pharmacology: nalidixic acid
Citations:
  • https://www.pnas.org/doi/10.1073/pnas.74.11.4767
  • https://pubs.acs.org/doi/abs/10.1021/jm01240a021

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