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CAS 389-08-2

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Nalidixic acid

Description:
Nalidixic acid is a synthetic antibacterial agent belonging to the quinolone class of antibiotics. It is primarily used to treat urinary tract infections caused by susceptible bacteria. The compound is characterized by its bicyclic structure, which includes a naphthyridine ring system, and features a carboxylic acid functional group that contributes to its solubility and biological activity. Nalidixic acid exhibits broad-spectrum activity against Gram-negative bacteria, inhibiting bacterial DNA gyrase, an essential enzyme for DNA replication and transcription. Its pharmacokinetics include oral absorption, with peak plasma concentrations typically occurring within a few hours post-administration. The drug is metabolized in the liver and excreted primarily through the kidneys. Common side effects may include gastrointestinal disturbances and, in rare cases, central nervous system effects. Due to the emergence of bacterial resistance and the development of newer fluoroquinolones with improved efficacy and safety profiles, nalidixic acid is less commonly used today but remains a significant historical antibiotic in the treatment of specific infections.
Formula:C12H12N2O3
InChI:InChI=1/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)/p-1
InChI key:InChIKey=MHWLWQUZZRMNGJ-UHFFFAOYSA-N
SMILES:C(C)N1C=2C(C(=O)C(C(O)=O)=C1)=CC=C(C)N2
Synonyms:
  • 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
  • 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-
  • 1-Ethyl-1,4-Dihydro-7-Methyl-4-Oxo-1,8-Naphthyridine-3-Carboxylic Acid
  • 1-Ethyl-7-Methyl-4-Oxo-1,4-Dihydro-1,8-Naphthyridine-3-Carboxylate
  • 1-Ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid
  • 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
  • 1-Ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
  • 3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one
  • Acide Nalidixique
  • Acido Nalidixico
  • See more synonyms
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