Nalidixic acid

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Nalidixic acid
Clinical data
Trade namesNegGram, Wintomylon, others
AHFS/Drugs.comConsumer Drug Information
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • US: Not FDA approved
renal
impairment
Identifiers
  • 1-Ethyl-7-methyl-4-oxo-[1,8]naphthyridine-3-carboxylic acid
JSmol)
  • O=C\2c1c(nc(cc1)C)N(/C=C/2C(=O)O)CC
  • 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) checkY
  • Key:MHWLWQUZZRMNGJ-UHFFFAOYSA-N checkY
  (verify)

Nalidixic acid (tradenames Nevigramon, NegGram, Wintomylon and WIN 18,320) is the first of the synthetic quinolone antibiotics.

In a technical sense, it is a naphthyridone, not a quinolone: its ring structure is a 1,8-naphthyridine nucleus that contains two nitrogen atoms, unlike quinoline, which has a single nitrogen atom.[1]

Synthetic quinolone antibiotics were discovered by George Lesher and coworkers as a byproduct of chloroquine manufacture in the 1960s;[2] nalidixic acid itself was used clinically, starting in 1967.

Nalidixic acid is effective primarily against

bacteriostatic
manner; that is, it inhibits growth and reproduction. In higher concentrations, it is bactericidal, meaning that it kills bacteria instead of merely inhibiting their growth.

It has historically been used for treating

urinary tract infections, caused, for example, by Escherichia coli, Proteus, Shigella, Enterobacter, and Klebsiella. It is no longer clinically used for this indication in the US as less toxic and more effective agents are available. The marketing authorization for nalidixic acid has been suspended throughout the EU.[3]

It is also a tool in studies as a regulation of bacterial division. It selectively and reversibly blocks DNA replication in susceptible bacteria. Nalidixic acid and related antibiotics inhibit a subunit of DNA gyrase and topoisomerase IV and induce formation of cleavage complexes.[4] It also inhibits the nicking-closing activity on the subunit of DNA gyrase that releases the positive binding stress on the supercoiled DNA.

Adverse effects

Hives, rash, intense itching, or fainting soon after a dose may be a sign of

infants and young children, has been reported occasionally increased intracranial pressure.[10][11][12]

Overdose

In case of overdose the patient experiences

seizures.[13]

Spectrum of bacterial susceptibility and resistance

Bifidobacteria, Lactobacillus, Pseudomonas and Staphylococcus are resistant.[14] Salmonella enterica serovar Typhimurium strain ATCC14028 acquires nalidixic acid resistance when gyrB gene is mutated (strain IR715).[15]

See also

References

  1. PMID 12702699
    .
  2. PMID 14056431
    .
  3. ^ "Disabling and potentially permanent side effects lead to suspension or restrictions of quinolone and fluoroquinolone antibiotics". European Medicines Agency. 11 March 2019.
  4. PMID 20534341
    .
  5. PMID 589309
    .
  6. PMID 4733958
    .
  7. PMID 4653901
    .
  8. PMID 6811074
    .
  9. PMID 6435742
    .
  10. PMID 6025983
    .
  11. PMID 6055749
    .
  12. PMID 4419059
    .
  13. PMID 17175866
    .
  14. ^ "Nalidixic acid spectrum of bacterial susceptibility and Resistance" (PDF). Toku-E. 2011-09-14. Archived from the original (PDF) on 2016-01-10. Retrieved 2012-05-14.
  15. PMID 7868611
    .

External links
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