Nalidixic acid
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Oral |
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| Protein binding | 90% |
| Metabolism | Partially Hepatic |
| Biological half-life | 6-7 hours, significantly longer in renal impairment |
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| ECHA InfoCard | 100.006.241 |
| Chemical and physical data | |
| Formula | C12H12N2O3 |
| Molar mass | 232.235 g/mol |
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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.
Synthetic quinolone antibiotics were discovered by George Lesher and coworkers as a byproduct of chloroquine manufacture in the 1960s. Used clinically from 1967.
Nalidixic acid is effective primarily against gram-negative bacteria, with minor anti-gram-positive activity. In lower concentrations, it acts in a 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 USA as less toxic and more effective agents are available.
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. It also inhibits the nicking-closing activity on the subunit of DNA gyrase that releases the positive binding stress on the supercoiled DNA.
Hives, rash, intense itching, or fainting soon after a dose may be a sign of anaphylaxis. Common adverse effects include rash, itchy skin, blurred or double vision, halos around lights, changes in color vision, nausea, vomiting, and diarrhea. Nalidixic acid may also cause convulsions and hyperglycaemia, photosensitivity reactions, and sometimes haemolytic anaemia, thrombocytopenia or leukopenia. Particularly in infants and young children, has been reported occasionally increased intracranial pressure.
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Wikipedia