Nalidixic acid

Nalidixic acid
Systematic (IUPAC) name
1-ethyl-7-methyl-4-oxo-[1,8]naphthyridine-3-carboxylic acid
Clinical data
AHFS/Drugs.com Consumer Drug Information
Pregnancy cat. B U.S.
Legal status  ?
Routes Oral
Pharmacokinetic data
Protein binding 90%
Metabolism Partially Hepatic
Half-life 6-7 hours, significantly longer in renal impairment
Identifiers
CAS number 389-08-2 Y
ATC code J01MB02
PubChem CID 4421
DrugBank APRD01133
ChemSpider 4268 Y
UNII 3B91HWA56M Y
KEGG D00183 Y
ChEBI CHEBI:100147 Y
ChEMBL CHEMBL5 Y
Chemical data
Formula C12H12N2O3 
Mol. mass 232.235 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Nalidixic acid (tradenames Nevigramon, Neggram, Wintomylon and WIN 18,320) is the first of the synthetic quinolone antibiotics. In the technical sense, it is a naphthyridone, not a quinolone: its ring structure is a 1,8-naphthyridines 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.[1]

Nalidixic acid is effective against both gram-positive and gram-negative bacteria. 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 is especially used in treating urinary tract infections, caused, for example, by Escherichia coli, Proteus, Shigella, Enterobacter, and Klebsiella.. 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 induce formation of relaxation complex analogue. It also inhibits the nicking dosing activity on the subunit of DNA gyrase that releases the positive binding stress on the supercoiled DNA. It is the only FDA approved quinolone for treating UTI infections in children (3).

Contents

Adverse effects

Convulsions and hyperglycaemia[2]

See also

References

  1. ^ a b Emmerson, A.; Jones, A. (2003). "The quinolones: decades of development and use". The Journal of antimicrobial chemotherapy 51 Suppl 1 (90001): 13–20. doi:10.1093/jac/dkg208. PMID 12702699.  edit
  2. ^ Fraser AG, Harrower AD (December 1977). "Convulsions and hyperglycaemia associated with nalidixic acid". Br Med J 2 (6101): 1518. doi:10.1136/bmj.2.6101.1518. PMC 1632822. PMID 589309. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1632822. 
3 Barkley, Nghiem, (Sept. 2011) "AAP reviews

use of systemic and topical Quinolones" Medscape educational briefs

External links

Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis)
Other/ungrouped
Combinations
Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)
Cinoxacin‡ • Flumequine • Nalidixic acid • Oxolinic acid • Pipemidic acid • Piromidic acid • Rosoxacin
Related (DG)
Anaerobic DNA
inhibitors
Nitro- imidazole derivatives
Nitrofuran derivatives
RNA synthesis

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)