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Nalidixic acid

Clinical data
AHFS/Drugs.com	Consumer Drug Information
Pregnancy category	B U.S.
Routes of administration	Oral
ATC code	J01MB02 (WHO)
Pharmacokinetic data
Protein binding	90%
Metabolism	Partially Hepatic
Elimination half-life	6-7 hours, significantly longer in renal impairment
Identifiers
IUPAC name 1-ethyl-7-methyl-4-oxo-naphthyridine-3-carboxylic acid
CAS Number	389-08-2
PubChem CID	4421
DrugBank	APRD01133
ChemSpider	4268
UNII	3B91HWA56M
KEGG	D00183
ChEBI	CHEBI:100147
ChEMBL	ChEMBL5
CompTox Dashboard (EPA)	DTXSID3020912
ECHA InfoCard	100.006.241
Chemical and physical data
Formula	C12H12N2O3
Molar mass	232.235 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C\2c1c(nc(cc1)C)N(/C=C/2C(=O)O)CC
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) Key:MHWLWQUZZRMNGJ-UHFFFAOYSA-N
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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.

Synthetic quinolone antibiotics were discovered by George Lesher and coworkers as a byproduct of chloroquine manufacture in the 1960s.

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).

Adverse effects

Convulsions and hyperglycaemia

See also

• Fluoroquinolone toxicity
• Fluoroquinolone
• DNA gyrase

References

1. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1093/jac/dkg208, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1093/jac/dkg208 instead.
2. Fraser AG, Harrower AD (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. {{cite journal}}: Unknown parameter |month= ignored (help)

3 Barkley, Nghiem, (Sept. 2011) "AAP reviews 

use of systemic and topical Quinolones" Medscape educational briefs

External links

• MedlinePlus DrugInfo medmaster-a682042
• HealthDigest.org: Nalidixic acid

• Quinolone antibiotics
• 1,8 Naphthyridines
• WIN compounds