Synthetic antimicrobial related to oxolinic acid and nalidixic acid and used in urinary tract infections. [PubChem]
Indication
For the treatment of initial and recurrent urinary tract infections in adults caused by the following susceptible microorganisms: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella species (including K. pneumoniae), and Enterobacter species.
Pharmacology
Cinoxacin is a synthetic antibacterial agent with in vitro activity against many gram-negative aerobic bacteria, particularly strains of the Enterobacteriaceae family. Cinoxacin inhibits bacterial deoxyribonucleic acid (DNA) synthesis, is bactericidal, and is active over the entire urinary pH range. Cross resistance with nalidixic acid has been demonstrated.
Toxicity
Oral, subcutaneous, and intravenous LD50 in the rat is 3610 mg/kg, 1380 mg/kg, and 860 mg/kg, respectively. Oral, subcutaneous, and intravenous LD50 in the mouse is 2330 mg/kg, 900 mg/kg, and 850 mg/kg, respectively.Symptoms following an overdose of cinoxacin may include anorexia, nausea, vomiting, epigastric distress, and diarrhea. The severity of the epigastric distress and the diarrhea are dose related. Headache, dizziness, insomnia, photophobia, tinnitus, and a tingling sensation have been reported in some patients.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation
Hepatic, with approximately 30-40% metabolized to inactive metabolites.
Absorption
Rapidly absorbed after oral administration. The presence of food delays absorption but does does not affect total absorption.
Half Life
The mean serum half-life is 1.5 hours. Half-life in patients with impaired renal function may exceed 10 hours.
Application Cinoxacin is a synthetic antimicrobial commonly used in urinary tract infections that are caused by Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella species, and Enterobacter species.. It is a quinolone gyrase inhibitor. It is used to study the rat renal organic anion transporter 1 (OAT1)1. It is used to study fluoroquinolone-resistant Streptococcus pyogenes2. Biochem/physiol Actions Cinoxacin interferes with DNA replication by inhibiting DNA gyrase and topoisomerase IV (topo IV) through tight DNA binding. Cinoxacin allows for proper replicated DNA separation. Therefore, the inhibition of Cinoxacin inhibits DNA replication and cell division. Cinoxacin interferes with DNA replication by inhibiting DNA gyrase and topoisomerase IV (topo IV) through tight DNA binding. Other Notes Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8645.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
A member of the class of cinnolines that is 6,7-methylenedioxycinnolin-4(1H)-one bearing an ethyl group at position 1 and a carboxylic acid group at position 3. An analogue of oxolinic acid, it has similar antibacterial actions. It was formerly used for the treatment of urinary tract infections.
