Cinoxacin

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Cinoxacin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601013
ATC code	J01MB06 (WHO)
Legal status
Legal status	UK: discontinued US: discontinued
Pharmacokinetic data
Protein binding	60 to 80%
Identifiers
IUPAC name 1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
CAS Number	28657-80-9 Y
PubChem CID	2762
DrugBank	DB00827 Y
ChemSpider	2660 Y
UNII	LMK22VUH23
KEGG	D00872 Y
ChEBI	CHEBI:3716 Y
ChEMBL	ChEMBL1208 Y
CompTox Dashboard (EPA)	DTXSID8022822
ECHA InfoCard	100.044.652
Chemical and physical data
Formula	C12H10N2O5
Molar mass	262.221 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C1c3c(N(\N=C1\C(=O)O)CC)cc2OCOc2c3
InChI InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17) Y Key:VDUWPHTZYNWKRN-UHFFFAOYSA-N Y
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Cinoxacin is a quinolone antibiotic that has been discontinued in the U.K. as well the United States, both as a branded drug or a generic. The marketing authorization of cinoxacin has been suspended throughout the EU.^[1]

Cinoxacin was an older synthetic antimicrobial related to the quinolone class of antibiotics with activity similar to oxolinic acid and nalidixic acid. It was commonly used thirty years ago to treat urinary tract infections in adults. There are reports that cinoxacin had also been used to treat initial and recurrent urinary tract infections and bacterial prostatitis in dogs.^[2] however this veterinary use was never approved by the United States Food and Drug Administration (FDA). In complicated UTI, the older gyrase-inhibitors such as cinoxacin are no longer indicated.^[3]