Cinoxacin

Class: Quinolone

Spectrum of activity:	Gram-negative
Details of activity:	Binds to type II topoisomerases, gyrase and topoisomerase IV and thus, inhibits DNA cleavage and ligation reactions. It kills bacterial cells by increasing the concentration of enzyme–DNA cleavage complexes, thereby inhibiting cell replication.
Description:	Synthetic oxolinic acid derivative, closely related to oxolinic acid and nalidixic acid
Institute where first reported:	Lilly
Year first mentioned:	1972
Highest developmental phase:	Approved by FDA in 1980
Development status:	Discontinued
Reason Dropped:	Causes serious, disabling and potentially permanent side effects as with other quinolone and fluoroquinolone antibiotics when given by mouth, injection or inhalation

Chemical structure(s):
Canonical SMILES:	CCN1C2=C(C=C3C(=C2)OCO3)C(=O)C(=N1)C(=O)O
Isomeric SMILES:	CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3
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)
InChI Key:	VDUWPHTZYNWKRN-UHFFFAOYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/2762

External links:
Guide to Pharmacology:	cinoxacin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/6763208/
Citation:	https://www.ema.europa.eu/en/medicines/human/referrals/quinolone-fluoroquinolone-containing-medicinal-products