Compound ID | 2028

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Cinoxacin

Class: Quinolone

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: DNA synthesis inhibitor. Binds to type II topoisomerases, gyrase and topoisomerase IV to inhibitor DNA cleavage and ligation reactions; bacterial topoisomerase inhibitor
Description: Synthetic oxolinic acid derivative, closely related to oxolinic acid and nalidixic acid
Institute where first reported: Lilly
Year first mentioned: 1972
Highest development stage: Approved by FDA in 1980
Development status: Withdrawn
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):
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Molecular weight: 262.22
Iso. SMILES: CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3
InChI Key: VDUWPHTZYNWKRN-UHFFFAOYSA-N
Can. SMILES: CCN1C2=C(C=C3C(=C2)OCO3)C(=O)C(=N1)C(=O)O
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)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/2762
Guide to Pharmacology: cinoxacin
Citations:
  • https://www.ema.europa.eu/en/medicines/human/referrals/quinolone-fluoroquinolone-containing-medicinal-products
  • https://pubmed.ncbi.nlm.nih.gov/6763208/

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