Compound ID | 2052

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Flumequine

Class: Fluoroquinolone

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 quinoline derivative. Used for uncomplicated urinary tract infections
Year first mentioned: 1973
Highest development stage: Approved, primarily used in veterinary medicine
Development status: Withdrawn
Reason dropped: Ocular toxicity, liver toxicity, genotoxic carcinogen
Chemical structure(s):
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Molecular weight: 261.25
Iso. SMILES: CC1CCC2=C3N1C=C(C(=O)C3=CC(=C2)F)C(=O)O
InChI Key: DPSPPJIUMHPXMA-UHFFFAOYSA-N
Can. SMILES: CC1CCC2=C3C(=CC(=C2)F)C(=O)C(=CN13)C(=O)O
InChI: InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/3374
Guide to Pharmacology: flumequine
Citations:
  • https://www.ema.europa.eu/en/documents/mrl-report/flumequine-summary-report-2-committee-veterinary-medicinal-products_en.pdf
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8399897/

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