Compound ID | 2029

Prulifloxacin

Class: Fluoroquinolone

Spectrum of activity: Gram-positive  &  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 quinoline derivative, prodrug of ulifloxacin. Very similar to ciprofloxacin.
Year first mentioned: 1987
Development status: Approved in Japan, off-patent, available in some countries
Chemical structure(s):
Canonical SMILES: CC1=C(CN2CCN(CC2)C3=CC4=C(C=C3F)C(=O)C(=C5N4C(C)S5)C(=O)O)OC(=O)O1
Isomeric SMILES: CC1N2C3=CC(=C(C=C3C(=O)C(=C2S1)C(=O)O)F)N4CCN(CC4)CC5=C(OC(=O)O5)C
InChI: InChI=1S/C21H20FN3O6S/c1-10-16(31-21(29)30-10)9-23-3-5-24(6-4-23)15-8-14-12(7-13(15)22)18(26)17(20(27)28)19-25(14)11(2)32-19/h7-8,11H,3-6,9H2,1-2H3,(H,27,28)
InChI Key: PWNMXPDKBYZCOO-UHFFFAOYSA-N
Structure link: https://pubchem.ncbi.nlm.nih.gov/compound/65947
External links:
Guide to Pharmacology: prulifloxacin
Main Source: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2650572/
Citation: https://www.ema.europa.eu/en/news/disabling-potentially-permanent-side-effects-lead-suspension-restrictions-quinolone-fluoroquinolone

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