Compound ID | 2024

Ciprofloxacin

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. Oral, intravenous and topical application.
Year first mentioned: 1980
Development status: Approved, off-patent
Chemical structure(s):
Canonical SMILES: C1CC1N2C=C(C(=O)C3=C2C=C(C(=C3)F)N4CCNCC4)C(=O)O
Isomeric SMILES: C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)N4CCNCC4)F)C(=O)O
InChI: InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)
InChI Key: MYSWGUAQZAJSOK-UHFFFAOYSA-N
Structure link: https://pubchem.ncbi.nlm.nih.gov/compound/2764
External links:
Guide to Pharmacology: ciprofloxacin
Main Source: https://pubs.acs.org/doi/10.1021/bi5000564
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/16970512/
  • https://www.ema.europa.eu/en/medicines/human/referrals/quinolone-fluoroquinolone-containing-medicinal-products
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC90866/
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