Chemical formula:
C17H18FN3O3
SAR:
Ciprofloxacin is a fluoroquinolone antibiotic.
The key elements in its structure are the quinolone ring, a carboxylic acid group, a fluorine atom at the C-6 position, and a cyclopropyl group at the N-1 position.
Fluorine contributes significantly to its antibacterial activity and the cyclopropyl group enhances activity against gram-negative bacteria.
The carboxyl group is necessary for antibacterial activity and is believed to be involved in the chelation of metal ions that could interfere with bacterial DNA synthesis.
Mechanism of action:
Ciprofloxacin inhibits bacterial DNA replication by targeting DNA gyrase and topoisomerase IV.
Synthesis:
The synthesis of Ciprofloxacin involves a multi-step reaction:
1. Ethyl piperazine-1-carboxylate reacts with a bromoquinoline derivative to yield a cyclopropylquinoline ester:
Ethyl piperazine-1-carboxylate + Bromoquinoline → Cyclopropylquinoline ester
2. The ester group is then hydrolyzed to give the corresponding carboxylic acid:
Cyclopropylquinoline ester + H2O → Cyclopropylquinoline carboxylic acid
3. The final step is a condensation with piperazine:
Cyclopropylquinoline carboxylic acid + Piperazine → Ciprofloxacin
Uses:
iprofloxacin is used to treat a wide range of bacterial infections, including urinary tract infections, respiratory infections, gastrointestinal infections, and skin infections.
Side effects:
Side effects can include gastrointestinal disturbances, CNS effects (e.g., headache, dizziness), phototoxicity, tendonitis or tendon rupture, and hypersensitivity reactions.