Ciprofloxacin
- BP-S-6-Medicinal Chemistry III
- Mar 31
- 1 min read
Chemical Structure / Formula of Ciprofloxacin
Formula: C17H18FN3O3
Structure: Fluorinated quinolone with piperazine ring, increasing bioavailability and potency.
Mechanism of Action
Inhibits DNA gyrase (topoisomerase II) and topoisomerase IV, preventing bacterial DNA replication.
Bactericidal – effective against both Gram-positive and Gram-negative bacteria.
Uses
UTIs, pyelonephritis, bacterial prostatitis.
Respiratory infections (pseudomonas coverage in CF patients).
Gastrointestinal infections (traveler’s diarrhea, typhoid fever, cholera).
Side Effects
GI upset (nausea, diarrhea, abdominal pain).
CNS effects (dizziness, headache, confusion in elderly patients).
Tendon rupture and tendinitis (higher risk in elderly and corticosteroid users).
QT prolongation, arrhythmias.
Structure-Activity Relationship (SAR) of Ciprofloxacin
Structural Feature | SAR Insight |
Fluorine at position 6 | Enhances lipophilicity and cell wall penetration; crucial for activity. |
Carboxylic acid at position 3 & ketone at 4 | Essential for binding to DNA-gyrase-DNA complex. |
Piperazinyl ring at position 7 | Enhances Gram-negative activity and broadens antibacterial spectrum. |
Substituent at position 1 (cyclopropyl in ciprofloxacin) | Enhances potency and broadens activity. |
Structural Feature | SAR Insight |
Fluorine at position 6 | Enhances lipophilicity and cell wall penetration; crucial for activity. |
Carboxylic acid at position 3 & ketone at 4 | Essential for binding to DNA-gyrase-DNA complex. |
Piperazinyl ring at position 7 | Enhances Gram-negative activity and broadens antibacterial spectrum. |
Substituent at position 1 (cyclopropyl in ciprofloxacin) | Enhances potency and broadens activity. |
Substitution at position 8 (e.g., methoxy, halogens) | Affects phototoxicity and resistance profile. |
Synthesis of Ciprofloxacin
