Synthesis of fluorine-18-labeled ciprofloxacin for PET studies in humans.
Ciprofloxacin (1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid), a widely-prescribed antibiotic, was labeled with fluorine-18 with the aim to perform positron emission tomography studies in humans for pharmacokinetic measurements. Due to a lack of chemical activation of ciprofloxacin for a direct nucleophilic exchange reaction a novel two-step synthetic approach, which employed an activated 6-fluoro-7-chloro substituted precursor molecule, was developed. The radiosynthesis yielded, starting from 52.5 +/- 11.3 GBq of [(18)F]fluoride, 1.3 +/- 0.6 GBq (n = 13) [(18)F]ciprofloxacin ready for intravenous administration in about 130 min synthesis time. A series of analytical tests was performed in order to prove the identity of the radiolabeled compound and its suitability for human applications.
Langer
Oliver
O
Department of Clinical Pharmacology, Division of Clinical Pharmacokinetics, Vienna University Medical School, Vienna, Austria. Claus.Oliver.Langer@univie.ac.at
Mitterhauser
Markus
M
Brunner
Martin
M
Zeitlinger
Markus
M
Wadsak
Wolfgang
W
Mayer
Bernhard X
BX
Kletter
Kurt
K
Müller
Markus
M
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000493:pharmacokinetics; D002851:Chromatography, High Pressure Liquid; D002939:Ciprofloxacin / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D019275:Radiopharmaceuticals / Q000138:chemical synthesis / Q000493:pharmacokinetics; D014018:Tissue Distribution; D014055:Tomography, Emission-Computed
D000890:Anti-Infective Agents; D019275:Radiopharmaceuticals; D002939:Ciprofloxacin