Cipro is oxidized to oxo-Cipro

Stable Identifier
R-HSA-9794840
Type
Reaction [uncertain]
Species
Homo sapiens
Compartment
cytosol
ReviewStatus
5/5
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Cipro is oxidized to oxo-Cipro
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Oxo-Cipro (oxociprofloxacin, M3) is a major metabolite of Cipro (ciprofloxacine) from which it is formed by several phase I biotransformations in hepatic cells (Joos et al, 1985; reviewed by Campoli-Richards et al, 1988; Sörgel, 1989; Sörgel & Kinzig, 1993). The steps probably involve oxidation to the intermediate hydroxyciprofloxacin, reactions catalyzed by cytochrome P450 enzymes and monoaminooxidases, followed by dehydrogenation catalyzed by either cytochrome P450 enzymes or aldehyde oxidases, yielding the lactam (reviewed by Bolleddula et al, 2014; Vickers & Polsky, 2000; reviewed by Lynch & Price, 2007). Cipro inhibits Cytochrome P450 1A2 (CYP1A2) (Batty et al, 1995; Granfors et al, 2004) but its role as a CYP1A2 ligand has not been shown.
Literature References
PubMed ID Title Journal Year
15592331 Ciprofloxacin greatly increases concentrations and hypotensive effect of tizanidine by inhibiting its cytochrome P450 1A2-mediated presystemic metabolism

Granfors, MT, Backman, JT, Neuvonen, M, Neuvonen, PJ

Clin Pharmacol Ther 2004
8383921 Pharmacokinetics of gyrase inhibitors, Part 2: Renal and hepatic elimination pathways and drug interactions

Sörgel, F, Kinzig, M

Am J Med 1993
7619673 The effect of ciprofloxacin on theophylline pharmacokinetics in healthy subjects

Batty, KT, Davis, TM, Ilett, KF, Dusci, LJ, Langton, SR

Br J Clin Pharmacol 1995
2549606 Metabolism of gyrase inhibitors

Sörgel, F

Rev Infect Dis 1989
3292209 Ciprofloxacin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use

Campoli-Richards, DM, Monk, JP, Price, A, Benfield, P, Todd, PA, Ward, A

Drugs 1988
11465044 The biotransformation of nitrogen containing xenobiotics to lactams

Vickers, S, Polsky, SL

Curr Drug Metab 2000
17708140 The effect of cytochrome P450 metabolism on drug response, interactions, and adverse effects

Lynch, T, Price, A

Am Fam Physician 2007
3158274 Comparison of high-pressure liquid chromatography and bioassay for determination of ciprofloxacin in serum and urine

Joos, B, Ledergerber, B, Flepp, M, Bettex, JD, Lüthy, R, Siegenthaler, W

Antimicrob Agents Chemother 1985
24909234 Biotransformation and bioactivation reactions of alicyclic amines in drug molecules

Bolleddula, J, DeMent, K, Driscoll, JP, Worboys, P, Brassil, PJ, Bourdet, DL

Drug Metab Rev 2014
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Authored
Stephan, R  (2022-07-21)
Reviewed
Thorn, CF  (2022-11-09)
Created
Stephan, R  (2022-07-21)
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