Substance
ID:420
Names and Identifiers
IUPAC Traditional name
ciprofloxacin
IUPAC name
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
Synonyms
CiprofloxacinCiprofloxacin hydrochlorideCiprofloxacin dihydrochlorideCiprofloxacinaCiprofloxacin monohydrochlorideCiprofloxacin HClciprofloxacin
Brand Name
Cipro XLVelomonitBaycipBernofloxCifloxCiprinolCipromycinCiproquinolFloxinOcufloxProquin XRSepticideCifloxinCiloxanCiproCiprobayCiprocinolBacquinorCipro XRCiprodarFlociprinCipro I.V.CiproxanCiproxin
Properties
Physical Property
Hydrophobicity(logP)
2.3
Solubility
1.1 mg/L
Molecule Details
Drug Groups
approved; investigational
Description
A broad-spectrum antimicrobial carboxyfluoroquinoline. [PubChem]
Indication
For the treatment of the following infections caused by susceptible organisms: urinary tract infections, acute uncomplicated cystitis, chronic bacterial prostatitis, lower respiratory tract infections, acute sinusitis, skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections (used in combination with metronidazole), infectious diarrhea, typhoid fever (enteric fever), uncomplicated cervical and urethral gonorrhea, and inhalational anthrax (post-exposure).
Pharmacology
Ciprofloxacin is a broad-spectrum antiinfective agent of the fluoroquinolone class. Ciprofloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. The mechanism of action of quinolones, including ciprofloxacin, is different from that of other antimicrobial agents such as beta-lactams, macrolides, tetracyclines, or aminoglycosides; therefore, organisms resistant to these drugs may be susceptible to ciprofloxacin. There is no known cross-resistance between ciprofloxacin and other classes of antimicrobials. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian.
Toxicity
The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation
Hepatic. Four metabolites have been identified in human urine which together account for approximately 15% of an oral dose. The metabolites have antimicrobial activity, but are less active than unchanged ciprofloxacin.
Absorption
Rapidly and well absorbed from the gastrointestinal tract after oral administration. The absolute bioavailability is approximately 70% with no substantial loss by first pass metabolism.
Half Life
4 hours
Protein Binding
20 to 40%
Elimination
Approximately 40 to 50% of an orally administered dose is excreted in the urine as unchanged drug.
Clearance
* Renal cl=300 mL/min
References
•
Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J: Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother. 1986 Sep;30(3):444-6.
[Pubmed]
•
Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF: A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69.
[Pubmed]
•
Spivey JM, Cummings DM, Pierson NR: Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy. 1996 Mar-Apr;16(2):314-6.
[Pubmed]
•
Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81.
[Pubmed]
External Links
Molecular Spectra
No Data Available
Click here to submit data
References
• Spivey JM, Cummings DM, Pierson NR: Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy. 1996 Mar-Apr;16(2):314-6. Pubmed
• Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF: A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69. Pubmed
• Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81. Pubmed
• Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J: Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother. 1986 Sep;30(3):444-6. Pubmed