Overview
| Generic Names: | Ciprofloxacin HCl; Ciprofloxacin dihydrochloride; Ciprofloxacin hydrochloride; Ciprofloxacin monohydrochloride; Ciprofloxacina; ciprofloxacin |
|---|---|
| IUPAC Name: | 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid |
| Trade Names: | Bacquinor; Baycip; Bernoflox; Ciflox; Cifloxin; Ciloxan; Ciprinol; Cipro; Cipro I.V.; Cipro XL; Cipro XR; Ciprobay; Ciprocinol; Ciprodar; Cipromycin; Ciproquinol; Ciproxan; Ciproxin; Flociprin; Floxin; Ocuflox; Proquin XR; Septicide; Velomonit |
| Brand Mixtures: | Cipro HC Otic Suspension (Ciprofloxacin hydrochloride + Hydrocortisone); Ciprodex (Ciprofloxacin hydrochloride + Dexamethasone) |
| PharmGKB Accession Id: | PA449009 |
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).
ATC Therapeutic Categories
- J01MA:Fluoroquinolones
- S01AX:Other antiinfectives
- S02AA:Antiinfectives
- S03AA:Antiinfectives
Pharmacology and Interactions
Mechanism Of Action
The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
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.
Food Interactions
Avoid excessive quantities of coffee or tea (Caffeine). Avoid milk, calcium containing dairy products, iron, magnesium, zinc, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication. Take with a full glass of water. Take without regard to meals.
Absorption, Distribution, Metabolism, Elimination & Toxicity
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.
Protein Binding
20 to 40%
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
Toxicity
The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics.
Chemical Properties
Chemical Formula:
C17H18FN3O3
SMILES Code:
C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)N4CCNCC4)F)C(=O)O
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
331.3415 / 331.1332
Curated Information
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
|---|---|---|---|
|
CYP3A4 |
|
Publications |
|
SLCO1A2 |
|
Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| acenocoumarol | The quinolone increases the anticoagulant effect |
| aluminium | Formation of non-absorbable complexes |
| aminophylline | The quinolone increases the effect of theophylline |
| anisindione | The quinolone increases the anticoagulant effect |
| bismuth | Formation of non-absorbable complexes |
| caffeine | The quinolone increases the effect and toxicity of caffeine |
| calcium | Formation of non-absorbable complexes |
| clozapine | Ciprofloxacin may increase clozapine serum levels |
| cyclosporine | The quinolone increases the effect and toxicity of cyclosporine |
| dicumarol | The quinolone increases the anticoagulant effect |
| dihydroxyaluminium | Formation of non-absorbable complexes |
| duloxetine | Increases the effect/toxicity of duloxetine |
| dyphylline | The quinolone increases the effect of theophylline |
| ethotoin | Decreases the hydantoin effect |
| foscarnet | Increased risk of convulsions |
| fosphenytoin | Decreases the hydantoin effect |
| iron | Formation of non-absorbable complexes |
| magnesium | Formation of non-absorbable complexes |
| magnesium oxide | Formation of non-absorbable complexes |
| mephenytoin | Decreases the hydantoin effect |
| methotrexate | Increases methotrexate toxicity |
| oxtriphylline | The quinolone increases the effect of theophylline |
| phenytoin | Decreases the hydantoin effect |
| procainamide | The quinolone increases the effect of procainamide |
| rasagiline | Increases effect/toxicity of rasagiline |
| ropinirole | The quinolone increases the effect and toxicity of ropinirole |
| sevelamer | Sevelamer decreases ciprofloxacin bioavailability |
| sildenafil | The quinolone increases sildenafil levels |
| sucralfate | Formation of non-absorbable complexes |
| theophylline | The quinolone increases the effect of theophylline |
| tizanidine | Increases the effect/toxicity of tizanidine |
| warfarin | The quinolone increases the anticoagulant effect |
| zinc | Formation of non-absorbable complexes |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
Common Searches
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.