Drug/Small Molecule:
ciprofloxacin

2D structure

Overview

Generic Names: Ciprofloxacin HCl; Ciprofloxacin dihydrochloride; Ciprofloxacin hydrochloride; Ciprofloxacin monohydrochloride; Ciprofloxacina; ciprofloxacin
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 (source: Drug Bank)

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). (source: Drug Bank)

ATC Therapeutic Categories

  • J01MA:Fluoroquinolones
  • S01AX:Other antiinfectives
  • S02AA:Antiinfectives
  • S03AA:Antiinfectives

Pharmacology, Interactions, and Contraindications

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. (source: Drug Bank)

Pharmacology

Ciprofloxacin is a broad-spectrum antiinfective agent of the fluoroquinolone class. Ciprofloxacin has <i>in vitro</i> 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. (source: Drug Bank)

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. (source: Drug Bank)

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. (source: Drug Bank)

Protein Binding

20 to 40% (source: Drug Bank)

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. (source: Drug Bank)

Toxicity

The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics. (source: Drug Bank)

Isomeric SMILES Code:

C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)N4CCNCC4)F)C(=O)O (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
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  • PK
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
SLCO1A2
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  • FA
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Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
ALB Uncurated Annotation (source: Drug Bank)
TOP2A Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation The quinolone increases the anticoagulant effect (source: Drug Bank)
caffeine Uncurated Annotation The quinolone increases the effect and toxicity of caffeine (source: Drug Bank)
calcium Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
clozapine Uncurated Annotation Ciprofloxacin may increase clozapine serum levels (source: Drug Bank)
cyclosporine Uncurated Annotation The quinolone increases the effect and toxicity of cyclosporine (source: Drug Bank)
dicumarol Uncurated Annotation The quinolone increases the anticoagulant effect (source: Drug Bank)
duloxetine Uncurated Annotation Increases the effect/toxicity of duloxetine (source: Drug Bank)
foscarnet Uncurated Annotation Increased risk of convulsions (source: Drug Bank)
iron Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
magnesium Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
magnesium oxide Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
mephenytoin Uncurated Annotation Decreases the hydantoin effect (source: Drug Bank)
methotrexate Uncurated Annotation Increases methotrexate toxicity (source: Drug Bank)
phenytoin Uncurated Annotation Decreases the hydantoin effect (source: Drug Bank)
procainamide Uncurated Annotation The quinolone increases the effect of procainamide (source: Drug Bank)
sildenafil Uncurated Annotation The quinolone increases sildenafil levels (source: Drug Bank)
sucralfate Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
theophylline Uncurated Annotation The quinolone increases the effect of theophylline (source: Drug Bank)
tizanidine Uncurated Annotation Increases the effect/toxicity of tizanidine (source: Drug Bank)
warfarin Uncurated Annotation The quinolone increases the anticoagulant effect (source: Drug Bank)
zinc Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00537
KEGG Compound ID:
C05349
KEGG Drug ID:
D00186
PubChem Compound ID:
2764
PubChem Substance ID:
192835

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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