QuickView for Ciprofloxacin (compound)

Summary
General Info

PubChem

PubChem Compound 10336735

Name:	Ciprofloxacin
PubChem Compound ID:	10336735
Description:	A broad-spectrum antimicrobial carboxyfluoroquinoline.
Molecular formula:	C₁₇H₁₈FN₃O₃
Molecular weight:	330.344 g/mol

DrugBank

Identification

Name:	Ciprofloxacin
Name (isomeric):	DB00537
Drug Type:	small molecule
Description:	A broad-spectrum antimicrobial carboxyfluoroquinoline.
Synonyms:	Ciprofloxacin monohydrochloride; Ciprofloxacina; Ciprofloxacin dihydrochloride; Ciprofloxacin hydrochloride; Ciprofloxacin HCl
Brand:	Velomonit, Ciflox, Ciprinol, Ciprobay, Ciproxan, Ciproquinol, Bacquinor, Cipro XL, Bernoflox, Flociprin, Ciloxan, Septicide, Cipromycin, Cifloxin, Cipro, Ciprodar, Ciprocinol, Proquin XR, Cipro I.V., Cipro XR, Ocuflox, Baycip, Ciproxin, Floxin
Brand name mixture:	Cipro HC Otic Suspension(Ciprofloxacin hydrochloride + Hydrocortisone), Ciprodex(Ciprofloxacin hydrochloride + Dexamethasone)
Category:	Anti-Infective Agents, Quinolones, Nucleic Acid Synthesis Inhibitors, Anti-Infectives
CAS number:	85721-33-1

Pharmacology

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, ... show more » 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. show less «
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, strand supercoiling repair, and recombination.
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.
Protein binding:	20 to 40%
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.
Route of elimination:	Approximately 40 to 50% of an orally administered dose is excreted in the urine as unchanged drug.
Half Life:	4 hours
Clearance:	Renal cl=300 mL/min
Toxicity:	The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics.
Affected organisms:	Enteric bacteria and other eubacteria

Interactions

Food interaction:

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 without regard to meals.

Take with a full glass of water.

Avoid excessive quantities of coffee or tea (Caffeine).

Drug interaction:

Methotrexate	Ciprofloxacine may decrease the metabolism of methotrexate. Monitor for changes adverse effects of methotrexate if ciprofloxacin is initiated.
Oxtriphylline	Ciprofloxacin may increase the effect of oxtriphylline.
Iron	Formation of non-absorbable complexes
Dihydroxyaluminium	Formation of non-absorbable complexes
Ethotoin	Decreases the hydantoin effect

Methotrexate	Ciprofloxacine may decrease the metabolism of methotrexate. Monitor for changes adverse effects of methotrexate if ciprofloxacin is initiated.
Oxtriphylline	Ciprofloxacin may increase the effect of oxtriphylline.
Iron	Formation of non-absorbable complexes
Dihydroxyaluminium	Formation of non-absorbable complexes
Ethotoin	Decreases the hydantoin effect
Calcium	Formation of non-absorbable complexes
Magnesium oxide	Formation of non-absorbable complexes
Zinc	Formation of non-absorbable complexes
Sucralfate	Formation of non-absorbable complexes
Magnesium	Formation of non-absorbable complexes
Caffeine	Ciprofloxacin may increase the effect and toxicity of caffeine.
Ramelteon	Ciprofloxacin increases levels/toxicity of ramelteon
Dyphylline	Ciprofloxacin may increase the effect of dyphylline.
Aminophylline	Ciprofloxacin may increase the effect of aminophylline.
Warfarin	The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of warfarin.
Sildenafil	Ciprofloxacin may increase the serum level of sildenafil.
Clozapine	Ciprofloxacin may increase clozapine serum levels
Foscarnet	Increased risk of convulsions
Aluminium	Formation of non-absorbable complexes
Mephenytoin	Decreases the hydantoin effect
Rasagiline	Ciprofloxacin, a strong CYP1A2 inhibitor, may decrease the metabolism of rasagiline. Monitor for changes in the therapeutic and adverse effects of rasagiline if ciprofloxacin is initiated or discontinued.
Dicumarol	The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of dicumarol.
Cyclosporine	Ciprofloxacin may increase the effect and toxicity of cyclosporine.
Tacrine	The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by strong CYP1A2 inhibitors such as Ciprofloxacin. Consider modifying therapy to avoid Tacrine toxicity. Monitor the efficacy and toxicity of Tacrine if Ciprofloxacin is initiated, discontinued or if the dose is changed.
Anisindione	The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of anisindione.
Acenocoumarol	The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of acenocoumarol.
Sevelamer	Sevelamer decreases ciprofloxacin bioavailability
Iron Dextran	Formation of non-absorbable complexes
Procainamide	Ciprofloxacin may increase the effect of procainamide.
Calcium Acetate	Calcium salts such as calcium acetate may decrease the absorption of quinolone antibiotics such as ciprofloxacin. Of concern only with oral administration of both agents. Interactions can be minimized by administering oral quinolone at least 2 hours before, or 6 hours after, the dose of an oral calcium supplement. Monitor for decreased therapeutic effects of oral quinolones if administered with oral calcium supplements.
Ropinirole	Ciprofloxacin may increase the effect and toxicity of ropinirole.
Thiothixene	The strong CYP1A2 inhibitor, Ciprofloxacin, may decrease the metabolism and clearance of Thiothixene, a CYP1A2 substrate. Consider alternate therapy or monitor for changes in Thiothixene therapeutic and adverse effects if Ciprofloxacin is initiated, discontinued or dose changed.
Duloxetine	Ciprofloxacin, a strong CYP1A2 inhibitor, may decrease the metabolism of duloxetine. Monitor for changes in the therapeutic and adverse effects of duloxetine if ciprofloxacin is initiated or discontinued.
Tizanidine	Ciprofloxacin inhibits the metabolism and clearance of Tizanidine. Concomitant therapy is contraindicated.
Theophylline	Ciprofloxacin may increase the effect of theophylline.
Phenytoin	Ciprofloxacin may decrease the therapeutic effect of phenytoin.

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Targets

DNA topoisomerase 4 subunit A

DNA gyrase subunit A

DNA topoisomerase 2-alpha

Enzymes

Transporters

Multidrug resistance protein 1