Ciprofloxacin

Ciprofloxacin

Clinical data
Trade names	Ciloxan, Cipro, Neofloxin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a688016
License data	US FDA: Ciprofloxacin
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	By mouth, intravenous, topical (ear drops, eye drops)
ATC code	J01MA02 (WHO) S01AE03 (WHO) S02AA15 (WHO) S03AA07 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	70%
Protein binding	30%
Metabolism	Liver (incl. CYP1A2)
Biological half-life	3.5 hours
Excretion	Kidney
Identifiers
IUPAC name 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-quinoline-3-carboxylic acid
CAS Number	85721-33-1 Y
PubChem (CID)	2764
DrugBank	DB00537 Y
ChemSpider	2662 Y
UNII	5E8K9I0O4U Y
KEGG	D00186 Y
ChEBI	CHEBI:100241 Y
ChEMBL	CHEMBL8 Y
NIAID ChemDB	001992
ECHA InfoCard	100.123.026
Chemical and physical data
Formula	C17H18FN3O3
Molar mass	331.346 g/mol
3D model (Jmol)	Interactive image
SMILES c1c2c(cc(c1F)N3CCNCC3)n(cc(c2=O)C(=O)O)C4CC4
InChI InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24) Y Key:MYSWGUAQZAJSOK-UHFFFAOYSA-N Y

Ciprofloxacin is an antibiotic used to treat a number of bacterial infections. This includes bone and joint infections, intra abdominal infections, certain type of infectious diarrhea, respiratory tract infections, skin infections, typhoid fever, and urinary tract infections, among others. For some infections it is used in addition to other antibiotics. It can be taken by mouth or used intravenously.

Common side effects include nausea, vomiting, diarrhea, and rash. Ciprofloxacin increases the risk of tendon rupture and worsening muscle weakness in people with the neurological disorder myasthenia gravis. Rates of side effects appear to be higher than some groups of antibiotics such as cephalosporins but lower than others such as clindamycin. Studies in other animals raise concerns regarding use in pregnancy. No problems were identified, however, in the children of a small number of women who took the medication. It appears to be safe during breastfeeding. It is a second-generation fluoroquinolone with a broad spectrum of activity that usually results in the death of the bacteria.

Ciprofloxacin was introduced in 1987. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication and not very expensive. The wholesale cost in the developing world is between 0.03 and 0.13 USD a dose. In the United States it is sold for about 0.40 USD per dose.