Ofloxacin

Ofloxacin
Clinical data
Trade names	Floxin, Ocuflox, others
Other names	(±)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid
AHFS/Drugs.com	Monograph
MedlinePlus	a691005
License data	US DailyMed: Ofloxacin;
Routes of; administration	By mouth, intravenous therapy, topical (eye drops and ear drops)
ATC code	J01MA01 (WHO) J01RA17 (WHO), J01RA18 (WHO), S01AE01 (WHO), S02AA16 (WHO);
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	85% – 95%
Protein binding	32%
Elimination half-life	8–9 hours
Identifiers
	IUPAC name (RS)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid;
CAS Number	82419-36-1 ;
PubChem CID	4583;
DrugBank	DB01165 ;
ChemSpider	4422 ;
UNII	A4P49JAZ9H;
KEGG	D00453 ;
ChEBI	CHEBI:7731 ;
ChEMBL	ChEMBL4 ;
CompTox Dashboard (EPA)	DTXSID3041085 ;
ECHA InfoCard	100.205.209
Chemical and physical data
Formula	C18H20FN3O4
Molar mass	361.373 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Melting point	250–257 °C (482–495 °F)
	SMILES Fc4cc1c2N(/C=C(\C1=O)C(=O)O)C(COc2c4N3CCN(C)CC3)C;
	InChI InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25) ; Key:GSDSWSVVBLHKDQ-UHFFFAOYSA-N ;
	(verify)

Ofloxacin is a quinolone antibiotic useful for the treatment of a number of bacterial infections. When taken by mouth or injection into a vein, these include pneumonia, cellulitis, urinary tract infections, prostatitis, plague, and certain types of infectious diarrhea. Other uses, along with other medications, include treating multidrug resistant tuberculosis. An eye drop may be used for a superficial bacterial infection of the eye and an ear drop may be used for otitis media when a hole in the ear drum is present.

When taken by mouth, common side effects include vomiting, diarrhea, headache, and rash. Other serious side effect include tendon rupture, numbness due to nerve damage, seizures, and psychosis. Use in pregnancy is typically not recommended. Ofloxacin is in the fluoroquinolone family of medications. It works by interfering with the bacterium's DNA.

Ofloxacin was patented in 1980 and approved for medical use in 1985. It is on the World Health Organization's List of Essential Medicines. Ofloxacin is available as a generic medication. In 2022, it was the 206th most commonly prescribed medication in the United States, with more than 1 million prescriptions.