Ofloxacin

Ofloxacin
Clinical data


Trade names	Floxin, Ocuflox, others
AHFS/Drugs.com	Monograph
MedlinePlus	a691005
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	by mouth, IV, topical (eye drops and ear drops)
ATC code	J01MA01 (WHO) S01AE01 (WHO), S02AA16 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	85% - 95%
Protein binding	32%
Biological half-life	8–9 hours
Identifiers
IUPAC name (RS)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
Synonyms	(±)-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
CAS Number	82419-36-1^Y
PubChem (CID)	4583
DrugBank	DB01165^Y
ChemSpider	4422^Y
UNII	A4P49JAZ9H^Y
KEGG	D00453^Y
ChEBI	CHEBI:7731^Y
ChEMBL	CHEMBL4^Y
ECHA InfoCard	100.205.209
Chemical and physical data
Formula	C₁₈H₂₀FN₃O₄
Molar mass	361.368 g/mol
3D model (Jmol)	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)^Y Key:GSDSWSVVBLHKDQ-UHFFFAOYSA-N^Y

Ofloxacin is an antibiotic useful for the treatment of a number of bacterial infections. When taken by mouth or injection into a vein this includes pneumonia, cellulitis, urinary tract infections, prostatitis, plague and certain types of infectious diarrhea. Other uses, along with other medications, include 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 there is a hole in the ear drum.

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 bacteria'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, the most effective and safe medicines needed in a health system. Ofloxacin is available as a generic medication. The wholesale cost in the developing world is about 3.27 USD per month. In the United States a course of treatment costs about 50 to 100 USD.

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