Levofloxacin

Levofloxacin
Clinical data


Trade names	Levaquin, Tavanic, Iquix, others
AHFS/Drugs.com	Monograph
MedlinePlus	a697040
License data	US FDA: Levofloxacin
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	By mouth, IV, eye drops
ATC code	J01MA12 (WHO) S01AE05 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	99%
Protein binding	31%
Metabolism	<5% desmethyl and N-oxide metabolites
Biological half-life	6.9 hours
Excretion	Renal, mostly unchanged (83%)
Identifiers
IUPAC name (S)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid
CAS Number	100986-85-4^Y
PubChem (CID)	149096
DrugBank	DB01137^Y
ChemSpider	131410^Y
UNII	RIX4E89Y14^N
KEGG	D08120^Y
ChEMBL	CHEMBL33^Y
NIAID ChemDB	002307
ECHA InfoCard	100.115.581
Chemical and physical data
Formula	C₁₈H₂₀FN₃O₄
Molar mass	361.368 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@H]1COc2c3n1cc(c(=O)c3cc(c2N4CCN(CC4)C)F)C(=O)O
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)/t10-/m0/s1^Y Key:GSDSWSVVBLHKDQ-JTQLQIEISA-N^Y
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Levofloxacin, sold under the trade names Levaquin among others, is an antibiotic. It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, urinary tract infections, chronic prostatitis, and some types of gastroenteritis. Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease. It is available by mouth, intravenously, and in eye drop form.

Common side effects include nausea, diarrhea, and trouble sleeping. Serious side effects may include tendon rupture, tendon inflammation, seizures, psychosis, and potentially permanent peripheral nerve damage. Tendon damage may appear months after treatment is completed. People may also sunburn more easily. In people with myasthenia gravis, muscle weakness and breathing problems may worsen. The risk of use during pregnancy is low and it is probably okay during breastfeeding. Levofloxacin is a broad-spectrum antibiotic of the fluoroquinolone drug class. It usually results in death of the bacteria. It is the left sided isomer of the medication ofloxacin.