Levofloxacin

Levofloxacin
Clinical data
Trade namesLevaquin, others
AHFS/Drugs.comMonograph
MedlinePlusa697040
License data
Routes of
administration		By mouth, intravenous (IV), eye drops
Drug classFluoroquinolone
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability99%[3]
Protein binding31%[3]
Metabolism<5% desmethyl and N-oxide metabolites
Elimination half-life6.9 hours[3]
ExcretionKidney, mostly unchanged (83%)[3]
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.115.581
Chemical and physical data
FormulaC18H20FN3O4
Molar mass361.373 g·mol−1
3D model (JSmol)
Density1.5±0.1[4] g/cm3
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
 NY (what is this?)  (verify)

Levofloxacin, sold under the brand name Levaquin among others, is a broad-spectrum antibiotic of the fluoroquinolone drug class.[5] It is the left-handed isomer of the medication ofloxacin.[5][6] It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, H. pylori (in combination with other medications), urinary tract infections, Legionnaires' disease, chronic bacterial prostatitis, and some types of gastroenteritis.[6] Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease.[6] It is available by mouth, intravenously,[6] and in eye drop form.[7]

Common side effects include nausea, diarrhea, and trouble sleeping.[6] A warning concerning all fluoroquinolones was issued in 2016: "An FDA safety review has shown that fluoroquinolones when used systemically (i.e. tablets, capsules, and injectable) are associated with disabling and potentially permanent serious adverse effects that can occur together. These adverse effects can involve the tendons, muscles, joints, nerves, and central nervous system."[8]

Other serious side effects may include tendon rupture, tendon inflammation, seizures, psychosis, and potentially permanent peripheral nerve damage.[6] Tendon damage may appear months after treatment is completed.[6] People may also sunburn more easily.[6] In people with myasthenia gravis, muscle weakness and breathing problems may worsen.[6] While use during pregnancy is not recommended, risk appears to be low.[5] The use of other medications in this class appear to be safe while breastfeeding; however, the safety of levofloxacin is unclear.[5]

Levofloxacin was patented in 1985 and approved for medical use in the United States in 1996.[6][9] It is on the World Health Organization's List of Essential Medicines.[10] It is available as a generic medication.[6] In 2022, it was the 251st most commonly prescribed medication in the United States, with more than 1 million prescriptions.[11][12]

  1. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  2. ^ Cite error: The named reference Levaquin FDA label was invoked but never defined (see the help page).
  3. ^ a b c d Zhanel GG, Fontaine S, Adam H, Schurek K, Mayer M, Noreddin AM, et al. (2006). "A Review of New Fluoroquinolones: Focus on their Use in Respiratory Tract Infections". Treat Respir Med. 5 (6): 437–65. doi:10.2165/00151829-200605060-00009. PMID 17154673. S2CID 26955572.
  4. ^ "Levofloxacin". Material Safety Data Sheet. ChemSrc.
  5. ^ a b c d Yaffe GB, Freeman RK, Sumner J (2011). Drugs in pregnancy and lactation: a reference guide to fetal and neonatal risk (9th ed.). Philadelphia: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 828. ISBN 978-1-60831-708-0. Archived from the original on 1 February 2016.
  6. ^ a b c d e f g h i j k "Levofloxacin". The American Society of Health-System Pharmacists. Archived from the original on 1 May 2016. Retrieved 25 August 2016.
  7. ^ "Levofloxacin ophthalmic medical facts from Drugs.com". Drugs.com. Archived from the original on 2 February 2017. Retrieved 23 January 2017.
  8. ^ Cite error: The named reference FDA2016 was invoked but never defined (see the help page).
  9. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 978-3-527-60749-5.
  10. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  11. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  12. ^ "Levofloxacin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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