Moxifloxacin

Moxifloxacin
Clinical data
Trade namesAvelox, Vigamox, Moxiflox, others
Other namesMoxifloxacine; BAY 12-8039
AHFS/Drugs.comMonograph
MedlinePlusa600002
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, intravenous, eye drops
Drug classAntibiotic (fluoroquinolone)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability86%[1]
Protein binding47%[1]
MetabolismGlucuronide and sulfate conjugation; CYP450Tooltip cytochrome P450 system not involved[2]
Elimination half-life12.1 hours[1]
ExcretionUrine, feces
Identifiers
IUPAC name
  • 1-Cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.129.459
Chemical and physical data
FormulaC21H24FN3O4
Molar mass401.438 g·mol−1
3D model (JSmol)
SMILES
  • COc1c2c(cc(c1N3C[C@@H]4CCCN[C@@H]4C3)F)c(=O)c(cn2C5CC5)C(=O)O
InChI
  • InChI=1S/C21H24FN3O4/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,16+/m0/s1 Y
  • Key:FABPRXSRWADJSP-MEDUHNTESA-N Y
  (verify)

Moxifloxacin is an antibiotic, used to treat bacterial infections,[3] including pneumonia, conjunctivitis, endocarditis, tuberculosis, and sinusitis.[3][4] It can be given by mouth, by injection into a vein, and as an eye drop.[4]

Common side effects include diarrhea, dizziness, and headache.[3] Severe side effects may include spontaneous tendon ruptures, nerve damage, and worsening of myasthenia gravis.[3] Safety of use in pregnancy and breastfeeding is unclear.[5] Moxifloxacin is in the fluoroquinolone family of medications.[3] It usually kills bacteria by blocking their ability to duplicate DNA.[3]

Moxifloxacin was patented in 1988 and approved for use in the United States in 1999.[6][7] It is on the World Health Organization's List of Essential Medicines.[8] In 2022, it was the 273rd most commonly prescribed medication in the United States, with more than 800,000 prescriptions.[9][10]

  1. ^ a b c 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". Treatments in Respiratory Medicine. 5 (6): 437–465. doi:10.2165/00151829-200605060-00009. PMID 17154673. S2CID 26955572.
  2. ^ World Health Organization (2008). Guidelines for the Programmatic Management of Drug-resistant Tuberculosis. World Health Organization. pp. 189–. ISBN 978-92-4-154758-1.
  3. ^ a b c d e f "Moxifloxacin Hydrochloride". The American Society of Health-System Pharmacists. Retrieved 29 August 2017.
  4. ^ a b British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 408, 757. ISBN 9780857111562.
  5. ^ "Moxifloxacin Use During Pregnancy". Drugs.com. Retrieved 10 December 2017.
  6. ^ "Details for NDA:021085". DrugPatentWatch. Retrieved 17 July 2009.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 501. ISBN 9783527607495.
  8. ^ 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.
  9. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  10. ^ "Moxifloxacin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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