Ofloxacin

Ofloxacin
Clinical data
Trade namesFloxin, 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.comMonograph
MedlinePlusa691005
License data
Routes of
administration		By mouth, intravenous therapy, topical (eye drops and ear drops)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability85% – 95%
Protein binding32%
Elimination half-life8–9 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.205.209
Chemical and physical data
FormulaC18H20FN3O4
Molar mass361.373 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point250–257 °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
  (verify)

Ofloxacin is a quinolone antibiotic useful for the treatment of a number of bacterial infections.[1] When taken by mouth or injection into a vein, these include pneumonia, cellulitis, urinary tract infections, prostatitis, plague, and certain types of infectious diarrhea.[1][2] Other uses, along with other medications, include treating multidrug resistant tuberculosis.[3] 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.[2]

When taken by mouth, common side effects include vomiting, diarrhea, headache, and rash.[1] Other serious side effect include tendon rupture, numbness due to nerve damage, seizures, and psychosis.[1] Use in pregnancy is typically not recommended.[4] Ofloxacin is in the fluoroquinolone family of medications.[1] It works by interfering with the bacterium's DNA.[1]

Ofloxacin was patented in 1980 and approved for medical use in 1985.[5] It is on the World Health Organization's List of Essential Medicines.[6] Ofloxacin is available as a generic medication.[1] In 2022, it was the 206th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[7][8]

  1. ^ a b c d e f g "Ofloxacin". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  2. ^ a b British national formulary: BNF 69 (69 ed.). British Medical Association. 2015. pp. 409, 757, 782. ISBN 9780857111562.
  3. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 140. hdl:10665/44053. ISBN 9789241547659.
  4. ^ "Ofloxacin Use During Pregnancy | Drugs.com". www.drugs.com. Archived from the original on 28 December 2016. Retrieved 28 December 2016.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 9783527607495. Archived from the original on 2016-12-29.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  8. ^ "Ofloxacin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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