Drug/Small Molecule:
levofloxacin

2D structure

Overview

Generic Names: L-Ofloxacin; levofloxacin
IUPAC Name: (-)-(S)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7Hpyrido[1,2,3-de]-1,4 benzoxazine-6-carboxylic acid hemihydrate
Trade Names: Cravit; Cravit Ophthalmic; Elequine; Floxel; Iquix; Leroxacin; Lesacin; Levaquin; Levokacin; Levox; Levoxacin; Mosardal; Nofaxin; Quixin; Reskuin; Tavanic; Volequin
PharmGKB Accession Id: PA450214

Description

A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. [PubChem]

Indication

For the treatment of bacterial conjunctivitis caused by susceptible strains of the following organisms: Corynebacterium species, Staphylococus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, Streptococcus (Groups C/F/G), Viridans group streptococci, Acinetobacter lwoffii, Haemophilus influenzae, Serratia marcescens.

ATC Therapeutic Categories

  • J01MA:Fluoroquinolones
  • S01AX:Other antiinfectives

Pharmacology and Interactions

Mechanism Of Action

Levofloxacin inhibits bacterial type II topoisomerases, topoisomerase IV and DNA gyrase. Levofloxacin, like other fluoroquinolones, inhibits the A subunits of DNA gyrase, two subunits encoded by the gyrA gene. This results in strand breakage on a bacterial chromosome, supercoiling, and resealing; DNA replication and transcription is inhibited.

Pharmacology

Levofloxacin, a fluoroquinolone antiinfective, is the optically active L-isomer of ofloxacin. Levofloxacin is used to treat bacterial conjunctivitis, sinusitis, chronic bronchitis, community-acquired pneumonia and pneumonia caused by penicillin-resistant strains of Streptococcus pneumoniae, skin and skin structure infections, complicated urinary tract infections and acute pyelonephritis.

Food Interactions

Take without regard to meals. Take with water, drink lliberally. Taking this product with orange juice can result in reduced quinolone plasma levels.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Protein Binding

24-38% (to plasma proteins)

Absorption

Absorption of ofloxacin after single or multiple doses of 200 to 400 mg is predictable, and the amount of drug absorbed increases proportionately with the dose.

Half Life

6-8 hours

Toxicity

Side effects include disorientation, dizziness, drowsiness, hot and cold flashes, nausea, slurring of speech, swelling and numbness in the face

Chemical Properties

Chemical Formula:

C18H20FN3O4

SMILES Code:

C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

361.3675 / 361.1438

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
ABCB1
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  • FA
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
SLCO1A2
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  •   
  •   
  • FA
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Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

acenocoumarol The quinolone increases the anticoagulant effect
aluminium Formation of non-absorbable complexes
amiodarone Increased risk of cardiotoxicity and arrhythmias
anisindione The quinolone increases the anticoagulant effect
bepridil Increased risk of cardiotoxicity and arrhythmias
bismuth Formation of non-absorbable complexes
bretylium Increased risk of cardiotoxicity and arrhythmias
calcium Formation of non-absorbable complexes
chlorpromazine Increased risk of cardiotoxicity and arrhythmias
dicumarol The quinolone increases the anticoagulant effect
dihydroquinidine barbiturate Increased risk of cardiotoxicity and arrhythmias
disopyramide Increased risk of cardiotoxicity and arrhythmias
erythromycin Increased risk of cardiotoxicity and arrhythmias
fluphenazine Increased risk of cardiotoxicity and arrhythmias
iron Formation of non-absorbable complexes
josamycin Increased risk of cardiotoxicity and arrhythmias
magnesium Formation of non-absorbable complexes
magnesium oxide Formation of non-absorbable complexes
mesoridazine Increased risk of cardiotoxicity and arrhythmias
methotrimeprazine Increased risk of cardiotoxicity and arrhythmias
perphenazine Increased risk of cardiotoxicity and arrhythmias
procainamide The quinolone increases the effect of procainamide
prochlorperazine Increased risk of cardiotoxicity and arrhythmias
promazine Increased risk of cardiotoxicity and arrhythmias
promethazine Increased risk of cardiotoxicity and arrhythmias
propiomazine Increased risk of cardiotoxicity and arrhythmias
quinidine Increased risk of cardiotoxicity and arrhythmias
quinidine barbiturate Increased risk of cardiotoxicity and arrhythmias
quinupristin This combination presents an increased risk of toxicity
sotalol Increased risk of cardiotoxicity and arrhythmias
sucralfate Formation of non-absorbable complexes
thiethylperazine Increased risk of cardiotoxicity and arrhythmias
thioridazine Increased risk of cardiotoxicity and arrhythmias
trifluoperazine Increased risk of cardiotoxicity and arrhythmias
triflupromazine Increased risk of cardiotoxicity and arrhythmias
warfarin The quinolone increases the anticoagulant effect
zinc Formation of non-absorbable complexes

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. Physicochemical determinants of human renal clearance

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB01137
KEGG Compound ID:
C07660
PubChem Compound ID:
149096
PubChem Substance ID:
195031

Common Searches

Search PubMed
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Search PubChem
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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
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