levofloxacin db01137

7/30/2019 Levofloxacin DB01137

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DrugBank: Levofloxacin (DB01137)

drugbank.ca /drugs/DB01137

Identification Name Levofloxacin Accession NumberDB01137 (APRD00477) Type small molecule Groups approved

Description

A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA

gyrase, halting DNA replication. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI

Display: 2D Structure | 3D Structure

Synonyms

L-Ofloxacin

Salts Not Available Brand names

Name Company

Cravit

Cravit Ophthalmic

Elequine

Floxel

Iquix

Leroxacin

Lesacin

Levaquin

Levokacin

Levox

Levoxacin

Mosardal

Nofaxin

Quixin

Reskuin

Tavanic

Volequin

Brand mixtures Not Available Categories

Anti-Bacterial Agents

Quinolones

Nucleic Acid Synthesis Inhibitors
http://www.drugbank.ca/drugs/DB01137/structure?dim=3dhttp://www.drugbank.ca/drugs/DB01137/structurehttp://www.drugbank.ca/drugs/DB01137.inchihttp://www.drugbank.ca/drugs/DB01137.smileshttp://www.drugbank.ca/drugs/DB01137.sdfhttp://www.drugbank.ca/drugs/DB01137.molhttp://www.drugbank.ca/drugs/DB01137


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Anti-Infective Agents, Urinary

CAS number 100986-85-4 Weight Average: 361.3675

Monoisotopic: 361.143784348 Chemical Formula C18H20FN3O4 InChI Key InChIKey=GSDSWSVVBLHKDQ-JTQLQIEISA

N 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

Plain Text IUPAC Name

(2S)-7-fluoro-2-methyl-6-(4-methylpiperaz in-1-yl)- 10-oxo- 4-oxa- 1-azatricyclo[7.3.1.0 {5,13}]trideca-5(13),6,8,11-

tetraene- 11-carboxylic acid

SMILES

C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1

Plain Text Mass Spec Not Available Taxonomy Kingdom Organic Classes

Fluoroquinolones and Quinolones

Aminoquinolines and Derivatives

Hydroxyquinolines

Substructures

Hydroxy Compounds

Acetates

Phenols and Derivatives

Aliphatic and Aryl Amines

Pyridines and Derivatives

Piperazines

Fluoroquinolones and Quinolones

Ethers

Benzene and Derivatives

Oxazines

Aminoquinolines and Derivatives

Carboxylic Acids and Derivatives

Hydroxyquinolines

Halobenzenes

Heterocyclic compounds

Aromatic compounds

Anisoles

(Iso)quinolines and Derivatives

Aryl Halides

Phenyl Esters

Anilines

Pharmacology 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
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marcescens. Pharmacodynamics 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 ofStreptococcus pneumoniae, skin and skin structure

infections, complicated urinary tract infections and acute pyelonephritis. 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. 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. Volume of distribution Not Available Protein binding 24-38% (to p lasma proteins)

Metabolism

Mainly excreted as unchanged drug (87%); undergoes limited metabolism in humans.

Route o f elimination Mainly excreted as unchanged drug in the urine. Half life 6- 8 hours Clearance Not Available Toxici

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

and numbness in the face Affected organisms

Enteric bacteria and other eubacteria

Pathways Not Available Pharmacoeconomics Manufacturers

Ortho mcneil pharmaceutical inc

Santen inc

Ortho mcneil janssen pharmaceuticals inc

Packagers Dosage forms

Form Route St rength

Solution Intravenous 125 mg/5 ml

Tablet, film coated Oral 250 mg



Prices

Unit descript ion Cost Unit

Iquix 1.5% Solution 5ml Bottle 81.68 USD bo ttle

Levofloxacin hemihydr 100% powder 42.69 USD g

Levaquin 750 mg tablet 28.06 USD each

Levaquin 750 mg leva-pak tablet 27.51 USD tablet

Levaquin 500 mg tablet 16.57 USD tablet

Iquix 1.5% eye drops 15.71 USD ml

Levaquin 250 mg tablet 13.71 USD tablet

Quixin 0.5% eye drops 12.21 USD ml

Quixin 0.5% Solution 11.4 USD ml

Levaquin i.v. 25 mg/ml vial 1.94 USD ml

Levaquin 500 mg/100 ml d5w 0.44 USD ml


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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Country Patent Number Approved Expires (estimated)

United States 6806256 2002- 08- 26 2022- 08- 26

United States 5053407 1993- 12- 20 2010- 12- 20

Properties State solid Experimental Properties

Propert y Value Source

water solubility Insoluble Not Available

logP 2.1 Not Available

Predicted Properties

Property Value Source

water solubility 1.44e+00 g/l ALOGPS

logP -0.02 ALOGPS

logP 0.65 ChemAxon

logS -2.4 ALOGPS

pKa (strongest acid ic) 5.45 ChemAxon

pKa (strongest basic) 6.2 ChemAxon

physiological charge - 1 ChemAxon

hydrogen acceptor count 7 ChemAxon

hydrogen donor count 1 ChemAxon

polar surface area 73.32 ChemAxon

rotatable bond count 2 ChemAxon

refractivity 94.94 ChemAxon

polarizability 36.69 ChemAxon

References Synthesis Reference Not Available General Reference Not Available External Links

Resource Link

KEGG Compound C07660

PubChem Compound 149096

PubChem Substance 46505134

ChemSpider 131410

BindingDB 50167506

Therapeutic Targets Database DAP000160
http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000160http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50167506http://www.chemspider.com/Chemical-Structure.131410.htmlhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505134http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=149096http://www.genome.jp/dbget-bin/www_bget?cpd:C07660http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#refractivityhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysishttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#topolgical_surfacehttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bondhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bondhttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.vcclab.org/lab/alogps/http://www.chemaxon.com/products/calculator-plugins/property-predictors/#logp_logdhttp://www.vcclab.org/lab/alogps/http://www.vcclab.org/lab/alogps/


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PharmGKB PA450214

Drug Product Database 2248263

RxList http://www.rxlist.com/cgi/generic2/quixin.htm

Drugs.com http://www.drugs.com/cdi/levofloxacin-drops.html

PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/flo1181.shtml

Wikipedia http://en.wikipedia.org/wiki/Levofloxacin

ATC Codes

J01MA12

S01AE05

AHFS Codes

08:12.18

PDB Entries Not Available FDA label show (139 KB) MSDS Not Available Interactions Drug Interactions

Drug Interact ion

Acenocoumarol The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of acenocoumarol.

Aluminium Formation of non-absorbable complexes

Amiodarone Increased risk of cardiotoxicity and arrhythmias

Anisindione The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of anisindione.

Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.

Bepridil Increased risk of cardiotoxicity and arrhythmias

Bretylium Increased risk of cardiotoxicity and arrhythmias

Calcium Formation of non-absorbable complexes

Calcium Acetate Calcium salts such as calcium acetate may decrease the absorption of quinolone antibiotics suchas levofloxacin. Of concern only with oral administration of both agents. Interactions can beminimized by administering oral quinolone at least 2 hours before, or 6 hours after, the dose of anoral calcium supplement. Monitor for decreased therapeutic effects of oral quinolones ifadministered with oral calcium supplements.

Chlorpromazine Increased risk of cardiotoxicity and arrhythmias

Dicumarol The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of dicumarol.

Dihydroquinidinebarbiturate

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

Iron Dextran Formation of non-absorbable complexes

Josamycin Increased risk of cardiotoxicity and arrhythmias
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Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.

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 Levofloxacin may increase 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

Quinidinebarbiturate 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

Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias.Concomitant therapy should be used with caution.

Thiethylperazine Increased risk of cardiotoxicity and arrhythmias

Thioridazine Increased risk of cardiotoxicity and arrhythmias

Thiothixene May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consideralternate therapy. Thorough risk:benefit assessment is required prior to co- administration.

Toremifene Additive QTc-prolongation may occur, increasing the risk o f serious ventricular arrhythmias.Consider a lternate therapy. A thorough risk:benefit assessment is required prior to co-administration.

Trifluoperazine Increased risk of cardiotoxicity and arrhythmias

Triflupromazine Increased risk of cardiotoxicity and arrhythmias

Trimipramine Additive QTc-prolongation may occur, increasing the risk o f serious ventricular arrhythmias.

Concomitant therapy should be used with caution.

Voriconazole Additive QTc prolongation may occur. Consider a lternate therapy or monitor for QTc prolongationas this can lead to Torsade de Pointes (TdP).

Vorinostat Additive QTc prolongation may occur. Consider a lternate therapy or monitor for QTc prolongationas this can lead to Torsade de Pointes (TdP).

Warfarin The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of warfarin.

Zinc Formation of non-absorbable complexes

Ziprasidone Additive QTc-prolonging e ffects may increase the risk o f severe arrhythmias. Concomitanttherapy is contraindicated.
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Zuclopenthixol Additive QTc prolongation may occur. Consider a lternate therapy or use caution and monitor forQTc prolongation as this can lead to Torsade de Pointes (TdP).

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.
http://www.drugbank.ca/drugs/DB01624

levofloxacin db01137

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