DrugBank: Levofloxacin (DB01137)

drugbank.ca /drugs/DB01137
Identification Name Levof loxacin Accession Number DB01137 (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 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 Company

Anti- Infective Agents, Urinary CAS number 100986- 85- 4 Weight Average: 361.3675 Monoisotopic: 361.143784348 Chemical Formula C18H20FN3O 4 InChI Key InChIKey=GSDSWSVVBLHKDQ- JTQLQIEISAN 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/h78,10H,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- az atricyclo[7.3.1.0^{5,13}]trideca- 5(13),6,8,11tetraene- 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 Piperaz ines Fluoroquinolones and Quinolones Ethers Benz ene and Derivatives Oxaz ines Aminoquinolines and Derivatives Carboxylic Acids and Derivatives Hydroxyquinolines Halobenz enes 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

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 of Streptococcus 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 plasma proteins) Metabolism Mainly excreted as unchanged drug (87%); undergoes limited metabolism in humans. Route of elimination Mainly excreted as unchanged drug in the urine. Half life 6- 8 hours Clearance Not Available Toxicity Side effects include disorientation, diz z iness, 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 Solution Rout e St rengt h

Intravenous 125 mg/5 ml 250 mg 500 mg 750 mg

Tablet, film coated Oral Tablet, film coated Oral Tablet, film coated Oral Prices Unit descript ion Iquix 1.5% Solution 5ml Bottle

Cost

Unit

81.68 USD bottle

Levofloxacin hemihydr 100% powder 42.69 USD g Levaquin 750 mg tablet Levaquin 750 mg leva- pak tablet Levaquin 500 mg tablet Iquix 1.5% eye drops Levaquin 250 mg tablet Quixin 0.5% eye drops Quixin 0.5% Solution Levaquin i.v. 25 mg/ml vial Levaquin 500 mg/100 ml d5w 28.06 USD each 27.51 USD tablet 16.57 USD tablet 15.71 USD ml 13.71 USD tablet 12.21 USD ml 11.4 USD 1.94 USD 0.44 USD ml ml ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only. Patents Count ry Pat ent Number Approved Expires (est imat ed)

United States 6806256 United States 5053407

2002- 08- 26 2022- 08- 26 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 Propert y water solubility logP logP logS pKa (strongest acidic) pKa (strongest basic) physiological charge Value Source

1.44e+00 g/l ALOGPS - 0.02 0.65 - 2.4 5.45 6.2 -1 ALOGPS ChemAxon ALOGPS ChemAxon ChemAxon ChemAxon ChemAxon ChemAxon ChemAxon ChemAxon ChemAxon ChemAxon

hydrogen acceptor count 7 hydrogen donor count polar surface area rotatable bond count refractivity polariz ability 1 73.32 2 94.94 36.69

References Synthesis Reference Not Available General Reference Not Available External Links Resource KEGG Compound PubChem Compound PubChem Substance ChemSpider BindingDB C07660 149096 46505134 131410 50167506 Link

Therapeutic Targets Database DAP000160

PharmGKB Drug Product Database RxList Drugs.com PDRhealth Wikipedia ATC Codes J01MA12 S01AE05 AHFS Codes 08:12.18

PA450214 2248263 http://www.rxlist.com/cgi/generic2/quixin.htm http://www.drugs.com/cdi/levofloxacin- drops.html http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/flo1181.shtml http://en.wikipedia.org/wiki/Levofloxacin

PDB Entries Not Available FDA label show (139 KB) MSDS Not Available Interactions Drug Interactions Drug Acenocoumarol Aluminium Amiodarone Anisindione Artemether Bepridil Bretylium Calcium Calcium Acetate Int eract ion The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of acenocoumarol. Formation of non- absorbable complexes Increased risk of cardiotoxicity and arrhythmias The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of anisindione. Additive QTc- prolongation may occur. Concomitant therapy should be avoided. Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Formation of non- absorbable complexes Calcium salts such as calcium acetate may decrease the absorption of quinolone antibiotics such as levofloxacin. Of concern only with oral administration of both agents. Interactions can be minimiz ed by administering oral quinolone at least 2 hours before, or 6 hours after, the dose of an oral calcium supplement. Monitor for decreased therapeutic effects of oral quinolones if administered with oral calcium supplements. Increased risk of cardiotoxicity and arrhythmias The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of dicumarol. Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Formation of non- absorbable complexes Formation of non- absorbable complexes Increased risk of cardiotoxicity and arrhythmias

Chlorpromaz ine Dicumarol Dihydroquinidine barbiturate Disopyramide Erythromycin Fluphenaz ine Iron Iron Dextran Josamycin

Lumefantrine Magnesium Magnesium oxide Mesoridaz ine

Additive QTc- prolongation may occur. Concomitant therapy should be avoided. Formation of non- absorbable complexes Formation of non- absorbable complexes Increased risk of cardiotoxicity and arrhythmias

Methotrimepraz ine Increased risk of cardiotoxicity and arrhythmias Perphenaz ine Procainamide Prochlorperaz ine Promaz ine Promethaz ine Propiomaz ine Quinidine Quinidine barbiturate Quinupristin Sotalol Sucralfate Tacrolimus Thiethylperaz ine Thioridaz ine Thiothixene Toremifene Increased risk of cardiotoxicity and arrhythmias Levofloxacin may increase the effect of procainamide. Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias This combination presents an increased risk of toxicity Increased risk of cardiotoxicity and arrhythmias Formation of non- absorbable complexes Additive QTc- prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias May cause additive QTc- prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co- administration. Additive QTc- prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to coadministration. Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias Additive QTc- prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of warfarin. Formation of non- absorbable complexes Additive QTc- prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.

Trifluoperaz ine Triflupromaz ine Trimipramine Voriconaz ole Vorinostat Warfarin Zinc Ziprasidone

Zuclopenthixol

Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc 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.