Levofloxacin

Identification

Summary

Levofloxacin is a fluoroquinolone antibiotic used to treat infections caused by susceptible bacteria of the upper respiratory tract, skin and skin structures, urinary tract, and prostate, as well as for post-exposure treatment of inhaled anthrax and the plague.

Brand Names
Levaquin, Quinsair
Generic Name
Levofloxacin
DrugBank Accession Number
DB01137
Background

Levofloxacin is a fluoroquinolone antibiotic and the optical S-(-) isomer of racemic ofloxacin.1 It reportedly carries 8 to 128-fold more activity against both gram-negative and gram-positive bacteria compared to R-(+)-ofloxacin1 and remains stereochemically stable following administration (i.e. it does not invert to the inactive isomer).9 Levofloxacin, along with other quinolones such as gatifloxacin and moxifloxacin, is a member of the third generation of fluoroquinolones, colloquially referred to as the "respiratory quinolones" due to improved activity against gram-positive bacteria commonly implicated in respiratory infections.7,8

Levofloxacin was first approved by the FDA in 1996, and was approved in Canada and several South American countries soon after.1

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 361.3675
Monoisotopic: 361.143784348
Chemical Formula
C18H20FN3O4
Synonyms
  • (-)-Ofloxacin
  • (3S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid
  • (S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylic acid
  • (S)-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
  • (S)-Ofloxacin
  • L-Ofloxacin
  • Levofloxacin
  • Levofloxacin anhydrous
  • Levofloxacine
  • Levofloxacino
  • Levofloxacinum
  • Ofloxacin S-(-)-form
External IDs
  • MP-376

Pharmacology

Indication

In oral and intravenous formulations, levofloxacin is indicated in adults for the treatment of various infections caused by susceptible bacteria, including infections of the upper respiratory tract, lower respiratory tract, skin, skin structures, urinary tract, and prostate.9,13 The oral formulation is also indicated in both adults and children 6 months of age and older for the post-exposure management of inhalational anthrax caused by Bacillus anthracis and for the treatment and/or prophylaxis of plague caused by Yersinia pestis.9

In its ophthalmic formulation, levofloxacin is indicated for the treatment of bacterial conjunctivitis caused by susceptible organisms.10 An inhalational solution available in Canada is indicated for the management of cystic fibrosis patients aged 18 years or older with chronic pulmonary Pseudomonas aeruginosa infections.12

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAbscesses caused by susceptible bacteria•••••••••••••••••••••••• ••••••• •••• ••••••
Treatment ofAcute bacterial exacerbation of chronic bronchitis (abecb) caused by susceptible bacteria••••••••••••••••••••••••••• ••••••••••• ••••••••• •••••••••••••• ••••••• •••• ••••••
Treatment ofAcute pyelonephritis caused by infection due to escherichia coli••••••••••••••••••• ••••••• •••• ••••••
Treatment ofBacterial conjunctivitis caused by susceptible bacteria••••••••••••••••••••• •••••••• • •••••
Treatment ofCellulitis caused by susceptible bacteria•••••••••••••••••••••••• ••••••• •••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Levofloxacin is bactericidal and exerts its antimicrobial effects via inhibition of bacterial DNA replication.9 It has a relatively long duration of action in comparison with other antibiotics that allows for once or twice daily dosing. Levofloxacin is associated with QTc-interval prolongation and should be used with caution in patients with other risk factors for prolongation (e.g. hypokalemia, concomitant medications).9

Levofloxacin has demonstrated in vitro activity against a number of aerobic gram-positive and gram-negative bacteria and may carry some activity against certain species of anaerobic bacteria9 and other pathogens such as Chlamydia and Legionella.1 Resistance to levofloxacin may develop, and is generally due to mutations in DNA gyrase or topoisomerase IV, or via alterations to drug efflux.9,7 Cross-resistance may occur between levofloxacin and other fluoroquinolones, but is unlikely to develop between levofloxacin and other antibiotic classes (e.g. macrolides) due to significant differences in chemical structure and mechanism of action.9

As antimicrobial susceptibility patterns are geographically distinct, local antibiograms should be consulted to ensure adequate coverage of relevant pathogens prior to use.

Mechanism of action

Levofloxacin, like other fluoroquinolone antibiotics, exerts its antimicrobial activity via the inhibition of two key bacterial enzymes: DNA gyrase and topoisomerase IV.9 Both targets are type II topoisomerases, but have unique functions within the bacterial cell. DNA gyrase is an enzyme found only in bacteria that introduces negative supercoils into DNA during replication - this helps to relieve torsional strain caused by the introduction of positive supercoils during replication, and these negative supercoils are essential for chromosome condensation and the promotion of transcription initiation.7 It is comprised of four subunits (two A subunits and two B subunits) of which the A subunits appear to be the target of fluoroquinolone antibiotics.1 Bacterial topoisomerase IV, in addition to contributing to the relaxation of positive supercoils, is essential at the terminal stages of DNA replication and functions to “unlink” newly replicated chromosomes to allow for the completion of cell division.7

Inhibition of these enzymes by levofloxacin likely occurs via complexation with the topoisomerase enzymes.7 The end result is a blockade of DNA replication, thus inhibiting cell division and resulting in cell death.

TargetActionsOrganism
ADNA gyrase subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA topoisomerase 4 subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Absorption

Absorption of levofloxacin following oral administration is rapid and essentially complete, with an oral bioavailability of approximately 99%.9 Due to its nearly complete absorption, the intravenous and oral formulations of levofloxacin may be interchangeable.13 The Tmax is generally attained 1-2 hours following administration and the Cmax is proportional to the given dose - an intravenous dose of 500mg infused over 60 minutes resulted in a Cmax of 6.2 ± 1.0 µg/mL whereas a 750mg dose infused over 90 minutes resulted in a Cmax of 11.5 ± 4.0 µg/mL.9 Oral administration with food prolongs the Tmax by approximately 1 hour and slightly decreases the Cmax, but these changes are not likely to be clinically significant.9

Systemic absorption following oral inhalation is approximately 50% lower than that observed following oral administration.12

Volume of distribution

Levofloxacin is widely distributed in the body, with an average volume of distribution following oral administration between 1.09-1.26 L/kg (~89-112 L).1,9 Concentrations in many tissues and fluids may exceed those observed in plasma.1 Levofloxacin is known to penetrate well into skin tissue, fluids (e.g. blisters), lung tissue, and prostatic tissue, amongst others.1

Protein binding

Levofloxacin is 24-38% protein-bound in plasma, primarily to albumin. The extent of protein-binding is independent of its plasma concentration.9

Metabolism

Only 2 metabolites, desmethyl-levofloxacin and levofloxacin-N-oxide, have been identified in humans, neither of which appears to carry any relevant pharmacological activity.9 Following oral administration, less than 5% of the administered dose was recovered in the urine as these metabolites, indicating very little metabolism of levofloxacin in humans.9 The specific enzymes responsible for the demethylation and oxidation of levofloxacin have yet to be ascertained.

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Route of elimination

The majority of administered levofloxacin is excreted unchanged in the urine.9 Following the administration of a single oral dose of levofloxacin, approximately 87% was eliminated unchanged in the urine within 48 hours and less than 4% was eliminated in the feces within 72 hours.9

Half-life

The average terminal elimination half-life of levofloxacin is 6-8 hours.1,9

Clearance

The average apparent total body clearance of levofloxacin ranges from 8.64-13.56 L/h, and its renal clearance ranges from 5.76-8.52 L/h.1,9 The relative similarity of these ranges indicates a small degree of non-renal clearance.1

Adverse Effects
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Toxicity

The LD50 following oral administration in mice and rats is 1803 mg/kg and 1478 mg/kg, respectively.14

Levofloxacin exhibits low potential for acute toxicity - following a single high dose of levofloxacin in several different test animals (e.g. mice, rats, monkeys) observed symptoms included ataxia, ptosis, decreased motor activity, dyspnea, tremors, and convulsions.9 Treatment of acute overdosage should involve stomach emptying (e.g. with activated charcoal) and general supportive measures. Consider monitoring of the patient's ECG to ensure QTc values remain within range.13 Levofloxacin is not efficiently removed by dialysis (peritoneal or hemodialysis) and is therefore of little benefit in cases of overdose.9

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Levofloxacin which could result in a higher serum level.
AbemaciclibThe excretion of Abemaciclib can be decreased when combined with Levofloxacin.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Levofloxacin.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Levofloxacin.
AcemetacinAcemetacin may increase the neuroexcitatory activities of Levofloxacin.
Food Interactions
  • Take with or without food. Food slightly alters kinetics but not to any clinically significant extent.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Levofloxacin hemihydrate6GNT3Y5LMF138199-71-0SUIQUYDRLGGZOL-RCWTXCDDSA-N
Product Images
International/Other Brands
Cravit / Elequine / Floxel / Leroxacin / Levokacin / Levox / Levoxacin / Mosardal / Nofaxin / Reskuin / Tavanic
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act LevofloxacinTablet250 mgOralTEVA Canada Limited2009-06-24Not applicableCanada flag
Act LevofloxacinTablet750 mgOralTEVA Canada Limited2009-06-24Not applicableCanada flag
Act LevofloxacinTablet500 mgOralTEVA Canada Limited2009-06-24Not applicableCanada flag
IquixSolution15 mg/1mLOphthalmicVistakon Pharmaceuticals2004-06-012017-04-13US flag
LevaquinTablet, film coated500 mg/1OralMcNeil Pharmaceuticals1996-12-202012-03-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-levofloxacinTablet500 mgOralApotex Corporation2009-06-24Not applicableCanada flag
Apo-levofloxacinTablet750 mgOralApotex Corporation2009-06-24Not applicableCanada flag
Apo-levofloxacinTablet250 mgOralApotex Corporation2009-06-24Not applicableCanada flag
Auro-levofloxacinTablet750 mgOralAuro Pharma Inc2016-04-12Not applicableCanada flag
Auro-levofloxacinTablet500 mgOralAuro Pharma Inc2016-04-12Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
LevodexaLevofloxacin hemihydrate (0.5 % w/v) + Dexamethasone sodium phosphate (0.1 % w/v)SolutionOphthalmicXediton Pharmaceuticals IncNot applicableNot applicableCanada flag
TRILEVO 500 MG+30 MG+ 1000 MG TEDAVİ PAKETİLevofloxacin hemihydrate (500 mg) + Amoxicillin (1000 mg) + Lansoprazole (30 mg)TabletOralDeva Holding A.S.2012-02-13Not applicableTurkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
LEVONAT 500 MG FILM TABLET, 7 ADETLevofloxacin hemihydrate (500 mg)Tablet, film coatedOralATABAY KİMYA SAN. VE TİC. A.Ş.2013-01-29Not applicableTurkey flag

Categories

ATC Codes
J01MA12 — LevofloxacinA02BD10 — Lansoprazole, amoxicillin and levofloxacinJ01RA05 — Levofloxacin and ornidazoleS01AE05 — Levofloxacin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Fluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Benzoxazines / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / N-methylpiperazines
show 15 more
Substituents
1,4-diazinane / Alkyl aryl ether / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolone antibiotic, fluoroquinolone antibiotic, ofloxacin (CHEBI:63598)
Affected organisms
  • Pseudomonas aeruginosa
  • Bacillus anthracis
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Streptococcus agalactiae
  • Staphylococcus saprophyticus
  • Clostridium perfringens
  • Haemophilus influenzae
  • Mycoplasma pneumoniae
  • Yersinia pestis
  • Escherichia coli
  • Legionella pneumophila
  • Bordetella pertussis
  • Staphylococcus aureus
  • Enterococcus faecalis
  • Moraxella catarrhalis
  • Staphylococcus epidermidis
  • Serratia marcescens
  • Proteus vulgaris
  • Proteus mirabilis
  • Providencia stuartii
  • Streptococcus viridans
  • Providencia rettgeri
  • Morganella morganii
  • Enterobacter cloacae
  • Klebsiella pneumoniae
  • Staphylococcus haemolyticus
  • Enterobacter aerogenes
  • Haemophilus parainfluenzae
  • Klebsiella oxytoca
  • Pseudomonas fluorescens
  • Chlamydophila pneumoniae
  • Citrobacter freundii
  • Streptococcus sp. group G
  • Acinetobacter baumannii
  • Acinetobacter lwoffii
  • Group C Streptococcus sp.
  • Streptococcus milleri
  • Citrobacter koseri
  • Cronobacter sakazakii
  • Pantoea agglomerans

Chemical Identifiers

UNII
RIX4E89Y14
CAS number
100986-85-4
InChI Key
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
IUPAC Name
(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-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

References

Synthesis Reference

Valerie Niddam-Hildesheim, "Preparation of levofloxacin and forms thereof." U.S. Patent US20030130507, issued July 10, 2003.

US20030130507
General References
  1. Fish DN, Chow AT: The clinical pharmacokinetics of levofloxacin. Clin Pharmacokinet. 1997 Feb;32(2):101-19. doi: 10.2165/00003088-199732020-00002. [Article]
  2. Giri P, Naidu S, Patel N, Patel H, Srinivas NR: Evaluation of In Vitro Cytochrome P450 Inhibition and In Vitro Fate of Structurally Diverse N-Oxide Metabolites: Case Studies with Clozapine, Levofloxacin, Roflumilast, Voriconazole and Zopiclone. Eur J Drug Metab Pharmacokinet. 2017 Aug;42(4):677-688. doi: 10.1007/s13318-016-0385-7. [Article]
  3. Sato T, Mishima E, Mano N, Abe T, Yamaguchi H: Potential Drug Interactions Mediated by Renal Organic Anion Transporter OATP4C1. J Pharmacol Exp Ther. 2017 Aug;362(2):271-277. doi: 10.1124/jpet.117.241703. Epub 2017 May 26. [Article]
  4. Parvez MM, Kaisar N, Shin HJ, Jung JA, Shin JG: Inhibitory Interaction Potential of 22 Antituberculosis Drugs on Organic Anion and Cation Transporters of the SLC22A Family. Antimicrob Agents Chemother. 2016 Oct 21;60(11):6558-6567. doi: 10.1128/AAC.01151-16. Print 2016 Nov. [Article]
  5. Maeda T, Takahashi K, Ohtsu N, Oguma T, Ohnishi T, Atsumi R, Tamai I: Identification of influx transporter for the quinolone antibacterial agent levofloxacin. Mol Pharm. 2007 Jan-Feb;4(1):85-94. doi: 10.1021/mp060082j. [Article]
  6. Nies AT, Damme K, Schaeffeler E, Schwab M: Multidrug and toxin extrusion proteins as transporters of antimicrobial drugs. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1565-77. doi: 10.1517/17425255.2012.722996. Epub 2012 Sep 13. [Article]
  7. Fabrega A, Madurga S, Giralt E, Vila J: Mechanism of action of and resistance to quinolones. Microb Biotechnol. 2009 Jan;2(1):40-61. doi: 10.1111/j.1751-7915.2008.00063.x. Epub 2008 Oct 13. [Article]
  8. Fish DN: Levofloxacin: update and perspectives on one of the original 'respiratory quinolones'. Expert Rev Anti Infect Ther. 2003 Oct;1(3):371-87. doi: 10.1586/14787210.1.3.371. [Article]
  9. FDA Approved Drug Products: Levaquin (levofloxacin) oral tablets [Link]
  10. FDA Approved Drug Products: Quixin (levofloxacin) ophthalmic solution [Link]
  11. Health Canada Product Monograph: Levofloxacin oral tablets [Link]
  12. Health Canada Product Monograph: Quinsair (levofloxacin hemihydrate) solution for inhalation [Link]
  13. Health Canada Product Monograph: Levofloxacin in 5% dextrose for injection [Link]
  14. CaymanChem: Levofloxacin MSDS [Link]
Human Metabolome Database
HMDB0001929
KEGG Drug
D08120
KEGG Compound
C07660
PubChem Compound
149096
PubChem Substance
46505134
ChemSpider
131410
BindingDB
50366826
RxNav
82122
ChEBI
63598
ChEMBL
CHEMBL33
ZINC
ZINC000000538273
Therapeutic Targets Database
DAP000160
PharmGKB
PA450214
PDBe Ligand
LFX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Levofloxacin
PDB Entries
3k9f / 3rae / 4juo / 4z2d / 5btg / 5bti / 5eix / 7b8t
FDA label
Download (139 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAcute Exacerbation of Bronchiectasis1
4CompletedBasic ScienceCataracts1
4CompletedBasic ScienceHealthy Volunteers (HV)1
4CompletedDiagnosticHealthy Volunteers (HV)1
4CompletedOtherAge Related Cataracts / Antibiotic Side Effect / Endophthalmitis / Safety Issues1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • H.J. Harkins Co. Inc.
  • Hospira Inc.
  • Innoviant Pharmacy Inc.
  • Janssen-Ortho Inc.
  • Lake Erie Medical and Surgical Supply
  • Letco Medical Inc.
  • Liberty Pharmaceuticals
  • McNeil Laboratories
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • OMJ Pharmaceuticals
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Santen Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • Vistakon Pharmaceuticals LLC
  • Yuhan Chemical Industrial Co. Ltd.
Dosage Forms
FormRouteStrength
Tablet, coatedOral768.75 mg
Tablet, film coatedOral250.0 mg
TabletOral512.466 mg
SolutionIntravenous500.000 mg
TabletOral768.700 mg
Tablet, film coatedOral750 mg
InjectionIntravenous5 mg/ml
SolutionOphthalmic0.5 % w/v
SolutionOphthalmic15 mg/ml
Solution / dropsOphthalmic5 MG/ML
TabletOral500.00 mg
SolutionIntravenous250.000 mg
TabletOral500.000 mg
SolutionIntravenous500 mg/100ml
SolutionOphthalmic5.000 mg
SolutionOphthalmic15 mg/1mL
SolutionOphthalmic5 mg
Injection, solutionIntravenous
TabletOral259.30 mg
TabletOral512.460 mg
Tablet, coatedOral500 mg
Injection, solutionIntravenous5 mg/1mL
Injection, solution, concentrateIntravenous25 mg/1mL
SolutionOral25 mg/1mL
TabletOral250 mg
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral750 mg/1
SolutionIntravenous25 mg / mL
TabletOral500 mg
SolutionIntravenous5 mg / mL
TabletOral750 mg
Tablet, film coatedOral250.000 mg
Tablet, film coatedOral500.00 mg
Tablet, film coatedOral
InjectionIntravenous25 mg/1mL
InjectionIntravenous5 mg/1mL
Injection, solutionIntravenous25 mg/1mL
Injection, solutionIntravenous250 mg/50mL
Injection, solutionIntravenous500 mg/100mL
Injection, solutionIntravenous750 mg/200mL
Injection, solutionIntravenous750 mg/150mL
Injection, solution, concentrateIntravenous500 mg/20mL
Injection, solution, concentrateIntravenous750 mg/30mL
Solution / dropsOphthalmic15 mg/1mL
Solution / dropsOphthalmic5 mg/1mL
Solution / dropsTopical5 mg/1mL
TabletOral250 mg/1
TabletOral500 mg/1
TabletOral750 mg/1
SolutionIntravenous5 mg/ml
Tablet, film coatedOral256.23 mg
Tablet, film coatedOral512.46 mg
InjectionIntravenous500 mg/100ml
Tablet, film coatedOral512.5 MG
InjectionParenteral500 mg/100ml
SolutionParenteral5 mg/ml
Injection, solution5 MG/ML
Injection, solution
Injection, solutionIntravenous5 MG/ML
Injection, solutionParenteral500 MG/100ML
Tablet, film coatedOral500 mg
InjectionIntravenous
Solution / dropsOphthalmic0.5 %
SolutionConjunctival; Ophthalmic5 mg
Solution / dropsAuricular (otic); Ophthalmic0.5 %
TabletOral768.680 mg
SolutionOphthalmic
Solution / dropsOphthalmic
SolutionIntravenous
Tablet, coatedOral75000000 mg
SolutionIntramuscular512.500 mg
Tablet, film coatedOral512 MG
Tablet, coatedOral750 mg
SolutionIntravenous512.000 mg
Tablet, film coatedOral512.58 MG
SolutionRespiratory (inhalation)240 MG
SolutionRespiratory (inhalation)240 mg / 2.4 mL
SolutionOphthalmic5 mg/1mL
Solution / dropsOphthalmic
SolutionIntravenous500 mg
TabletOral768.670 mg
Injection, solutionParenteral5 MG/ML
TabletOral
SolutionIntravenous
InjectionIntravenous500 mg
TabletOral
InjectionIntravenous750 mg/150ml
Tablet, film coatedOral100 mg
LiquidOphthalmic5 mg/1ml
Solution5 mg/1ml
Tablet, coatedOral100 mg
Tablet, coatedOral250 mg
Tablet, film coatedOral250 mg
Injection, solution5 mg/1ml
Prices
Unit descriptionCostUnit
Iquix 1.5% Solution 5ml Bottle81.68USD bottle
Levofloxacin hemihydr 100% powder42.69USD g
Levaquin 750 mg tablet28.06USD each
Levaquin 750 mg leva-pak tablet27.51USD tablet
Levaquin 500 mg tablet16.57USD tablet
Iquix 1.5% eye drops15.71USD ml
Levaquin 250 mg tablet13.71USD tablet
Quixin 0.5% eye drops12.21USD ml
Quixin 0.5% Solution11.4USD ml
Levaquin i.v. 25 mg/ml vial1.94USD ml
Levaquin 500 mg/100 ml d5w0.44USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5053407No1991-10-012010-12-20US flag
US6806256Yes2004-10-192022-08-26US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)225-227CCanadian label
water solubilitySparingly solubleCanadian label
logP2.1Not Available
pKa6.25Canadian label
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP-0.02ALOGPS
logP0.09Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.35Chemaxon
pKa (Strongest Basic)6.72Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area73.32 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity94.94 m3·mol-1Chemaxon
Polarizability36.69 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-2019000000-30d77332fe9feb70a82d
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-00gm-1315975420-b0c4e6cdef799fda69b4
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-0abc-3459425420-e8a4ecd2f8aea93fa660
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-0h9p-3513893500-1d5c8069419fa2c37ebb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0009000000-63138044688fa3ab0792
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-02t9-0019000000-265eec70cbb77077fbfa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1290000000-3ff2c315dfac97ded8c5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0axr-1980000000-e31472e2487627c51cea
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0adl-1930000000-3cd445f16118ecf3f610
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0049000000-3cbab894a4b0d1165e7d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-2492000000-62b30ac9148b06791816
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0009000000-36259e1f93e7f0591ff8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0029000000-575d0b555ec70a134ced
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-a4319ee2062d2e84d33e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0292-0059000000-d39f6e7bcbdc53f172d1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-0019000000-52f593d297a6cb46de27
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pic-0398000000-41f0181effb1e475d616
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-194.4593641
predicted
DarkChem Lite v0.1.0
[M-H]-180.04735
predicted
DeepCCS 1.0 (2019)
[M+H]+194.6161641
predicted
DarkChem Lite v0.1.0
[M+H]+182.41982
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.3068641
predicted
DarkChem Lite v0.1.0
[M+Na]+189.58098
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Note: The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
Gene Name
gyrA
Uniprot ID
P43700
Uniprot Name
DNA gyrase subunit A
Molecular Weight
97817.145 Da
References
  1. Fabrega A, Madurga S, Giralt E, Vila J: Mechanism of action of and resistance to quinolones. Microb Biotechnol. 2009 Jan;2(1):40-61. doi: 10.1111/j.1751-7915.2008.00063.x. Epub 2008 Oct 13. [Article]
  2. FDA Approved Drug Products: Levaquin (levofloxacin) oral tablets [Link]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Note: The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name
parC
Uniprot ID
P43702
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
83366.24 Da
References
  1. Fabrega A, Madurga S, Giralt E, Vila J: Mechanism of action of and resistance to quinolones. Microb Biotechnol. 2009 Jan;2(1):40-61. doi: 10.1111/j.1751-7915.2008.00063.x. Epub 2008 Oct 13. [Article]
  2. FDA Approved Drug Products: Levaquin (levofloxacin) oral tablets [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhang L, Wei MJ, Zhao CY, Qi HM: Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes. Acta Pharmacol Sin. 2008 Dec;29(12):1507-14. doi: 10.1111/j.1745-7254.2008.00908.x. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: Levaquin (levofloxacin) oral tablets [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Ito T, Yano I, Tanaka K, Inui KI: Transport of quinolone antibacterial drugs by human P-glycoprotein expressed in a kidney epithelial cell line, LLC-PK1. J Pharmacol Exp Ther. 1997 Aug;282(2):955-60. [Article]
  2. Yamaguchi H, Yano I, Hashimoto Y, Inui KI: Secretory mechanisms of grepafloxacin and levofloxacin in the human intestinal cell line caco-2. J Pharmacol Exp Ther. 2000 Oct;295(1):360-6. [Article]
  3. Yamaguchi H, Yano I, Saito H, Inui K: Effect of cisplatin-induced acute renal failure on bioavailability and intestinal secretion of quinolone antibacterial drugs in rats. Pharm Res. 2004 Feb;21(2):330-8. [Article]
  4. Zimmermann ES, Laureano JV, Dos Santos CN, Schmidt S, Lagishetty CV, de Castro WV, Dalla Costa T: Simultaneous Semimechanistic Population Analyses of Levofloxacin in Plasma, Lung, and Prostate To Describe the Influence of Efflux Transporters on Drug Distribution following Intravenous and Intratracheal Administration. Antimicrob Agents Chemother. 2015 Nov 30;60(2):946-54. doi: 10.1128/AAC.02317-15. Print 2016 Feb. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. Nies AT, Damme K, Schaeffeler E, Schwab M: Multidrug and toxin extrusion proteins as transporters of antimicrobial drugs. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1565-77. doi: 10.1517/17425255.2012.722996. Epub 2012 Sep 13. [Article]
  2. Ohta KY, Imamura Y, Okudaira N, Atsumi R, Inoue K, Yuasa H: Functional characterization of multidrug and toxin extrusion protein 1 as a facilitative transporter for fluoroquinolones. J Pharmacol Exp Ther. 2009 Feb;328(2):628-34. doi: 10.1124/jpet.108.142257. Epub 2008 Nov 12. [Article]
  3. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data for this transporter inhibition are limited to an in vitro study.
General Function
Drug transmembrane transporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name
SLC47A2
Uniprot ID
Q86VL8
Uniprot Name
Multidrug and toxin extrusion protein 2
Molecular Weight
65083.915 Da
References
  1. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Parvez MM, Kaisar N, Shin HJ, Jung JA, Shin JG: Inhibitory Interaction Potential of 22 Antituberculosis Drugs on Organic Anion and Cation Transporters of the SLC22A Family. Antimicrob Agents Chemother. 2016 Oct 21;60(11):6558-6567. doi: 10.1128/AAC.01151-16. Print 2016 Nov. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Parvez MM, Kaisar N, Shin HJ, Jung JA, Shin JG: Inhibitory Interaction Potential of 22 Antituberculosis Drugs on Organic Anion and Cation Transporters of the SLC22A Family. Antimicrob Agents Chemother. 2016 Oct 21;60(11):6558-6567. doi: 10.1128/AAC.01151-16. Print 2016 Nov. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Maeda T, Takahashi K, Ohtsu N, Oguma T, Ohnishi T, Atsumi R, Tamai I: Identification of influx transporter for the quinolone antibacterial agent levofloxacin. Mol Pharm. 2007 Jan-Feb;4(1):85-94. doi: 10.1021/mp060082j. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Note: Inhibition was observed only at concentrations well above those seen with typical therapeutic use. Relevance to clinical practice is unclear.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Organic anion transporter, capable of transporting pharmacological substances such as digoxin, ouabain, thyroxine, methotrexate and cAMP. May participate in the regulation of membrane transport of ...
Gene Name
SLCO4C1
Uniprot ID
Q6ZQN7
Uniprot Name
Solute carrier organic anion transporter family member 4C1
Molecular Weight
78947.525 Da
References
  1. Sato T, Mishima E, Mano N, Abe T, Yamaguchi H: Potential Drug Interactions Mediated by Renal Organic Anion Transporter OATP4C1. J Pharmacol Exp Ther. 2017 Aug;362(2):271-277. doi: 10.1124/jpet.117.241703. Epub 2017 May 26. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48