You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameLevofloxacin
Accession NumberDB01137  (APRD00477, DB06085)
TypeSmall Molecule
GroupsApproved, Investigational
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
(-)-OfloxacinNot AvailableNot Available
(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 acidNot AvailableNot Available
(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 acidNot AvailableNot Available
(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 acidNot AvailableNot Available
(S)-OfloxacinNot AvailableNot Available
L-ofloxacinNot AvailableNot Available
LevofloxacineNot AvailableNot Available
LevofloxacinoNot AvailableNot Available
LevofloxacinumNot AvailableNot Available
Ofloxacin S-(-)-formNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Levaquinsolution25 mg/mLoralPatriot Pharmaceuticals, Inc.2013-07-01Not AvailableUs
Levaquintablet, film coated500 mgoralRebel Distributors Corp1996-12-20Not AvailableUs
Levaquintablet, film coated750 mgoralRebel Distributors Corp1996-12-20Not AvailableUs
Levaquintablet, film coated500 mgoralPd Rx Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated500 mgoralREMEDYREPACK INC.2013-04-10Not AvailableUs
Levaquintablet, film coated500 mgoralREMEDYREPACK INC.2013-07-03Not AvailableUs
Levaquintablet, film coated250 mgoralREMEDYREPACK INC.2013-04-11Not AvailableUs
Levaquintablet, film coated500 mgoralLake Erie Medical DBA Quality Care Products LLC2011-01-27Not AvailableUs
Levaquininjection, solution5 mg/mLintravenousJanssen Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquininjection, solution5 mg/mLintravenousJanssen Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquininjection, solution5 mg/mLintravenousJanssen Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquinsolution25 mg/mLoralJanssen Pharmaceuticals, Inc.2004-10-21Not AvailableUs
Levaquintablet, film coated250 mgoralJanssen Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated500 mgoralJanssen Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated750 mgoralJanssen Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated500 mgoralPhysicians Total Care, Inc.2000-05-11Not AvailableUs
Levaquintablet, film coated250 mgoralPhysicians Total Care, Inc.2000-05-12Not AvailableUs
Levaquintablet, film coated750 mgoralPhysicians Total Care, Inc.2005-08-02Not AvailableUs
Levaquintablet, film coated500 mgoralCardinal Health1996-12-20Not AvailableUs
Levaquintablet, film coated750 mgoralCardinal Health1996-12-20Not AvailableUs
Levaquintablet, film coated250 mgoralCardinal Health1996-12-20Not AvailableUs
Levaquintablet, film coated750 mgoralPd Rx Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated500 mgoralPd Rx Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated500 mgoralPd Rx Pharmaceuticals, Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated500 mgoralbryant ranch prepack1996-12-20Not AvailableUs
Levaquintablet, film coated500 mgoralRed Pharm Drug Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated750 mgoralRed Pharm Drug Inc.1996-12-20Not AvailableUs
Levaquintablet, film coated250 mgoralRed Pharm Drug Inc.1996-12-20Not AvailableUs
Quixinsolution5 mg/mLophthalmicVistakon Pharmaceuticals LLC2000-10-01Not AvailableUs
Iquixsolution15 mg/mLophthalmicVistakon Pharmaceuticals LLC2004-06-01Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Levofloxacintablet, film coated250 mgoralTeva Pharmaceuticals USA Inc2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralTeva Pharmaceuticals USA Inc2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralTeva Pharmaceuticals USA Inc2011-06-20Not AvailableUs
Levofloxacininjection, solution750 mg/150mLintravenousWest ward Pharmaceutical Corp2011-09-16Not AvailableUs
Levofloxacininjection, solution500 mg/100mLintravenousWest ward Pharmaceutical Corp2011-09-16Not AvailableUs
Levofloxacininjection, solution250 mg/50mLintravenousWest ward Pharmaceutical Corp2011-09-16Not AvailableUs
Levofloxacintablet750 mgoralWest ward Pharmaceutical Corp2011-06-21Not AvailableUs
Levofloxacintablet500 mgoralWest ward Pharmaceutical Corp2011-06-21Not AvailableUs
Levofloxacintablet250 mgoralWest ward Pharmaceutical Corp2011-06-21Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousSandoz Inc2011-07-07Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousSandoz Inc2011-07-07Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousSandoz Inc2011-07-07Not AvailableUs
Levofloxacintablet, film coated250 mgoralSandoz Inc2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralSandoz Inc2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralSandoz Inc2011-06-20Not AvailableUs
Levofloxacintablet250 mgoralMajor Pharmaceuticals2011-06-23Not AvailableUs
Levofloxacintablet500 mgoralMajor Pharmaceuticals2011-06-23Not AvailableUs
Levofloxacintablet750 mgoralMajor Pharmaceuticals2011-06-23Not AvailableUs
Levofloxacintablet, film coated250 mgoralMajor Pharmaceuticals2013-12-01Not AvailableUs
Levofloxacintablet, film coated500 mgoralMajor Pharmaceuticals2013-12-01Not AvailableUs
Levofloxacintablet, film coated750 mgoralMajor Pharmaceuticals2013-12-01Not AvailableUs
Levofloxacintablet, film coated750 mgoralBlenheim Pharmacal, Inc.2013-11-15Not AvailableUs
Levofloxacintablet, film coated500 mgoralBlenheim Pharmacal, Inc.2013-11-13Not AvailableUs
Levofloxacintablet250 mgoralTorrent Pharmaceuticals Limited2011-06-20Not AvailableUs
Levofloxacintablet500 mgoralTorrent Pharmaceuticals Limited2011-06-20Not AvailableUs
Levofloxacintablet750 mgoralTorrent Pharmaceuticals Limited2011-06-20Not AvailableUs
Levofloxacinsolution/ drops5 mg/mLtopicalPACK Pharmaceuticals, LLC2010-12-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralSTAT Rx USA LLC2011-08-13Not AvailableUs
Levofloxacinsolution5 mg/mLophthalmicAkorn Inc.2011-03-01Not AvailableUs
Levofloxacininjection25 mg/mLintravenousAkorn, Inc.2011-07-01Not AvailableUs
Levofloxacintablet, film coated250 mgoralRebel Distributors Corp2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralRebel Distributors Corp2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralRebel Distributors Corp2011-06-20Not AvailableUs
Levofloxacininjection25 mg/mLintravenousHeritage Pharmaceuticals Inc.2013-02-04Not AvailableUs
Levofloxacininjection, solution25 mg/mLintravenousSagent Pharmaceuticals2012-01-05Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousSagent Pharmaceuticals2011-06-20Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousSagent Pharmaceuticals2013-07-15Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousSagent Pharmaceuticals2011-12-05Not AvailableUs
Levofloxacintablet, film coated250 mgoralCamber Pharmaceuticals, Inc.2015-01-09Not AvailableUs
Levofloxacintablet, film coated500 mgoralCamber Pharmaceuticals, Inc.2015-01-09Not AvailableUs
Levofloxacintablet, film coated750 mgoralCamber Pharmaceuticals, Inc.2015-01-09Not AvailableUs
Levofloxacintablet500 mgoralAidarex Pharmaceuticals LLC2011-06-20Not AvailableUs
Levofloxacintablet750 mgoralAidarex Pharmaceuticals LLC2011-06-20Not AvailableUs
Levofloxacintablet250 mgoralAidarex Pharmaceuticals LLC2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralMacleods Pharmaceuticals Limited2012-03-22Not AvailableUs
Levofloxacintablet, film coated500 mgoralMacleods Pharmaceuticals Limited2012-03-22Not AvailableUs
Levofloxacintablet, film coated750 mgoralMacleods Pharmaceuticals Limited2012-03-22Not AvailableUs
Levofloxacintablet, film coated750 mgoralLake Erie Medical DBA Quality Care Products LLC2011-06-21Not AvailableUs
Levofloxacintablet, film coated500 mgoralLake Erie Medical DBA Quality Care Products LLC2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralLake Erie Medical DBA Quality Care Products LLC2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralLake Erie Medical DBA Quality Care Products LLC2011-06-20Not AvailableUs
Levofloxacininjection, solution25 mg/mLintravenousClaris Lifesciences Inc.2013-07-01Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousClaris Lifesciences Inc.2013-07-01Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousClaris Lifesciences Inc.2013-07-01Not AvailableUs
Levofloxacininjection, solution5 mg/mLintravenousClaris Lifesciences Inc.2013-07-01Not AvailableUs
Levofloxacintablet, film coated250 mgoralAv Kare, Inc.2013-07-12Not AvailableUs
Levofloxacintablet, film coated500 mgoralAv Kare, Inc.2013-07-12Not AvailableUs
Levofloxacintablet, film coated750 mgoralAv Kare, Inc.2013-07-12Not AvailableUs
Levofloxacintablet, film coated500 mgoralPd Rx Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralPd Rx Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralPd Rx Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralPd Rx Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralPd Rx Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacinsolution/ drops5 mg/mLophthalmicHi Tech Pharmacal Co., Inc.2011-02-10Not AvailableUs
Levofloxacinsolution25 mg/mLoralHi Tech Pharmacal Co., Inc.2011-06-21Not AvailableUs
Levofloxacintablet, film coated500 mgoralUnit Dose Services2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralMylan Institutional Inc.2012-08-27Not AvailableUs
Levofloxacintablet, film coated500 mgoralMylan Institutional Inc.2012-08-27Not AvailableUs
Levofloxacintablet, film coated500 mgoralNorthwind Pharmaceuticals2014-03-03Not AvailableUs
Levofloxacintablet, film coated250 mgoralREMEDYREPACK INC.2013-03-08Not AvailableUs
Levofloxacintablet, film coated500 mgoralREMEDYREPACK INC.2013-09-19Not AvailableUs
Levofloxacintablet, film coated500 mgoralREMEDYREPACK INC.2013-12-11Not AvailableUs
Levofloxacintablet, film coated500 mgoralREMEDYREPACK INC.2013-09-19Not AvailableUs
Levofloxacintablet, film coated250 mgoralREMEDYREPACK INC.2013-12-31Not AvailableUs
Levofloxacintablet, film coated250 mgoralPhysicians Total Care, Inc.2011-09-15Not AvailableUs
Levofloxacintablet, film coated500 mgoralPhysicians Total Care, Inc.2011-06-22Not AvailableUs
Levofloxacintablet, film coated750 mgoralPhysicians Total Care, Inc.2011-06-22Not AvailableUs
Levofloxacintablet, film coated250 mgoralDr. Reddy's Laboratories Limited2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralDr. Reddy's Laboratories Limited2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralDr. Reddy's Laboratories Limited2011-06-20Not AvailableUs
Levofloxacininjection, solution, concentrate500 mg/20mLintravenousAuro Medics Pharma Llc2013-01-24Not AvailableUs
Levofloxacininjection, solution, concentrate750 mg/30mLintravenousAuro Medics Pharma Llc2013-01-24Not AvailableUs
Levofloxacintablet750 mgoralCardinal Health2011-06-23Not AvailableUs
Levofloxacintablet500 mgoralCardinal Health2011-06-23Not AvailableUs
Levofloxacintablet250 mgoralCardinal Health2011-06-23Not AvailableUs
Levofloxacintablet, film coated500 mgoralCardinal Health2013-12-01Not AvailableUs
Levofloxacintablet, film coated750 mgoralCardinal Health2013-12-01Not AvailableUs
Levofloxacintablet250 mgoralWockhardt Limited2011-06-20Not AvailableUs
Levofloxacintablet500 mgoralWockhardt Limited2011-06-20Not AvailableUs
Levofloxacintablet750 mgoralWockhardt Limited2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralCitron Pharma LLC2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralCitron Pharma LLC2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralCitron Pharma LLC2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralClinical Solutions Wholesale2011-06-20Not AvailableUs
Levofloxacintablet500 mgoralNew Horizon Rx Group, LLC2013-08-25Not AvailableUs
Levofloxacintablet250 mgoralHikma Pharmaceutical2011-06-21Not AvailableUs
Levofloxacintablet500 mgoralHikma Pharmaceutical2011-06-21Not AvailableUs
Levofloxacintablet750 mgoralHikma Pharmaceutical2011-06-21Not AvailableUs
Levofloxacintablet, film coated250 mgoralGreenstone LLC2011-06-202015-02-28Us
Levofloxacintablet, film coated500 mgoralGreenstone LLC2011-06-202015-04-30Us
Levofloxacintablet, film coated750 mgoralDIRECT RX2014-01-01Not AvailableUs
Levofloxacintablet, film coated250 mgoralDIRECT RX2014-01-01Not AvailableUs
Levofloxacintablet, film coated500 mgoralDIRECT RX2014-01-01Not AvailableUs
Levofloxacintablet, film coated500 mgoralProficient Rx2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralProficient Rx2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralProficient Rx LP2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralProficient Rx LP2011-06-20Not AvailableUs
Levofloxacininjection5 mg/mLintravenousFresenius Kabi USA, LLC2013-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralbryant ranch prepack2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralbryant ranch prepack2011-06-20Not AvailableUs
Levofloxacintablet250 mgoralbryant ranch prepack2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralReady Meds2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralBoca Pharmacal, LLC2012-08-17Not AvailableUs
Levofloxacintablet, film coated500 mgoralBoca Pharmacal, LLC2012-08-17Not AvailableUs
Levofloxacintablet, film coated750 mgoralBoca Pharmacal, LLC2012-08-17Not AvailableUs
Levofloxacintablet250 mgoralWockhardt USA LLC.2011-06-20Not AvailableUs
Levofloxacintablet500 mgoralWockhardt USA LLC.2011-06-20Not AvailableUs
Levofloxacintablet750 mgoralWockhardt USA LLC.2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralCadila Healthcare Limited2012-11-10Not AvailableUs
Levofloxacintablet, film coated500 mgoralCadila Healthcare Limited2012-11-10Not AvailableUs
Levofloxacintablet, film coated750 mgoralCadila Healthcare Limited2012-11-10Not AvailableUs
Levofloxacintablet, film coated250 mgoralAurobindo Pharma Limited2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralAurobindo Pharma Limited2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralAurobindo Pharma Limited2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralAmerican Health Packaging2011-07-01Not AvailableUs
Levofloxacintablet, film coated500 mgoralAmerican Health Packaging2011-07-01Not AvailableUs
Levofloxacintablet, film coated750 mgoralAmerican Health Packaging2011-07-01Not AvailableUs
Levofloxacintablet, film coated250 mgoralLupin Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralLupin Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralLupin Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated250 mgoralZydus Pharmaceuticals (USA) Inc.2012-11-10Not AvailableUs
Levofloxacintablet, film coated500 mgoralZydus Pharmaceuticals (USA) Inc.2012-11-10Not AvailableUs
Levofloxacintablet, film coated750 mgoralZydus Pharmaceuticals (USA) Inc.2012-11-10Not AvailableUs
Levofloxacintablet, film coated750 mgoralPreferred Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated500 mgoralPreferred Pharmaceuticals, Inc.2011-06-20Not AvailableUs
Levofloxacintablet, film coated750 mgoralPreferred Pharmaceuticals, Inc.2015-01-08Not AvailableUs
Levofloxacintablet, film coated750 mgoralPreferred Pharmaceuticals, Inc.2013-11-14Not AvailableUs
Levofloxacintablet750 mgoralPreferred Pharmaceuticals, Inc.2013-03-27Not AvailableUs
Levofloxacintablet, film coated500 mgoralPreferred Pharmaceuticals, Inc.2011-08-12Not AvailableUs
Levofloxacintablet750 mgoralPreferred Pharmaceuticals, Inc.2013-02-04Not AvailableUs
Levofloxacintablet, film coated500 mgoralH.J. Harkins Company, Inc.2011-11-22Not AvailableUs
Levofloxacintablet500 mgoralPro Doc LimiteeNot AvailableNot AvailableCanada
Over the Counter ProductsNot Available
International Brands
NameCompany
CravitNot Available
ElequineNot Available
FloxelNot Available
LeroxacinNot Available
LevokacinNot Available
LevoxNot Available
LevoxacinNot Available
MosardalNot Available
NofaxinNot Available
ReskuinNot Available
TavanicNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Levofloxacin hemihydrate
ThumbNot applicableDBSALT001001
Categories
CAS number100986-85-4
WeightAverage: 361.3675
Monoisotopic: 361.143784348
Chemical FormulaC18H20FN3O4
InChI KeyGSDSWSVVBLHKDQ-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[7.3.1.0⁵,¹³]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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-3-carboxylic acid
  • N-arylpiperazine
  • Fluoroquinolone
  • Hydroxyquinoline
  • Dihydroquinolone
  • Aminoquinoline
  • Dihydroquinoline
  • Benzoxazine
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Dialkylarylamine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Fluorobenzene
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsLevofloxacin, 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 actionLevofloxacin 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.
AbsorptionAbsorption 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 distributionNot Available
Protein binding24-38% (to plasma proteins)
Metabolism

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

Route of eliminationMainly excreted as unchanged drug in the urine.
Half life6-8 hours
ClearanceNot Available
ToxicitySide 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 2C19 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injectionintravenous25 mg/mL
Injectionintravenous5 mg/mL
Injection, solutionintravenous25 mg/mL
Injection, solutionintravenous250 mg/50mL
Injection, solutionintravenous5 mg/mL
Injection, solutionintravenous500 mg/100mL
Injection, solutionintravenous750 mg/150mL
Injection, solution, concentrateintravenous500 mg/20mL
Injection, solution, concentrateintravenous750 mg/30mL
Solutionophthalmic15 mg/mL
Solutionophthalmic5 mg/mL
Solutionoral25 mg/mL
Solution/ dropsophthalmic5 mg/mL
Solution/ dropstopical5 mg/mL
Tabletoral250 mg
Tabletoral500 mg
Tabletoral750 mg
Tablet, film coatedoral250 mg
Tablet, film coatedoral500 mg
Tablet, film coatedoral750 mg
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
CountryPatent NumberApprovedExpires (estimated)
United States50534071993-12-202010-12-20
United States68062562002-08-262022-08-26
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP-0.02ALOGPS
logP0.65ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.45ChemAxon
pKa (Strongest Basic)6.2ChemAxon
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS/MS1D NMR2D NMR
References
Synthesis Reference

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

US20030130507
General ReferenceNot Available
External Links
ATC CodesJ01MA12S01AE05
AHFS Codes
  • 08:12.18
PDB EntriesNot Available
FDA labelDownload (139 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolThe quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of acenocoumarol.
AluminiumFormation of non-absorbable complexes
AmiodaroneIncreased risk of cardiotoxicity and arrhythmias
AnisindioneThe quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of anisindione.
ArtemetherAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
BepridilIncreased risk of cardiotoxicity and arrhythmias
BretyliumIncreased risk of cardiotoxicity and arrhythmias
CalciumFormation of non-absorbable complexes
Calcium AcetateCalcium 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 minimized 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.
ChlorpromazineIncreased risk of cardiotoxicity and arrhythmias
DicoumarolThe quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of dicumarol.
Dihydroquinidine barbiturateIncreased risk of cardiotoxicity and arrhythmias
DisopyramideIncreased risk of cardiotoxicity and arrhythmias
ErythromycinIncreased risk of cardiotoxicity and arrhythmias
FluphenazineIncreased risk of cardiotoxicity and arrhythmias
IronFormation of non-absorbable complexes
Iron DextranFormation of non-absorbable complexes
JosamycinIncreased risk of cardiotoxicity and arrhythmias
LumefantrineAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
MagnesiumFormation of non-absorbable complexes
Magnesium oxideFormation of non-absorbable complexes
MesoridazineIncreased risk of cardiotoxicity and arrhythmias
MethotrimeprazineIncreased risk of cardiotoxicity and arrhythmias
PerphenazineIncreased risk of cardiotoxicity and arrhythmias
ProcainamideLevofloxacin may increase the effect of procainamide.
ProchlorperazineIncreased risk of cardiotoxicity and arrhythmias
PromazineIncreased risk of cardiotoxicity and arrhythmias
PromethazineIncreased risk of cardiotoxicity and arrhythmias
PropiomazineIncreased risk of cardiotoxicity and arrhythmias
QuinidineIncreased risk of cardiotoxicity and arrhythmias
Quinidine barbiturateIncreased risk of cardiotoxicity and arrhythmias
QuinupristinThis combination presents an increased risk of toxicity
SotalolIncreased risk of cardiotoxicity and arrhythmias
SucralfateFormation of non-absorbable complexes
TacrolimusAdditive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
ThiethylperazineIncreased risk of cardiotoxicity and arrhythmias
ThioridazineIncreased risk of cardiotoxicity and arrhythmias
ThiothixeneMay cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
ToremifeneAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
TrifluoperazineIncreased risk of cardiotoxicity and arrhythmias
TriflupromazineIncreased risk of cardiotoxicity and arrhythmias
TrimipramineAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
VoriconazoleAdditive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
VorinostatAdditive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
WarfarinThe quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of warfarin.
ZincFormation of non-absorbable complexes
ZiprasidoneAdditive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
ZuclopenthixolAdditive 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.

Targets

1. DNA gyrase subunit A

Kind: protein

Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
DNA gyrase subunit A P43700 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Schmitz FJ, Hofmann B, Hansen B, Scheuring S, Luckefahr M, Klootwijk M, Verhoef J, Fluit A, Heinz HP, Kohrer K, Jones ME: Relationship between ciprofloxacin, ofloxacin, levofloxacin, sparfloxacin and moxifloxacin (BAY 12-8039) MICs and mutations in grlA, grlB, gyrA and gyrB in 116 unrelated clinical isolates of Staphylococcus aureus. J Antimicrob Chemother. 1998 Apr;41(4):481-4. Pubmed
  4. Brisse S, Milatovic D, Fluit AC, Verhoef J, Martin N, Scheuring S, Kohrer K, Schmitz FJ: Comparative in vitro activities of ciprofloxacin, clinafloxacin, gatifloxacin, levofloxacin, moxifloxacin, and trovafloxacin against Klebsiella pneumoniae, Klebsiella oxytoca, Enterobacter cloacae, and Enterobacter aerogenes clinical isolates with alterations in GyrA and ParC proteins. Antimicrob Agents Chemother. 1999 Aug;43(8):2051-5. Pubmed
  5. Messina C, Cafiso V, Campanile F, Santagati M, Stefani S: Rapid method for detection of gyrA and grlA mutations in unrelated strains of Staphylococci susceptible and resistant to levofloxacin. New Microbiol. 2001 Oct;24(4):347-53. Pubmed

2. DNA topoisomerase 4 subunit A

Kind: protein

Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
DNA topoisomerase 4 subunit A P43702 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Zheng X, Johnson C, Lu Y, Yanagihara R, Hollingshead S, Crain M, Benjamin W Jr, Waites KB: Clinical isolates of Streptococcus pneumoniae resistant to levofloxacin contain mutations in both gyrA and parC genes. Int J Antimicrob Agents. 2001 Oct;18(4):373-8. Pubmed
  4. Schafer J, Hovde LB, Simonson D, Rotschafer JC: In vitro pharmacodynamics of moxifloxacin versus levofloxacin against 4 strains of Streptococcus pneumoniae: 1 wild type, 2 first-step parC mutants, and 1 pump mutant. Diagn Microbiol Infect Dis. 2007 Oct 1;. Pubmed
  5. Deryke CA, Du X, Nicolau DP: Evaluation of bacterial kill when modelling the bronchopulmonary pharmacokinetic profile of moxifloxacin and levofloxacin against parC-containing isolates of Streptococcus pneumoniae. J Antimicrob Chemother. 2006 Sep;58(3):601-9. Epub 2006 Jul 19. Pubmed

3. DNA topoisomerase 2-alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
DNA topoisomerase 2-alpha P11388 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Bellon A, Perez-Garcia G, Coverdale JH, Chacko RC: Seizures associated with levofloxacin: case presentation and literature review. Eur J Clin Pharmacol. 2009 Oct;65(10):959-62. Epub 2009 Aug 26. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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. Pubmed
  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. Pubmed
  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. Pubmed

2. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Uwai Y, Okuda M, Takami K, Hashimoto Y, Inui K: Functional characterization of the rat multispecific organic anion transporter OAT1 mediating basolateral uptake of anionic drugs in the kidney. FEBS Lett. 1998 Nov 6;438(3):321-4. Pubmed

3. Solute carrier family 22 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 2 O15244 Details

References:

  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. Pubmed
  2. Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. Pubmed

4. Solute carrier family 22 member 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 4 Q9H015 Details

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. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13