Identification

Name
Levofloxacin
Accession Number
DB01137  (APRD00477, DB06085)
Type
Small Molecule
Groups
Approved, Investigational
Description

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

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Levofloxacin hemihydrate6GNT3Y5LMF138199-71-0SUIQUYDRLGGZOL-RCWTXCDDSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act LevofloxacinTablet500 mgOralTeva2009-06-24Not applicableCanada
Act LevofloxacinTablet750 mgOralTeva2009-06-24Not applicableCanada
Act LevofloxacinTablet250 mgOralTeva2009-06-24Not applicableCanada
IquixSolution15 mg/1mLOphthalmicVistakon Pharmaceuticals2004-06-012017-04-13Us
LevaquinTablet, film coated500 mg/1OralRebel Distributors1996-12-20Not applicableUs
LevaquinTablet, film coated500 mg/1OralJanssen Pharmaceuticals, Inc.1996-12-202020-05-31Us
LevaquinTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.1996-12-20Not applicableUs
LevaquinInjection, solution5 mg/1mLIntravenousOrtho-McNeil-Janssen Pharmaceuticals Inc.1996-12-202009-07-27Us
LevaquinTablet, film coated750 mg/1OralMcNeil Pharmaceuticals1996-12-202012-03-31Us
LevaquinInjection, solution5 mg/1mLIntravenousMcNeil Pharmaceuticals1996-12-202011-12-31Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-levofloxacinTablet250 mgOralApotex Corporation2009-06-24Not applicableCanada
Apo-levofloxacinTablet500 mgOralApotex Corporation2009-06-24Not applicableCanada
Apo-levofloxacinTablet750 mgOralApotex Corporation2009-06-24Not applicableCanada
Auro-levofloxacinTablet500 mgOralAuro Pharma Inc2016-04-12Not applicableCanada
Auro-levofloxacinTablet250 mgOralAuro Pharma Inc2016-04-12Not applicableCanada
Auro-levofloxacinTablet750 mgOralAuro Pharma Inc2016-04-12Not applicableCanada
Ava-levofloxacinTablet250 mgOralAvanstra Inc2011-09-152014-08-21Canada
Ava-levofloxacinTablet500 mgOralAvanstra Inc2011-09-152014-08-21Canada
Dom-levofloxacinTablet250 mgOralDominion PharmacalNot applicableNot applicableCanada
Dom-levofloxacinTablet750 mgOralDominion PharmacalNot applicableNot applicableCanada
International/Other Brands
Cravit / Elequine / Floxel / Leroxacin / Levokacin / Levox / Levoxacin / Mosardal / Nofaxin / Reskuin / Tavanic
Categories
UNII
RIX4E89Y14
CAS number
100986-85-4
Weight
Average: 361.3675
Monoisotopic: 361.143784348
Chemical Formula
C18H20FN3O4
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[7.3.1.0⁵,¹³]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

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.

Associated Conditions
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.

TargetActionsOrganism
ADNA topoisomerase 4 subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA gyrase subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA topoisomerase 2-alpha
inhibitor
Human
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, 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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Levofloxacin.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Levofloxacin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Levofloxacin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Levofloxacin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Levofloxacin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Levofloxacin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Levofloxacin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Levofloxacin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Levofloxacin.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Levofloxacin.
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.

References

Synthesis Reference

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

US20030130507
General References
Not Available
External Links
Human Metabolome Database
HMDB0001929
KEGG Drug
D08120
KEGG Compound
C07660
PubChem Compound
149096
PubChem Substance
46505134
ChemSpider
131410
BindingDB
50366826
ChEBI
63598
ChEMBL
CHEMBL33
Therapeutic Targets Database
DAP000160
PharmGKB
PA450214
HET
LFX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Levofloxacin
ATC Codes
J01RA05 — Levofloxacin and ornidazoleA02BD10 — Lansoprazole, amoxicillin and levofloxacinS01AE05 — LevofloxacinJ01MA12 — Levofloxacin
AHFS Codes
  • 08:12.18 — Quinolones
PDB Entries
3k9f / 3rae / 4juo / 4z2d / 5btg / 5bti / 5eix
FDA label
Download (139 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingPreventionComplications of Surgical Procedures1
0RecruitingTreatmentOsteomyelitis1
1CompletedDiagnosticLung Function / Sarcoidosis, Pulmonary1
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedPreventionChronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentCystic Fibrosis (CF)2
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers / The Focus of This Study Was to Assess the Effect of Food Following a Single Oral Dose of Levofloxacin Solution1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
1CompletedTreatmentKidney Diseases1
1RecruitingTreatmentConjunctivitis / Conjunctivitis, Bacterial1
1TerminatedNot AvailableEscherichia Coli Infections1
1TerminatedTreatmentUrinary Bladder, Overactive1
1, 2CompletedTreatmentMulti-Drug Resistant Tuberculosis / Tuberculosis Infection1
1, 2RecruitingTreatmentTuberculous Meningitis1
1, 2Unknown StatusTreatmentCorneal Diseases / Hypermetropia / Myopia / Pterygium1
2Active Not RecruitingTreatmentTuberculosis, Multidrug Resistant1
2CompletedNot AvailableHealthy Volunteers1
2CompletedTreatmentAcute Pyelonephritis / Complicated Urinary Tract Infections1
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
2CompletedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP)1
2CompletedTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentDiabetic Foot Ulcers (DFU)2
2CompletedTreatmentFoot Ulcer, Diabetic1
2Not Yet RecruitingTreatmentAppendicitis Acute1
2RecruitingOtherCataracts1
2RecruitingSupportive CareStem Cell Transplant Complications1
2RecruitingTreatmentAcute Pyelonephritis1
2RecruitingTreatmentChronic Bacterial Prostatitis1
2RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)2
2RecruitingTreatmentSarcoidosis; Antimycobacterial Therapy1
2RecruitingTreatmentTuberculosis, Multidrug Resistant1
2TerminatedTreatmentCommunity Acquired Pneumonia (CAP)1
2TerminatedTreatmentInfected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee1
2TerminatedTreatmentMalignancies / Non-Hodgkin's Lymphoma (NHL)1
2, 3CompletedTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease1
2, 3CompletedTreatmentBronchitis / Chronic Bronchitis1
2, 3CompletedTreatmentCellulitis / Skin Diseases, Infectious1
2, 3CompletedTreatmentPneumonia1
2, 3Not Yet RecruitingTreatmentPulmonary Tuberculosis (TB)1
2, 3RecruitingTreatmentExtensively Drug Resistant Tuberculosis / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
2, 3Unknown StatusPreventionAllogeneic Stem Cell Transplantation / Malignancies1
3CompletedNot AvailableProstatic Hyperplasia / Prostatitis1
3CompletedPreventionCataract operation1
3CompletedSupportive CareAcute Leukemias of Ambiguous Lineage / Bacterial Infections / Infections, Fungal / Musculoskeletal Complications / Neutropenias / Recurrent Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Severe or persistent diarrhea / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies1
3CompletedSupportive CareBrain and Central Nervous System Tumors / Cancer of the Ovary / Cancer, Breast / Extragonadal Germ Cell Tumor / Infection NOS / Lung Cancers / Malignant Lymphomas / Small Intestine Cancer / Testicular germ cell tumour / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedTreatmentAcute Lower Urinary Tract Infection1
3CompletedTreatmentAcute Pyelonephritis / Complicated Urinary Tract Infections1
3CompletedTreatmentAcute Pyelonephritis / Urinary Tract Infection Complicated1
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
3CompletedTreatmentBacterial Infections / Bacteriuria / Urinary Tract Infections (UTIs) / Urologic Diseases1
3CompletedTreatmentBacteriuria / Neurogenic Bladder Dysfunction / Pyelonephritis / Urinary Tract Infections (UTIs) / Urologic Diseases1
3CompletedTreatmentChronic Bronchitis2
3CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
3CompletedTreatmentCommunity-Acquired Infections / Cross Infection / Pneumonia, Bacterial1
3CompletedTreatmentComplicated Urinary Tract Infections1
3CompletedTreatmentComplicated Urinary Tract Infections (cUTIs) / CUTI1
3CompletedTreatmentComplicated Urinary Tract Infections / Pyelonephritis1
3CompletedTreatmentCystic Fibrosis (CF)2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3CompletedTreatmentMaxillary Sinusitis2
3CompletedTreatmentMaxillary Sinusitis / Sinusitis1
3CompletedTreatmentOtitis Media (OM)2
3CompletedTreatmentPelvic Inflammatory Disease (PID)1
3CompletedTreatmentPneumonia6
3CompletedTreatmentPneumonia, Bacterial1
3CompletedTreatmentProstatitis3
3CompletedTreatmentPyelonephritis / Urinary Tract Infections (UTIs)1
3CompletedTreatmentSinusitis1
3CompletedTreatmentSkin Diseases, Bacterial1
3CompletedTreatmentSkin Diseases, Infectious1
3CompletedTreatmentHospital-acquired bacterial pneumonia1
3Not Yet RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
3RecruitingPreventionChronic Systolic Heart Failure / Complete atrioventricular heart block / Sick Sinus Syndrome / Syncope1
3RecruitingPreventionLeukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndromes1
3RecruitingPreventionPrevention1
3RecruitingSupportive CareChronic Rhinosinusitis / Chronic Sinusitis - Ethmoidal Anterior / Chronic Sinusitis - Ethmoidal, Posterior / Chronic Sinusitis - Frontoethmoidal / Chronic Sinusitis, Ethmoidal / Chronic Sinusitis, Sphenoidal / Nasal Polyp - Posterior / Polyps, Nasal1
3RecruitingTreatmentChronic Rhinosinusitis1
3RecruitingTreatmentHelicobacter-associated Gastritis1
3RecruitingTreatmentIndigestion1
3RecruitingTreatmentInfective Endocarditis1
3RecruitingTreatmentKeratitis; Infectious Disease (Manifestation)1
3RecruitingTreatmentMulti-Drug Resistant Tuberculosis1
3RecruitingTreatmentTuberculosis, Multidrug Resistant1
3TerminatedTreatmentInfection NOS1
3TerminatedTreatmentInfection in Solid Organ Transplant Recipients / Latent Tuberculosis Infection (LTI)1
3TerminatedTreatmentStaphylococcus1
3TerminatedTreatmentTuberculosis Infection1
3Unknown StatusSupportive CareFever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Malignant Lymphomas / Neutropenias / Unspecified Adult Solid Tumor, Protocol Specific1
3Unknown StatusTreatmentAcute Exacerbation of Chronic Bronchitis (AECB)1
3WithdrawnTreatmentTuberculosis Multi Drug Resistant Active1
4Active Not RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4CompletedNot AvailableBacteremia / Endocarditis / Sepsis / Staphylococcus Aureus1
4CompletedNot AvailableHelicobacter Infections1
4CompletedBasic ScienceCataracts1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedPreventionDisease Due to BK Polyomavirus / Kidney Transplant Infection1
4CompletedTreatmentAcute Bacterial Sinusitis (ABS)1
4CompletedTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease2
4CompletedTreatmentBK Viremia1
4CompletedTreatmentBMI >30 kg/m2 / Critical Illness1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
4CompletedTreatmentCataract Extraction1
4CompletedTreatmentCataracts1
4CompletedTreatmentCataracts / Dry Eye Syndromes1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP) / Intensive Care Unit Syndrome1
4CompletedTreatmentCommunity-acquired / Pneumonia, Bacterial1
4CompletedTreatmentCure Rate of Helicobacter Pylori Infection1
4CompletedTreatmentFevers / Urinary Tract Infections (UTIs)1
4CompletedTreatmentFunctional Dyspepsia / Peptic Ulcers1
4CompletedTreatmentHelicobacter Infections1
4CompletedTreatmentPneumonia1
4CompletedTreatmentPulmonary Tuberculosis (TB)1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Triple Therapy1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4Not Yet RecruitingTreatmentUrinary Tract Infection Lower Acute1
4RecruitingPreventionProstate Cancer1
4RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4RecruitingTreatmentBacillus Calmette-Guerin (BCG) Cystitis / Intra-vesical Instillation / Non-Muscle-invasive Bladder Cancer (NMIBC)1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4RecruitingTreatmentCholangitis1
4RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingTreatmentMycoplasma Pneumoniae Pneumonia1
4RecruitingTreatmentPulmonary Tuberculosis (TB)1
4RecruitingTreatmentUrinary Tract Infections (UTIs)2
4TerminatedBasic ScienceTransplantation, Corneal1
4TerminatedTreatmentAcute Uncomplicated Pyelonephritis1
4TerminatedTreatmentAppendicitis1
4TerminatedTreatmentComplicated Urinary Infection1
4TerminatedTreatmentPneumonia, Pneumococcal1
4Unknown StatusTreatmentCommunity Acquired Pneumonia (CAP)1
4Unknown StatusTreatmentEradication Rate for Helicobacter1
4Unknown StatusTreatmentUrinary Tract Infections (UTIs)1
4WithdrawnTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
Not AvailableActive Not RecruitingOtherAnti-Bacterial Agents / Microbiota1
Not AvailableCompletedNot AvailableAcute maxillary sinusitis caused by M. catarrhalis1
Not AvailableCompletedNot AvailableEnd Stage Renal Disease (ESRD) / Infection NOS1
Not AvailableCompletedPreventionEndophthalmitis1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableCompletedTreatmentGastritis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
Not AvailableCompletedTreatmentOsteoarticular Infections1
Not AvailableEnrolling by InvitationTreatmentAppendicitis Acute1
Not AvailableNot Yet RecruitingTreatmentAntibiotics / Infection NOS / Percutaneous Nephrolithotomy / Sepsis1
Not AvailableRecruitingNot AvailableTuberculosis Infection1
Not AvailableRecruitingTreatmentAppendicitis Acute1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
Not AvailableRecruitingTreatmentBronchiectasis1
Not AvailableRecruitingTreatmentProsthetic Joint Infection1
Not AvailableTerminatedTreatmentAcute Watery Diarrhea / Dysentery/Febrile Diarrhea1
Not AvailableUnknown StatusNot AvailableAsymptomatic Infections / Bacteriuria / Transplantation Infection / Urinary Tract Infections (UTIs)1
Not AvailableUnknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1

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
SolutionOphthalmic15 mg/1mL
Injection, solutionIntravenous5 mg/1mL
Injection, solution, concentrateIntravenous25 mg/1mL
SolutionOral25 mg/1mL
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral750 mg/1
SolutionIntravenous25 mg
SolutionIntravenous5 mg
InjectionIntravenous25 mg/1mL
InjectionIntravenous5 mg/1mL
Injection, solutionIntravenous25 mg/1mL
Injection, solutionIntravenous250 mg/50mL
Injection, solutionIntravenous500 mg/100mL
Injection, solutionIntravenous750 mg/150mL
Injection, solutionIntravenous750 mg/200mL
Injection, solution, concentrateIntravenous500 mg/20mL
Injection, solution, concentrateIntravenous750 mg/30mL
Solution / dropsOphthalmic5 mg/1mL
Solution / dropsTopical5 mg/1mL
TabletOral250 mg/1
TabletOral500 mg/1
TabletOral750 mg/1
TabletOral250 mg
TabletOral500 mg
SolutionRespiratory (inhalation)240 mg
SolutionOphthalmic5 mg/1mL
TabletOral750 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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5053407No1991-10-012010-12-20Us
US6806256Yes2004-10-192022-08-26Us

Properties

State
Solid
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 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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Benzoxazine / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolone antibiotic, fluoroquinolone antibiotic, ofloxacin (CHEBI:63598)

Targets

Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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:17016423]
  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:11691571]
  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. 2008 Feb;60(2):155-61. Epub 2007 Oct 29. [PubMed:17910998]
  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:16857688]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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:17016423]
  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:9598779]
  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:10428935]
  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:11718372]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
Gene Name
TOP2A
Uniprot ID
P11388
Uniprot Name
DNA topoisomerase 2-alpha
Molecular Weight
174383.88 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
This drug is a fluoroquinolone, and these agents are known to inhibit CYP1A2.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
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. doi: 10.1007/s00228-009-0717-5. Epub 2009 Aug 26. [PubMed:19707748]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Shahzadi A, Javed I, Aslam B, Muhammad F, Asi MR, Ashraf MY, Zia-ur-Rahman: Therapeutic effects of ciprofloxacin on the pharmacokinetics of carbamazepine in healthy adult male volunteers. Pak J Pharm Sci. 2011 Jan;24(1):63-8. [PubMed:21190921]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-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 performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Nakamura H, Ohtsuka T, Enomoto H, Hasegawa A, Kawana H, Kuriyama T, Ohmori S, Kitada M: Effect of levofloxacin on theophylline clearance during theophylline and clarithromycin combination therapy. Ann Pharmacother. 2001 Jun;35(6):691-3. doi: 10.1345/aph.10307. [PubMed:11408986]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:9262363]
  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:10992002]
  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:15032316]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
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:9827570]
Kind
Protein
Organism
Human
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. 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:12089365]
  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:10082798]
Kind
Protein
Organism
Human
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. [PubMed:10215651]
Kind
Protein
Organism
Human
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. 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. [PubMed:17509534]
  2. 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. [PubMed:22970772]
  3. 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. [PubMed:19004926]
Kind
Protein
Organism
Human
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. [PubMed:17509534]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 05:46