Identification

Name
Ofloxacin
Accession Number
DB01165  (APRD00502)
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • 8-Fluoro-3-methyl-9-(4-methyl-piperazin-1-yl)-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid
  • Ofloxacine
  • Ofloxacino
  • Ofloxacinum
  • OFLX
External IDs
DL-8280 / HOE 280 / HOE-280
Product Ingredients
IngredientUNIICASInChI Key
Ofloxacin hydrochlorideI2UWV315WA118120-51-7CAOOISJXWZMLBN-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Floxin I.V. Liq 20mg/mlLiquid20 mgIntravenousOrtho Pharmaceutical, Division Of Janssen Ortho Inc.Not applicableNot applicableCanada
Floxin Tablets 200mgTablet200 mgOralJanssen Pharmaceuticals1992-12-312002-07-31Canada
Floxin Tablets 300mgTablet300 mgOralJanssen Pharmaceuticals1990-12-312006-12-21Canada
Floxin Tablets 400mgTablet400 mgOralJanssen Pharmaceuticals1990-12-312007-01-10Canada
Novo-ofloxacinTablet400 mgOralNovopharm Limited2004-06-112012-05-08Canada
Novo-ofloxacinTablet200 mgOralNovopharm Limited2004-06-112012-05-08Canada
Novo-ofloxacinTablet300 mgOralNovopharm Limited2004-06-112012-05-08Canada
OcufloxSolution0.3 %OphthalmicAllergan1995-12-31Not applicableCanada
OcufloxSolution / drops3 mg/mLOphthalmicAllergan1993-08-01Not applicableUs
Ofloxacin TabletsTablet200 mgOralAa Pharma Inc1998-02-042016-08-02Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ofloxacinSolution0.3 %OphthalmicApotex Corporation2004-01-22Not applicableCanada
Floxin OticSolution / drops3 mg/mLAuricular (otic)ALMATICA PHARMA INC.2016-07-252017-02-14Us
OfloxacinSolution3 mg/mLOphthalmicRemedy Repack2016-10-112017-02-25Us
OfloxacinSolution / drops3 mg/mLOphthalmicRemedy Repack2014-02-262017-11-17Us
OfloxacinSolution3 mg/mLAuricular (otic)A S Medication Solutions2008-03-312017-06-20Us
OfloxacinSolution / drops3 mg/mLOphthalmicPreferreed Pharmaceuticals Inc.2013-05-14Not applicableUs
OfloxacinSolution3 mg/mLAuricular (otic)Aidarex Pharmaceuticals LLC2008-03-17Not applicableUs
OfloxacinTablet, film coated400 mg/1OralCadila Pharnmaceuticals2015-12-29Not applicableUs
OfloxacinSolution / drops3 mg/mLOphthalmicRebel Distributors2004-05-14Not applicableUs
OfloxacinSolution / drops3 mg/mLAuricular (otic)Physicians Total Care, Inc.2009-05-21Not applicableUs
International/Other Brands
Floxin / Floxstat / Zanocin
Categories
UNII
A4P49JAZ9H
CAS number
82419-36-1
Weight
Average: 361.3675
Monoisotopic: 361.143784348
Chemical Formula
C18H20FN3O4
InChI Key
GSDSWSVVBLHKDQ-UHFFFAOYSA-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)
IUPAC Name
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
CC1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1

Pharmacology

Indication

For the treatment of infections (respiratory tract, kidney, skin, soft tissue, UTI), urethral and cervical gonorrhoea.

Structured Indications
Pharmacodynamics

Ofloxacin is a quinolone/fluoroquinolone antibiotic. Ofloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Ofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.

Mechanism of action

Ofloxacin acts on DNA gyrase and toposiomerase IV, enzymes which, like human topoisomerase, prevents the excessive supercoiling of DNA during replication or transcription. By inhibiting their function, the drug thereby inhibits normal cell division.

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)
UDNA topoisomerase 2-alpha
inhibitor
Human
Absorption

Bioavailability of ofloxacin in the tablet formulation is approximately 98%

Volume of distribution
Not Available
Protein binding

32%

Metabolism

Hepatic

Route of elimination

Elimination is mainly by renal excretion. Between 65% and 80% of an administered oral dose of ofloxacin is excreted unchanged via the kidneys within 48 hours of dosing. Four to eight percent of an ofloxacin dose is excreted in the feces. This indicates a small degree of biliary excretion of ofloxacin.

Half life

9 hours

Clearance
Not Available
Toxicity

LD50=5450 mg/kg (orally in mice)

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Ofloxacin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Ofloxacin.Experimental
AlfuzosinAlfuzosin may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
AmantadineAmantadine may increase the QTc-prolonging activities of Ofloxacin.Approved
AmiodaroneOfloxacin may increase the QTc-prolonging activities of Amiodarone.Approved, Investigational
AmitriptylineAmitriptyline may increase the QTc-prolonging activities of Ofloxacin.Approved
AmoxapineAmoxapine may increase the QTc-prolonging activities of Ofloxacin.Approved
AnagrelideOfloxacin may increase the QTc-prolonging activities of Anagrelide.Approved
ApomorphineApomorphine may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
ArformoterolArformoterol may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
AripiprazoleAripiprazole may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
Arsenic trioxideOfloxacin may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherOfloxacin may increase the QTc-prolonging activities of Artemether.Approved
AsenapineOfloxacin may increase the QTc-prolonging activities of Asenapine.Approved
AtazanavirAtazanavir may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
AtomoxetineAtomoxetine may increase the QTc-prolonging activities of Ofloxacin.Approved
AzithromycinAzithromycin may increase the QTc-prolonging activities of Ofloxacin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Ofloxacin.Investigational
BedaquilineOfloxacin may increase the QTc-prolonging activities of Bedaquiline.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Ofloxacin.Approved, Investigational
BortezomibBortezomib may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
BuserelinBuserelin may increase the QTc-prolonging activities of Ofloxacin.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Ofloxacin.Approved
CeritinibOfloxacin may increase the QTc-prolonging activities of Ceritinib.Approved
ChloroquineChloroquine may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
ChlorpromazineChlorpromazine may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
CiprofloxacinCiprofloxacin may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
CisaprideOfloxacin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramOfloxacin may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinOfloxacin may increase the QTc-prolonging activities of Clarithromycin.Approved
ClomipramineClomipramine may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
ClozapineClozapine may increase the QTc-prolonging activities of Ofloxacin.Approved
CrizotinibOfloxacin may increase the QTc-prolonging activities of Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Ofloxacin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Ofloxacin.Experimental
DabrafenibDabrafenib may increase the QTc-prolonging activities of Ofloxacin.Approved
DasatinibDasatinib may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
DegarelixDegarelix may increase the QTc-prolonging activities of Ofloxacin.Approved
DesfluraneDesflurane may increase the QTc-prolonging activities of Ofloxacin.Approved
DesipramineDesipramine may increase the QTc-prolonging activities of Ofloxacin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Ofloxacin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Ofloxacin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Ofloxacin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Ofloxacin.Approved
DiphenhydramineDiphenhydramine may increase the QTc-prolonging activities of Ofloxacin.Approved
DisopyramideOfloxacin may increase the QTc-prolonging activities of Disopyramide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Ofloxacin.Approved, Investigational
DofetilideOfloxacin may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronDolasetron may increase the QTc-prolonging activities of Ofloxacin.Approved
DomperidoneOfloxacin may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DoxepinDoxepin may increase the QTc-prolonging activities of Ofloxacin.Approved
DronedaroneOfloxacin may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolDroperidol may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
EliglustatOfloxacin may increase the QTc-prolonging activities of Eliglustat.Approved
EribulinEribulin may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
ErythromycinErythromycin may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
EscitalopramOfloxacin may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
EzogabineEzogabine may increase the QTc-prolonging activities of Ofloxacin.Approved
FamotidineFamotidine may increase the QTc-prolonging activities of Ofloxacin.Approved
FelbamateFelbamate may increase the QTc-prolonging activities of Ofloxacin.Approved
FingolimodFingolimod may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
FlecainideOfloxacin may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FluconazoleFluconazole may increase the QTc-prolonging activities of Ofloxacin.Approved
FluoxetineOfloxacin may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolOfloxacin may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FormoterolFormoterol may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
FoscarnetFoscarnet may increase the QTc-prolonging activities of Ofloxacin.Approved
Gadobenic acidGadobenic acid may increase the QTc-prolonging activities of Ofloxacin.Approved
GalantamineGalantamine may increase the QTc-prolonging activities of Ofloxacin.Approved
GemifloxacinGemifloxacin may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Ofloxacin.Experimental
GoserelinGoserelin may increase the QTc-prolonging activities of Ofloxacin.Approved
GranisetronGranisetron may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
HaloperidolHaloperidol may increase the QTc-prolonging activities of Ofloxacin.Approved
HistrelinHistrelin may increase the QTc-prolonging activities of Ofloxacin.Approved
HydroxyzineHydroxyzine may increase the QTc-prolonging activities of Ofloxacin.Approved
IbandronateIbandronate may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
IbutilideOfloxacin may increase the QTc-prolonging activities of Ibutilide.Approved
IloperidoneOfloxacin may increase the QTc-prolonging activities of Iloperidone.Approved
ImipramineImipramine may increase the QTc-prolonging activities of Ofloxacin.Approved
IndacaterolIndacaterol may increase the QTc-prolonging activities of Ofloxacin.Approved
IndapamideIndapamide may increase the QTc-prolonging activities of Ofloxacin.Approved
IsofluraneIsoflurane may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
IsradipineIsradipine may increase the QTc-prolonging activities of Ofloxacin.Approved
ItraconazoleItraconazole may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
IvabradineIvabradine may increase the QTc-prolonging activities of Ofloxacin.Approved
KetoconazoleKetoconazole may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Ofloxacin.Experimental
LapatinibLapatinib may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
LenvatinibOfloxacin may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideLeuprolide may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
LevofloxacinLevofloxacin may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
LithiumLithium may increase the QTc-prolonging activities of Ofloxacin.Approved
LopinavirOfloxacin may increase the QTc-prolonging activities of Lopinavir.Approved
LumefantrineOfloxacin may increase the QTc-prolonging activities of Lumefantrine.Approved
MaprotilineMaprotiline may increase the QTc-prolonging activities of Ofloxacin.Approved
MefloquineMefloquine may increase the QTc-prolonging activities of Ofloxacin.Approved
MethadoneMethadone may increase the QTc-prolonging activities of Ofloxacin.Approved
MethotrimeprazineMethotrimeprazine may increase the QTc-prolonging activities of Ofloxacin.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Ofloxacin.Experimental
MetoclopramideMetoclopramide may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
MetronidazoleMetronidazole may increase the QTc-prolonging activities of Ofloxacin.Approved
MifepristoneMifepristone may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
MirabegronMirabegron may increase the QTc-prolonging activities of Ofloxacin.Approved
MirtazapineMirtazapine may increase the QTc-prolonging activities of Ofloxacin.Approved
MoexiprilMoexipril may increase the QTc-prolonging activities of Ofloxacin.Approved
MoxifloxacinMoxifloxacin may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
NelfinavirNelfinavir may increase the QTc-prolonging activities of Ofloxacin.Approved
NicardipineNicardipine may increase the QTc-prolonging activities of Ofloxacin.Approved
NilotinibOfloxacin may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NorfloxacinNorfloxacin may increase the QTc-prolonging activities of Ofloxacin.Approved
NortriptylineNortriptyline may increase the QTc-prolonging activities of Ofloxacin.Approved
OctreotideOctreotide may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
OlanzapineOlanzapine may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Ofloxacin.Experimental, Investigational
OlodaterolOlodaterol may increase the QTc-prolonging activities of Ofloxacin.Approved
OndansetronOndansetron may increase the QTc-prolonging activities of Ofloxacin.Approved
OuabainOuabain may decrease the cardiotoxic activities of Ofloxacin.Approved
OxytocinOxytocin may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Ofloxacin.Approved, Vet Approved
PaliperidoneOfloxacin may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatOfloxacin may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
ParoxetineParoxetine may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
PasireotidePasireotide may increase the QTc-prolonging activities of Ofloxacin.Approved
PazopanibOfloxacin may increase the QTc-prolonging activities of Pazopanib.Approved
PentamidinePentamidine may increase the QTc-prolonging activities of Ofloxacin.Approved
PerflutrenPerflutren may increase the QTc-prolonging activities of Ofloxacin.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Ofloxacin.Experimental
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Ofloxacin.Approved
PimozideOfloxacin may increase the QTc-prolonging activities of Pimozide.Approved
PosaconazolePosaconazole may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational, Vet Approved
PrimaquinePrimaquine may increase the QTc-prolonging activities of Ofloxacin.Approved
ProcainamideOfloxacin may increase the QTc-prolonging activities of Procainamide.Approved
PromazinePromazine may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
PromethazinePromethazine may increase the QTc-prolonging activities of Ofloxacin.Approved
PropafenoneOfloxacin may increase the QTc-prolonging activities of Propafenone.Approved
PropofolPropofol may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Ofloxacin.Experimental
ProtriptylineProtriptyline may increase the QTc-prolonging activities of Ofloxacin.Approved
QuetiapineOfloxacin may increase the QTc-prolonging activities of Quetiapine.Approved
QuinidineOfloxacin may increase the QTc-prolonging activities of Quinidine.Approved
QuinineOfloxacin may increase the QTc-prolonging activities of Quinine.Approved
RanolazineRanolazine may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
RilpivirineRilpivirine may increase the QTc-prolonging activities of Ofloxacin.Approved
RisperidoneRisperidone may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
RitonavirRitonavir may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
SalbutamolSalbutamol may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
SalmeterolSalmeterol may increase the QTc-prolonging activities of Ofloxacin.Approved
SaquinavirOfloxacin may increase the QTc-prolonging activities of Saquinavir.Approved, Investigational
SertralineSertraline may increase the QTc-prolonging activities of Ofloxacin.Approved
SevofluraneSevoflurane may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
SolifenacinSolifenacin may increase the QTc-prolonging activities of Ofloxacin.Approved
SorafenibSorafenib may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
SotalolOfloxacin may increase the QTc-prolonging activities of Sotalol.Approved
SulfamethoxazoleSulfamethoxazole may increase the QTc-prolonging activities of Ofloxacin.Approved
SulfisoxazoleSulfisoxazole may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
SunitinibSunitinib may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
TamoxifenTamoxifen may increase the QTc-prolonging activities of Ofloxacin.Approved
TelavancinOfloxacin may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinTelithromycin may increase the QTc-prolonging activities of Ofloxacin.Approved
TerbutalineTerbutaline may increase the QTc-prolonging activities of Ofloxacin.Approved
TetrabenazineOfloxacin may increase the QTc-prolonging activities of Tetrabenazine.Approved
ThioridazineOfloxacin may increase the QTc-prolonging activities of Thioridazine.Approved, Withdrawn
ThiothixeneThiothixene may increase the QTc-prolonging activities of Ofloxacin.Approved
TizanidineTizanidine may increase the QTc-prolonging activities of Ofloxacin.Approved
TolterodineTolterodine may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
ToremifeneOfloxacin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Ofloxacin.Approved, Investigational
TrazodoneTrazodone may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
TreprostinilTreprostinil may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
TrimethoprimTrimethoprim may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
TrimipramineTrimipramine may increase the QTc-prolonging activities of Ofloxacin.Approved
TriptorelinTriptorelin may increase the QTc-prolonging activities of Ofloxacin.Approved, Vet Approved
VandetanibOfloxacin may increase the QTc-prolonging activities of Vandetanib.Approved
VardenafilVardenafil may increase the QTc-prolonging activities of Ofloxacin.Approved
VemurafenibOfloxacin may increase the QTc-prolonging activities of Vemurafenib.Approved
VenlafaxineVenlafaxine may increase the QTc-prolonging activities of Ofloxacin.Approved
VilanterolVilanterol may increase the QTc-prolonging activities of Ofloxacin.Approved
VoriconazoleVoriconazole may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
VorinostatVorinostat may increase the QTc-prolonging activities of Ofloxacin.Approved, Investigational
ZiprasidoneOfloxacin may increase the QTc-prolonging activities of Ziprasidone.Approved
ZuclopenthixolOfloxacin may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
  • Avoid high doses of caffeine.
  • Take without regard to meals.

References

Synthesis Reference
US4382892
General References
Not Available
External Links
Human Metabolome Database
HMDB15296
KEGG Drug
D00453
KEGG Compound
C07321
PubChem Compound
4583
PubChem Substance
46507574
ChemSpider
4422
BindingDB
50045004
ChEBI
7731
ChEMBL
CHEMBL4
Therapeutic Targets Database
DAP000655
PharmGKB
PA450684
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ofloxacin
ATC Codes
J01MA01 — OfloxacinS02AA16 — OfloxacinJ01RA09 — Ofloxacin and ornidazoleS01AE01 — Ofloxacin
AHFS Codes
  • 52:04.04 — Antibacterials
  • 08:12.18 — Quinolones
FDA label
Download (198 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1WithdrawnTreatmentHard of Hearing1
2TerminatedTreatmentMinor Intra-uterine Abnormalities1
3CompletedSupportive CareInfection NOS / Multiple Myeloma (MM)1
3CompletedTreatmentAcute Otitis Media1
3CompletedTreatmentConjunctivitis, Bacterial1
3CompletedTreatmentDiabetic Foot Ulcers (DFU)2
3CompletedTreatmentOtitis Media (OM)1
3CompletedTreatmentPelvic Inflammatory Disease (PID)1
3RecruitingTreatmentAcute Male Urinary Tract Infection1
3RecruitingTreatmentKeratitis; Infectious Disease (Manifestation)1
4Active Not RecruitingTreatmentCorneal Transplant / Grafting, Corneal / Keratoplasty, Lamellar / Transplantation, Cornea / Transplantation, Corneal1
4CompletedTreatmentCataracts1
4CompletedTreatmentFevers / Urinary Tract Infections (UTIs)1
4CompletedTreatmentPelvic Inflammatory Disease (PID)1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4Unknown StatusPreventionInfection NOS1
Not AvailableCompletedTreatmentReactive Arthritis1
Not AvailableRecruitingTreatmentMyopia / Refractive Errors1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
LiquidIntravenous20 mg
TabletOral200 mg
TabletOral300 mg
TabletOral400 mg
SolutionOphthalmic0.3 %
SolutionAuricular (otic)3 mg/mL
SolutionOphthalmic3 mg/mL
Solution / dropsAuricular (otic)3 mg/mL
Solution / dropsOphthalmic3 mg/mL
Tablet, coatedOral200 mg/1
Tablet, coatedOral300 mg/1
Tablet, coatedOral400 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral400 mg/1
Prices
Unit descriptionCostUnit
Floxin Otic 0.3% Solution 10ml Bottle142.91USD bottle
Ofloxacin 10ml Otic (ear) Solution132.19USD bottle
Ofloxacin 10ml. Ophthalmic (eye) Solution87.6USD bottle
Floxin Otic 0.3% Solution 5ml Bottle86.49USD bottle
Ofloxacin 5ml Otic (ear) Solution77.21USD bottle
Ofloxacin 5ml. Ophthalmic (eye) Solution43.86USD bottle
Ocuflox 0.3% eye drops11.35USD ml
Floxin 400 mg tablet9.55USD tablet
Ofloxacin 0.3% eye drops8.08USD ml
Floxin 200 mg tablet6.6USD tablet
Ofloxacin 400 mg tablet6.12USD tablet
Ofloxacin 300 mg tablet5.81USD tablet
Floxin 300 mg tablet5.61USD tablet
Ofloxacin 200 mg tablet4.88USD tablet
Floxin otic singles4.28USD each
Ocuflox 0.3 % Solution2.75USD ml
Apo-Ofloxacin 0.3 % Solution1.04USD ml
Pms-Ofloxacin 0.3 % Solution1.04USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5401741No1995-03-272012-03-27Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)254 dec °CPhysProp
water solubility28.3 mg/mLNot Available
logP-0.39HANSCH,C ET AL. (1995)
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
PropertyValueProbability
Human Intestinal Absorption+0.9545
Blood Brain Barrier-0.9659
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.7489
CYP450 2C9 substrateNon-substrate0.8468
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6386
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9268
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7726
Ames testAMES toxic0.7844
CarcinogenicityNon-carcinogens0.9033
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.1639 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8402
hERG inhibition (predictor II)Non-inhibitor0.866
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-066u-4849000000-62a3272bb7a7b0465316
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-044i-4069000000-fc2f3ccfc4622b82671d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0009000000-8ca4d2a7e1305755f3d3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-02t9-0019000000-a2e5b08b64a9acd1d2f8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1093000000-8403d1bb463eb3fb6e3e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1090000000-ee50b73ec2b046ce37ca
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ck9-1490000000-8b09e639f03f4aa7a14a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0adl-1950000000-0c369c959a56510a5ff7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-02t9-0029000000-3b84ed4e6dd24267cf5d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-07r0-1590000000-4be12443c6e428a5b6b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0091000000-a74a0303807ced89f7cc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0cml-0590000000-c08e9fca2077fb0daa17
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0009000000-9046beaae10bda8773cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0009000000-97824faaceab754612c9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0159000000-de443922130ae95667e4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0089-0920000000-16bd425ab62950a6c1f7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1269000000-01b22da2e2e9a9fdbc27
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-2492000000-e0ea454a6ebaa02d7ae9

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
N-arylpiperazine, organic heterotricyclic compound, N-alkylpiperazine, quinolone antibiotic, fluoroquinolone antibiotic, 3-oxo monocarboxylic acid, oxazinoquinoline (CHEBI:7731)

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
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. 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]
  2. Cambau E, Sougakoff W, Besson M, Truffot-Pernot C, Grosset J, Jarlier V: Selection of a gyrA mutant of Mycobacterium tuberculosis resistant to fluoroquinolones during treatment with ofloxacin. J Infect Dis. 1994 Nov;170(5):1351. [PubMed:7963747]
  3. Shi R, Zhang J, Li C, Kazumi Y, Sugawara I: Emergence of ofloxacin resistance in Mycobacterium tuberculosis clinical isolates from China as determined by gyrA mutation analysis using denaturing high-pressure liquid chromatography and DNA sequencing. J Clin Microbiol. 2006 Dec;44(12):4566-8. Epub 2006 Oct 11. [PubMed:17035499]
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. Turner AK, Nair S, Wain J: The acquisition of full fluoroquinolone resistance in Salmonella Typhi by accumulation of point mutations in the topoisomerase targets. J Antimicrob Chemother. 2006 Oct;58(4):733-40. Epub 2006 Aug 8. [PubMed:16895934]
  2. Chau TT, Campbell JI, Galindo CM, Van Minh Hoang N, Diep TS, Nga TT, Van Vinh Chau N, Tuan PQ, Page AL, Ochiai RL, Schultsz C, Wain J, Bhutta ZA, Parry CM, Bhattacharya SK, Dutta S, Agtini M, Dong B, Honghui Y, Anh DD, Canh do G, Naheed A, Albert MJ, Phetsouvanh R, Newton PN, Basnyat B, Arjyal A, La TT, Rang NN, Phuong le T, Van Be Bay P, von Seidlein L, Dougan G, Clemens JD, Vinh H, Hien TT, Chinh NT, Acosta CJ, Farrar J, Dolecek C: Antimicrobial drug resistance of Salmonella enterica serovar typhi in asia and molecular mechanism of reduced susceptibility to the fluoroquinolones. Antimicrob Agents Chemother. 2007 Dec;51(12):4315-23. Epub 2007 Oct 1. [PubMed:17908946]
  3. Ishiguro F, Toho M, Yamazaki M, Matsuyuki S, Moriya K, Tanaka D, Isobe J, Kyota Y, Muraoka M: [Mutations of gyrA gene and parC gene in fluoroquinolone-resistant Escherichia coli isolates from sporadic diarrheal cases]. Kansenshogaku Zasshi. 2006 Sep;80(5):507-12. [PubMed:17073264]
  4. Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [PubMed:9293187]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Divo AA, Sartorelli AC, Patton CL, Bia FJ: Activity of fluoroquinolone antibiotics against Plasmodium falciparum in vitro. Antimicrob Agents Chemother. 1988 Aug;32(8):1182-6. [PubMed:2847647]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. 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]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Terashi K, Oka M, Soda H, Fukuda M, Kawabata S, Nakatomi K, Shiozawa K, Nakamura T, Tsukamoto K, Noguchi Y, Suenaga M, Tei C, Kohno S: Interactions of ofloxacin and erythromycin with the multidrug resistance protein (MRP) in MRP-overexpressing human leukemia cells. Antimicrob Agents Chemother. 2000 Jun;44(6):1697-700. [PubMed:10817732]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Sasabe H, Tsuji A, Sugiyama Y: Carrier-mediated mechanism for the biliary excretion of the quinolone antibiotic grepafloxacin and its glucuronide in rats. J Pharmacol Exp Ther. 1998 Mar;284(3):1033-9. [PubMed:9495864]
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]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33