IDPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomy
Targets (3)Enzymes (6)Transporters (2)
Targets (3)Enzymes (6)Transporters (2)Biointeractions (11)

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Identification
NameNorfloxacin
Accession NumberDB01059  (APRD00469)
TypeSmall Molecule
GroupsApproved
Description

A synthetic fluoroquinolone (fluoroquinolones) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA gyrase. [PubChem]

Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
1-Ethyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsaeure
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
1,4-Dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
NFLX
Norfloxacine
Norfloxacino
Norfloxacinum
External IDs MK-366
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ava-norfloxacinTablet400 mgOralAvanstra Inc2011-11-232014-08-21Canada
Co NorfloxacinTablet400 mgOralCobalt Laboratories2006-07-18Not applicableCanada
NorfloxacinTablet400 mgOralPharmel IncNot applicableNot applicableCanada
NorfloxacinTablet400 mgOralCobalt LaboratoriesNot applicableNot applicableCanada
Norfloxacine-400Tablet400 mgOralPro Doc Limitee1999-08-232010-07-13Canada
NoroxinSolution3 mgOphthalmicMerck Ltd.1990-12-312005-06-18Canada
NoroxinTablet400 mgOralMerck Ltd.1986-12-312005-06-18Canada
Ntp-norfloxacinTablet400 mgOralTevaNot applicableNot applicableCanada
PMS-norfloxacinTablet400 mgOralPharmascience Inc2002-09-26Not applicableCanada
Riva-norfloxacinTablet400 mgOralLaboratoire Riva Inc2008-06-132013-07-31Canada
Riva-norfloxacinTablet400 mgOralLaboratoire Riva Inc2000-01-312013-07-31Canada
Teva-norfloxacinTablet400 mgOralTeva1998-08-20Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-norflox - 400mgTablet400 mgOralApotex Corporation1998-07-20Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ChibroxinNot Available
Brand mixturesNot Available
Categories
UNIIN0F8P22L1P
CAS number70458-96-7
WeightAverage: 319.3308
Monoisotopic: 319.133219662
Chemical FormulaC16H18FN3O3
InChI KeyOGJPXUAPXNRGGI-UHFFFAOYSA-N
InChI
InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
IUPAC Name
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCNCC1
Pharmacology
Indication

For the treatment of urinary tract infection

Structured Indications
Pharmacodynamics

Norfloxacin is a quinolone/fluoroquinolone antibiotic. Norfloxacin 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.

Mechanism of action

The bactericidal action of Norfloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination. Norfloxacin is a broad-spectrum antibiotic that is active against both gram-positive and gram-negative bacterias. The fluorine atom at the 6 position increases potency against gram-negative organisms, and the piperazine moiety at the 7 position is responsible for anti-pseudomonal activity

TargetKindPharmacological actionActionsOrganismUniProt ID
DNA gyrase subunit AProteinyes
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)P43700 details
DNA topoisomerase 4 subunit AProteinyes
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)P43702 details
DNA topoisomerase 2-alphaProteinunknown
inhibitor
HumanP11388 details
Related Articles
Absorption

Rapid

Volume of distributionNot Available
Protein binding

10 and 15% (Serum protein binding)

Metabolism

Via liver and kidney

Route of elimination

Norfloxacin is eliminated through metabolism, biliary excretion, and renal excretion. Renal excretion occurs by both glomerular filtration and tubular secretion as evidenced by the high rate of renal clearance (approximately 275 mL/min).

Half life

3-4 hours

ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Norfloxacin.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Norfloxacin.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Norfloxacin.Experimental, Illicit
AcarboseNorfloxacin may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AceclofenacAceclofenac may increase the neuroexcitatory activities of Norfloxacin.Approved
AcenocoumarolNorfloxacin may increase the anticoagulant activities of Acenocoumarol.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Norfloxacin.Approved
Acetylsalicylic acidAcetylsalicylic acid may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
AdapaleneAdapalene may increase the neuroexcitatory activities of Norfloxacin.Approved
AlbiglutideNorfloxacin may increase the hypoglycemic activities of Albiglutide.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Norfloxacin.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Norfloxacin.Experimental
AlogliptinNorfloxacin may increase the hypoglycemic activities of Alogliptin.Approved
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Ambroxol acefyllinateThe metabolism of Ambroxol acefyllinate can be decreased when combined with Norfloxacin.Experimental
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Norfloxacin.Approved
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Norfloxacin.Approved
AmiodaroneNorfloxacin may increase the QTc-prolonging activities of Amiodarone.Approved, Investigational
AnagrelideNorfloxacin may increase the QTc-prolonging activities of Anagrelide.Approved
AndrographolideHMPL-004 may increase the neuroexcitatory activities of Norfloxacin.Investigational
AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Norfloxacin.Experimental, Illicit
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Norfloxacin.Investigational
AnisodamineAnisodamine may increase the neuroexcitatory activities of Norfloxacin.Investigational
AntipyrineAntipyrine may increase the neuroexcitatory activities of Norfloxacin.Approved
ApocyninAcetovanillone may increase the neuroexcitatory activities of Norfloxacin.Investigational
ApremilastApremilast may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
Arsenic trioxideNorfloxacin may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherNorfloxacin may increase the QTc-prolonging activities of Artemether.Approved
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Norfloxacin resulting in a loss in efficacy.Approved
AsenapineNorfloxacin may increase the QTc-prolonging activities of Asenapine.Approved
AzapropazoneAzapropazone may increase the neuroexcitatory activities of Norfloxacin.Withdrawn
AzelastineAzelastine may increase the neuroexcitatory activities of Norfloxacin.Approved
AzithromycinNorfloxacin may increase the QTc-prolonging activities of Azithromycin.Approved
BalsalazideBalsalazide may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with Norfloxacin.Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Norfloxacin.Approved, Investigational
BedaquilineNorfloxacin may increase the QTc-prolonging activities of Bedaquiline.Approved
BenoxaprofenBenoxaprofen may increase the neuroexcitatory activities of Norfloxacin.Withdrawn
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Norfloxacin.Approved, Vet Approved
Betulinic AcidBetulinic Acid may increase the neuroexcitatory activities of Norfloxacin.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Norfloxacin.Approved, Investigational
Bismuth SubcitrateBismuth Subcitrate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
BromfenacBromfenac may increase the neuroexcitatory activities of Norfloxacin.Approved
BromocriptineNorfloxacin may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BucillamineBucillamine may increase the neuroexcitatory activities of Norfloxacin.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Norfloxacin.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Norfloxacin.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Norfloxacin.Approved
CalciumCalcium can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Nutraceutical
Calcium AcetateCalcium Acetate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium CarbonateCalcium carbonate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium ChlorideCalcium Chloride can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium CitrateCalcium citrate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium glubionateCalcium glubionate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium GluceptateCalcium Gluceptate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium gluconateCalcium gluconate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
CanagliflozinNorfloxacin may increase the hypoglycemic activities of Canagliflozin.Approved
CarprofenCarprofen may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may increase the neuroexcitatory activities of Norfloxacin.Experimental
CelecoxibCelecoxib may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
CeritinibNorfloxacin may increase the QTc-prolonging activities of Ceritinib.Approved
ChloroquineChloroquine may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
ChlorpromazineNorfloxacin may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
ChlorpropamideNorfloxacin may increase the hypoglycemic activities of Chlorpropamide.Approved
Choline magnesium trisalicylateTrisalicylate-choline may increase the neuroexcitatory activities of Norfloxacin.Approved
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Norfloxacin.Approved, Investigational
CiprofloxacinNorfloxacin may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideNorfloxacin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramNorfloxacin may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinNorfloxacin may increase the QTc-prolonging activities of Clarithromycin.Approved
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Norfloxacin.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Norfloxacin.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Norfloxacin.Approved
ClonixinClonixin may increase the neuroexcitatory activities of Norfloxacin.Approved
ClozapineNorfloxacin may increase the QTc-prolonging activities of Clozapine.Approved
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Norfloxacin.Approved
CrizotinibNorfloxacin may increase the QTc-prolonging activities of Crizotinib.Approved
CurcuminCurcumin may increase the neuroexcitatory activities of Norfloxacin.Investigational
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Norfloxacin.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Norfloxacin.Approved, Investigational, Vet Approved
DapagliflozinNorfloxacin may increase the hypoglycemic activities of Dapagliflozin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Norfloxacin.Approved
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Norfloxacin.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Norfloxacin.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Norfloxacin.Approved, Investigational, Vet Approved
DiclofenacDiclofenac may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
DicoumarolNorfloxacin may increase the anticoagulant activities of Dicoumarol.Approved
DidanosineThe serum concentration of Didanosine can be decreased when it is combined with Norfloxacin.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Norfloxacin.Approved
DiflunisalDiflunisal may increase the neuroexcitatory activities of Norfloxacin.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Norfloxacin.Approved
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Norfloxacin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Norfloxacin.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Norfloxacin.Approved
DisopyramideNorfloxacin may increase the QTc-prolonging activities of Disopyramide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Norfloxacin.Approved, Investigational
DofetilideNorfloxacin may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronNorfloxacin may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneNorfloxacin may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DronedaroneNorfloxacin may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolNorfloxacin may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
DroxicamDroxicam may increase the neuroexcitatory activities of Norfloxacin.Approved
DulaglutideNorfloxacin may increase the hypoglycemic activities of Dulaglutide.Approved
DuvelisibDuvelisib may increase the neuroexcitatory activities of Norfloxacin.Investigational
DyphyllineThe metabolism of Dyphylline can be decreased when combined with Norfloxacin.Approved
E-6201E6201 may increase the neuroexcitatory activities of Norfloxacin.Investigational
EbselenEbselen may increase the neuroexcitatory activities of Norfloxacin.Investigational
EliglustatNorfloxacin may increase the QTc-prolonging activities of Eliglustat.Approved
EmpagliflozinNorfloxacin may increase the hypoglycemic activities of Empagliflozin.Approved
EpirizoleEpirizole may increase the neuroexcitatory activities of Norfloxacin.Approved
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Norfloxacin.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Norfloxacin.Approved
ErythromycinNorfloxacin may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramNorfloxacin may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Norfloxacin.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Norfloxacin.Approved
EtanerceptEtanercept may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
Ethyl biscoumacetateNorfloxacin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may increase the neuroexcitatory activities of Norfloxacin.Approved
EtoricoxibEtoricoxib may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
ExenatideNorfloxacin may increase the hypoglycemic activities of Exenatide.Approved, Investigational
FenbufenFenbufen may increase the neuroexcitatory activities of Norfloxacin.Approved
FenoprofenFenoprofen may increase the neuroexcitatory activities of Norfloxacin.Approved
Ferric CarboxymaltoseThe serum concentration of Norfloxacin can be decreased when it is combined with Ferric Carboxymaltose.Approved
Ferric CitrateThe serum concentration of Norfloxacin can be decreased when it is combined with Ferric Citrate.Approved
Ferric pyrophosphateThe serum concentration of Norfloxacin can be decreased when it is combined with Ferric pyrophosphate.Approved
FlecainideNorfloxacin may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FloctafenineFloctafenine may increase the neuroexcitatory activities of Norfloxacin.Approved, Withdrawn
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Norfloxacin.Approved
FluindioneNorfloxacin may increase the anticoagulant activities of Fluindione.Investigational
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Norfloxacin.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Norfloxacin.Approved, Investigational
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Norfloxacin.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Norfloxacin.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Norfloxacin.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Norfloxacin.Approved
FluoxetineNorfloxacin may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolNorfloxacin may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Norfloxacin.Approved, Withdrawn
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Norfloxacin.Approved
FlurbiprofenFlurbiprofen may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Norfloxacin.Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Norfloxacin.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Norfloxacin.Approved, Investigational, Withdrawn
Gadobenic acidNorfloxacin may increase the QTc-prolonging activities of Gadobenic acid.Approved
GemifloxacinNorfloxacin may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GliclazideNorfloxacin may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideNorfloxacin may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideNorfloxacin may increase the hypoglycemic activities of Glipizide.Approved
GlyburideNorfloxacin may increase the hypoglycemic activities of Glyburide.Approved
GoserelinNorfloxacin may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronNorfloxacin may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
HaloperidolNorfloxacin may increase the QTc-prolonging activities of Haloperidol.Approved
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Norfloxacin.Investigational
HigenamineHigenamine may increase the neuroexcitatory activities of Norfloxacin.Investigational
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Norfloxacin.Approved, Vet Approved
IbuprofenIbuprofen may increase the neuroexcitatory activities of Norfloxacin.Approved
IbuproxamIbuproxam may increase the neuroexcitatory activities of Norfloxacin.Withdrawn
IbutilideNorfloxacin may increase the QTc-prolonging activities of Ibutilide.Approved
IcatibantIcatibant may increase the neuroexcitatory activities of Norfloxacin.Approved
IloperidoneNorfloxacin may increase the QTc-prolonging activities of Iloperidone.Approved
IndomethacinIndomethacin may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
IndoprofenIndoprofen may increase the neuroexcitatory activities of Norfloxacin.Withdrawn
Insulin AspartNorfloxacin may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirNorfloxacin may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineNorfloxacin may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineNorfloxacin may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanNorfloxacin may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproNorfloxacin may increase the hypoglycemic activities of Insulin Lispro.Approved
IronThe serum concentration of Norfloxacin can be decreased when it is combined with Iron.Approved
Iron DextranThe serum concentration of Norfloxacin can be decreased when it is combined with Iron Dextran.Approved, Vet Approved
Iron saccharateThe serum concentration of Norfloxacin can be decreased when it is combined with Iron saccharate.Approved
IsoxicamIsoxicam may increase the neuroexcitatory activities of Norfloxacin.Withdrawn
KebuzoneKebuzone may increase the neuroexcitatory activities of Norfloxacin.Experimental
KetoprofenKetoprofen may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
KetorolacKetorolac may increase the neuroexcitatory activities of Norfloxacin.Approved
LanreotideNorfloxacin may increase the hypoglycemic activities of Lanreotide.Approved
Lanthanum carbonateThe serum concentration of Norfloxacin can be decreased when it is combined with Lanthanum carbonate.Approved
LeflunomideLeflunomide may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
LenvatinibNorfloxacin may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideNorfloxacin may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevofloxacinNorfloxacin may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LiraglutideNorfloxacin may increase the hypoglycemic activities of Liraglutide.Approved
LisofyllineLisofylline may increase the neuroexcitatory activities of Norfloxacin.Investigational
LopinavirNorfloxacin may increase the QTc-prolonging activities of Lopinavir.Approved
LornoxicamLornoxicam may increase the neuroexcitatory activities of Norfloxacin.Approved
LoxoprofenLoxoprofen may increase the neuroexcitatory activities of Norfloxacin.Approved
LumefantrineNorfloxacin may increase the QTc-prolonging activities of Lumefantrine.Approved
LumiracoxibLumiracoxib may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
MagaldrateMagaldrate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Withdrawn
Magnesium carbonateMagnesium carbonate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium HydroxideMagnesium hydroxide can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium salicylateThe serum concentration of Norfloxacin can be decreased when it is combined with Magnesium salicylate.Approved
Magnesium SulfateThe serum concentration of Norfloxacin can be decreased when it is combined with Magnesium Sulfate.Approved, Vet Approved
Magnesium TrisilicateMagnesium Trisilicate can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
MasoprocolMasoprocol may increase the neuroexcitatory activities of Norfloxacin.Approved
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Norfloxacin.Investigational
MecaserminNorfloxacin may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
Meclofenamic acidMeclofenamic acid may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Norfloxacin.Approved
Mefenamic acidMefenamic acid may increase the neuroexcitatory activities of Norfloxacin.Approved
MeloxicamMeloxicam may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
MesalazineMesalazine may increase the neuroexcitatory activities of Norfloxacin.Approved
MetamizoleMetamizole may increase the neuroexcitatory activities of Norfloxacin.Withdrawn
MetforminNorfloxacin may increase the hypoglycemic activities of Metformin.Approved
MethadoneNorfloxacin may increase the QTc-prolonging activities of Methadone.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Norfloxacin.Approved, Vet Approved
MifepristoneMifepristone may increase the QTc-prolonging activities of Norfloxacin.Approved, Investigational
MiglitolNorfloxacin may increase the hypoglycemic activities of Miglitol.Approved
MizoribineMizoribine may increase the neuroexcitatory activities of Norfloxacin.Investigational
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Norfloxacin.Approved, Vet Approved
MoxifloxacinNorfloxacin may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
Mycophenolate mofetilMycophenolate mofetil may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Norfloxacin.Approved
NabumetoneNabumetone may increase the neuroexcitatory activities of Norfloxacin.Approved
NafamostatNafamostat may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
NaftifineNaftifine may increase the neuroexcitatory activities of Norfloxacin.Approved
NaproxenNaproxen may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
NateglinideNorfloxacin may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Norfloxacin.Investigational
NCX 4016NCX 4016 may increase the neuroexcitatory activities of Norfloxacin.Investigational
NepafenacNepafenac may increase the neuroexcitatory activities of Norfloxacin.Approved
Niflumic AcidNiflumic Acid may increase the neuroexcitatory activities of Norfloxacin.Approved
NilotinibNorfloxacin may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NimesulideNimesulide may increase the neuroexcitatory activities of Norfloxacin.Approved, Withdrawn
NitroaspirinNitroaspirin may increase the neuroexcitatory activities of Norfloxacin.Investigational
NitrofurantoinThe therapeutic efficacy of Norfloxacin can be decreased when used in combination with Nitrofurantoin.Approved, Vet Approved
OctreotideNorfloxacin may increase the hypoglycemic activities of Octreotide.Approved, Investigational
OfloxacinNorfloxacin may increase the QTc-prolonging activities of Ofloxacin.Approved
OleandrinAnvirzel may decrease the cardiotoxic activities of Norfloxacin.Experimental
Oleoyl-estroneThe risk or severity of adverse effects can be increased when Oleoyl estrone is combined with Norfloxacin.Investigational
OlopatadineOlopatadine may increase the neuroexcitatory activities of Norfloxacin.Approved
OlsalazineOlsalazine may increase the neuroexcitatory activities of Norfloxacin.Approved
OndansetronNorfloxacin may increase the QTc-prolonging activities of Ondansetron.Approved
OuabainOuabain may decrease the cardiotoxic activities of Norfloxacin.Approved
OxaprozinOxaprozin may increase the neuroexcitatory activities of Norfloxacin.Approved
OxyphenbutazoneOxyphenbutazone may increase the neuroexcitatory activities of Norfloxacin.Withdrawn
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Norfloxacin.Approved, Vet Approved
PaliperidoneNorfloxacin may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatNorfloxacin may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Norfloxacin.Approved
ParecoxibParecoxib may increase the neuroexcitatory activities of Norfloxacin.Approved
PasireotideNorfloxacin may increase the hypoglycemic activities of Pasireotide.Approved
PazopanibNorfloxacin may increase the QTc-prolonging activities of Pazopanib.Approved
PentamidineNorfloxacin may increase the QTc-prolonging activities of Pentamidine.Approved
PerflutrenNorfloxacin may increase the QTc-prolonging activities of Perflutren.Approved
PhenindioneNorfloxacin may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonNorfloxacin may increase the anticoagulant activities of Phenprocoumon.Approved
PhenylbutazonePhenylbutazone may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Norfloxacin.Approved
PimecrolimusPimecrolimus may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
PimozideNorfloxacin may increase the QTc-prolonging activities of Pimozide.Approved
PioglitazoneNorfloxacin may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PirfenidonePirfenidone may increase the neuroexcitatory activities of Norfloxacin.Investigational
PiroxicamPiroxicam may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
PramlintideNorfloxacin may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Norfloxacin.Approved, Nutraceutical
Prasterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Norfloxacin.Investigational
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Norfloxacin.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Norfloxacin.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Norfloxacin.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Norfloxacin.Experimental
PrimaquineNorfloxacin may increase the QTc-prolonging activities of Primaquine.Approved
ProbenecidThe serum concentration of Norfloxacin can be increased when it is combined with Probenecid.Approved
ProcainamideNorfloxacin may increase the QTc-prolonging activities of Procainamide.Approved
PromazineNorfloxacin may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PropacetamolPropacetamol may increase the neuroexcitatory activities of Norfloxacin.Approved
PropafenoneNorfloxacin may increase the QTc-prolonging activities of Propafenone.Approved
PTC299PTC299 may increase the neuroexcitatory activities of Norfloxacin.Investigational
QuetiapineNorfloxacin may increase the QTc-prolonging activities of Quetiapine.Approved
QuinaprilThe serum concentration of Norfloxacin can be decreased when it is combined with Quinapril.Approved, Investigational
QuinidineNorfloxacin may increase the QTc-prolonging activities of Quinidine.Approved
QuinineNorfloxacin may increase the QTc-prolonging activities of Quinine.Approved
RepaglinideNorfloxacin may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
ResveratrolResveratrol may increase the neuroexcitatory activities of Norfloxacin.Experimental, Investigational
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Norfloxacin.Approved
RofecoxibRofecoxib may increase the neuroexcitatory activities of Norfloxacin.Investigational, Withdrawn
RosiglitazoneNorfloxacin may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SalicylamideSalicylamide may increase the neuroexcitatory activities of Norfloxacin.Approved
Salicylic acidSalicylic acid may increase the neuroexcitatory activities of Norfloxacin.Approved, Vet Approved
SalsalateSalsalate may increase the neuroexcitatory activities of Norfloxacin.Approved
SaquinavirNorfloxacin may increase the QTc-prolonging activities of Saquinavir.Approved, Investigational
SaxagliptinNorfloxacin may increase the hypoglycemic activities of Saxagliptin.Approved
SevelamerSevelamer can cause a decrease in the absorption of Norfloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SitagliptinNorfloxacin may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SotalolNorfloxacin may increase the QTc-prolonging activities of Sotalol.Approved
SRT501SRT501 may increase the neuroexcitatory activities of Norfloxacin.Investigational
Strontium ranelateThe serum concentration of Norfloxacin can be decreased when it is combined with Strontium ranelate.Approved
SucralfateThe serum concentration of Norfloxacin can be decreased when it is combined with Sucralfate.Approved
SulfadiazineNorfloxacin may increase the hypoglycemic activities of Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleNorfloxacin may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfasalazineSulfasalazine may increase the neuroexcitatory activities of Norfloxacin.Approved
SulfisoxazoleNorfloxacin may increase the QTc-prolonging activities of Sulfisoxazole.Approved, Vet Approved
SulindacSulindac may increase the neuroexcitatory activities of Norfloxacin.Approved
SunitinibNorfloxacin may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
SuprofenSuprofen may increase the neuroexcitatory activities of Norfloxacin.Approved, Withdrawn
TelavancinNorfloxacin may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinNorfloxacin may increase the QTc-prolonging activities of Telithromycin.Approved
TenoxicamTenoxicam may increase the neuroexcitatory activities of Norfloxacin.Approved
TeriflunomideTeriflunomide may increase the neuroexcitatory activities of Norfloxacin.Approved
TetrabenazineNorfloxacin may increase the QTc-prolonging activities of Tetrabenazine.Approved
TheophyllineThe metabolism of Theophylline can be decreased when combined with Norfloxacin.Approved
ThioridazineNorfloxacin may increase the QTc-prolonging activities of Thioridazine.Withdrawn
Tiaprofenic acidTiaprofenic acid may increase the neuroexcitatory activities of Norfloxacin.Approved
TinoridineTinoridine may increase the neuroexcitatory activities of Norfloxacin.Investigational
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Norfloxacin.Approved
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Norfloxacin.Approved
TolazamideNorfloxacin may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideNorfloxacin may increase the hypoglycemic activities of Tolbutamide.Approved
Tolfenamic AcidTolfenamic Acid may increase the neuroexcitatory activities of Norfloxacin.Approved
TolmetinTolmetin may increase the neuroexcitatory activities of Norfloxacin.Approved
ToremifeneNorfloxacin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TranilastTranilast may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Norfloxacin.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Norfloxacin.Approved, Vet Approved
ValdecoxibValdecoxib may increase the neuroexcitatory activities of Norfloxacin.Investigational, Withdrawn
VandetanibNorfloxacin may increase the QTc-prolonging activities of Vandetanib.Approved
VareniclineThe serum concentration of Varenicline can be increased when it is combined with Norfloxacin.Approved, Investigational
VemurafenibNorfloxacin may increase the QTc-prolonging activities of Vemurafenib.Approved
WarfarinNorfloxacin may increase the anticoagulant activities of Warfarin.Approved
ZaltoprofenZaltoprofen may increase the neuroexcitatory activities of Norfloxacin.Approved
ZileutonZileuton may increase the neuroexcitatory activities of Norfloxacin.Approved, Investigational, Withdrawn
ZiprasidoneNorfloxacin may increase the QTc-prolonging activities of Ziprasidone.Approved
ZomepiracZomepirac may increase the neuroexcitatory activities of Norfloxacin.Withdrawn
ZuclopenthixolNorfloxacin may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
  • Avoid high doses of caffeine.
  • Take on an empty stomach. Drink liberally.
References
Synthesis ReferenceUS4146719
General References
  1. Goldstein EJ: Norfloxacin, a fluoroquinolone antibacterial agent. Classification, mechanism of action, and in vitro activity. Am J Med. 1987 Jun 26;82(6B):3-17. [PubMed:3111257 ]
External Links
ATC CodesS01AE02 — NorfloxacinJ01RA13 — Norfloxacin and tinidazoleJ01MA06 — Norfloxacin
AHFS Codes
  • 08:12.18
PDB EntriesNot Available
FDA labelDownload (599 KB)
MSDSDownload (42.5 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
2CompletedTreatmentHepatopulmonary Syndrome1
2, 3Unknown StatusPreventionLiver Cirrhosis / Spontaneous Bacterial Peritonitis (SBP)1
3CompletedPreventionCirrhosis With Ascites1
3RecruitingPreventionAscites / Liver Cirrhosis / Spontaneous Bacterial Peritonitis (SBP)1
3TerminatedPreventionLiver Cirrhosis1
3WithdrawnTreatmentCystitis1
4CompletedPreventionAdverse Reaction to Other Drugs and Medicines1
4CompletedPreventionHepatorenal Syndrome / Liver Cirrhosis / Spontaneous Bacterial Peritonitis (SBP)1
4TerminatedTreatmentUrinary Tract Infections (UTIs)1
Not AvailableUnknown StatusTreatmentPortal Hypertension1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral400 mg
SolutionOphthalmic3 mg
Prices
Unit descriptionCostUnit
Noroxin 400 mg tablet4.21USD tablet
Apo-Norflox 400 mg Tablet1.44USD tablet
Co Norfloxacin 400 mg Tablet1.28USD tablet
Novo-Norfloxacin 400 mg Tablet1.28USD tablet
Pms-Norfloxacin 400 mg Tablet1.28USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)227-228 °CPhysProp
water solubility1.78E+005 mg/LNot Available
logP-1.03HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.01 mg/mLALOGPS
logP-0.47ALOGPS
logP-0.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)5.77ChemAxon
pKa (Strongest Basic)8.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.88 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.48 m3·mol-1ChemAxon
Polarizability32.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9916
Blood Brain Barrier-0.9824
Caco-2 permeable-0.8683
P-glycoprotein substrateSubstrate0.8554
P-glycoprotein inhibitor INon-inhibitor0.849
P-glycoprotein inhibitor IINon-inhibitor0.8657
Renal organic cation transporterNon-inhibitor0.7588
CYP450 2C9 substrateNon-substrate0.8301
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9268
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9148
CYP450 3A4 inhibitorNon-inhibitor0.8988
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5702
Ames testAMES toxic0.9108
CarcinogenicityNon-carcinogens0.7923
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8785 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7034
hERG inhibition (predictor II)Non-inhibitor0.5292
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0019000000-209bfb114ccbb6d9e304View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0069000000-4d54becdaa4caedbe3b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0391000000-a84cfa736c2dcec4d545View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ufr-0069000000-246d2ae5a6ec6a55d6b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009000000-f809266e62551b06d730View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fmi-0039000000-b7128cd18b98a04daf9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0069000000-d5c4d2c4b68d5f6d03a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ue9-0095000000-901dbfc8f7d02a135c4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0491000000-be9683c47fbf7a3cb0baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0970000000-90dc103f49990c57d26fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009000000-13d5054c01078e14d8f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fmi-0039000000-74150f6e5c4d2dcba6abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0059000000-dd2ee816e5228385835dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0195000000-596094ef32a4ddd39544View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0491000000-20c74694b378fdb752b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0970000000-06c84236dac00c44e42eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ufr-0069000000-5c4650a9bab59ded6701View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0910000000-71f0a353a8e37a26b402View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1398000000-86efb47466226acbabf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassQuinolines and derivatives
Direct ParentQuinoline carboxylic acids
Alternative ParentsFluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Benzenoids / Aryl fluorides
SubstituentsQuinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Tertiary aliphatic/aromatic amine
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsN-arylpiperazine, quinolone antibiotic, fluoroquinolone antibiotic, quinolone, quinolinemonocarboxylic acid (CHEBI:100246 ) / Fluoroquinolones (C06687 )

Targets

Details
1. DNA gyrase subunit A
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, including catenanes and knotted rings.
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. Hombrouck C, Capmau ML, Moreau N: Overexpression, purification and photoaffinity labeling with a 3H-analogue of norfloxacin, of the GyrA and GyrB subunits of the DNA gyrase. Cell Mol Biol (Noisy-le-grand). 1999 May;45(3):347-52. [PubMed:10386791 ]
  4. Hooper DC: Quinolone mode of action--new aspects. Drugs. 1993;45 Suppl 3:8-14. [PubMed:7689456 ]
  5. Fukuda H, Hori S, Hiramatsu K: Antibacterial activity of gatifloxacin (AM-1155, CG5501, BMS-206584), a newly developed fluoroquinolone, against sequentially acquired quinolone-resistant mutants and the norA transformant of Staphylococcus aureus. Antimicrob Agents Chemother. 1998 Aug;42(8):1917-22. [PubMed:9687384 ]
  6. Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [PubMed:9293187 ]
Details
2. DNA topoisomerase 4 subunit A
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. Rafii F, Park M, Novak JS: Alterations in DNA gyrase and topoisomerase IV in resistant mutants of Clostridium perfringens found after in vitro treatment with fluoroquinolones. Antimicrob Agents Chemother. 2005 Feb;49(2):488-92. [PubMed:15673722 ]
  4. Vila J, Sanchez-Cespedes J, Sierra JM, Piqueras M, Nicolas E, Freixas J, Giralt E: Antibacterial evaluation of a collection of norfloxacin and ciprofloxacin derivatives against multiresistant bacteria. Int J Antimicrob Agents. 2006 Jul;28(1):19-24. Epub 2006 Jun 14. [PubMed:16781123 ]
  5. Oyamada Y, Ito H, Fujimoto K, Asada R, Niga T, Okamoto R, Inoue M, Yamagishi J: Combination of known and unknown mechanisms confers high-level resistance to fluoroquinolones in Enterococcus faecium. J Med Microbiol. 2006 Jun;55(Pt 6):729-36. [PubMed:16687591 ]
  6. Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [PubMed:9293187 ]
Details
3. DNA topoisomerase 2-alpha
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 segregation of daughter chromosomes. May play a role in regulating the period length of ARNTL/BMAL1 transcriptional oscillation (By similarity).
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

Details
1. Cytochrome P450 1A2
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
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 ]
Details
2. Cytochrome P450 3A4
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Details
3. Cytochrome P450 3A5
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Uniprot Name:
Cytochrome P450 3A5
Molecular Weight:
57108.065 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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Details
4. Cytochrome P450 3A7
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Uniprot Name:
Cytochrome P450 3A7
Molecular Weight:
57525.03 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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Details
5. Cytochrome P450 1A1
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Uniprot Name:
Cytochrome P450 1A1
Molecular Weight:
58164.815 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 ]
Details
6. Cytochrome P450 2A6
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Uniprot Name:
Cytochrome P450 2A6
Molecular Weight:
56501.005 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

Details
1. Solute carrier family 22 member 5
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 cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
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 ]
Details
2. Solute carrier family 22 member 6
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
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 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:55