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Identification
NameCinoxacin
Accession NumberDB00827  (APRD00873)
TypeSmall Molecule
GroupsApproved, Withdrawn
DescriptionSynthetic antimicrobial related to oxolinic acid and nalidixic acid and used in urinary tract infections. [PubChem]
Structure
Thumb
Synonyms
1-Ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid
5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylic acid
Cinoxacin
Cinoxacine
Cinoxacino
Cinoxacinum
External Identifiers
  • 64716
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CinobacOclassen
MeciconChung Mei
TatsulexinTatsumi Kagaku
UrocinoxBioHealth Pharmaceuticals
Brand mixturesNot Available
SaltsNot Available
Categories
UNIILMK22VUH23
CAS number28657-80-9
WeightAverage: 262.2182
Monoisotopic: 262.05897144
Chemical FormulaC12H10N2O5
InChI KeyVDUWPHTZYNWKRN-UHFFFAOYSA-N
InChI
InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)
IUPAC Name
1-ethyl-4-oxo-1H,4H,7H-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
SMILES
CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12
Pharmacology
IndicationFor the treatment of initial and recurrent urinary tract infections in adults caused by the following susceptible microorganisms: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella species (including K. pneumoniae), and Enterobacter species.
Structured Indications Not Available
PharmacodynamicsCinoxacin is a synthetic antibacterial agent with in vitro activity against many gram-negative aerobic bacteria, particularly strains of the Enterobacteriaceae family. Cinoxacin inhibits bacterial deoxyribonucleic acid (DNA) synthesis, is bactericidal, and is active over the entire urinary pH range. Cross resistance with nalidixic acid has been demonstrated.
Mechanism of actionEvidence exists that cinoxacin binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis. It appears to also inhibit DNA gyrase. This enzyme is necessary for proper replicated DNA separation. By inhibiting this enzyme, DNA replication and cell division is inhibited.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNA gyrase subunit AProteinyes
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)P43700 details
DNANucleotideunknown
intercalation
Humannot applicabledetails
Related Articles
AbsorptionRapidly absorbed after oral administration. The presence of food delays absorption but does does not affect total absorption.
Volume of distributionNot Available
Protein binding60 to 80%
Metabolism

Hepatic, with approximately 30-40% metabolized to inactive metabolites.

Route of eliminationNot Available
Half lifeThe mean serum half-life is 1.5 hours. Half-life in patients with impaired renal function may exceed 10 hours.
ClearanceNot Available
ToxicityOral, subcutaneous, and intravenous LD50 in the rat is 3610 mg/kg, 1380 mg/kg, and 860 mg/kg, respectively. Oral, subcutaneous, and intravenous LD50 in the mouse is 2330 mg/kg, 900 mg/kg, and 850 mg/kg, respectively.Symptoms following an overdose of cinoxacin may include anorexia, nausea, vomiting, epigastric distress, and diarrhea. The severity of the epigastric distress and the diarrhea are dose related. Headache, dizziness, insomnia, photophobia, tinnitus, and a tingling sensation have been reported in some patients.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Cinoxacin.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Cinoxacin.Experimental, Illicit
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Cinoxacin.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Cinoxacin.Experimental, Illicit
AcarboseCinoxacin may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AceclofenacAceclofenac may increase the neuroexcitatory activities of Cinoxacin.Approved
AcenocoumarolCinoxacin may increase the anticoagulant activities of Acenocoumarol.Approved
AcetovanilloneAcetovanillone may increase the neuroexcitatory activities of Cinoxacin.Investigational
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Cinoxacin.Approved
Acetylsalicylic acidAcetylsalicylic acid may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
AdapaleneAdapalene may increase the neuroexcitatory activities of Cinoxacin.Approved
AlbiglutideCinoxacin may increase the hypoglycemic activities of Albiglutide.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Cinoxacin.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Cinoxacin.Experimental
AlogliptinCinoxacin may increase the hypoglycemic activities of Alogliptin.Approved
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Aluminum phosphateAluminum phosphate can cause a decrease in the absorption of Cinoxacin 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 Cinoxacin.Experimental
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Cinoxacin.Approved
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Cinoxacin.Approved
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Cinoxacin.Investigational
AnisodamineAnisodamine may increase the neuroexcitatory activities of Cinoxacin.Investigational
AntipyrineAntipyrine may increase the neuroexcitatory activities of Cinoxacin.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Cinoxacin.Investigational
ApremilastApremilast may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
AzapropazoneAzapropazone may increase the neuroexcitatory activities of Cinoxacin.Withdrawn
AzelastineAzelastine may increase the neuroexcitatory activities of Cinoxacin.Approved
BalsalazideBalsalazide may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
BeclomethasoneThe risk or severity of adverse effects can be increased when Beclomethasone is combined with Cinoxacin.Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Cinoxacin.Approved, Investigational
BenoxaprofenBenoxaprofen may increase the neuroexcitatory activities of Cinoxacin.Withdrawn
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Cinoxacin.Approved, Vet Approved
Betulinic AcidBetulinic Acid may increase the neuroexcitatory activities of Cinoxacin.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Cinoxacin.Approved, Investigational
Bismuth SubcitrateBismuth Subcitrate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
BromfenacBromfenac may increase the neuroexcitatory activities of Cinoxacin.Approved
BromocriptineCinoxacin may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BucillamineBucillamine may increase the neuroexcitatory activities of Cinoxacin.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Cinoxacin.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Cinoxacin.Approved
CalciumCalcium can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Nutraceutical
Calcium AcetateCalcium Acetate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium ChlorideCalcium Chloride can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium citrateCalcium citrate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium glubionateCalcium glubionate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium GluceptateCalcium Gluceptate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium gluconateCalcium gluconate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
CanagliflozinCinoxacin may increase the hypoglycemic activities of Canagliflozin.Approved
CarprofenCarprofen may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may increase the neuroexcitatory activities of Cinoxacin.Experimental
CelecoxibCelecoxib may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
ChloroquineChloroquine may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
ChlorpropamideCinoxacin may increase the hypoglycemic activities of Chlorpropamide.Approved
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Cinoxacin.Approved, Investigational
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Cinoxacin.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Cinoxacin.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Cinoxacin.Approved
ClonixinClonixin may increase the neuroexcitatory activities of Cinoxacin.Approved
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Cinoxacin.Approved
CurcuminCurcumin may increase the neuroexcitatory activities of Cinoxacin.Investigational
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Cinoxacin.Approved, Investigational
D-LimoneneD-Limonene may increase the neuroexcitatory activities of Cinoxacin.Investigational
DapagliflozinCinoxacin may increase the hypoglycemic activities of Dapagliflozin.Approved
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Cinoxacin.Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Cinoxacin.Approved
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Cinoxacin.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Cinoxacin.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Cinoxacin.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Cinoxacin.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Cinoxacin.Vet Approved
DiclofenacDiclofenac may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
DicoumarolCinoxacin may increase the anticoagulant activities of Dicoumarol.Approved
DidanosineThe serum concentration of Didanosine can be decreased when it is combined with Cinoxacin.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Cinoxacin.Approved
DiflunisalDiflunisal may increase the neuroexcitatory activities of Cinoxacin.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Cinoxacin.Approved
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Cinoxacin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Cinoxacin.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Cinoxacin.Approved
DisopyramideCinoxacin may increase the hypoglycemic activities of Disopyramide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Cinoxacin.Approved, Investigational
DroxicamDroxicam may increase the neuroexcitatory activities of Cinoxacin.Approved
DulaglutideCinoxacin may increase the hypoglycemic activities of Dulaglutide.Approved
DuvelisibDuvelisib may increase the neuroexcitatory activities of Cinoxacin.Investigational
DyphyllineThe metabolism of Dyphylline can be decreased when combined with Cinoxacin.Approved
E6201E6201 may increase the neuroexcitatory activities of Cinoxacin.Investigational
EbselenEbselen may increase the neuroexcitatory activities of Cinoxacin.Investigational
EmpagliflozinCinoxacin may increase the hypoglycemic activities of Empagliflozin.Approved
EpirizoleEpirizole may increase the neuroexcitatory activities of Cinoxacin.Approved
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Cinoxacin.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Cinoxacin.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Cinoxacin.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Cinoxacin.Approved
EtanerceptEtanercept may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
Ethyl biscoumacetateCinoxacin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may increase the neuroexcitatory activities of Cinoxacin.Approved
EtoricoxibEtoricoxib may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
Evening primrose oilEvening primrose oil may increase the neuroexcitatory activities of Cinoxacin.Approved
ExenatideCinoxacin may increase the hypoglycemic activities of Exenatide.Approved, Investigational
exisulindexisulind may increase the neuroexcitatory activities of Cinoxacin.Investigational
FenbufenFenbufen may increase the neuroexcitatory activities of Cinoxacin.Approved
FenoprofenFenoprofen may increase the neuroexcitatory activities of Cinoxacin.Approved
Ferric CarboxymaltoseThe serum concentration of Cinoxacin can be decreased when it is combined with Ferric Carboxymaltose.Approved
Ferric CitrateThe serum concentration of Cinoxacin can be decreased when it is combined with Ferric Citrate.Approved
Ferric pyrophosphateThe serum concentration of Cinoxacin can be decreased when it is combined with Ferric pyrophosphate.Approved
FloctafenineFloctafenine may increase the neuroexcitatory activities of Cinoxacin.Approved, Withdrawn
fluasteroneThe risk or severity of adverse effects can be increased when fluasterone is combined with Cinoxacin.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Cinoxacin.Approved
FluindioneCinoxacin may increase the anticoagulant activities of Fluindione.Investigational
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Cinoxacin.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Cinoxacin.Approved, Investigational
FlunixinFlunixin may increase the neuroexcitatory activities of Cinoxacin.Vet Approved
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Cinoxacin.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Cinoxacin.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Cinoxacin.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Cinoxacin.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Cinoxacin.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Cinoxacin.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Cinoxacin.Approved
FlurbiprofenFlurbiprofen may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Cinoxacin.Approved
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Cinoxacin.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Cinoxacin.Approved, Investigational, Withdrawn
GliclazideCinoxacin may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideCinoxacin may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideCinoxacin may increase the hypoglycemic activities of Glipizide.Approved
GlyburideCinoxacin may increase the hypoglycemic activities of Glyburide.Approved
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Cinoxacin.Investigational
HigenamineHigenamine may increase the neuroexcitatory activities of Cinoxacin.Investigational
HMPL-004HMPL-004 may increase the neuroexcitatory activities of Cinoxacin.Investigational
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Cinoxacin.Approved, Vet Approved
IbuprofenIbuprofen may increase the neuroexcitatory activities of Cinoxacin.Approved
IbuproxamIbuproxam may increase the neuroexcitatory activities of Cinoxacin.Withdrawn
IcatibantIcatibant may increase the neuroexcitatory activities of Cinoxacin.Approved
IndomethacinIndomethacin may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
IndoprofenIndoprofen may increase the neuroexcitatory activities of Cinoxacin.Withdrawn
Insulin AspartCinoxacin may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirCinoxacin may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineCinoxacin may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineCinoxacin may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanCinoxacin may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproCinoxacin may increase the hypoglycemic activities of Insulin Lispro.Approved
IronThe serum concentration of Cinoxacin can be decreased when it is combined with Iron.Approved
Iron DextranThe serum concentration of Cinoxacin can be decreased when it is combined with Iron Dextran.Approved, Vet Approved
Iron saccharateThe serum concentration of Cinoxacin can be decreased when it is combined with Iron saccharate.Approved
IsoxicamIsoxicam may increase the neuroexcitatory activities of Cinoxacin.Withdrawn
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Cinoxacin.Investigational
KebuzoneKebuzone may increase the neuroexcitatory activities of Cinoxacin.Experimental
KetoprofenKetoprofen may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
KetorolacKetorolac may increase the neuroexcitatory activities of Cinoxacin.Approved
LanreotideCinoxacin may increase the hypoglycemic activities of Lanreotide.Approved
Lanthanum carbonateThe serum concentration of Cinoxacin can be decreased when it is combined with Lanthanum carbonate.Approved
LeflunomideLeflunomide may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
LiraglutideCinoxacin may increase the hypoglycemic activities of Liraglutide.Approved
LisofyllineLisofylline may increase the neuroexcitatory activities of Cinoxacin.Investigational
LornoxicamLornoxicam may increase the neuroexcitatory activities of Cinoxacin.Approved
LoxoprofenLoxoprofen may increase the neuroexcitatory activities of Cinoxacin.Approved
LumiracoxibLumiracoxib may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
MagaldrateMagaldrate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Withdrawn
Magnesium carbonateMagnesium carbonate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium hydroxideMagnesium hydroxide can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium salicylateThe serum concentration of Cinoxacin can be decreased when it is combined with Magnesium salicylate.Approved
Magnesium SulfateThe serum concentration of Cinoxacin can be decreased when it is combined with Magnesium Sulfate.Approved, Vet Approved
Magnesium TrisilicateMagnesium Trisilicate can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
MasoprocolMasoprocol may increase the neuroexcitatory activities of Cinoxacin.Approved
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Cinoxacin.Investigational
MecaserminCinoxacin may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
Meclofenamic acidMeclofenamic acid may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Cinoxacin.Approved
Mefenamic acidMefenamic acid may increase the neuroexcitatory activities of Cinoxacin.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Cinoxacin.Vet Approved
MeloxicamMeloxicam may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
MesalazineMesalazine may increase the neuroexcitatory activities of Cinoxacin.Approved
MetamizoleMetamizole may increase the neuroexcitatory activities of Cinoxacin.Withdrawn
MetforminCinoxacin may increase the hypoglycemic activities of Metformin.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Cinoxacin.Approved, Vet Approved
MifepristoneCinoxacin may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
MiglitolCinoxacin may increase the hypoglycemic activities of Miglitol.Approved
MizoribineMizoribine may increase the neuroexcitatory activities of Cinoxacin.Investigational
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Cinoxacin.Approved, Vet Approved
Mycophenolate mofetilMycophenolate mofetil may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Cinoxacin.Approved
NabumetoneNabumetone may increase the neuroexcitatory activities of Cinoxacin.Approved
NafamostatNafamostat may increase the neuroexcitatory activities of Cinoxacin.Investigational
NaftifineNaftifine may increase the neuroexcitatory activities of Cinoxacin.Approved
NaproxenNaproxen may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
NateglinideCinoxacin 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 Cinoxacin.Investigational
NCX 4016NCX 4016 may increase the neuroexcitatory activities of Cinoxacin.Investigational
NepafenacNepafenac may increase the neuroexcitatory activities of Cinoxacin.Approved
Niflumic AcidNiflumic Acid may increase the neuroexcitatory activities of Cinoxacin.Approved
NimesulideNimesulide may increase the neuroexcitatory activities of Cinoxacin.Approved, Withdrawn
NitroaspirinNitroaspirin may increase the neuroexcitatory activities of Cinoxacin.Investigational
OctreotideCinoxacin may increase the hypoglycemic activities of Octreotide.Approved, Investigational
Oleoyl estroneThe risk or severity of adverse effects can be increased when Oleoyl estrone is combined with Cinoxacin.Investigational
OlopatadineOlopatadine may increase the neuroexcitatory activities of Cinoxacin.Approved
OlsalazineOlsalazine may increase the neuroexcitatory activities of Cinoxacin.Approved
OrgoteinOrgotein may increase the neuroexcitatory activities of Cinoxacin.Vet Approved
OuabainOuabain may decrease the cardiotoxic activities of Cinoxacin.Approved
OxaprozinOxaprozin may increase the neuroexcitatory activities of Cinoxacin.Approved
OxyphenbutazoneOxyphenbutazone may increase the neuroexcitatory activities of Cinoxacin.Withdrawn
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Cinoxacin.Approved, Vet Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Cinoxacin.Approved
ParecoxibParecoxib may increase the neuroexcitatory activities of Cinoxacin.Approved
PasireotideCinoxacin may increase the hypoglycemic activities of Pasireotide.Approved
PentamidineCinoxacin may increase the hypoglycemic activities of Pentamidine.Approved
PhenindioneCinoxacin may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonCinoxacin may increase the anticoagulant activities of Phenprocoumon.Approved
PhenylbutazonePhenylbutazone may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
PimecrolimusPimecrolimus may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
PioglitazoneCinoxacin may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PirfenidonePirfenidone may increase the neuroexcitatory activities of Cinoxacin.Investigational
PiroxicamPiroxicam may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
PramlintideCinoxacin may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Cinoxacin.Approved, Nutraceutical
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Cinoxacin.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Cinoxacin.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Cinoxacin.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Cinoxacin.Experimental
ProbenecidThe serum concentration of Cinoxacin can be increased when it is combined with Probenecid.Approved
PropacetamolPropacetamol may increase the neuroexcitatory activities of Cinoxacin.Approved
PTC299PTC299 may increase the neuroexcitatory activities of Cinoxacin.Investigational
QuinaprilThe serum concentration of Cinoxacin can be decreased when it is combined with Quinapril.Approved, Investigational
QuinineCinoxacin may increase the hypoglycemic activities of Quinine.Approved
RepaglinideCinoxacin may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
ResveratrolResveratrol may increase the neuroexcitatory activities of Cinoxacin.Experimental, Investigational
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Cinoxacin.Approved
RofecoxibRofecoxib may increase the neuroexcitatory activities of Cinoxacin.Investigational, Withdrawn
RosiglitazoneCinoxacin may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SalicylamideSalicylamide may increase the neuroexcitatory activities of Cinoxacin.Approved
Salicylic acidSalicylic acid may increase the neuroexcitatory activities of Cinoxacin.Approved, Vet Approved
SalsalateSalsalate may increase the neuroexcitatory activities of Cinoxacin.Approved
SaxagliptinCinoxacin may increase the hypoglycemic activities of Saxagliptin.Approved
SeratrodastSeratrodast may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
SevelamerSevelamer can cause a decrease in the absorption of Cinoxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SitagliptinCinoxacin may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SRT501SRT501 may increase the neuroexcitatory activities of Cinoxacin.Investigational
Strontium ranelateThe serum concentration of Cinoxacin can be decreased when it is combined with Strontium ranelate.Approved
SucralfateThe serum concentration of Cinoxacin can be decreased when it is combined with Sucralfate.Approved
SulfadiazineCinoxacin may increase the hypoglycemic activities of Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleCinoxacin may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfasalazineSulfasalazine may increase the neuroexcitatory activities of Cinoxacin.Approved
SulfisoxazoleCinoxacin may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SulindacSulindac may increase the neuroexcitatory activities of Cinoxacin.Approved
SunitinibCinoxacin may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
SuprofenSuprofen may increase the neuroexcitatory activities of Cinoxacin.Approved, Withdrawn
TenoxicamTenoxicam may increase the neuroexcitatory activities of Cinoxacin.Approved
TepoxalinTepoxalin may increase the neuroexcitatory activities of Cinoxacin.Vet Approved
TeriflunomideTeriflunomide may increase the neuroexcitatory activities of Cinoxacin.Approved
TheophyllineThe metabolism of Theophylline can be decreased when combined with Cinoxacin.Approved
Tiaprofenic acidTiaprofenic acid may increase the neuroexcitatory activities of Cinoxacin.Approved
TinoridineTinoridine may increase the neuroexcitatory activities of Cinoxacin.Investigational
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Cinoxacin.Approved
TolazamideCinoxacin may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideCinoxacin may increase the hypoglycemic activities of Tolbutamide.Approved
Tolfenamic AcidTolfenamic Acid may increase the neuroexcitatory activities of Cinoxacin.Approved
TolmetinTolmetin may increase the neuroexcitatory activities of Cinoxacin.Approved
TranilastTranilast may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Cinoxacin.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Cinoxacin.Approved, Vet Approved
Trisalicylate-cholineTrisalicylate-choline may increase the neuroexcitatory activities of Cinoxacin.Approved
ValdecoxibValdecoxib may increase the neuroexcitatory activities of Cinoxacin.Investigational, Withdrawn
VareniclineThe serum concentration of Varenicline can be increased when it is combined with Cinoxacin.Approved, Investigational
WarfarinCinoxacin may increase the anticoagulant activities of Warfarin.Approved
ZaltoprofenZaltoprofen may increase the neuroexcitatory activities of Cinoxacin.Approved
ZileutonZileuton may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational, Withdrawn
ZomepiracZomepirac may increase the neuroexcitatory activities of Cinoxacin.Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

White, W.A.; U.S. Patent 3,669,965; June 13, 1972; assigned to Eli Lilly & Company.

US3669965
General ReferencesNot Available
External Links
ATC CodesJ01MB06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (37.2 KB)
MSDSDownload (53.7 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9902
Blood Brain Barrier+0.7001
Caco-2 permeable-0.515
P-glycoprotein substrateNon-substrate0.5087
P-glycoprotein inhibitor INon-inhibitor0.8358
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.7213
CYP450 2C9 substrateNon-substrate0.8137
CYP450 2D6 substrateNon-substrate0.8119
CYP450 3A4 substrateNon-substrate0.5503
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6
Ames testAMES toxic0.9106
CarcinogenicityNon-carcinogens0.8656
BiodegradationNot ready biodegradable0.8917
Rat acute toxicity1.8922 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8812
hERG inhibition (predictor II)Non-inhibitor0.9074
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Teva pharmaceuticals usa inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point261-262White, W.A.; U.S. Patent 3,669,965; June 13, 1972; assigned to Eli Lilly & Company.
logP1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.961 mg/mLALOGPS
logP1.25ALOGPS
logP1.72ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.93ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.43 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity73.6 m3·mol-1ChemAxon
Polarizability24.72 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
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 organic compounds known as cinnolines. These are organic aromatic compounds containing a benzene fused to a pyridazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthyridines
Sub ClassCinnolines
Direct ParentCinnolines
Alternative Parents
Substituents
  • Cinnoline
  • Benzodioxole
  • Benzenoid
  • Pyridazine
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

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, including catenanes and knotted rings.
Gene Name:
gyrA
Uniprot ID:
P43700
Molecular Weight:
97817.145 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 ]
  2. Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [PubMed:9293187 ]
  3. Neugebauer U, Szeghalmi A, Schmitt M, Kiefer W, Popp J, Holzgrabe U: Vibrational spectroscopic characterization of fluoroquinolones. Spectrochim Acta A Mol Biomol Spectrosc. 2005 May;61(7):1505-17. [PubMed:15820884 ]
  4. Tuma J, Connors WH, Stitelman DH, Richert C: On the effect of covalently appended quinolones on termini of DNA duplexes. J Am Chem Soc. 2002 Apr 24;124(16):4236-46. [PubMed:11960452 ]
2. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
unknown
Actions
intercalation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 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. Tuma J, Connors WH, Stitelman DH, Richert C: On the effect of covalently appended quinolones on termini of DNA duplexes. J Am Chem Soc. 2002 Apr 24;124(16):4236-46. [PubMed:11960452 ]

Transporters

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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23