You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameNalidixic Acid
Accession NumberDB00779  (APRD01133)
TypeSmall Molecule
GroupsApproved
DescriptionA synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase. [PubChem]
Structure
Thumb
Synonyms
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
1,4-dihydro-1-Ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one
Acide nalidixique
Acido nalidixico
Acidum Nalidixicum
Nalidixic acid
Nalidixinsäure
External Identifiers
  • Win 18320
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NeggramTablet500 mgOralSanofi Aventis Canada Inc1964-12-312007-03-28Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AdixNenza Pharma
CuriemylonPanion & BF
DegramDoctor's Chemical Works
DelugiWashington
DixiconJayson
GlanegaMeider
GramazineJohnson
GramonegRanbaxy
Huei YiChen Ho
LisalenbSan Tong
LitalonLi Ta
NadixinPei Jin
NadonCentury
NagominMing Ta
Nal-acidFarmanic Chemipharma
NalicYu Sheng
NalicidTorrent
NalidSquare
NalidinFu Yuan
NalidixDar-Al-Dawa
NaligramAcme
NalitomylonThe Central
NalixAristopharma
NalixidZentiva
NalixinYung Sine
NebactilBeximco
NegachineHor Chen
NevigramonSanofi-Aventis
UnaserusIsei
WintomylonSanofi Aventis
WintorinSankei Yakuhin
YoudixYoshindo
Zuno-NathasidYung Chang
Brand mixturesNot Available
SaltsNot Available
Categories
UNII3B91HWA56M
CAS number389-08-2
WeightAverage: 232.2353
Monoisotopic: 232.08479226
Chemical FormulaC12H12N2O3
InChI KeyMHWLWQUZZRMNGJ-UHFFFAOYSA-N
InChI
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)
IUPAC Name
1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
SMILES
CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2
Pharmacology
IndicationFor the treatment of urinary tract infections caused by susceptible gram-negative microorganisms, including the majority of E. Coli, Enterobacter species, Klebsiella species, and Proteus species.
Structured Indications Not Available
PharmacodynamicsNalidixic acid is a quinolone antibacterial agent for oral administration. Nalidixic acid has marked antibacterial activity against gram-negative bacteria including Enterobacter species, Escherichia coli, Morganella Morganii; Proteus Mirabilis, Proteus vulgaris, and Providencia rettgeri. Pseudomonas species are generally resistant to the drug. Nalidixic acid is bactericidal and is effective over the entire urinary pH range. Conventional chromosomal resistance to nalidixic acid taken in full dosage has been reported to emerge in approximately 2 to 14 percent of patients during treatment; however, bacterial resistance to nalidixic acid has not been shown to be transferable via R factor.
Mechanism of actionEvidence exists for Nalidixic acid that its active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideyes
other
Humannot applicabledetails
Related Articles
AbsorptionFollowing oral administration, nalidixic acid is rapidly absorbed from the gastrointestinal tract. Bioavailability is approximately 96%. Absorption may be delayed if taken with antacids.
Volume of distributionNot Available
Protein bindingNalidixic acid is 93% bound to protein in the blood, and the active metabolite, hydroxynalidixic acid is 63% bound.
Metabolism

Hepatic. 30% of administered dose is metabolized to the active metabolite, hydroxynalidixic acid. Rapid conjugation of parent drug and active metabolite to inactive metabolites. Metabolism may vary widely among individuals. In the urine, hydroxynalidixic acid represents 80 to 85% of the antibacterial activity.

SubstrateEnzymesProduct
Nalidixic Acid
Not Available
Hydroxynalidixic acidDetails
Route of eliminationFollowing oral administration, NegGram is rapidly absorbed from the gastrointestinal tract, partially metabolized in the liver, and rapidly excreted through the kidneys. Approximately four percent of NegGram is excreted in the feces.
Half life1.1 to 2.5 hours in healthy adult patients, and up to 21 hours in patients with impaired renal function.
ClearanceNot Available
ToxicityORAL (LD50): Acute: 1160 mg/kg [Rat]. 572 mg/kg [Mouse]. Toxic psychosis, convulsions, increased intracranial pressure, or metabolic acidosis may occur in patients taking more than the recommended dosage. Vomiting, nausea, and lethargy may also occur following overdosage.
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 Nalidixic Acid.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Nalidixic Acid.Experimental, Illicit
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Nalidixic Acid.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Nalidixic Acid.Experimental, Illicit
AcarboseNalidixic Acid may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AceclofenacAceclofenac may increase the neuroexcitatory activities of Nalidixic Acid.Approved
AcenocoumarolNalidixic Acid may increase the anticoagulant activities of Acenocoumarol.Approved
AcetovanilloneAcetovanillone may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Nalidixic Acid.Approved
Acetylsalicylic acidAcetylsalicylic acid may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
AdapaleneAdapalene may increase the neuroexcitatory activities of Nalidixic Acid.Approved
AlbiglutideNalidixic Acid may increase the hypoglycemic activities of Albiglutide.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Nalidixic Acid.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Nalidixic Acid.Experimental
AlogliptinNalidixic Acid may increase the hypoglycemic activities of Alogliptin.Approved
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Aluminum phosphateAluminum phosphate can cause a decrease in the absorption of Nalidixic Acid 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 Nalidixic Acid.Experimental
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Nalidixic Acid.Approved
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Nalidixic Acid.Approved
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Nalidixic Acid.Investigational
AnisodamineAnisodamine may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
AntipyrineAntipyrine may increase the neuroexcitatory activities of Nalidixic Acid.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Nalidixic Acid.Investigational
ApremilastApremilast may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
AzapropazoneAzapropazone may increase the neuroexcitatory activities of Nalidixic Acid.Withdrawn
AzelastineAzelastine may increase the neuroexcitatory activities of Nalidixic Acid.Approved
BalsalazideBalsalazide may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Nalidixic Acid.Investigational
BeclomethasoneThe risk or severity of adverse effects can be increased when Beclomethasone is combined with Nalidixic Acid.Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Nalidixic Acid.Approved, Investigational
BenoxaprofenBenoxaprofen may increase the neuroexcitatory activities of Nalidixic Acid.Withdrawn
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Nalidixic Acid.Approved, Vet Approved
Betulinic AcidBetulinic Acid may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Nalidixic Acid.Approved, Investigational
Bismuth SubcitrateBismuth Subcitrate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
BromfenacBromfenac may increase the neuroexcitatory activities of Nalidixic Acid.Approved
BromocriptineNalidixic Acid may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BucillamineBucillamine may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Nalidixic Acid.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Nalidixic Acid.Approved
CalciumCalcium can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Nutraceutical
Calcium AcetateCalcium Acetate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium ChlorideCalcium Chloride can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium citrateCalcium citrate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium glubionateCalcium glubionate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium GluceptateCalcium Gluceptate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium gluconateCalcium gluconate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
CanagliflozinNalidixic Acid may increase the hypoglycemic activities of Canagliflozin.Approved
CarprofenCarprofen may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may increase the neuroexcitatory activities of Nalidixic Acid.Experimental
CelecoxibCelecoxib may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
ChloroquineChloroquine may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
ChlorpropamideNalidixic Acid may increase the hypoglycemic activities of Chlorpropamide.Approved
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Nalidixic Acid.Approved, Investigational
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Nalidixic Acid.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Nalidixic Acid.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Nalidixic Acid.Approved
ClonixinClonixin may increase the neuroexcitatory activities of Nalidixic Acid.Approved
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Nalidixic Acid.Approved
CurcuminCurcumin may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Nalidixic Acid.Approved, Investigational
D-LimoneneD-Limonene may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
DapagliflozinNalidixic Acid 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 Nalidixic Acid.Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Nalidixic Acid.Approved
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Nalidixic Acid.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Nalidixic Acid.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Nalidixic Acid.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Nalidixic Acid.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Nalidixic Acid.Vet Approved
DiclofenacDiclofenac may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
DicoumarolNalidixic Acid may increase the anticoagulant activities of Dicoumarol.Approved
DidanosineThe serum concentration of Didanosine can be decreased when it is combined with Nalidixic Acid.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Nalidixic Acid.Approved
DiflunisalDiflunisal may increase the neuroexcitatory activities of Nalidixic Acid.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Nalidixic Acid.Approved
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Nalidixic Acid.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Nalidixic Acid.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Nalidixic Acid.Approved
DisopyramideNalidixic Acid may increase the hypoglycemic activities of Disopyramide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Nalidixic Acid.Approved, Investigational
DroxicamDroxicam may increase the neuroexcitatory activities of Nalidixic Acid.Approved
DulaglutideNalidixic Acid may increase the hypoglycemic activities of Dulaglutide.Approved
DuvelisibDuvelisib may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
DyphyllineThe metabolism of Dyphylline can be decreased when combined with Nalidixic Acid.Approved
E6201E6201 may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
EbselenEbselen may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
EmpagliflozinNalidixic Acid may increase the hypoglycemic activities of Empagliflozin.Approved
EpirizoleEpirizole may increase the neuroexcitatory activities of Nalidixic Acid.Approved
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Nalidixic Acid.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Nalidixic Acid.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Nalidixic Acid.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Nalidixic Acid.Approved
EtanerceptEtanercept may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
Ethyl biscoumacetateNalidixic Acid may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may increase the neuroexcitatory activities of Nalidixic Acid.Approved
EtoricoxibEtoricoxib may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
Evening primrose oilEvening primrose oil may increase the neuroexcitatory activities of Nalidixic Acid.Approved
ExenatideNalidixic Acid may increase the hypoglycemic activities of Exenatide.Approved, Investigational
exisulindexisulind may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
FenbufenFenbufen may increase the neuroexcitatory activities of Nalidixic Acid.Approved
FenoprofenFenoprofen may increase the neuroexcitatory activities of Nalidixic Acid.Approved
Ferric CarboxymaltoseThe serum concentration of Nalidixic Acid can be decreased when it is combined with Ferric Carboxymaltose.Approved
Ferric CitrateThe serum concentration of Nalidixic Acid can be decreased when it is combined with Ferric Citrate.Approved
Ferric pyrophosphateThe serum concentration of Nalidixic Acid can be decreased when it is combined with Ferric pyrophosphate.Approved
FloctafenineFloctafenine may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Withdrawn
fluasteroneThe risk or severity of adverse effects can be increased when fluasterone is combined with Nalidixic Acid.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Nalidixic Acid.Approved
FluindioneNalidixic Acid may increase the anticoagulant activities of Fluindione.Investigational
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Nalidixic Acid.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Nalidixic Acid.Approved, Investigational
FlunixinFlunixin may increase the neuroexcitatory activities of Nalidixic Acid.Vet Approved
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Nalidixic Acid.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Nalidixic Acid.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Nalidixic Acid.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Nalidixic Acid.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Nalidixic Acid.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Nalidixic Acid.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Nalidixic Acid.Approved
FlurbiprofenFlurbiprofen may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Nalidixic Acid.Approved
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Nalidixic Acid.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Nalidixic Acid.Approved, Investigational, Withdrawn
GliclazideNalidixic Acid may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideNalidixic Acid may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideNalidixic Acid may increase the hypoglycemic activities of Glipizide.Approved
GlyburideNalidixic Acid may increase the hypoglycemic activities of Glyburide.Approved
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Nalidixic Acid.Investigational
HigenamineHigenamine may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
HMPL-004HMPL-004 may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Nalidixic Acid.Approved, Vet Approved
IbuprofenIbuprofen may increase the neuroexcitatory activities of Nalidixic Acid.Approved
IbuproxamIbuproxam may increase the neuroexcitatory activities of Nalidixic Acid.Withdrawn
IcatibantIcatibant may increase the neuroexcitatory activities of Nalidixic Acid.Approved
IndomethacinIndomethacin may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
IndoprofenIndoprofen may increase the neuroexcitatory activities of Nalidixic Acid.Withdrawn
Insulin AspartNalidixic Acid may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirNalidixic Acid may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineNalidixic Acid may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineNalidixic Acid may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanNalidixic Acid may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproNalidixic Acid may increase the hypoglycemic activities of Insulin Lispro.Approved
IronThe serum concentration of Nalidixic Acid can be decreased when it is combined with Iron.Approved
Iron DextranThe serum concentration of Nalidixic Acid can be decreased when it is combined with Iron Dextran.Approved, Vet Approved
Iron saccharateThe serum concentration of Nalidixic Acid can be decreased when it is combined with Iron saccharate.Approved
IsoxicamIsoxicam may increase the neuroexcitatory activities of Nalidixic Acid.Withdrawn
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Nalidixic Acid.Investigational
KebuzoneKebuzone may increase the neuroexcitatory activities of Nalidixic Acid.Experimental
KetoprofenKetoprofen may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
KetorolacKetorolac may increase the neuroexcitatory activities of Nalidixic Acid.Approved
LanreotideNalidixic Acid may increase the hypoglycemic activities of Lanreotide.Approved
Lanthanum carbonateThe serum concentration of Nalidixic Acid can be decreased when it is combined with Lanthanum carbonate.Approved
LeflunomideLeflunomide may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
LiraglutideNalidixic Acid may increase the hypoglycemic activities of Liraglutide.Approved
LisofyllineLisofylline may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
LornoxicamLornoxicam may increase the neuroexcitatory activities of Nalidixic Acid.Approved
LoxoprofenLoxoprofen may increase the neuroexcitatory activities of Nalidixic Acid.Approved
LumiracoxibLumiracoxib may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
MagaldrateMagaldrate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Withdrawn
Magnesium carbonateMagnesium carbonate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium hydroxideMagnesium hydroxide can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium salicylateThe serum concentration of Nalidixic Acid can be decreased when it is combined with Magnesium salicylate.Approved
Magnesium SulfateThe serum concentration of Nalidixic Acid can be decreased when it is combined with Magnesium Sulfate.Approved, Vet Approved
Magnesium TrisilicateMagnesium Trisilicate can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
MasoprocolMasoprocol may increase the neuroexcitatory activities of Nalidixic Acid.Approved
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Nalidixic Acid.Investigational
MecaserminNalidixic Acid may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
Meclofenamic acidMeclofenamic acid may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Nalidixic Acid.Approved
Mefenamic acidMefenamic acid may increase the neuroexcitatory activities of Nalidixic Acid.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Nalidixic Acid.Vet Approved
MeloxicamMeloxicam may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
MelphalanThe risk or severity of adverse effects can be increased when Nalidixic Acid is combined with Melphalan.Approved
MesalazineMesalazine may increase the neuroexcitatory activities of Nalidixic Acid.Approved
MetamizoleMetamizole may increase the neuroexcitatory activities of Nalidixic Acid.Withdrawn
MetforminNalidixic Acid may increase the hypoglycemic activities of Metformin.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Nalidixic Acid.Approved, Vet Approved
MifepristoneNalidixic Acid may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
MiglitolNalidixic Acid may increase the hypoglycemic activities of Miglitol.Approved
MizoribineMizoribine may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Nalidixic Acid.Approved, Vet Approved
Mycophenolate mofetilMycophenolate mofetil may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Nalidixic Acid.Approved
NabumetoneNabumetone may increase the neuroexcitatory activities of Nalidixic Acid.Approved
NafamostatNafamostat may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
NaftifineNaftifine may increase the neuroexcitatory activities of Nalidixic Acid.Approved
NaproxenNaproxen may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
NateglinideNalidixic Acid 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 Nalidixic Acid.Investigational
NCX 4016NCX 4016 may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
NepafenacNepafenac may increase the neuroexcitatory activities of Nalidixic Acid.Approved
Niflumic AcidNiflumic Acid may increase the neuroexcitatory activities of Nalidixic Acid.Approved
NimesulideNimesulide may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Withdrawn
NitroaspirinNitroaspirin may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
OctreotideNalidixic Acid 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 Nalidixic Acid.Investigational
OlopatadineOlopatadine may increase the neuroexcitatory activities of Nalidixic Acid.Approved
OlsalazineOlsalazine may increase the neuroexcitatory activities of Nalidixic Acid.Approved
OrgoteinOrgotein may increase the neuroexcitatory activities of Nalidixic Acid.Vet Approved
OuabainOuabain may decrease the cardiotoxic activities of Nalidixic Acid.Approved
OxaprozinOxaprozin may increase the neuroexcitatory activities of Nalidixic Acid.Approved
OxyphenbutazoneOxyphenbutazone may increase the neuroexcitatory activities of Nalidixic Acid.Withdrawn
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Nalidixic Acid.Approved, Vet Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Nalidixic Acid.Approved
ParecoxibParecoxib may increase the neuroexcitatory activities of Nalidixic Acid.Approved
PasireotideNalidixic Acid may increase the hypoglycemic activities of Pasireotide.Approved
PentamidineNalidixic Acid may increase the hypoglycemic activities of Pentamidine.Approved
PhenindioneNalidixic Acid may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonNalidixic Acid may increase the anticoagulant activities of Phenprocoumon.Approved
PhenylbutazonePhenylbutazone may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Nalidixic Acid.Approved
PimecrolimusPimecrolimus may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
PioglitazoneNalidixic Acid may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PirfenidonePirfenidone may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
PiroxicamPiroxicam may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
PramlintideNalidixic Acid may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Nalidixic Acid.Approved, Nutraceutical
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Nalidixic Acid.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Nalidixic Acid.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Nalidixic Acid.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Nalidixic Acid.Experimental
ProbenecidThe serum concentration of Nalidixic Acid can be increased when it is combined with Probenecid.Approved
PropacetamolPropacetamol may increase the neuroexcitatory activities of Nalidixic Acid.Approved
PTC299PTC299 may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
QuinaprilThe serum concentration of Nalidixic Acid can be decreased when it is combined with Quinapril.Approved, Investigational
QuinineNalidixic Acid may increase the hypoglycemic activities of Quinine.Approved
RepaglinideNalidixic Acid may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
ResveratrolResveratrol may increase the neuroexcitatory activities of Nalidixic Acid.Experimental, Investigational
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Nalidixic Acid.Approved
RofecoxibRofecoxib may increase the neuroexcitatory activities of Nalidixic Acid.Investigational, Withdrawn
RosiglitazoneNalidixic Acid may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SalicylamideSalicylamide may increase the neuroexcitatory activities of Nalidixic Acid.Approved
Salicylic acidSalicylic acid may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Vet Approved
SalsalateSalsalate may increase the neuroexcitatory activities of Nalidixic Acid.Approved
SaxagliptinNalidixic Acid may increase the hypoglycemic activities of Saxagliptin.Approved
SeratrodastSeratrodast may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
SevelamerSevelamer can cause a decrease in the absorption of Nalidixic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SitagliptinNalidixic Acid may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SRT501SRT501 may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
Strontium ranelateThe serum concentration of Nalidixic Acid can be decreased when it is combined with Strontium ranelate.Approved
SucralfateThe serum concentration of Nalidixic Acid can be decreased when it is combined with Sucralfate.Approved
SulfadiazineNalidixic Acid may increase the hypoglycemic activities of Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleNalidixic Acid may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfasalazineSulfasalazine may increase the neuroexcitatory activities of Nalidixic Acid.Approved
SulfisoxazoleNalidixic Acid may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SulindacSulindac may increase the neuroexcitatory activities of Nalidixic Acid.Approved
SunitinibNalidixic Acid may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
SuprofenSuprofen may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Withdrawn
TenoxicamTenoxicam may increase the neuroexcitatory activities of Nalidixic Acid.Approved
TepoxalinTepoxalin may increase the neuroexcitatory activities of Nalidixic Acid.Vet Approved
TeriflunomideTeriflunomide may increase the neuroexcitatory activities of Nalidixic Acid.Approved
TheophyllineThe metabolism of Theophylline can be decreased when combined with Nalidixic Acid.Approved
Tiaprofenic acidTiaprofenic acid may increase the neuroexcitatory activities of Nalidixic Acid.Approved
TinoridineTinoridine may increase the neuroexcitatory activities of Nalidixic Acid.Investigational
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Nalidixic Acid.Approved
TolazamideNalidixic Acid may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideNalidixic Acid may increase the hypoglycemic activities of Tolbutamide.Approved
Tolfenamic AcidTolfenamic Acid may increase the neuroexcitatory activities of Nalidixic Acid.Approved
TolmetinTolmetin may increase the neuroexcitatory activities of Nalidixic Acid.Approved
TranilastTranilast may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Nalidixic Acid.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Nalidixic Acid.Approved, Vet Approved
Trisalicylate-cholineTrisalicylate-choline may increase the neuroexcitatory activities of Nalidixic Acid.Approved
ValdecoxibValdecoxib may increase the neuroexcitatory activities of Nalidixic Acid.Investigational, Withdrawn
VareniclineThe serum concentration of Varenicline can be increased when it is combined with Nalidixic Acid.Approved, Investigational
WarfarinNalidixic Acid may increase the anticoagulant activities of Warfarin.Approved
ZaltoprofenZaltoprofen may increase the neuroexcitatory activities of Nalidixic Acid.Approved
ZileutonZileuton may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational, Withdrawn
ZomepiracZomepirac may increase the neuroexcitatory activities of Nalidixic Acid.Withdrawn
Food Interactions
  • Take with food to reduce irritation. Drink liberally.
References
Synthesis Reference

Charles L. Fox, Jr., Shanta Modak, Keith Reemtsma, “Injection-resistant materials and method of making same through use of nalidixic acid derivatives.” U.S. Patent US4563485, issued July, 1984.

US4563485
General ReferencesNot Available
External Links
ATC CodesJ01MB02
AHFS Codes
  • 08:12.18
PDB EntriesNot Available
FDA labelDownload (47.9 KB)
MSDSDownload (73.2 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9873
Blood Brain Barrier+0.8945
Caco-2 permeable+0.6315
P-glycoprotein substrateNon-substrate0.5071
P-glycoprotein inhibitor INon-inhibitor0.8838
P-glycoprotein inhibitor IINon-inhibitor0.8566
Renal organic cation transporterNon-inhibitor0.8104
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7202
CYP450 1A2 substrateNon-inhibitor0.7888
CYP450 2C9 inhibitorNon-inhibitor0.8934
CYP450 2D6 inhibitorNon-inhibitor0.9115
CYP450 2C19 inhibitorNon-inhibitor0.7834
CYP450 3A4 inhibitorNon-inhibitor0.9531
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8555
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8815
BiodegradationNot ready biodegradable0.8553
Rat acute toxicity2.0874 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9392
hERG inhibition (predictor II)Non-inhibitor0.8534
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Mutual pharmaceutical co inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral500 mg
Prices
Unit descriptionCostUnit
Nalidixic acid powder7.2USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point229.5 °CPhysProp
water solubility100 mg/L (at 23 °C)MERCK INDEX (1996)
logP1.59BIOBYTE (1995)
logS-3.37ADME Research, USCD
pKa8.6OSOL,A & HOOVER,JE (1975)
Predicted Properties
PropertyValueSource
Water Solubility2.3 mg/mLALOGPS
logP0.95ALOGPS
logP1.01ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)5.95ChemAxon
pKa (Strongest Basic)4.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area70.5 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.82 m3·mol-1ChemAxon
Polarizability23.65 Å3ChemAxon
Number of Rings2ChemAxon
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 naphthyridine carboxylic acids and derivatives. These are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthyridines
Sub ClassNaphthyridine carboxylic acids and derivatives
Direct ParentNaphthyridine carboxylic acids and derivatives
Alternative Parents
Substituents
  • Naphthyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Methylpyridine
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
other
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. 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 ]
  2. Avsaroglu MD, Helmuth R, Junker E, Hertwig S, Schroeter A, Akcelik M, Bozoglu F, Guerra B: Plasmid-mediated quinolone resistance conferred by qnrS1 in Salmonella enterica serovar Virchow isolated from Turkish food of avian origin. J Antimicrob Chemother. 2007 Nov;60(5):1146-50. Epub 2007 Sep 19. [PubMed:17881633 ]
  3. Jain A, Rajeswari MR: Preferential binding of quinolones to DNA with alternating G, C / A, T sequences: a spectroscopic study. J Biomol Struct Dyn. 2002 Oct;20(2):291-9. [PubMed:12354080 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Tryptophan 2,3-dioxygenase activity
Specific Function:
Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
Gene Name:
TDO2
Uniprot ID:
P48775
Molecular Weight:
47871.215 Da
References
  1. Sanzey B: Modulation of gene expression by drugs affecting deoxyribonucleic acid gyrase. J Bacteriol. 1979 Apr;138(1):40-7. [PubMed:108253 ]

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. Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [PubMed:9228014 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23