Identification

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Name
Nitrofurantoin
Accession Number
DB00698  (APRD00191)
Type
Small Molecule
Groups
Approved, Vet approved
Description

Nitrofurantoin is a nitrofuran antibiotic used to treat uncomplicated urinary tract infections.8,9,10 Nitrofurantoin is converted by bacterial nitroreductases to electrophilic intermediates which inhibit the citric acid cycle as well as synthesis of DNA, RNA, and protein.2 This drug is more resistant to the development of bacterial resistance because it acts on many targets at once.2 Nitrofurantoin is a second line treatment to trimethoprim/sulfamethoxazole.3

Nitrofurantoin was granted FDA approval on 6 February 1953.11

Structure
Thumb
Synonyms
  • 1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione
  • 1-((5-nitrofurfurylidene)amino)hydantoin
  • 5-Nitrofurantoin
  • N-(5-Nitrofurfurylidene)-1-aminohydantoin
  • Nitrofurantoin
  • Nitrofurantoin anhydrous
  • Nitrofurantoin macrocrystal
  • Nitrofurantoin macrocrystalline
  • Nitrofurantoin, macrocrystalline
  • Nitrofurantoin, macrocrystals
  • nitrofurantoina
  • nitrofurantoine
  • nitrofurantoinum
  • Nitrofurantoinum anhydrous
External IDs
NSC-2107 / NSC-44150 / USAF EA-2
Product Ingredients
IngredientUNIICASInChI Key
Nitrofurantoin monohydrateE1QI2CQQ1I17140-81-7NHBPVLAHAVEISO-JSGFVSQVSA-N
Nitrofurantoin sodiumMAL9M0T5LV54-87-5AFDJQFFKYDCYIG-JSGFVSQVSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FuradantinSuspension25 mg/5mLOralCasper Pharma Llc2018-01-22Not applicableUs
FuradantinSuspension25 mg/5mLOralShionogi1953-12-23Not applicableUs
MacrobidCapsule100 mgOralAllergan1993-12-31Not applicableCanada
MacrodantinCapsule50 mg/1OralProcter & Gamble Pharmaceuticals2009-03-23Not applicableUs
MacrodantinCapsule50 mg/1OralALMATICA PHARMA INC.2010-09-27Not applicableUs
MacrodantinCapsule25 mg/1OralProcter & Gamble Pharmaceuticals2009-03-23Not applicableUs0149 000720180819 11162 7dlgpq
MacrodantinCapsule25 mg/1OralALMATICA PHARMA INC.2010-09-27Not applicableUs
MacrodantinCapsule100 mg/1OralProcter & Gamble Pharmaceuticals2009-03-23Not applicableUs
MacrodantinCapsule100 mg/1OralALMATICA PHARMA INC.2010-09-27Not applicableUs
MacrodantinCapsule25 mgOralAlza1993-12-311999-08-06Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-nitrofurantoinCapsuleOralAuro Pharma Inc2017-10-23Not applicableCanada
NitrofurantionCapsule100 mg/1OralBluePoint Labortories2019-05-14Not applicableUs
NitrofurantionCapsule50 mg/1OralSun Pharmaceutical Industries, Inc.2016-04-15Not applicableUs
NitrofurantionCapsule50 mg/1OralBluePoint Labortories2019-05-14Not applicableUs
NitrofurantionCapsule25 mg/1OralSun Pharmaceutical Industries, Inc.2016-04-15Not applicableUs
NitrofurantionCapsule100 mg/1OralNuCare Pharmaceuticals Industries, Inc.2016-04-15Not applicableUs
NitrofurantionCapsule100 mg/1OralProficient Rx LP2016-04-15Not applicableUs
NitrofurantionCapsule25 mg/1OralBluePoint Labortories2019-05-14Not applicableUs
NitrofurantionCapsule50 mg/1Oralbryant ranch prepack2016-04-15Not applicableUs
NitrofurantionCapsule100 mg/1Oralbryant ranch prepack2016-04-152018-01-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MacrobidNitrofurantoin monohydrate (75 mg/1) + Nitrofurantoin (25 mg/1)CapsuleOralProcter and Gamble Pharmaceuticals, Inc.2009-03-23Not applicableUs
MacrobidNitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1)CapsuleOralPhysicians Total Care, Inc.1991-12-242010-06-30Us
MacrobidNitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1)CapsuleOralALMATICA PHARMA INC.2011-05-31Not applicableUs
MacrobidNitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (80.7 mg/1)CapsuleOralSunny Pharmtech Inc.2018-01-012018-06-01Us
MacrobidNitrofurantoin monohydrate (75 mg/1) + Nitrofurantoin (25 mg/1)CapsuleOralProcter and Gamble Pharmaceuticals, Inc.2009-03-23Not applicableUs
MacrobidNitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1)CapsuleOralALMATICA PHARMA INC.2011-05-31Not applicableUs
MacrobidNitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (80.7 mg/1)CapsuleOralSunny Pharmtech Inc.2018-01-012018-06-01Us
MacrobidNitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1)CapsuleOralCentral Texas Community Health Centers2011-05-31Not applicableUs
MacrobidNitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1)CapsuleOralCentral Texas Community Health Centers2011-05-31Not applicableUs
MacrobidNitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1)CapsuleOralPhysicians Total Care, Inc.1991-12-242010-06-30Us
International/Other Brands
Furabid (Goldshield) / Niftran / Siraliden / Urantoin (Basel) / Urolong (Thiemann)
Categories
UNII
927AH8112L
CAS number
67-20-9
Weight
Average: 238.159
Monoisotopic: 238.033819309
Chemical Formula
C8H6N4O5
InChI Key
NXFQHRVNIOXGAQ-YCRREMRBSA-N
InChI
InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
IUPAC Name
1-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
SMILES
[O-][N+](=O)C1=CC=C(O1)\C=N\N1CC(=O)NC1=O

Pharmacology

Indication

Nitrofurantoin is indicated to treat acute uncomplicated urinary tract infections.8,9,10

Associated Conditions
Pharmacodynamics

Nitrofurantoin interferes with vital processes in bacteria, which leads to their death.2 Nitrofurantoin rapidly reaches therapeutic concentrations in the urine and is also cleared rapidly.3

Mechanism of action

Nitrofurantoin is converted by bacterial nitroreductases to electrophilic intermediates which inhibit the citric acid cycle as well as synthesis of DNA, RNA, and protein.2

TargetActionsOrganism
AProbable pyruvate-flavodoxin oxidoreductase
potentiator
Escherichia coli (strain K12)
AOxygen-insensitive NADPH nitroreductase
potentiator
Escherichia coli (strain K12)
U30S ribosomal protein S10
inhibitor
Escherichia coli (strain K12)
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Nitrofurantoin reaches a Cmax of 0.875-0.963mg/L with an AUC of 2.21-2.42mg*h/L.3 It is 38.8-44.3% bioavailable.3 Taking nitrofurantoin with food increases the absorption and duration of therapeutic concentrations in the urine.5

Volume of distribution

Data regarding the volume of distribution in humans is scarce but it has been reported as 0.46L/kg in dogs.6

Protein binding

Nitrofurantoin could be up to 90% protein bound in plasma.1

Metabolism

0.8-1.8% of a dose is metabolized to aminofurantoin, and ≤0.9% of a dose is metabolized to other metabolites.7

Route of elimination

27-50% of an oral dose is excreted in the urine as unchanged nitrofurantoin.3 90% of the total dose is eliminated in the urine.4

Half life

The half life of nitrofurantoin is 0.72-0.78h.3

Clearance

The clearance of nitrofurantoin is 16.7-19.4L/h.3

Toxicity

Symptoms of overdose include vomiting.8,9,10 In case of overdose, induce vomiting if it has not already occurred and increase fluid intake to promote urination.8,9,10 In extreme cases, nitrofurantoin can be removed from circulation by dialysis.8,9,10

Affected organisms
  • Gram negative and gram positive bacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Glucose-6-phosphate 1-dehydrogenaseVilleurbanneNot Available1000_1002delACCADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseTorunNot Available1006A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSunderlandNot Available105_107delCATADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseIwatsukiNot Available1081G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSerresNot Available1082C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseTondelaNot Available1084_1101delCTGAACGAGCGCAAGGCCADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseLoma LindaNot Available1089C->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAachenNot Available1089C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseTenriNot Available1096A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMontpellierNot Available1132G>AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCalvo MackennaNot Available1138A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseRileyNot Available1139T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseOlomoucNot Available1141T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseTomahNot Available1153T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseLynwoodNot Available1154G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMadridNot Available1155C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseIowa, Walter Reed, SpringfieldNot Available1156A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBeverly Hills, Genova, Iwate, Niigata, YamaguchiNot Available1160G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseHartfordNot Available1162A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenasePrahaNot Available1166A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseKrakowNot Available1175T>CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseWisconsinNot Available1177C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNashville, Anaheim, PorticiNot Available1178G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAlhambraNot Available1180G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBariNot Available1187C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenasePuerto LimonNot Available1192G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCovao do LoboNot Available1205C>AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseClinicNot Available1215G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseUtrechtNot Available1225C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSuwalkiNot Available1226C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseRiversideNot Available1228G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseJapan, ShinagawaNot Available1229G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseKawasakiNot Available1229G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMunichNot Available1231A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseGeorgiaNot Available1284C->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSumareNot Available1292T->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseTelti/KobeNot Available1318C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSantiago de Cuba, MoriokaNot Available1339G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseHarimaNot Available1358T->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseFiguera da FozNot Available1366G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAmiensNot Available1367A>TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBangkok NoiNot Available1376G->T, 1502T->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseFukayaNot Available1462G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCampinasNot Available1463G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBuenos AiresNot Available1465C>TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseArakawaNot Available1466C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBrightonNot Available1488_1490delGAAADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseKozukataNot Available159G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAmsterdamNot Available180_182delTCTADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNo nameNot Available202G->A, 376A->G, 1264C>GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSwanseaNot Available224T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseUrayasuNot Available281_283delAGAADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseVancouverNot Available317C->G544C->T592C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMt SinaiNot Available376A->G, 1159C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenasePlymouthNot Available488G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseVolendamNot Available514C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseShinshuNot Available527A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseChikugoNot Available535A->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseTsukuiNot Available561_563delCTCADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenasePedoplis-CkaroNot Available573C>GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSantiagoNot Available593G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMinnesota, Marion, Gastonia, LeJeuneNot Available637G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCincinnatiNot Available637G->T, 1037A->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseHarilaouNot Available648T->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNorth DallasNot Available683_685delACAADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAsahikawaNot Available695G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseDurhamNot Available713A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseStonybrookNot Available724_729delGGCACTADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseWayneNot Available769C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAveiroNot Available806G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCleveland CorumNot Available820G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseLilleNot Available821A>TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBangkokNot Available825G>CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSugaoNot Available826C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseLa JollaNot Available832T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseWexhamNot Available833C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenasePiotrkowNot Available851T>CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseWest VirginiaNot Available910G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseOmiyaNot Available921G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNaraNot Available953_976delCCACCAAAGGGTACCTGGAC GACCADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseManhattanNot Available962G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseRehevotNot Available964T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseHoniaraNot Available99A->G / 1360C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseTokyo, FukushimaNot Available1246G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseChathamNot Available1003G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseFushanNot Available1004C->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenasePartenopeNot Available1052G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseIerapetraNot Available1057C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAnadiaNot Available1193A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAbenoNot Available1220A->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSurabayaNot Available1291G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenasePawneeNot Available1316G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseS. AntiocoNot Available1342A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCassanoNot Available1347G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseHermoupolisNot Available1347G->C / 1360C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseUnion,Maewo, Chinese-2, KaloNot Available1360C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAndalusNot Available1361G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCosenzaNot Available1376G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCanton, Taiwan- Hakka, Gifu-like, Agrigento-likeNot Available1376G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseFloresNot Available1387C->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseKaiping, Anant, Dhon, Sapporo-like, WoseraNot Available1388G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseKamogawaNot Available169C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCostanzoNot Available179T>CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAmazoniaNot Available185C->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSongklanagarindNot Available196T->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseHechiNot Available202G->A / 871G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNamouruNot Available208T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBao LocNot Available352T>CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCrispimNot Available375G->T, 379G->T383T->C384C>TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAcrokorinthosNot Available376A->G / 463C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSanta MariaNot Available376A->G / 542A->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAnanindeuaNot Available376A->G / 871G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseVanua LavaNot Available383T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseValladolidNot Available406C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBelemNot Available409C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseLiuzhouNot Available442G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseShenzenNot Available473G>AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseTaipei “Chinese- 3”Not Available493A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseToledoNot Available496C>TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNaoneNot Available497G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNankangNot Available517T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMiaoliNot Available519C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMediterranean, Dallas, Panama‚ Sassari, Cagliari, BirminghamNot Available563C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseCoimbra ShundeNot Available592C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNilgiriNot Available593G>AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseRadlowoNot Available679C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseRoubaixNot Available811G>CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseHaikouNot Available835A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseChinese-1Not Available835A->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMizushimaNot Available848A>GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseOsakaNot Available853C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseViangchan, JammuNot Available871G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSeoulNot Available916G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseLudhianaNot Available929G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseFarroupilhaNot Available977C->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseChinese-5Not Available1024C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseRignanoNot Available130G>AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseOrissaNot Available131C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseG6PDNiceNot Available1380G>CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseKamiube, KeelungNot Available1387C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNeapolisNot Available1400C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAuresNot Available143T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSplitNot Available1442C->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseKambosNot Available148C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenasePalestrinaNot Available170G>AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMetapontoNot Available172G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMusashinoNot Available185C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseAsahiNot Available202G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseA- (202), Ferrara INot Available202G->A / 376A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMurcia OristanoNot Available209A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseUbe KonanNot Available241C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseLagosantoNot Available242G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseGuangzhouNot Available274C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseHammersmithNot Available323T->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSinnaiNot Available34G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseA- (680)Not Available376A->G / 680G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseA- (968), Betica,Selma, GuantanamoNot Available376A->G / 968T->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSalerno PyrgosNot Available383T>GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseQuing YanNot Available392G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseLagesNot Available40G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseIleshaNot Available466G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMahidolNot Available487G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMalagaNot Available542A->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSibariNot Available634A->GADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMexico CityNot Available680G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseNanningNot Available703C->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseSeattle, Lodi, Modena, Ferrara II, Athens-likeNot Available844G->CADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseBajo MaumereNot Available844G->TADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseMontalbanoNot Available854G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseKalyan-Kerala, Jamnaga, RohiniNot Available949G->AADR InferredIncreased risk of hemolytic anemia.Details
Glucose-6-phosphate 1-dehydrogenaseGaoheNot Available95A->GADR InferredIncreased risk of hemolytic anemia.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Nitrofurantoin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Nitrofurantoin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Nitrofurantoin is combined with 4-hydroxycoumarin.
5-fluorouridineThe therapeutic efficacy of Nitrofurantoin can be decreased when used in combination with 5-fluorouridine.
AbacavirNitrofurantoin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibAbemaciclib may decrease the excretion rate of Nitrofurantoin which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Nitrofurantoin which could result in a higher serum level.
AcebutololThe risk or severity of hyperkalemia can be increased when Nitrofurantoin is combined with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Nitrofurantoin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Nitrofurantoin which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Do not take magnesium at the same time.
  • Take with food since it increases bioavailability and reduces irritation.

References

Synthesis Reference

Tara Bielski, Kerry Benson, "Novel orally administrable formulation of nitrofurantoin and a method for preparing said formulation." U.S. Patent US20050202079, issued September 15, 2005.

US20050202079
General References
  1. Mannisto PT, Lamminsivu U: Nitrofurantoin is highly bound to plasma protein. J Antimicrob Chemother. 1982 Apr;9(4):327-8. doi: 10.1093/jac/9.4.327. [PubMed:7085535]
  2. McOsker CC, Fitzpatrick PM: Nitrofurantoin: mechanism of action and implications for resistance development in common uropathogens. J Antimicrob Chemother. 1994 May;33 Suppl A:23-30. doi: 10.1093/jac/33.suppl_a.23. [PubMed:7928834]
  3. Novelli A, Rosi E: Pharmacological properties of oral antibiotics for the treatment of uncomplicated urinary tract infections. J Chemother. 2017 Dec;29(sup1):10-18. doi: 10.1080/1120009X.2017.1380357. [PubMed:29271734]
  4. Gupta K, Hooton TM, Stamm WE: Increasing antimicrobial resistance and the management of uncomplicated community-acquired urinary tract infections. Ann Intern Med. 2001 Jul 3;135(1):41-50. doi: 10.7326/0003-4819-135-1-200107030-00012. [PubMed:11434731]
  5. Rosenberg HA, Bates TR: The influence of food on nitrofurantoin bioavailability. Clin Pharmacol Ther. 1976 Aug;20(2):227-32. doi: 10.1002/cpt1976202227. [PubMed:7376]
  6. Niazi S, Vishnupad KS, Veng-Pedersen P: Absorption and disposition characteristics of nitrofurantoin in dogs. Biopharm Drug Dispos. 1983 Jul-Sep;4(3):213-23. [PubMed:6626697]
  7. Hoener B, Patterson SE: Nitrofurantoin disposition. Clin Pharmacol Ther. 1981 Jun;29(6):808-16. doi: 10.1038/clpt.1981.115. [PubMed:7226713]
  8. FDA Approved Drug Products: Macrocrystalline Nitrofurantoin Oral Capsule [Link]
  9. FDA Approved Drug Products: Nitrofurantoin and Macrocrystalline Nitrofurantoin Oral Capsule [Link]
  10. FDA Approved Drug Products: Nitrofurantoin Oral Suspension [Link]
  11. FDA Approved Drug Products: Nitrofurantoin Oral Tablet [Link]
External Links
KEGG Drug
D00439
KEGG Compound
C07268
PubChem Compound
6604200
PubChem Substance
46504447
ChemSpider
5036498
BindingDB
57045
ChEBI
71415
ChEMBL
CHEMBL572
Therapeutic Targets Database
DAP000998
PharmGKB
PA450640
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Nitrofurantoin
ATC Codes
J01XE01 — NitrofurantoinJ01XE51 — Nitrofurantoin, combinations
AHFS Codes
  • 08:36.00 — Urinary Anti-infectives
FDA label
Download (923 KB)
MSDS
Download (73.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingPreventionComplications of Surgical Procedures1
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableHealthy Volunteers3
2CompletedTreatmentCystitis / Uncomplicated Urinary Tract Infections1
2CompletedTreatmentUrinary Tract Infection1
3RecruitingPreventionChronic Kidney Disease (CKD) / Renal Hypodysplasia, Nonsyndromic, 1 / Vesicoureteral Reflux1
3RecruitingTreatmentBacterial Infections1
4Active Not RecruitingTreatmentCystitis / Urinary Tract Infection1
4CompletedPreventionCalcium Nephrolithiasis / Urinary Tract Infection1
4CompletedPreventionCatheter-Associated Urinary Tract Infection1
4CompletedPreventionPelvic Organ Prolapse (POP)1
4CompletedPreventionUrinary Tract Infection1
4CompletedPreventionUrinary Tract Infection: [Site Not Specified] or [Recurrent] / Urinary Tract Infections, Recurrent1
4CompletedTreatmentPost-Operative Urinary Tract Infection in Patients Undergoing Placement of a Sub-Urethral Sling for the Treatment of Stress Urinary Incontinence / Stress Urinary Incontinence (SUI)1
4CompletedTreatmentUncomplicated Bacterial Cystitis1
4CompletedTreatmentUrinary Tract Infection1
4Enrolling by InvitationPreventionKidney Stones1
4RecruitingHealth Services ResearchAntibiotic Resistant Infection / Uncomplicated Urinary Tract Infections1
4RecruitingPreventionKidney Stones1
4WithdrawnTreatmentCystitis1
4WithdrawnTreatmentUrinary Tract Infection1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableNight Wetting and Day Wetting, Menstruation's Disorders, Urolithiasis, Defects of Urinary / System and Hematuria / The Follow-up Duration Was 1-8 Years / The Main Reasons Behind Visiting the Hospital Were Recurrent Urinary Tract Infection / Urinary Urgencies, Pollakiuria, Difficulty in Initiating Micturition, Pain in Hypogastrium1
Not AvailableCompletedTreatmentComplications, Pregnancy1
Not AvailableRecruitingPreventionCalcium Nephrolithiasis / Sepsis / Urinary Tract Infection1
Not AvailableTerminatedTreatmentBacteriuria (Asymptomatic) in Pregnancy1
Not AvailableTerminatedTreatmentUrinary Tract Infection1
Not AvailableUnknown StatusNot AvailableAsymptomatic Infections / Bacteriuria / Transplantation Infection / Urinary Tract Infection1

Pharmacoeconomics

Manufacturers
  • Watson laboratories inc
  • Shionogi pharma inc
  • Procter and gamble pharmaceuticals inc sub procter and gamble co
  • Lannett co inc
  • Elkins sinn div ah robins co inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Sandoz inc
  • Whiteworth towne paulsen inc
  • Alvogen inc
  • Mylan pharmaceuticals inc
Packagers
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Buffalo Molasses LLC
  • Caremark LLC
  • Central Texas Community Health Centers
  • Comprehensive Consultant Services Inc.
  • Direct Dispensing Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • Gallipot
  • Goldline Laboratories Inc.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Liberty Pharmaceuticals
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Norwich Pharmaceuticals Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Promex Medical Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Sciele Pharma Inc.
  • Scruggs Pharmacal Co. Inc.
  • Shionogi Pharma Inc.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Warner Chilcott Co. Inc.
  • Watson Pharmaceuticals
  • WC Pharmaceuticals
Dosage forms
FormRouteStrength
SuspensionOral25 mg/5mL
CapsuleOral
CapsuleOral100 mg
CapsuleOral100 mg/1
CapsuleOral25 mg/1
CapsuleOral25 mg
CapsuleOral50 mg/1
TabletOral
PowderNot applicable1 kg/1kg
TabletOral100 mg
TabletOral50 mg
SuspensionOral
CapsuleOral
Prices
Unit descriptionCostUnit
Macrobid 100 mg capsule3.02USD capsule
Macrodantin 100 mg capsule2.67USD capsule
Furadantin 25 mg/5ml Suspension2.22USD ml
Furadantin 25 mg/5 ml susp2.13USD ml
Nitrofurantoin powder2.13USD g
Nitrofurantoin Monohyd Macro 100 mg capsule2.12USD capsule
Nitrofurantoin mono-mcr 100 mg2.04USD each
Nitrofurantoin-macro 100 mg2.04USD each
Nitrofurantoin Macrocrystal 100 mg capsule1.88USD capsule
Nitrofurantoin mcr 100 mg capsule1.86USD capsule
Macrodantin 50 mg capsule1.67USD capsule
Macrodantin 25 mg capsule1.3USD capsule
Nitrofurantoin Macrocrystal 50 mg capsule1.14USD capsule
Nitrofurantoin mcr 50 mg capsule1.09USD capsule
Macrobid 100 mg Capsule (Macrocrystals/Monohydrate)0.78USD capsule
Novo-Furantoin 100 mg Capsule (Macrocrystals)0.66USD capsule
Novo-Furantoin 50 mg Capsule (Macrocrystals)0.35USD capsule
Apo-Nitrofurantoin 100 mg Tablet0.23USD tablet
Apo-Nitrofurantoin 50 mg Tablet0.17USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)223-228Gever, G.; U.S. Patent 2,802,002; August 6, 1957; assigned to The Norwich Pharmacal Co.
water solubility79.5 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.47HANSCH,C ET AL. (1995)
pKa7.2SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.415 mg/mLALOGPS
logP0.03ALOGPS
logP-0.22ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.23ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area118.05 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.11 m3·mol-1ChemAxon
Polarizability20.49 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9832
Blood Brain Barrier+0.958
Caco-2 permeable-0.575
P-glycoprotein substrateNon-substrate0.6374
P-glycoprotein inhibitor INon-inhibitor0.8661
P-glycoprotein inhibitor IINon-inhibitor0.9834
Renal organic cation transporterNon-inhibitor0.8835
CYP450 2C9 substrateNon-substrate0.8373
CYP450 2D6 substrateNon-substrate0.8757
CYP450 3A4 substrateSubstrate0.5799
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9069
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8943
Ames testAMES toxic0.9231
CarcinogenicityNon-carcinogens0.8869
BiodegradationReady biodegradable0.7448
Rat acute toxicity2.5717 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7981
hERG inhibition (predictor II)Non-inhibitor0.94
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azolidines
Sub Class
Imidazolidines
Direct Parent
Hydantoins
Alternative Parents
Alpha amino acids and derivatives / Nitroaromatic compounds / Nitrofurans / Semicarbazones / Dicarboximides / Heteroaromatic compounds / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Oxacyclic compounds
show 6 more
Substituents
Hydantoin / Alpha-amino acid or derivatives / Nitroaromatic compound / 2-nitrofuran / Semicarbazone / Dicarboximide / Furan / Heteroaromatic compound / Semicarbazide / C-nitro compound
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organooxygen heterocyclic antibiotic, organonitrogen heterocyclic antibiotic, imidazolidine-2,4-dione, nitrofuran antibiotic (CHEBI:71415)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Potentiator
General Function
Thiamine pyrophosphate binding
Specific Function
Oxidoreductase required for the transfer of electrons from pyruvate to flavodoxin.
Gene Name
ydbK
Uniprot ID
P52647
Uniprot Name
Probable pyruvate-flavodoxin oxidoreductase
Molecular Weight
128823.205 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. Breeze AS, Obaseiki-Ebor EE: Nitrofuran reductase activity in nitrofurantoin-resistant strains of Escherichia coli K12: some with chromosomally determined resistance and others carrying R-plasmids. J Antimicrob Chemother. 1983 Dec;12(6):543-7. [PubMed:6363380]
  4. Sisson G, Goodwin A, Raudonikiene A, Hughes NJ, Mukhopadhyay AK, Berg DE, Hoffman PS: Enzymes associated with reductive activation and action of nitazoxanide, nitrofurans, and metronidazole in Helicobacter pylori. Antimicrob Agents Chemother. 2002 Jul;46(7):2116-23. [PubMed:12069963]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Potentiator
General Function
Oxidoreductase activity, acting on nad(p)h, nitrogenous group as acceptor
Specific Function
Reduction of nitroaromatic compounds using NADH. Reduces nitrofurazone by a ping-pong bi-bi mechanism possibly to generate a two-electron transfer product. Major component of the oxygen-insensitive...
Gene Name
nfsA
Uniprot ID
P17117
Uniprot Name
Oxygen-insensitive NADPH nitroreductase
Molecular Weight
26800.375 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. Kutty R, Bennett GN: Biochemical characterization of trinitrotoluene transforming oxygen-insensitive nitroreductases from Clostridium acetobutylicum ATCC 824. Arch Microbiol. 2005 Nov;184(3):158-67. Epub 2005 Nov 10. [PubMed:16187099]
  4. Lightfoot RT, Shuman D, Ischiropoulos H: Oxygen-insensitive nitroreductases of Escherichia coli do not reduce 3-nitrotyrosine. Free Radic Biol Med. 2000 Apr 1;28(7):1132-6. [PubMed:10832075]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Trna binding
Specific Function
Involved in the binding of tRNA to the ribosomes.
Gene Name
rpsJ
Uniprot ID
P0A7R5
Uniprot Name
30S ribosomal protein S10
Molecular Weight
11735.47 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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name
POR
Uniprot ID
P16435
Uniprot Name
NADPH--cytochrome P450 reductase
Molecular Weight
76689.12 Da
References
  1. Wang Y, Gray JP, Mishin V, Heck DE, Laskin DL, Laskin JD: Role of cytochrome P450 reductase in nitrofurantoin-induced redox cycling and cytotoxicity. Free Radic Biol Med. 2008 Mar 15;44(6):1169-79. doi: 10.1016/j.freeradbiomed.2007.12.013. Epub 2007 Dec 23. [PubMed:18206659]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Perez M, Real R, Mendoza G, Merino G, Prieto JG, Alvarez AI: Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones. J Vet Pharmacol Ther. 2009 Oct;32(5):498-502. doi: 10.1111/j.1365-2885.2008.01050.x. [PubMed:19754918]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Feinshtein V, Holcberg G, Amash A, Erez N, Rubin M, Sheiner E, Polachek H, Ben-Zvi Z: Nitrofurantoin transport by placental choriocarcinoma JAr cells: involvement of BCRP, OATP2B1 and other MDR transporters. Arch Gynecol Obstet. 2010 Jun;281(6):1037-44. doi: 10.1007/s00404-009-1286-7. Epub 2009 Nov 19. [PubMed:19924425]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Feinshtein V, Holcberg G, Amash A, Erez N, Rubin M, Sheiner E, Polachek H, Ben-Zvi Z: Nitrofurantoin transport by placental choriocarcinoma JAr cells: involvement of BCRP, OATP2B1 and other MDR transporters. Arch Gynecol Obstet. 2010 Jun;281(6):1037-44. doi: 10.1007/s00404-009-1286-7. Epub 2009 Nov 19. [PubMed:19924425]

Drug created on June 13, 2005 07:24 / Updated on November 16, 2019 10:27