Identification
- Summary
Nitrofurantoin is an antibiotic used to treat urinary tract infections.
- Brand Names
- Furadantin, Macrobid, Macrodantin
- Generic Name
- Nitrofurantoin
- DrugBank Accession Number
- DB00698
- Background
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
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Nitrofurantoin (DB00698)
- Weight
- Average: 238.159
Monoisotopic: 238.033819309 - Chemical Formula
- C8H6N4O5
- 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
Pharmacology
- Indication
Nitrofurantoin is indicated to treat acute uncomplicated urinary tract infections.8,9,10
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- Contraindications & Blackbox Warnings
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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
Target Actions Organism AProbable pyruvate-flavodoxin oxidoreductase potentiatorEscherichia coli (strain K12) AOxygen-insensitive NADPH nitroreductase potentiatorEscherichia coli (strain K12) U30S ribosomal protein S10 inhibitorEscherichia coli (strain K12) - 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
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- 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
- Adverse Effects
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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
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Glucose-6-phosphate 1-dehydrogenase Villeurbanne Not Available 1000_1002delACC ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Torun Not Available 1006A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sunderland Not Available 105_107delCAT ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Iwatsuki Not Available 1081G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Serres Not Available 1082C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tondela Not Available 1084_1101delCTGAACGAGCGCAAGGCC ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Loma Linda Not Available 1089C->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Aachen Not Available 1089C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tenri Not Available 1096A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Montpellier Not Available 1132G>A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Calvo Mackenna Not Available 1138A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Riley Not Available 1139T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Olomouc Not Available 1141T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tomah Not Available 1153T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Lynwood Not Available 1154G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Madrid Not Available 1155C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Iowa, Walter Reed, Springfield Not Available 1156A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Beverly Hills, Genova, Iwate, Niigata, Yamaguchi Not Available 1160G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Hartford Not Available 1162A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Praha Not Available 1166A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Krakow Not Available 1175T>C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Wisconsin Not Available 1177C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nashville, Anaheim, Portici Not Available 1178G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Alhambra Not Available 1180G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bari Not Available 1187C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Puerto Limon Not Available 1192G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Covao do Lobo Not Available 1205C>A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Clinic Not Available 1215G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Utrecht Not Available 1225C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Suwalki Not Available 1226C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Riverside Not Available 1228G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Japan, Shinagawa Not Available 1229G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kawasaki Not Available 1229G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Munich Not Available 1231A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Georgia Not Available 1284C->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sumare Not Available 1292T->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Telti/Kobe Not Available 1318C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Santiago de Cuba, Morioka Not Available 1339G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Harima Not Available 1358T->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Figuera da Foz Not Available 1366G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Amiens Not Available 1367A>T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Noi Not Available 1376G->T, 1502T->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Fukaya Not Available 1462G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Campinas Not Available 1463G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Buenos Aires Not Available 1465C>T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Arakawa Not Available 1466C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Brighton Not Available 1488_1490delGAA ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kozukata Not Available 159G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Amsterdam Not Available 180_182delTCT ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase No name Not Available 202G->A, 376A->G, 1264C>G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Swansea Not Available 224T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Urayasu Not Available 281_283delAGA ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Vancouver Not Available 317C->G544C->T592C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mt Sinai Not Available 376A->G, 1159C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Plymouth Not Available 488G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Volendam Not Available 514C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Shinshu Not Available 527A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Chikugo Not Available 535A->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tsukui Not Available 561_563delCTC ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Pedoplis-Ckaro Not Available 573C>G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Santiago Not Available 593G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Minnesota, Marion, Gastonia, LeJeune Not Available 637G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Cincinnati Not Available 637G->T, 1037A->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Harilaou Not Available 648T->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase North Dallas Not Available 683_685delACA ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Asahikawa Not Available 695G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Durham Not Available 713A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Stonybrook Not Available 724_729delGGCACT ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Wayne Not Available 769C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Aveiro Not Available 806G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Cleveland Corum Not Available 820G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Lille Not Available 821A>T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Not Available 825G>C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sugao Not Available 826C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase La Jolla Not Available 832T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Wexham Not Available 833C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Piotrkow Not Available 851T>C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase West Virginia Not Available 910G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Omiya Not Available 921G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nara Not Available 953_976delCCACCAAAGGGTACCTGGAC GACC ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Manhattan Not Available 962G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Rehevot Not Available 964T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Honiara Not Available 99A->G / 1360C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Tokyo, Fukushima Not Available 1246G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Chatham Not Available 1003G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Fushan Not Available 1004C->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Partenope Not Available 1052G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ierapetra Not Available 1057C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Anadia Not Available 1193A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Abeno Not Available 1220A->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Surabaya Not Available 1291G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Pawnee Not Available 1316G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase S. Antioco Not Available 1342A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Cassano Not Available 1347G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Hermoupolis Not Available 1347G->C / 1360C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Union,Maewo, Chinese-2, Kalo Not Available 1360C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Andalus Not Available 1361G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Cosenza Not Available 1376G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Canton, Taiwan- Hakka, Gifu-like, Agrigento-like Not Available 1376G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Flores Not Available 1387C->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kaiping, Anant, Dhon, Sapporo-like, Wosera Not Available 1388G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kamogawa Not Available 169C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Costanzo Not Available 179T>C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Amazonia Not Available 185C->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Songklanagarind Not Available 196T->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Hechi Not Available 202G->A / 871G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Namouru Not Available 208T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bao Loc Not Available 352T>C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Crispim Not Available 375G->T, 379G->T383T->C384C>T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Acrokorinthos Not Available 376A->G / 463C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Santa Maria Not Available 376A->G / 542A->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ananindeua Not Available 376A->G / 871G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Vanua Lava Not Available 383T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Valladolid Not Available 406C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Belem Not Available 409C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Liuzhou Not Available 442G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Shenzen Not Available 473G>A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Taipei ‚ÄúChinese- 3‚Äù Not Available 493A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Toledo Not Available 496C>T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Naone Not Available 497G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nankang Not Available 517T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Miaoli Not Available 519C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mediterranean, Dallas, Panama‚ Sassari, Cagliari, Birmingham Not Available 563C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Coimbra Shunde Not Available 592C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nilgiri Not Available 593G>A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Radlowo Not Available 679C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Roubaix Not Available 811G>C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Haikou Not Available 835A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Chinese-1 Not Available 835A->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mizushima Not Available 848A>G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Osaka Not Available 853C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Viangchan, Jammu Not Available 871G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Seoul Not Available 916G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ludhiana Not Available 929G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Farroupilha Not Available 977C->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Chinese-5 Not Available 1024C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Rignano Not Available 130G>A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Orissa Not Available 131C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase G6PDNice Not Available 1380G>C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kamiube, Keelung Not Available 1387C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Neapolis Not Available 1400C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Aures Not Available 143T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Split Not Available 1442C->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kambos Not Available 148C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Palestrina Not Available 170G>A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Metaponto Not Available 172G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Musashino Not Available 185C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Asahi Not Available 202G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase A- (202), Ferrara I Not Available 202G->A / 376A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Murcia Oristano Not Available 209A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ube Konan Not Available 241C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Lagosanto Not Available 242G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Guangzhou Not Available 274C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Hammersmith Not Available 323T->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sinnai Not Available 34G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase A- (680) Not Available 376A->G / 680G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase A- (968), Betica,Selma, Guantanamo Not Available 376A->G / 968T->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Salerno Pyrgos Not Available 383T>G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Quing Yan Not Available 392G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Lages Not Available 40G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Ilesha Not Available 466G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mahidol Not Available 487G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Malaga Not Available 542A->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Sibari Not Available 634A->G ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Mexico City Not Available 680G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Nanning Not Available 703C->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Seattle, Lodi, Modena, Ferrara II, Athens-like Not Available 844G->C ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Bajo Maumere Not Available 844G->T ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Montalbano Not Available 854G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Kalyan-Kerala, Jamnaga, Rohini Not Available 949G->A ADR Inferred Increased risk of hemolytic anemia. Details Glucose-6-phosphate 1-dehydrogenase Gaohe Not Available 95A->G ADR Inferred Increased 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Nitrofurantoin may decrease the excretion rate of Abacavir which could result in a higher serum level. Abemaciclib Abemaciclib may decrease the excretion rate of Nitrofurantoin which could result in a higher serum level. Acebutolol The risk or severity of hyperkalemia can be increased when Nitrofurantoin is combined with Acebutolol. Aceclofenac The risk or severity of hyperkalemia can be increased when Nitrofurantoin is combined with Aceclofenac. Acemetacin The risk or severity of hyperkalemia can be increased when Nitrofurantoin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Nitrofurantoin is combined with Acenocoumarol. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Nitrofurantoin. Acetazolamide Acetazolamide may increase the excretion rate of Nitrofurantoin which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid The risk or severity of hyperkalemia can be increased when Nitrofurantoin is combined with Acetylsalicylic acid. Aclidinium Nitrofurantoin may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take with food. Food decreases irritation and increases bioavailability.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Nitrofurantoin monohydrate E1QI2CQQ1I 17140-81-7 NHBPVLAHAVEISO-JSGFVSQVSA-N Nitrofurantoin sodium MAL9M0T5LV 54-87-5 AFDJQFFKYDCYIG-JSGFVSQVSA-M - Product Images
- International/Other Brands
- Furabid (Goldshield) / Niftran / Siraliden / Urantoin (Basel) / Urolong (Thiemann)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Furadantin Suspension 25 mg/5mL Oral Casper Pharma Llc 2020-12-23 Not applicable US 
Furadantin Suspension 50 mg/5mL Oral Casper Pharma Llc 2023-06-09 Not applicable US Furadantin Suspension 25 mg/5mL Oral SHIONOGI INC. 1953-12-23 2017-07-31 US Macrobid Capsule 100 mg Oral Allergan 1993-12-31 2021-08-12 Canada 
Macrodantin Capsule 25 mg / cap Oral Alza 1993-12-31 1999-08-06 Canada Macrodantin Capsule 50 mg/1 Oral Procter & Gamble Pharmaceuticals 2009-03-23 Not applicable US Macrodantin Capsule 50 mg/1 Oral Almatica Pharma LLC 2010-09-27 Not applicable US Macrodantin Capsule 25 mg/1 Oral Procter & Gamble Pharmaceuticals 2009-03-23 Not applicable US 
Macrodantin Capsule 100 mg/1 Oral Procter & Gamble Pharmaceuticals 2009-03-23 Not applicable US Macrodantin Capsule 25 mg/1 Oral Almatica Pharma LLC 2010-09-27 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Auro-nitrofurantoin Bid Capsule 100 mg Oral Auro Pharma Inc 2017-10-23 Not applicable Canada Jamp Nitrofurantoin Capsule 50 mg Oral Jamp Pharma Corporation Not applicable Not applicable Canada Jamp Nitrofurantoin Capsule 100 mg Oral Jamp Pharma Corporation Not applicable Not applicable Canada Nitrofurantion Capsule 100 mg/1 Oral A-S Medication Solutions 2016-04-15 Not applicable US Nitrofurantion Capsule 50 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2016-04-15 Not applicable US Nitrofurantion Capsule 100 mg/1 Oral Quality Care Products, LLC 2021-01-04 Not applicable US Nitrofurantion Capsule 100 mg/1 Oral Proficient Rx LP 2016-04-15 Not applicable US Nitrofurantion Capsule 100 mg/1 Oral Nucare Pharmaceuticals,inc. 2016-04-15 Not applicable US Nitrofurantion Capsule 50 mg/1 Oral bryant ranch prepack 2016-04-15 Not applicable US Nitrofurantion Capsule 100 mg/1 Oral NuCare Pharmaceuticals Industries, Inc. 2016-04-15 2019-12-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Macrobid Nitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1) Capsule Oral Central Texas Community Health Centers 2011-05-31 Not applicable US Macrobid Nitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1) Capsule Oral Physicians Total Care, Inc. 1991-12-24 2010-06-30 US Macrobid Nitrofurantoin monohydrate (75 mg/1) + Nitrofurantoin (25 mg/1) Capsule Oral Procter and Gamble Pharmaceuticals, Inc. 2009-03-23 Not applicable US Macrobid Nitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1) Capsule Oral Almatica Pharma LLC 2011-05-31 Not applicable US Macrobid Nitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1) Capsule Oral REMEDYREPACK INC. 2020-01-08 Not applicable US Macrobid Nitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (80.7 mg/1) Capsule Oral Sunny Pharmtech Inc. 2018-01-01 2018-06-01 US Macrobid Nitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1) Capsule Oral Central Texas Community Health Centers 2011-05-31 Not applicable US Macrobid Nitrofurantoin monohydrate (75 mg/1) + Nitrofurantoin (25 mg/1) Capsule Oral Procter and Gamble Pharmaceuticals, Inc. 2009-03-23 Not applicable US Macrobid Nitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1) Capsule Oral REMEDYREPACK INC. 2020-01-08 Not applicable US Macrobid Nitrofurantoin (25 mg/1) + Nitrofurantoin monohydrate (75 mg/1) Capsule Oral Almatica Pharma LLC 2011-05-31 Not applicable US
Categories
- ATC Codes
- J01XE01 — Nitrofurantoin
- J01XE — Nitrofuran derivatives
- J01X — OTHER ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Agents causing hyperkalemia
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- BCRP/ABCG2 Substrates
- BSEP/ABCB11 Substrates
- Drugs that are Mainly Renally Excreted
- Furans
- Methemoglobinemia Associated Agents
- Nitro Compounds
- Nitrofuran Antibacterial
- Nitrofuran Derivatives
- Nitrofurans
- P-glycoprotein substrates
- Renal Agents
- Thyroxine-binding globulin substrates
- Chemical TaxonomyProvided by Classyfire
- 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
- 2-nitrofuran / Allyl-type 1,3-dipolar organic compound / Alpha-amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / C-nitro compound / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dicarboximide show 19 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organooxygen heterocyclic antibiotic, organonitrogen heterocyclic antibiotic, imidazolidine-2,4-dione, nitrofuran antibiotic (CHEBI:71415)
- Affected organisms
- Gram negative and gram positive bacteria
Chemical Identifiers
- UNII
- 927AH8112L
- CAS number
- 67-20-9
- 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
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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Rosenberg HA, Bates TR: The influence of food on nitrofurantoin bioavailability. Clin Pharmacol Ther. 1976 Aug;20(2):227-32. doi: 10.1002/cpt1976202227. [Article]
- 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. [Article]
- Hoener B, Patterson SE: Nitrofurantoin disposition. Clin Pharmacol Ther. 1981 Jun;29(6):808-16. doi: 10.1038/clpt.1981.115. [Article]
- FDA Approved Drug Products: Macrocrystalline Nitrofurantoin Oral Capsule [Link]
- FDA Approved Drug Products: Nitrofurantoin and Macrocrystalline Nitrofurantoin Oral Capsule [Link]
- FDA Approved Drug Products: Nitrofurantoin Oral Suspension [Link]
- 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
- 235559
- ChEBI
- 71415
- ChEMBL
- CHEMBL572
- ZINC
- ZINC000003875368
- Therapeutic Targets Database
- DAP000998
- PharmGKB
- PA450640
- PDBe Ligand
- U6Z
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Nitrofurantoin
- PDB Entries
- 7nb9
- FDA label
- Download (923 KB)
- MSDS
- Download (73.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Health Services Research Antibiotic Resistant Infection / Uncomplicated Urinary Tract Infections 1 4 Completed Prevention Catheter Associated Urinary Tract Infections 1 4 Completed Prevention Kidney Stones / Urinary Tract Infection 1 4 Completed Prevention Pelvic Organ Prolapse (POP) 1 4 Completed Prevention Urinary Tract Infection 1 4 Completed Prevention Urinary Tract Infections, Recurrent 1 4 Completed Treatment Irreversible Pulpitis (Toothache) / Postoperative pain 1 4 Completed Treatment Pain / Symptomatic Irreversible Pulpitis (SIP) 1 4 Completed Treatment Stress Urinary Incontinence (SUI) 1 4 Completed Treatment Uncomplicated Cystitis 1
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
Form Route Strength Capsule Oral 100.000 mg Suspension Oral 50 mg/5mL Capsule Oral Suspension Oral 0.5 % Tablet Oral 50 MG Suspension Oral 0.500 g Capsule Oral 85.000 mg Capsule Oral Capsule Oral 100 mg/1 Capsule Oral 25 mg/1 Capsule Oral 25 mg / cap Capsule Oral 50 mg/1 Capsule Oral 100 mg / cap Capsule Oral 50 mg / cap Tablet Oral 50 mg / tab Tablet, coated Oral 100 MG Tablet, coated Oral 20 MG Powder Not applicable 1 kg/1kg Suspension Oral 25 mg/5mL Tablet Oral Capsule, extended release Oral 100 MG Syrup Capsule, coated Oral 100 mg Capsule, coated Oral 50 mg Tablet Oral 100 mg / tab Suspension Oral 5 mg / mL Capsule Oral 100.00 mg Capsule Oral 50.000 mg Capsule Oral 100 mg Capsule Oral 50 mg Tablet Oral 100 mg - Prices
Unit description Cost Unit Macrobid 100 mg capsule 3.02USD capsule Macrodantin 100 mg capsule 2.67USD capsule Furadantin 25 mg/5ml Suspension 2.22USD ml Furadantin 25 mg/5 ml susp 2.13USD ml Nitrofurantoin powder 2.13USD g Nitrofurantoin Monohyd Macro 100 mg capsule 2.12USD capsule Nitrofurantoin mono-mcr 100 mg 2.04USD each Nitrofurantoin-macro 100 mg 2.04USD each Nitrofurantoin Macrocrystal 100 mg capsule 1.88USD capsule Nitrofurantoin mcr 100 mg capsule 1.86USD capsule Macrodantin 50 mg capsule 1.67USD capsule Macrodantin 25 mg capsule 1.3USD capsule Nitrofurantoin Macrocrystal 50 mg capsule 1.14USD capsule Nitrofurantoin mcr 50 mg capsule 1.09USD 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 Tablet 0.23USD tablet Apo-Nitrofurantoin 50 mg Tablet 0.17USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 223-228 Gever, G.; U.S. Patent 2,802,002; August 6, 1957; assigned to The Norwich Pharmacal Co. water solubility 79.5 mg/L (at 24 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -0.47 HANSCH,C ET AL. (1995) pKa 7.2 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.415 mg/mL ALOGPS logP 0.03 ALOGPS logP -0.22 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 8.23 Chemaxon pKa (Strongest Basic) -2.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 118.05 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 52.11 m3·mol-1 Chemaxon Polarizability 20.49 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9832 Blood Brain Barrier + 0.958 Caco-2 permeable - 0.575 P-glycoprotein substrate Non-substrate 0.6374 P-glycoprotein inhibitor I Non-inhibitor 0.8661 P-glycoprotein inhibitor II Non-inhibitor 0.9834 Renal organic cation transporter Non-inhibitor 0.8835 CYP450 2C9 substrate Non-substrate 0.8373 CYP450 2D6 substrate Non-substrate 0.8757 CYP450 3A4 substrate Substrate 0.5799 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9069 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8943 Ames test AMES toxic 0.9231 Carcinogenicity Non-carcinogens 0.8869 Biodegradation Ready biodegradable 0.7448 Rat acute toxicity 2.5717 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7981 hERG inhibition (predictor II) Non-inhibitor 0.94
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- The exact mechanisms of nitrofurantoin are not fully known, but its mechanism of action includes inhibiting bacterial DNA/RNA synthesis, which may involve this target.
- 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
- Squadrito FJ, del Portal D: Nitrofurantoin . [Article]
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
- 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. [Article]
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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:54