Drug Information

Drug (ID: DG00647) and It's Reported Resistant Information

• Name: Nitrofurantoin
• Synonyms: Nitrofurantoin; 67-20-9; Furadantin; 5-Nitrofurantoin; Furadonine; Furadantine; Furadantoin; Furadoine; Furadontin; Furantoin; Nifurantin; Nitrofuradantin; Nitrofurantoine; Berkfurin; Chemiofuran; Furachel; Furadonin; Furatoin; Furobactina; Macrobid; Novofuran; Orafuran; Parfuran; Trantoin; Urantoin; Urofurin; Welfurin; Zoofurin; Cyantin; Cystit; Furalan; Furina; Ituran; Nitoin; Urizept; Urodin; Urolong; Furadantine mc; Uro-Tablinen; Fur-ren; Macrodantin; Macrofuran; Nitrofurantoina; Benkfuran; Dantafur; Furaloid; Nierofu; Macpac; Nitrex; Nitrofurantoinum; Fua Med; N-Toin; Usaf ea-2; 1-(5-Nitro-2-furfurylideneamino)hydantoin; N-(5-Nitrofurfurylidene)-1-aminohydantoin; NITROFURANTOIN, MACROCRYSTALLINE; N-(5-Nitro-2-furfurylidene)-1-aminohydantoin; 1-((5-Nitrofurfurylidene)amino)hydantoin; 1-[(5-Nitrofurfurylidene)amino]hydantoin; 1-(5-Nitro-2-furfurylidenamino)hydantoin; NCI-C55196; NSC 2107; NSC 44150; N-(5-Nitro-2-furfurylideno)-1-aminohydantoina; UNII-927AH8112L; Nitrofurantoin anhydrous; Furadoninum; Nitrofurantoin macrocrystal; 1-(((5-Nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione; 1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione; Nitrofurantoin, macrocrystals; MLS000028500; Cistofuran; Macrodantina; Macrofurin; Nifuretten; Alfuran; Berkfuran; Ceduran; Furabid; Furedan; Gerofuran; Phenurin; Siraliden; Uerineks; Urofuran; Urolisa; CHEBI:71415; Hydantoin, 1-((5-nitrofurfurylidene)amino)-; PiyEloseptyl; 1-[[(5-Nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione; Furadantina MC; Furadantine-MC; Furophen T; Nitrofur-C; Ro-Antoin; Furadantin Retard; Uro-Selz; Ivadantin; MFCD00003224; 927AH8112L; SMR000058271; 1-(((5-Nitrofuran-2-yl)methylene)-amino)imidazolidine-2,4-dione; 1-{[(1E)-(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione; Nitrofurantoina [DCIT]; 2,4-Imidazolidinedione, 1-[[(5-nitro-2-furanyl)methylene]amino]-; Nitrofurantoine [INN-French]; Nitrofurantoinum [INN-Latin]; Furodantin; 2,4-Imidazolidinedione, 1-(((5-nitro-2-furanyl)methylene)amino)-; Fuamed; NSC-2107; 1-{[(E)-(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione; Furadantin (TN); Macrobid (TN); CCRIS 1192; Hydantoin, 1-[(5-nitrofurfurylidene)amino]-; HSDB 3135; SR-05000001681; EINECS 200-646-5; NITROFURANTOIN MACROCRYSTALLINE; NSC2107; Furantoina; Furadoin; Furadoxyl; Uvamin; N-(5-Nitro-2-furfurylideno)-1-aminohydantoina [Polish]; NSC44150; 1-[[(5-nitrofuran-2-yl)methylene]amino]imidazolidine-2,4-dione; AI3-26388; Nitrofurantoin (JAN/USP/INN); Furophen T-Caps; NCGC00091505-01; NCGC00091505-07; Prestwick_358; Nitrofurantoin Macro; 5-Nitrofurantoindorn; J01XE01; Nitrofurantoin [USP:INN:BAN:JAN]; ND-3320; ND-7248; Nitrofurantoin, 97%; Nitrofurantoinum anhydrous; Prestwick2_000168; Prestwick3_000168; Spectrum5_001367; Nitrofurantoin, crystalline; CHEMBL572; Nitrofurantoin Macrocrystals; cid_4509; SCHEMBL29470; SCHEMBL29472; BSPBio_000035; BSPBio_002073; BIDD:GT0181; SPECTRUM1500433; BPBio1_000039; BDBM57045; CHEBI:95222; HMS500L06; HMS1568B17; HMS1920P21; HMS2091H16; HMS2095B17; HMS3712B17; Pharmakon1600-01500433; 1-[(E)-(5-nitro-2-furyl)methyleneamino]imidazolidine-2,4-dione; HY-A0090; ZINC7997568; 2,4-Imidazolidenedione, 1-(((5-nitro-2-furanyl)methylene)amino)-; CCG-40108; NSC757243; s4536; STK009471; STL454163; AKOS001678301; DB00698; NSC-757243; IDI1_000224; NCGC00091505-03; NCGC00091505-04; NCGC00091505-05; NCGC00091505-06; NCGC00091505-08; NCGC00091505-09; NCGC00091505-10; LS-13402; 1-((5-nitrofurfurylidene)amino)-hydantoin; SBI-0051457.P003; AB00513815; BB 0310231; N0883; A16008; C07268; D00439; J10193; AB00052052_03; A835659; Hydantoin, n-(5-nitro-2-furfurylidene)-1-amino-; Nitrofurantoin, VETRANAL(TM), analytical standard; Q-201479; SR-05000001681-1; SR-05000001681-2; SR-05000001681-3; SR-05000001681-4; BRD-K76927775-001-05-0; Nitrofurantoin, Antibiotic for Culture Media Use Only; Hydantoin, 1-[(5-nitrofurfurylidene)amino]- (7CI,8CI); 1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione; 1-{[(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione; (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione; 1-([(5-Nitro-2-furyl)methylidene]amino)-2,4-imidazolidinedione #; 1-[(E)-(5-nitro-2-furanyl)methylideneamino]imidazolidine-2,4-dione; 1-{[(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione; Nitrofurantoin, United States Pharmacopeia (USP) Reference Standard; 1-{[(E)-1-(5-nitro-2-furyl)methylidene]amino}-1H-imidazole-2,4(3H,5H)-dione; 4-hydroxy-1-{[(E)-(5-nitrofuran-2-yl)methylidene]amino}-1,5-dihydro-2H-imidazol-2-one; N-(5-Nitro-2-furfurylidine)-1-aminohydantoin; N-(5-Nitrofurfurylidene)-1aminohydantoin; Nitrofurantoin, Pharmaceutical Secondary Standard; Certified Reference Material; 178170-37-1
• Indication:
  In total 1 Indication(s)
  Urinary tract infection [ICD-11: GC08]; Approved; [1]
• Drug Resistance Disease(s):
  Disease(s) with Clinically Reported Resistance for This Drug (2 diseases)
  Tissue pyogenic bacterial infection [ICD-11: 1B7Y]; [1]
  Urinary tract infection [ICD-11: GC08]; [2]
• Target: Bacterial Deoxyribonucleic acid (Bact DNA); NOUNIPROTAC; [1]
• Formula: C8H6N4O5
• IsoSMILES: C1C(=O)NC(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-]
• 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+
• InChIKey: NXFQHRVNIOXGAQ-YCRREMRBSA-N
• PubChem CID: 6604200
• ChEBI ID: CHEBI:71415
• TTD Drug ID: D0R0BX
• VARIDT ID: DR00886
• INTEDE ID: DR1169
• DrugBank ID: DB00698

Type(s) of Resistant Mechanism of This Drug

  IDUE: Irregularity in Drug Uptake and Drug Efflux

Drug Resistance Data Categorized by Their Corresponding Diseases

ICD-01: Infectious/parasitic diseases

Tissue pyogenic bacterial infection [ICD-11: 1B7Y]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Irregularity in Drug Uptake and Drug Efflux (IDUE)

Key Molecule: Multidrug resistance protein 1 (ABCB1) [1]

• Molecule Alteration: Expression; Up-regulation
• Resistant Disease: Staphylococcus infection [ICD-11: 1B7Y.3]
• Experimental Note: Identified from the Human Clinical Data
• In Vitro Model: Pseudomonas aeruginosa isolates; 287
• In Vitro Model: Staphylococcus aureus isolates; 1280
• In Vitro Model: Klebsiella pneumoniae isolates; 573
• In Vitro Model: Acinetobacter isolates; 469
• In Vitro Model: Enterobacter cloacae isolates; 550
• Experiment for Drug Resistance: Disk diffusion method assay
• Mechanism Description: Up-regulation of P-glycoprotein led to nitrofurantoin resistance in the staphylococcus infection.

References

• Ref 1: Pathogen characteristics reveal novel antibacterial approaches for interstitial lung disease .Pulm Pharmacol Ther. 2014 Dec;29(2):250-4. doi: 10.1016/j.pupt.2014.03.005. Epub 2014 Apr 1. 10.1016/j.pupt.2014.03.005
• Ref 2: Resistance to nitrofurantoin is an indicator of extensive drug-resistant (XDR) Enterobacteriaceae .J Med Microbiol. 2021 Apr;70(4). doi: 10.1099/jmm.0.001347. 10.1099/jmm.0.001347