Details of the Drug

General Information of Drug (ID: DMSM2KE)

Drug Name
Nitrofurazone
Synonyms
nitrofurazone; Nitrofural; Furacilin; 59-87-0; Furacin; Furacillin; Furacine; Aldomycin; Furaldon; Nifuzon; Actin-N; Furacycline; Furacoccid; Otofuran; Nitrofurazan; Monafuracin; Furaziline; Furacinetten; Babrocid; Nitrozone; Mastofuran; Furazone; Chemofuran; Mammex; Amifur; Alfucin; Furesol; Furazol W; 5-Nitro-2-furaldehyde semicarbazone; Monofuracin; Dermofural; Monafuracis; Furaseptyl; Furatsilin; Nitrofurol; Fuvacillin; Furametral; Biofuracina; Becafurazone; Nifucin; Ibiofural; Hemofuran; Furalone; Furacort; Eldezol; Vadrocid; Vabrocid; Furazyme
Indication
Disease Entry ICD 11 Status REF
Skin burns ME65.0 Approved [1]
Bacterial infection 1A00-1C4Z Discontinued in Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 198.14
Logarithm of the Partition Coefficient (xlogp) 0.2
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Absorption
The drug is well absorbed []
Half-life
The concentration or amount of drug in body reduced by one-half in 5 hours [3]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Vitamin B complex deficiency Not Available TKT OTT5KPUB [4]
Chemical Identifiers
Formula
C6H6N4O4
IUPAC Name
[(E)-(5-nitrofuran-2-yl)methylideneamino]urea
Canonical SMILES
C1=C(OC(=C1)[N+](=O)[O-])/C=N/NC(=O)N
InChI
InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+
InChIKey
IAIWVQXQOWNYOU-FPYGCLRLSA-N
Cross-matching ID
PubChem CID
5447130
ChEBI ID
CHEBI:44368
CAS Number
59-87-0
DrugBank ID
DB00336
TTD ID
D0IE1E
INTEDE ID
DR1168
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial 30S ribosomal RNA (Bact 30S rRNA) TTOVFH2 NOUNIPROTAC Inhibitor [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [6]
NADPH-dependent oxidoreductase (nfrA) DE82GV7 NRFA_STAA8 Substrate [7], [8]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DE0QLUZ NFSB_ECOLI Substrate [9]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DEDPI65 NFSA_ECOLI Substrate [10]
NADPH-dependent nitroreductase (nfrA1) DE21PLI NFRA1_BACSU Substrate [11], [12]
Nitroreductase (NTR) DEUW4J0 A0A376H6M5_ENTGA Substrate [13]
Nitroreductase (NTR) DE3U2Y6 A0A377KR04_ENTCA Substrate [13]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [14]
Interleukin-1 beta (IL1B) OT0DWXXB IL1B_HUMAN Gene/Protein Processing [15]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [15]
Transketolase (TKT) OTT5KPUB TKT_HUMAN Drug Response [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800013595)
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
5 The antibiotic Furvina targets the P-site of 30S ribosomal subunits and inhibits translation initiation displaying start codon bias. Nucleic Acids Res. 2012 Nov 1;40(20):10366-74.
6 Nefazodone pharmacokinetics in depressed children and adolescents. J Am Acad Child Adolesc Psychiatry. 2000 Aug;39(8):1008-16.
7 Reduction of polynitroaromatic compounds: the bacterial nitroreductases. FEMS Microbiol Rev. 2008 May;32(3):474-500.
8 The human gut microbiota: metabolism and perspective in obesity. Gut Microbes. 2018 Jul 4;9(4):308-325.
9 Conversion of NfsB, a minor Escherichia coli nitroreductase, to a flavin reductase similar in biochemical properties to FRase I, the major flavin reductase in Vibrio fischeri, by a single amino acid substitution. J Bacteriol. 1996 Aug;178(15):4731-3.
10 Biochemical characterization of NfsA, the Escherichia coli major nitroreductase exhibiting a high amino acid sequence homology to Frp, a Vibrio harveyi flavin oxidoreductase. J Bacteriol. 1996 Aug;178(15):4508-14.
11 Conversion of NfsA, the major Escherichia coli nitroreductase, to a flavin reductase with an activity similar to that of Frp, a flavin reductase in Vibrio harveyi, by a single amino acid substitution. J Bacteriol. 1998 Jan;180(2):422-5.
12 Bacillus subtilis isolated from the human gastrointestinal tract. Res Microbiol. 2009 Mar;160(2):134-43.
13 Mechanism of metronidazole-resistance by isolates of nitroreductase-producing Enterococcus gallinarum and Enterococcus casseliflavus from the human intestinal tract. FEMS Microbiol Lett. 2003 Aug 29;225(2):195-200.
14 Mechanism of carcinogenesis induced by a veterinary antimicrobial drug, nitrofurazone, via oxidative DNA damage and cell proliferation. Cancer Lett. 2004 Nov 25;215(2):141-50. doi: 10.1016/j.canlet.2004.05.016.
15 Profiling the immunotoxicity of chemicals based on in vitro evaluation by a combination of the Multi-ImmunoTox assay and the IL-8 Luc assay. Arch Toxicol. 2018 Jun;92(6):2043-2054. doi: 10.1007/s00204-018-2199-7. Epub 2018 Mar 29.