Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1168)
Drug Name
Nitrofural
Synonyms
Actin-N; Aldomycin; Alfucin; Amifur; Babrocid; Becafurazone; Biofuracina; Chemofuran; Dermofural; Eldezol; Furacilin; Furacillin; Furacin; Furacine; Furacinetten; Furacoccid; Furacort; Furacycline; Furaldon; Furalone; Furametral; Furaseptyl; Furatsilin; Furaziline; Furazol W; Furazone; Furesol; Fuvacillin; Hemofuran; Ibiofural; Mammex; Mastofuran; Monafuracin; Monafuracis; Monofuracin; Nifucin; Nifuzon; Nitrofural; Nitrofurazan; Nitrofurol; Nitrozone; Otofuran; nitrofurazone; 5-Nitro-2-furaldehyde semicarbazone; 5-Nitrofurfural semicarbazone; 59-87-0
Indication Acute tonsillitis [ICD11: CA03] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 198.14 Topological Polar Surface Area 126
Heavy Atom Count 14 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5447130
ChEBI ID
CHEBI:44368
CAS Number
59-87-0
TTD Drug ID
D0IE1E
Formula
C6H6N4O4
Canonical SMILES
C1=C(OC(=C1)[N+](=O)[O-])C=NNC(=O)N
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Nitrofural cyano-metabolite DM003359 N. A. Unclear 1 [10]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003795 Nitrofural Nitrofural cyano-metabolite Unclear NTR [10]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
NADPH-dependent nitroreductase (nfrA1) DME1243 Bacillus subtilis
NFRA1_BACSU
1.5.1.38
[3] , [4]
NADPH-dependent oxidoreductase (nfrA) DME1242 Staphylococcus aureus
NRFA_STAA8
1.6.5.2
[5] , [6]
Nitroreductase (NTR) DME1327 Enterococcus casseliflavus
A0A377KR04_ENTCA
1.5.1.39
[7]
Nitroreductase (NTR) DME1328 Enterococcus gallinarum
A0A376H6M5_ENTGA
1.5.1.39
[7]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME1098 Escherichia coli
NFSA_ECOLI
1.5.1.38
[8]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME1048 Escherichia coli
NFSB_ECOLI
1.5.1.34
[9]
⏷ Show the Full List of 7  DME(s)
References
1 ClinicalTrials.gov (NCT00192985) Does a Nitrofurazone Coated Bladder Catheter Reduce the Number of Urinary Tract Infections in Trauma.
2 Nefazodone pharmacokinetics in depressed children and adolescents. J Am Acad Child Adolesc Psychiatry. 2000 Aug;39(8):1008-16.
3 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.
4 Bacillus subtilis isolated from the human gastrointestinal tract. Res Microbiol. 2009 Mar;160(2):134-43.
5 Reduction of polynitroaromatic compounds: the bacterial nitroreductases. FEMS Microbiol Rev. 2008 May;32(3):474-500.
6 The human gut microbiota: metabolism and perspective in obesity. Gut Microbes. 2018 Jul 4;9(4):308-325.
7 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.
8 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.
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 Cyano metabolite as a biomarker of nitrofurazone in channel catfish

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