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

General Information of Drug (ID: DR1169)
Drug Name
Nitrofurantoin
Synonyms
Nifurantin; Nitoin; Nitrex; Nitrofuradantin; Nitrofurantoina; Nitrofurantoine; Nitrofurantoinum; Novofuran; Orafuran; Parfuran; Benkfuran; Berkfurin; Chemiofuran; Cyantin; Cystit; Dantafur; Fur-ren; Furachel; Furadantin; Furadantine mc; Furadantoin; Furadoine; Furadonin; Furadoninum; Furadontin; Furalan; Furaloid; Furantoin; Furatoin; Furina; Furobactina; Ituran; Macpac; Macrobid; Macrodantin; Macrofuran; Nierofu; Trantoin; Urantoin; Urizept; Uro-Tablinen; Urodin; Urofurin; Urolong; Welfurin; Zoofurin; nitrofurantoin; 5-Nitrofurantoin; 67-20-9
Indication Infectious cystitis [ICD11: GC00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 238.16 Topological Polar Surface Area 121
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
6604200
PubChem SID
9477 ; 603042 ; 3347076 ; 7847505 ; 7980134 ; 8139874 ; 8149444 ; 10321408 ; 10532352 ; 14749496 ; 17389788 ; 24640067 ; 26611838 ; 26679707 ; 26747377 ; 43223979 ; 47425320 ; 47574396 ; 47796070 ; 47944823 ; 48170470 ; 48319506 ; 48394923 ; 48414143 ; 48416333 ; 48423850 ; 48425399 ; 49699064 ; 49855694 ; 50105610 ; 50105611 ; 50344367 ; 53788524 ; 57288795 ; 57371029 ; 72200890 ; 81041227 ; 81093030 ; 85787883 ; 88313616 ; 92124245 ; 92125001 ; 92307346 ; 93166339 ; 99301312 ; 103179088 ; 103913903 ; 104170019 ; 106225506 ; 114637257
ChEBI ID
CHEBI:71415
CAS Number
67-20-9
TTD Drug ID
D0R0BX
Formula
C8H6N4O5
Canonical SMILES
C1C(=O)NC(=O)N1N=CC2=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
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
Aminofurantoin DM002220
9577282
Unclear 1 [10]
Nitrofurantoin metabolite 8(M1/M2) DM002218 N. A. Oxidation - Oxidation 1 [11]
Nitrofurantoin metabolite 9(M1/M2) DM002219 N. A. Oxidation - Oxidation 1 [11]
Nitrofurantoin metabolite M10 DM002217 N. A. Oxidation - Oxidation 1 [11]
Nitrofurantoin metabolite 8(M1/M2) DM002218 N. A. Oxidation - Oxidation 2 [11]
Nitrofurantoin metabolite 9(M1/M2) DM002219 N. A. Oxidation - Oxidation 2 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001764 Nitrofurantoin Nitrofurantoin metabolite M10 Oxidation - Oxidation CYP3A5 ... [11]
MR001765 Nitrofurantoin Nitrofurantoin metabolite 8(M1/M2) Oxidation - Oxidation CYP3A5 ... [11]
MR001766 Nitrofurantoin Nitrofurantoin metabolite 9(M1/M2) Oxidation - Oxidation CYP3A5 ... [11]
MR001767 Nitrofurantoin Aminofurantoin Unclear Unclear [10]
MR001762 Nitrofurantoin metabolite M10 Nitrofurantoin metabolite 8(M1/M2) Oxidation - Oxidation CYP3A5 ... [11]
MR001763 Nitrofurantoin metabolite M10 Nitrofurantoin metabolite 9(M1/M2) Oxidation - Oxidation CYP3A5 ... [11]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
NADPH-cytochrome P450 reductase (CPR) DME0076 Homo sapiens
NCPR_HUMAN
1.6.2.4
[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) DME1246 Clostridium hiranonis
A0A351QTB1_CLOSP
1.5.1.39
[7]
Nitroreductase (NTR) DME1327 Enterococcus casseliflavus
A0A377KR04_ENTCA
1.5.1.39
[8]
Nitroreductase (NTR) DME1328 Enterococcus gallinarum
A0A376H6M5_ENTGA
1.5.1.39
[8]
Nitroreductase (NTR) DME1331 Clostridium sporogenes
A0A2X3BKF5_CLOSG
1.5.1.39
[9] , [7]
Nitroreductase (NTR) DME1070 Clostridium leptum
A0A412R9E4_9FIRM
1.5.1.39
[7]
Nitroreductase (NTR) DME1244 Clostridium paraputrificum
A0A174SJF2_9CLOT
1.5.1.39
[7]
Nitroreductase (NTR) DME1245 Clostridium perfringens
B1R7B9_CLOPF
1.5.1.39
[7]
⏷ Show the Full List of 10  DME(s)
References
1 Nitrofurantoin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Role of cytochrome P450 reductase in nitrofurantoin-induced redox cycling and cytotoxicity. Free Radic Biol Med. 2008 Mar 15;44(6):1169-79.
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 Isolation of nitrofurantoin-resistant mutants of nitroreductase-producing Clostridium sp. strains from the human intestinal tract. Antimicrob Agents Chemother. 1998 May;42(5):1121-6.
8 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.
9 Biotransformation of 1-nitropyrene in intestinal anaerobic bacteria. Microbiol Immunol. 1982;26(11):993-1005.
10 Nitrofurantoin disposition Clin Pharmacol Ther. 1981 Jun;29(6):808-16. doi: 10.1038/clpt.1981.115.
11 Oxidative bioactivation of nitrofurantoin in rat liver microsomes Xenobiotica. 2017 Feb;47(2):103-111. doi: 10.3109/00498254.2016.1164913.

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