Drugs Information: Nitrofurantoin

Basic Information

ID DDInter1303
Drug Type small molecule
Molecular Formula C8H6N4O5
Molecular Weight 238.159
Description Nitrofurantoin is a nitrofuran antibiotic used to treat uncomplicated urinary tract infections.[L6856,L6859,L6862] Nitrofurantoin is converted by bacterial nitroreductases to electrophilic intermediates which inhibit the citric acid cycle as well as synthesis of DNA, RNA, and protein.[A179824] This drug is more resistant to the development of bacterial resistance because it acts on many targets at once.[A179824] Nitrofurantoin is a second line treatment to [trimethoprim]/[sulfamethoxazole].[A179830] Nitrofurantoin was granted FDA approval on 6 February 1953.[L6895]
ATC Classification J01XE01 J01XE51
IUPAC Name 1-[(E)-[(5-Nitrofuran-2-Yl)Methylidene]Amino]Imidazolidine-2,4-Dione
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+
InChI Key NXFQHRVNIOXGAQ-YCRREMRBSA-N
Canonical SMILES [O-][N+](=O)C1=CC=C(O1)\C=N\N1CC(=O)NC1=O
Useful Links DrugBank ChEMBL

Interactions with Nitrofurantoin

Severity level ID Name Mechanism Detail