nitrofurantoin   Click here for help

GtoPdb Ligand ID: 10917

Synonyms: Furadantin® | Macrobid® | Macrodantin® | Nitro Macro® | NSC-2107 | NSC-44150
Approved drug PDB Ligand
nitrofurantoin is an approved drug (FDA (1953), UK (2000))
Compound class: Synthetic organic
Comment: The metabolically reduced form of nitrofurantoin is highly reactive, and disrupts many processes that are crucial for bacterial cell growth/survival. Structurally it is a nitrofuran antibacterial compound.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 118.05
Molecular weight 238.03
XLogP -0.09
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C1NC(=O)N(C1)/N=C/c1ccc(o1)[N+](=O)[O-]
Isomeric SMILES O=C1NC(=O)N(C1)/N=C/c1ccc(o1)[N+](=O)[O-]
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1953), UK (2000))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
488 nitrofurantoin
Synonyms Click here for help
Furadantin® | Macrobid® | Macrodantin® | Nitro Macro® | NSC-2107 | NSC-44150
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Nitrofurantoin
Other databases
BindingDB Ligand 57045
CAS Registry No. 67-20-9 (source: PubChem)
ChEMBL Ligand CHEMBL572
DrugBank Ligand DB00698
DrugCentral Ligand 1949
GtoPdb PubChem SID 405560358
PubChem CID 6604200
RCSB PDB Ligand U6Z
Search Google for chemical match using the InChIKey NXFQHRVNIOXGAQ-YCRREMRBSA-N
Search Google for chemicals with the same backbone NXFQHRVNIOXGAQ
Search PubMed clinical trials nitrofurantoin
Search PubMed titles nitrofurantoin
Search PubMed titles/abstracts nitrofurantoin
UniChem Compound Search for chemical match using the InChIKey NXFQHRVNIOXGAQ-YCRREMRBSA-N
UniChem Connectivity Search for chemical match using the InChIKey NXFQHRVNIOXGAQ-YCRREMRBSA-N