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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL572
CHEMBL572
Compound Name NITROFURANTOIN
ChEMBL Synonyms MACRODANTIN | Dantafur | BERKFURIN | CEDURAN | NITROFURANTOIN, MACROCRYSTALLINE | NITROFURANTOIN MACROCRYSTALLINE | IVADANTIN | NITROFURANTOIN | Ivadantin | GENFURA | NITROFURANTOIN (MONOHYDRATE/MACROCRYSTALS) | MACROBID | FURADANTIN | NITROFURANTOIN SODIUM | FURALAN
Max Phase 4 (Approved)
Trade Names NITROFURANTOIN MACROCRYSTALLINE | IVADANTIN | GENFURA | FURADANTIN | MACROBID | NITROFURANTOIN (MONOHYDRATE/MACROCRYSTALS) | Dantafur | BERKFURIN | FURALAN | MACRODANTIN | CEDURAN
Molecular Formula C8H6N4O5

Additional synonyms for CHEMBL572 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES [O-][N+](=O)c1oc(\C=N\N2CC(=O)NC2=O)cc1
Standard InChI InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(1 ...
Download InChI
Standard InChI Key NXFQHRVNIOXGAQ-YCRREMRBSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Gene Expression Atlas Compounds
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL572

Molecule Features

CHEMBL572 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials
Urinary Tract InfectionsD014552EFO:0003103urinary tract infection2ClinicalTrials

Clinical Data

ClinicalTrials.gov NITROFURANTOIN
The Cochrane Collaboration NITROFURANTOIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL572. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 1.000
CHEMBL1795168 CDGSH iron-sulfur domain-containing protein 1 Homo sapiens 1.000
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 1.000
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.996
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.991
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.989
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.987
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.956
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.940
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.940
CHEMBL2392 DNA polymerase beta Homo sapiens 0.936
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.913
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.858
CHEMBL5514 Huntingtin Homo sapiens 0.827
CHEMBL262 Glycogen synthase kinase-3 beta Homo sapiens 0.676
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.605
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.588
CHEMBL3081 Aldose reductase Bos taurus 0.571
CHEMBL2850 Glycogen synthase kinase-3 alpha Homo sapiens 0.497
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.428



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1795168 CDGSH iron-sulfur domain-containing protein 1 Homo sapiens 1.000
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.999
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.998
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.998
CHEMBL3151 Intestinal alkaline phosphatase Mus musculus 0.991
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.991
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.990
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.989
CHEMBL5514 Huntingtin Homo sapiens 0.972
CHEMBL2392 DNA polymerase beta Homo sapiens 0.969
CHEMBL2635 Dual specificity protein phosphatase 3 Homo sapiens 0.966
CHEMBL1741221 Cysteine protease ATG4B Homo sapiens 0.959
CHEMBL1293255 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens 0.952
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.944
CHEMBL1993 DNA (cytosine-5)-methyltransferase 1 Homo sapiens 0.919
CHEMBL4361 Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens 0.901
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.875
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.854
CHEMBL3880 Heat shock protein HSP 90-alpha Homo sapiens 0.830
CHEMBL3797 Serine-protein kinase ATM Homo sapiens 0.827

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
238.2 238.0338 0.07 3 118.05 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 1 0 9 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
7.55 - -.47 -.7 1 17 0.35

Structural Alerts

There are 6 structural alerts for CHEMBL572. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01X - OTHER ANTIBACTERIALS
J01XE - Nitrofuran derivatives
J01XE01 - nitrofurantoin

J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01X - OTHER ANTIBACTERIALS
J01XE - Nitrofuran derivatives
J01XE51 - nitrofurantoin, combinations

ChemSpider ChemSpider:NXFQHRVNIOXGAQ-YCRREMRBSA-N
DailyMed nitrofurantoin nitrofurantoin, macrocrystalline
PubChem SID: 17389788 SID: 26747377
Wikipedia Nitrofurantoin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL572



ACToR 67-20-9
Atlas nitrofurantoin
BindingDB 57045
ChEBI 71415
DrugBank DB00698
DrugCentral 1949
eMolecules 886566
FDA SRS 927AH8112L
KEGG Ligand C07268
MolPort MolPort-001-018-217
PubChem 6604200
PubChem: Thomson Pharma 14749496
SureChEMBL SCHEMBL29470
ZINC ZINC000003875368

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/NXFQHRVNIOXGAQ-YCRREMRBSA-N spacer
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