nifuroxazide   Click here for help

GtoPdb Ligand ID: 12358

Synonyms: NSC-759261 | RC-27109 | SJ000287313
Approved drug
nifuroxazide is an approved drug
Compound class: Synthetic organic
Comment: Nifuroxazide is a nitrofuran drug with broad-spectrum antibacterial activity. In addition to its antibacterial activity, nifuroxazide has been found to be a potent inhibitor of STAT3 and aldehyde dehydrogenase, and may have the potential to be repurposed as an antineoplastic therapy [1].

nifuroxazide is commercially available from our sponsors

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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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 117.97
Molecular weight 275.05
XLogP 2.35
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Oc1ccc(cc1)C(=O)N/N=C/c1ccc(o1)[N+](=O)[O-]
Isomeric SMILES c1cc(ccc1C(=O)N/N=C/c1ccc(o1)[N+](=O)[O-])O
InChI InChI=1S/C12H9N3O5/c16-9-3-1-8(2-4-9)12(17)14-13-7-10-5-6-11(20-10)15(18)19/h1-7,16H,(H,14,17)/b13-7+
InChI Key YCWSUKQGVSGXJO-NTUHNPAUSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
4-hydroxy-N-[(5-nitrofuran-2-yl)methylideneamino]benzamide
International Nonproprietary Names Click here for help
INN number INN
1578 nifuroxazide
Synonyms Click here for help
NSC-759261 | RC-27109 | SJ000287313
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Nifuroxazide
Other databases
CAS Registry No. 965-52-6 (source: Scifinder)
ChEBI CHEBI:135136
ChEMBL Ligand CHEMBL244888
DrugBank Ligand DB13855
DrugCentral Ligand 1928
GtoPdb PubChem SID 479821149
PubChem CID 5337997
Search Google for chemical match using the InChIKey YCWSUKQGVSGXJO-NTUHNPAUSA-N
Search Google for chemicals with the same backbone YCWSUKQGVSGXJO
Search PubMed clinical trials nifuroxazide
Search PubMed titles nifuroxazide
Search PubMed titles/abstracts nifuroxazide
UniChem Compound Search for chemical match using the InChIKey YCWSUKQGVSGXJO-NTUHNPAUSA-N
UniChem Connectivity Search for chemical match using the InChIKey YCWSUKQGVSGXJO-NTUHNPAUSA-N
Wikipedia Nifuroxazide

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MedChemExpress
Nifuroxazide (links to external site)
Cat. No. HY-B1436