furazolidone   Click here for help

GtoPdb Ligand ID: 12343

Synonyms: Furoxone®
Approved drug
furazolidone is an approved drug (FDA (1958))
Compound class: Synthetic organic
Comment: Furazolidone is an antimicrobial nitrofuran drug that exhibits antiprotozoal and broad-spectrum antibacterial activities.
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 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 4
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 98.18
Molecular weight 225.04
XLogP 0.9
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=C1OCCN1N=Cc1ccc(o1)[N+](=O)[O-]
Isomeric SMILES C1COC(=O)N1N=Cc1ccc(o1)[N+](=O)[O-]
InChI InChI=1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2
InChI Key PLHJDBGFXBMTGZ-UHFFFAOYSA-N
References
1. Dai G, Cheng N, Dong L, Muramatsu M, Xiao S, Wang MW, Zhu DX. (2005)
Bactericidal and morphological effects of NE-2001, a novel synthetic agent directed against Helicobacter pylori.
Antimicrob Agents Chemother, 49 (8): 3468-73. [PMID:16048962]
2. Mohammadi M, Attaran B, Malekzadeh R, Graham DY. (2017)
Furazolidone, an Underutilized Drug for H. pylori Eradication: Lessons from Iran.
Dig Dis Sci, 62 (8): 1890-1896. [PMID:28577244]
3. Timperio AM, Kuiper HA, Zolla L. (2003)
Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases.
Xenobiotica, 33 (2): 153-67. [PMID:12623758]
4. Wang Y, Xiang Y, Liao O, Wu Y, Li Y, Du Q, Ye J. (2022)
Short-term outcomes and intermediate-term follow-up of Helicobacter pylori infection treatment for naïve patients: a retrospective observational study.
BMJ Open, 12 (9): e062096. [PMID:36115671]
5. Xie Y, Zhu Y, Zhou H, Lu ZF, Yang Z, Shu X, Guo XB, Fan HZ, Tang JH, Zeng XP et al.. (2014)
Furazolidone-based triple and quadruple eradication therapy for Helicobacter pylori infection.
World J Gastroenterol, 20 (32): 11415-21. [PMID:25170230]