Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:44 UTC |
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HMDB ID | HMDB0014752 |
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Secondary Accession Numbers | - HMDB0029753
- HMDB14752
- HMDB29753
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Metabolite Identification |
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Common Name | Furazolidone |
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Description | Furazolidone is a nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone has been shown to exhibit antibiotic and anti-microbial functions (PMID 1476092 , 6651278 ). Furazolidone is also used as a poultry food additive. It is marketed by Roberts Laboratories under the brand name Furoxone and by GlaxoSmithKline as Dependal-M. Furoxone has a broad antibacterial spectrum covering the majority of gastrointestinal tract pathogens including E. coli, staphylococci, Salmonella, Shigella, Proteus, Aerobacter aerogenes, Vibrio cholerae and Giardia lamblia. Its bactericidal activity is based upon its interference with DNA replication and protein production. Furazolidone binds bacterial DNA which leads to the gradual inhibition of monoamine oxidase (From Martindale, The Extra Pharmacopoeia, 30th ed, p514). Furazolidone and its related free radical products are believed to bind DNA and induce cross-links. Bacterial DNA is particularly susceptible to this drug leading to high levels of mutations (transitions and transversions) in the bacterial chromosome. Furazolidone belongs to the family of Nitrofurans. These are compounds containing a furan ring which bears a nitro group. |
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Structure | [O-][N+](=O)C1=CC=C(O1)\C=N\N1CCOC1=O 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/b9-5+ |
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Synonyms | Value | Source |
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Furoxone | Kegg | 3-(5'-Nitrofurfuralamino)-2-oxazolidone | HMDB | 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinone | HMDB | 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidone | HMDB | 3-[(5-Nitrofurylidene)amino]-2-oxazolidone | HMDB | 3-{[(5-nitro-2-furanyl)methylene]amino}-2-oxazolidinone | HMDB | 5-Nitro-N-(2-oxo-3-oxazolidinyl)-2-furanmethanimine | HMDB | Furazolidona | HMDB | Furazolidonum | HMDB | FZL | HMDB | N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidone | HMDB | N-(5-Nitro-2-furfurylidene)-3-aminooxazolidine-2-one | HMDB | Nitrofurazolidone | HMDB | Nitrofurazolidonum | HMDB | 3-(((5-Nitro-2-furanyl)methylene)amino)-2-oxazolidinone | HMDB | 3-((5-Nitrofurfurylidene)amino)-2-oxazolidinone | HMDB | 3-((5-Nitrofurfurylidene)amino)-2-oxazolidone | HMDB | 3-((5-Nitrofurfurylidine)amino)-2-oxazolidinone | HMDB | 3-((5-Nitrofurylidene)amino)-2-oxazolidone | HMDB | 3-(5-Nitrofurfurylideneamino)-2-oxazolidinone | HMDB | 3-[(5-Nitrofurfurylidine)amino]-2-oxazolidinone | HMDB | 3-[(e)-(5-Nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one | HMDB | 3-[[(5-Nitro-2-furanyl)methylene]-amino]-2-oxazolidinone | HMDB | 3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinone | HMDB | 3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinone, 9ci | HMDB | Bifuron | HMDB | Corizium | HMDB | Coryzium | HMDB | Diafuron | HMDB | Enterotoxon | HMDB | Fiurox aerosol powder | HMDB | Furall | HMDB | Furaxon | HMDB | Furaxone | HMDB | Furazolidine | HMDB | Furazon | HMDB | Furidon | HMDB | Furovag | HMDB | Furox | HMDB | Furoxal | HMDB | Furoxane | HMDB | Furoxon | HMDB | Furoxone swine mix | HMDB | Furozolidine | HMDB | Giardil | HMDB | Giarlam | HMDB | Medaron | HMDB | Neftin | HMDB | Nicolen | HMDB | Nifulidone | HMDB | Nifuran | HMDB | Nifurazolidone | HMDB | Nitrofuroxon | HMDB | Optazol | HMDB | Ortazol | HMDB | Puradin | HMDB | Roptazol | HMDB | Sclaventerol | HMDB | Tikofuran | HMDB | Topazone | HMDB | Trichofuron | HMDB | Tricofuron | HMDB | Tricoron | HMDB | Trifurox | HMDB | USAF ea-1 | HMDB | Viofuragyn | HMDB | Furazol | HMDB |
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Chemical Formula | C8H7N3O5 |
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Average Molecular Weight | 225.16 |
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Monoisotopic Molecular Weight | 225.038570337 |
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IUPAC Name | 3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one |
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Traditional Name | furazolidone |
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CAS Registry Number | 67-45-8 |
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SMILES | [O-][N+](=O)C1=CC=C(O1)\C=N\N1CCOC1=O |
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InChI Identifier | 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/b9-5+ |
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InChI Key | PLHJDBGFXBMTGZ-WEVVVXLNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as nitrofurans. Nitrofurans are compounds containing a furan ring which bears a nitro group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Furans |
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Sub Class | Nitrofurans |
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Direct Parent | Nitrofurans |
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Alternative Parents | |
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Substituents | - Nitroaromatic compound
- 2-nitrofuran
- Oxazolidinone
- Oxazolidine
- Heteroaromatic compound
- C-nitro compound
- Carbonic acid derivative
- Organic nitro compound
- Organic oxoazanium
- Allyl-type 1,3-dipolar organic compound
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Oxacycle
- Azacycle
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Not Available | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 255 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.36 g/L | Not Available | LogP | 0.9 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Furazolidone GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-9610000000-ab960b06286d0ccd8c6c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Furazolidone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Furazolidone 10V, Positive-QTOF | splash10-004i-1390000000-6d4a20ff37556f08e13b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Furazolidone 20V, Positive-QTOF | splash10-004i-1390000000-3c18d9819c68dd1ecba9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Furazolidone 40V, Positive-QTOF | splash10-08mj-9500000000-9e58b2b1f6fd5b9343c5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Furazolidone 10V, Negative-QTOF | splash10-00di-2290000000-63a56a073d7d4f4cfd09 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Furazolidone 20V, Negative-QTOF | splash10-0fk9-9670000000-ddd3d4a03c2a3bc6ab9e | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Furazolidone 40V, Negative-QTOF | splash10-0fk9-9000000000-58fd85feae000f4153dd | 2016-08-04 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00614 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00614 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB000957 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4481255 |
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KEGG Compound ID | C07999 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Furazolidone |
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METLIN ID | Not Available |
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PubChem Compound | 5323714 |
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PDB ID | Not Available |
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ChEBI ID | 5195 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Ivanics E, Glavits R, Bodi T, Toth E: Demonstration of Clostridium septicum infection in a goose flock. Acta Vet Hung. 1992;40(1-2):71-4. [PubMed:1476092 ]
- Carlson JR, Thornton SA, DuPont HL, West AH, Mathewson JJ: Comparative in vitro activities of ten antimicrobial agents against bacterial enteropathogens. Antimicrob Agents Chemother. 1983 Oct;24(4):509-13. [PubMed:6651278 ]
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