Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:28:21 UTC |
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Update Date | 2014-12-24 20:25:54 UTC |
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Accession Number | T3D2983 |
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Identification |
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Common Name | Flucytosine |
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Class | Small Molecule |
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Description | Flucytosine is only found in individuals that have used or taken this drug. It is a fluorinated cytosine analog that is used as an antifungal agent. [PubChem]Although the exact mode of action is unknown, it has been proposed that flucytosine acts directly on fungal organisms by competitive inhibition of purine and pyrimidine uptake and indirectly by intracellular metabolism to 5-fluorouracil. Flucytosine enters the fungal cell via cytosine permease; thus, flucytosine is metabolized to 5-fluorouracil within fungal organisms. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and RNA. The result is unbalanced growth and death of the fungal organism. It also appears to be an inhibitor of fungal thymidylate synthase. |
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Compound Type | - Amine
- Antifungal Agent
- Antimetabolite
- Drug
- Metabolite
- Organic Compound
- Organofluoride
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 5-FC | 5-Fluorocystosine | 5-Fluorocytosin | 5-Fluorocytosine | 5-Flurocytosine | Ancobon | Ancotil | Flucytosin | Fluocytosine | Fluorcytosine | Flusine |
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Chemical Formula | C4H4FN3O |
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Average Molecular Mass | 129.093 g/mol |
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Monoisotopic Mass | 129.034 g/mol |
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CAS Registry Number | 2022-85-7 |
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IUPAC Name | 6-amino-5-fluoro-1,2-dihydropyrimidin-2-one |
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Traditional Name | flucytosine |
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SMILES | OC1=NC=C(F)C(=N)N1 |
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InChI Identifier | InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9) |
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InChI Key | InChIKey=XRECTZIEBJDKEO-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazines |
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Sub Class | Pyrimidines and pyrimidine derivatives |
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Direct Parent | Halopyrimidines |
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Alternative Parents | |
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Substituents | - Aminopyrimidine
- Halopyrimidine
- Pyrimidone
- Aryl fluoride
- Aryl halide
- Hydropyrimidine
- Heteroaromatic compound
- Azacycle
- Amine
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organofluoride
- Organohalogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 296°C | Boiling Point | Not Available | Solubility | 1.5E+004 mg/L (at 25°C) | LogP | -1.1 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-5900000000-62cd06162d248f459f77 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-002r-9400000000-acd1b588a4052f6fc2dd | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-002r-9400000000-a4e7dd3c4c886861c0ea | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-000i-9200000000-b3fb9cad9c2b375b08c6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-000i-9100000000-11fb61e55faa71878d87 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-000i-9000000000-13935b6ab4a3d8adaa08 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-000i-9000000000-cd981efe159dd44555f4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-0900000000-a228aa7f5ecaf516455f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-0900000000-ec5b7f7d9f3c75649dc2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03e9-0900000000-15df2a7b685c4dd4ca17 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-001i-0900000000-7110f8accb80c700a2a5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-001i-0900000000-89290e0501d587938afb | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-001i-0900000000-7248b6df062077397b61 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-001i-1900000000-df83e87e1bcbc8311be6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-01q9-3900000000-42649a5ceee8a4619fc3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-08gr-9800000000-8cb7a586d34dd7913561 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 0V, Positive | splash10-001i-0900000000-973610269bb11b2539b9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-f98fd5ea350e99bcbb13 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 0V, Positive | splash10-001i-0900000000-f0b5eaeae6c5f2a922c3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0bti-9300000000-c7808ed54724dbe0b4db | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-3daf46ab201d0847e716 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-4900000000-08676c044da012e58509 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0007-9000000000-fc78e7fb18ada3e97d98 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-2900000000-d0b2503a7f5865ac1efd | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00nu-9100000000-ee11917ba44963a8210b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-e5c5889e9b5cd0c8cae9 | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Rapidly and virtually completely absorbed following oral administration. Bioavailability 78% to 89%. |
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Mechanism of Toxicity | Although the exact mode of action is unknown, it has been proposed that flucytosine acts directly on fungal organisms by competitive inhibition of purine and pyrimidine uptake and indirectly by intracellular metabolism to 5-fluorouracil. Flucytosine enters the fungal cell via cytosine permease; thus, flucytosine is metabolized to 5-fluorouracil within fungal organisms. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and RNA. The result is unbalanced growth and death of the fungal organism. It also appears to be an inhibitor of fungal thymidylate synthase. |
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Metabolism | Flucytosine is deaminated, possibly by gut bacteria or by the fungal targets, to 5-fluorouracil, the active metabolite.
Route of Elimination: Flucytosine is excreted via the kidneys by means of glomerular filtration without significant tubular reabsorption.
A small portion of the dose is excreted in the feces.
Half Life: 2.4 to 4.8 hours. |
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Toxicity Values | LD50: 15 gm/kg (Oral, Rat) (1) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For the treatment (in combination with amphotericin B) of serious infections caused by susceptible strains of Candida (septicemia, endocarditis and urinary system infections) and/or Cryptococcus (meningitis and pulmonary infections). |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | In the management of overdosage, prompt gastric lavage or the use of an emetic is recommended. Adequate fluid intake should be maintained, by the intravenous route if necessary, since Ancobon is excreted unchanged via the renal tract. The hematologic parameters should be monitored frequently; liver and kidney function should be carefully monitored. Should any abnormalities appear in any of these parameters, appropriate therapeutic measures should be instituted. Since hemodialysis has been shown to rapidly reduce serum concentrations in anuric patients, this method may be considered in the management of overdosage. (5) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01099 |
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HMDB ID | HMDB15231 |
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PubChem Compound ID | 3366 |
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ChEMBL ID | CHEMBL1463 |
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ChemSpider ID | 3249 |
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KEGG ID | Not Available |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 5100 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Flucytosine |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Flucytosine |
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References |
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Synthesis Reference | Bernd Baasner, Erich Klauke, “Process for the preparation of 5-fluorocytosine.” U.S. Patent US4703121, issued September, 1961. |
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MSDS | Link |
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General References | - Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
- Bertout S, Dunyach C, Drakulovski P, Reynes J, Mallie M: Comparison of the Sensititre YeastOne(R) dilution method with the Clinical Laboratory Standards Institute (CLSI) M27-A3 microbroth dilution reference method for determining MIC of eight antifungal agents on 102 yeast strains. Pathol Biol (Paris). 2011 Feb;59(1):48-51. doi: 10.1016/j.patbio.2010.07.020. Epub 2010 Sep 16. [20843616 ]
- Kaouech E, Kallel K, Belhadj S, Anane S, Ben Chaabane T, Ben Fadhl K, Khedher A, Meddeb B, Ben Lakhal S, Chaker E: [Twenty-two cases of neuromeningeal cryptococcosis in Tunisia]. Med Mal Infect. 2009 Dec;39(12):914-9. doi: 10.1016/j.medmal.2009.02.004. Epub 2009 Apr 8. [19359114 ]
- Park BJ, Park JC, Taguchi H, Fukushima K, Hyon SH, Takatori K: Antifungal susceptibility of epigallocatechin 3-O-gallate (EGCg) on clinical isolates of pathogenic yeasts. Biochem Biophys Res Commun. 2006 Aug 25;347(2):401-5. Epub 2006 Jun 15. [16831406 ]
- RxList: The Internet Drug Index (2009). [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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