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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB120162 |
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Identification |
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| Name: |
5-fluorocytosine |
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| Description: | An organofluorine compound that is cytosine that is substituted at position 5 by a fluorine. A prodrug for the antifungal 5-fluorouracil, it is used for the treatment of systemic fungal infections. |
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Structure |
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| Synonyms: | - 5-FC
- 5-Fluorocystosine
- 5-Fluorocytosine
- Ancobon (TN)
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Chemical Formula: |
C4H4N3OF |
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| Average Molecular Weight: |
129.093 |
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| Monoisotopic Molecular
Weight: |
129.03384 |
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| InChI Key: |
XRECTZIEBJDKEO-UHFFFAOYSA-N |
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| InChI: | InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9) |
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| CAS
number: |
2022-85-7 |
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| IUPAC Name: | 4-amino-5-fluoropyrimidin-2(1H)-one |
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Traditional IUPAC Name: |
flucytosine |
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| SMILES: | C1(=C(F)C(N)=NC(=O)N1) |
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Chemical Taxonomy |
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Taxonomy Description | This compound 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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Physical Properties |
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| State: |
Solid |
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| Charge: | 0 |
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Melting point: |
296 °C |
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| Experimental Properties: |
| Property | Value | Reference |
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| Melting Point | 296 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 1.92e+00 g/L | Not Available | | LogP | -1.1 | Not Available |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Not Available |
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| Reactions: | |
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Pathways: |
Not Available |
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Spectra |
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| Spectra: |
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References |
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| References: |
- Einstein H (1973)Flucytosine, a major antifungal agent. California medicine 119, Pubmed: 18731030
- Fothergill AW, Sanders C, Wiederhold NP (2013)Comparison of MICs of fluconazole and flucytosine when dissolved in dimethyl sulfoxide or water. Journal of clinical microbiology 51, Pubmed: 23576540
- Markaki M, Craig RK, Savakis C (2004)Insect population control using female specific pro-drug activation. Insect biochemistry and molecular biology 34, Pubmed: 14871609
- Abuhammour W, Habte-Gabr E (2001)Systemic antifungal agents. Indian journal of pediatrics 68, Pubmed: 11519290
- Garcia H, Guitard J, Peltier J, Tligui M, Benbouzid S, Elhaj SA, Rondeau E, Hennequin C (2015)Caspofungin irrigation through percutaneous calicostomy catheter combined with oral flucytosine to treat fluconazole-resistant symptomatic candiduria. Journal de mycologie medicale 25, Pubmed: 25649231
- Ellepola AN, Chandy R, Khan ZU (2015)In vitro postantifungal effect, adhesion traits and haemolysin production of Candida dubliniensis isolates following exposure to 5-fluorocytosine. Mycoses 58, Pubmed: 26201447
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
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