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5-Flucytosine
drug data and news
5-Flucytosine drug data, resources, and news articles (when available). Onconews.org provides news on cancer research. This section, which includes profiles on medicines that may or not be cancer-related is in beta form. If things run smoothly we will be releasing a new format late in the summer of 2006.
| Generic name |
5-Flucytosine
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| Brand Names/Synonyms |
Ancobon; Ancotil; Flucytosin; Flucytosine; Fluocytosine; Fluorcytosine |
| Indication |
For treatment of (in combination with Amphotericin B) meningitis, endophthalmitis and pylelonephritis |
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Description |
Not Available |
| Pharmacology |
Flucytosine is an antimetabolite that acts as an antifungal agent with in vitro and in vivo activity against Candida and Cryptococcus. Flucytosine enters the fungal cell via cytosine permease; whereupon it is metabolized to 5-fluorouracil within fungal organisms. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and Antifungal synergism between Ancobon and polyene antibiotics, particularly amphotericin B, has been reported. |
| Mechanism Of Action |
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 monophosphate, a noncompetitive inhibitor of the fungal thymidylate synthetase which interferes with DNA synthesis. Flucytosine interrupts nucleic acid and protein synthesis. The cells of the host do not convert large quantities of flucytosine to fluorouracil, accounting for the selective toxicity of the compound against fungi. |
5-Flucytosine News
(When available) |
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| Dosage Forms |
Not Available |
| Drug_Category |
Antimetabolites; Antifungals; ATC:D01AE21; ATC:J02AX01 |
| Absorption |
Rapidly and completely absorbed, bioavailability is 78-90% |
| Interactions |
Interactions for 5-Flucytosine:
Cytosine arabinoside, a cytostatic agent, has been reported to inactivate the antifungal activity of flucytosine by competitive inhibition. Drugs which impair glomerular filtration may prolong the biological half-life of flucytosine.
Drug/Laboratory Test Interactions: Measurement of serum creatinine levels should be determined by the Jaffe reaction, since Ancobon does not interfere with the determination of creatinine values by this method. Most automated equipment for measurement of creatinine makes use of the Jaffe reaction.
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| Toxicity |
Not Available |
| Organisms Affected |
Yeast and other fungi |
| Chemical IUPAC Name |
4-amino-5-fluoro-3H-pyrimidin-2-one |
| Chemical Formula |
C4H4FN3O |
| Molecular Weight |
129.093 g/mol |
| Smiles String |
C1=C(C(=NC(=N1)O)N)F |
| Melting Point |
296 °C |
| Water Solubility |
15 mg/mL |
| State |
Solid |
| LogP/Hphobicity |
-0.062 |
| Isoelectric Point |
3.26 |
| Biotransformation |
Flucytosine is deaminated, possibly by gut bacteria or by the fungal targets, to |
| Half Life |
2.4 and 4.8 hours |
| Protein Binding [%] |
28-31% |
| RxList Link |
RXlist |
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| Drug Reference |
http://www.rxlist.com/cgi/generic3/flucytosine.htm |
| Drug Type |
Approved Drug |
| Accession No |
APRD00299 |
| CAS Registry Number |
2022-85-7 |
| KEGG Compound ID |
D00323 |
| PubChem ID |
SID:405592 |
| PharmGKB ID |
PA449654 |
| SwissProt ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
Not Available
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