CAS： 2022-85-7
MF： C4H4FN3O
Appearance： white crystalline solid
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Description |
Fluorocytosine (5-Fluorocytosine or 5-FC) is a synthetic fluorinated pyrimidine, initially developed as an anticancer agent. It was later discovered to be effective against fungal infections, particularly those caused by yeasts like Candida and Cryptococcus species. |
| Mechanism of Action | Fluorocytosine is converted into 5-fluorouracil (5-FU) by fungal cytosine deaminase, interfering with fungal RNA and DNA synthesis, leading to cell death. |
| Pharmacokinetics |
Absorption: Rapid and nearly complete oral absorption, with a bioavailability of 76-89%. |
| Mechanism of Action | Once inside susceptible fungal cells, Fluorocytosine is converted to 5-FU, which disrupts: RNA synthesis by misincorporation, leading to altered protein production. DNA synthesis by inhibiting thymidylate synthase, a key enzyme in nucleotide production. |
| Side Effects |
Common: Nausea, vomiting, abdominal pain, diarrhea. |
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Therapeutic Function |
Antifungal |
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Antimicrobial activity |
The spectrum of activity is restricted to Candida spp., Cryptococcus spp. and some fungi causing chromoblastomycosis. |
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Pharmaceutical Applications |
A synthetic fluorinated pyrimidine available for intravenous infusion or oral administration. |
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Drug interactions |
Potentially hazardous interactions with other drugs Cytarabine: concentration of flucytosine possibly reduced. |
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Definition |
ChEBI: 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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Brand name |
Ancobon (Valeant). |
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General Description |
Chemical structure: nucleoside |
InChI:InChI=1/C4H4FN3O/c5-8-2-1-3(6)7-4(8)9/h1-2H,(H2,6,7,9)
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Effective management and treatment of fungal diseases is hampered by poor diagnosis, limited options for antifungal therapy, and the emergence of antifungal drug resistance. An understanding of molecular mechanisms contributing to resistance is essential to optimize the efficacy of currently available antifungals. In this perspective, one of the oldest antifungals, 5-fluorocytosine (5-FC), has been the focus of recent studies applying advanced genomic and transcriptomic techniques to decipher the order of events at the molecular level that lead to resistance. These studies have highlighted the complexity of resistance and provided new insights that are reviewed in the present paper.
5-Fluorocytosine (5-FC) was investigated for the controlled synthesis of cocrystals by applying the pKa rule. Five cocrystals were designed and developed with adipic, succinic, terephtalic, benzoic, and malic acids, all exhibiting negative ΔpKa values ranging from close to zero up to roughly −1. The synthesized cocrystals were analyzed by single crystal X-ray diffraction, and the observed supramolecular synthons were compared to the reported structures containing 5-FC.
2-ethylsulfanyl-5-fluoro-pyrimidin-4-ylamine
Cytosine
β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine
2,5-difluoro-4-chloro-pyrimidine
N1-(4-benzoyl-2-butyn-1-yl)-5-fluorocytosine
1-(3,5-O-dibenzoyl-2-fluoro-β-D-arabinofuranosyl)-5-fluorocytosine
4-amino-5-fluoro-1-<<2-(benzoyloxy)-1-<(benzoyloxy)methyl>ethoxy>methyl>cytosine
5-fluorouracil
