Product Name

Flucytosine

CAS Number

2022-85-7

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Product Name:
Flucytosine
CAS Number:
2022-85-7
Indication:
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).
Mode 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 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.

Pharmacodynamics:

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; 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. Antifungal synergism between Ancobon and polyene antibiotics, particularly amphotericin B, has been reported.

Metabolism:

Flucytosine is deaminated, possibly by gut bacteria or by the fungal targets, to 5-fluorouracil, the active metabolite.

Toxicity:

Oral, rat: LD50 = >15 gm/kg.

IUPAC:
6-amino-5-fluoro-1, 2-dihydropyrimidin-2-one
ATC:
D01AE21 J02AX01
PubChem:
3366
DrugBank:
DB01099 (APRD00299)
Formula:
C22H29FO4
Molecular Mass:
129.0925
Synonyms:
5-FC 5-Fluorocystosine 5-Fluorocytosin 5-Fluorocytosine 5-Flurocytosine Flucytosin Fluocytosine Fluorcytosine
SMILES:
NC1=C(F)C=NC(=O)N1
InChi:
XRECTZIEBJDKEO-UHFFFAOYSA-N

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