Flucytosine

CAS No:
2022-85-7 Category:
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Product Details:

  • CAS No: 2022-85-7
  • AHFC code:
  • Synonyms: 5-FC 5-Fluorocystosine 5-Fluorocytosin 5-Fluorocytosine 5-Flurocytosine Flucytosin Fluocytosine Fluorcytosine
  • ATC Code: D01AE21 J02AX01
  • Chemical Formula: C22H29FO4
  • Molecular Weight: 129.0925
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB01099 (APRD00299)
  • SMILES: NC1=C(F)C=NC(=O)N1
  • InChl: XRECTZIEBJDKEO-UHFFFAOYSA-N
  • PubChem: 3366
  • IUPAC: 6-amino-5-fluoro-1,2-dihydropyrimidin-2-one

Additional Details

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).
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.
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.
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.
General Reference:
Products currently covered by valid US Patents are offered for R&D use in accordance with 35 USC 271(e)+A13(1). Any patent infringement and resulting liability is solely at buyer risk.

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