6-amino-5-fluoro-1,2-dihydropyrimidin-2-one

• ChemBase ID: 970
• Molecular Formular: C4H4FN3O
• Molecular Mass: 129.0924632
• Monoisotopic Mass: 129.03383998
• SMILES: Fc1c([nH]c(=O)nc1)N
• Canonical SMILES: Nc1c(F)cnc(=O)[nH]1
• InChI: InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
• InChIKey: XRECTZIEBJDKEO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-5-fluoro-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: flucytosine
• Brand Name: Ancobon; Ancotil
• Synonyms: 5-FC; 5-Fluorocystosine; 5-Fluorocytosin; 5-Fluorocytosine; 5-Flurocytosine; Flucytosin; Fluocytosine; Fluorcytosine; Flucytosine; 5-Fluoro cytosine; 6-amino-5-fluoro-1,2-dihydropyrimidin-2-one; 5-Fluorocytosine

Database IDs

• CAS Number: 2022-85-7
• MDL Number: MFCD00006035
• PubChem SID: 46504735; 160964433
• PubChem CID: 3366

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.163184
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.9489975
• LogD (pH = 7.4): -1.0088187
• Log P: -0.94816285
• Molar Refractivity: 38.2177 cm^3
• Polarizability: 10.144018 Å^3
• Polar Surface Area: 67.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.24
• LOG S: -1.83
• Solubility (Water): 1.92e+00 g/l

PROPERTIES

Physical Property

• Solubility: 10.5 g/L
• Apperance: white crystalline powder
• Melting Point: 295 - 297°C
• Hydrophobicity(logP): -1.1; -1.772

Product Information

• Purity: 95%; 98%; 99%

DETAILS

DrugBank - DB01099

• Drug Groups: approved
• Description: A fluorinated cytosine analog that is used as an antifungal agent. [PubChem]
• 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).
• 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; 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.
• Toxicity: Oral, rat: LD₅₀ = >15 gm/kg.
• Affected Organisms: Yeast and other fungi
• Biotransformation: Flucytosine is deaminated, possibly by gut bacteria or by the fungal targets, to 5-fluorouracil, the active metabolite.
• Absorption: Rapidly and virtually completely absorbed following oral administration. Bioavailability 78% to 89%.
• Half Life: 2.4 to 4.8 hours.
• Protein Binding: 28-31%
• Elimination: Flucytosine is excreted via the kidneys by means of glomerular filtration without significant tubular reabsorption.; A small portion of the dose is excreted in the feces.
• External Links: Wikipedia; RxList; Drugs.com