F7129
5-Fluorocytosine
nucleoside analog
Synonym(s):
4-amino-5-fluoro-2(1H)-pyrimidinone, Flucytosine
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About This Item
Empirical Formula (Hill Notation):
C4H4FN3O
CAS Number:
Molecular Weight:
129.09
UNSPSC Code:
41116107
NACRES:
NA.32
PubChem Substance ID:
EC Number:
217-968-7
Beilstein/REAXYS Number:
127285
MDL number:
Quality Segment
assay
≥99% (TLC)
form
powder
mol wt
129.09 g/mol
concentration
≤100% (Flucytosine)
color
white to off-white
mp
298-300 °C (dec.) (lit.)
solubility
formic acid: 50 mg/mL, colorless to faintly yellow
λmax
285-287 nm
fluorescence
(EmM Anhydrous 8.8 - 9.4, pH 1.0)
antibiotic activity spectrum
fungi
mode of action
DNA synthesis | interferes, protein synthesis | interferes
storage temp.
2-8°C
SMILES string
NC1=NC(=O)NC=C1F
InChI
1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
InChI key
XRECTZIEBJDKEO-UHFFFAOYSA-N
General description
Chemical structure: nucleoside
Application
Used in studies on TMP biosynthesis.
Biochem/physiol Actions
Nucleoside analog that has antifungal activities. 5-FC is deaminated by cytosine deaminase to product 5-fluorouracil, resulting in RNA miscoding. 5-Fluorocytosine inhibits DNA and RNA synthesis and interferes with ribosomal protein synthesis.
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