F7129

5-Fluorocytosine

nucleoside analog

• Synonym(s): 4-amino-5-fluoro-2(1H)-pyrimidinone, Flucytosine
• Empirical Formula (Hill Notation): C₄H₄FN₃O
• CAS Number: 2022-85-7
• Molecular Weight: 129.09
• UNSPSC Code: 41116107
• NACRES: NA.32
• PubChem Substance ID: 24894928
• EC Number: 217-968-7
• Beilstein/REAXYS Number: 127285
• MDL number: MFCD00006035

Properties

• Quality Segment: 200
• 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

Description

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.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Codes: H361
• Precautionary Statements: P281
• Hazard Classifications: Repr. 2
• Storage Class: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Gloves, type N95 (US)