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F7129

5-Fluorocytosine

Name: 5-Fluorocytosine
Brand: SIGMA

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:

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

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Properties

Quality Level

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

λ_max

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.

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pictograms

GHS08

signalword

Warning

hcodes

H361

pcodes

P281

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c