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F7129

Sigma-Aldrich

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:
2022-85-7
Molecular Weight:
129.09
Beilstein:
127285
EC Number:
217-968-7
MDL number:
MFCD00006035
UNSPSC Code:
41116107
PubChem Substance ID:
24894928
NACRES:
NA.32

Quality Level

200

Assay

≥99% (TLC)

mp

298-300 °C (dec.) (lit.)

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

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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.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361

Precautionary Statements

P281

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A Gomez-Lopez et al.
Antimicrobial agents and chemotherapy, 52(4), 1506-1509 (2008-02-21)
We describe the prevalences and susceptibility profiles of two recently described species, Candida metapsilosis and Candida orthopsilosis, related to Candida parapsilosis in candidemia. The prevalences of these species (1.7% for C. metapsilosis and 1.4% for C. orthopsilosis) are significant. Differences
Hong Jun Lee et al.
Cancer letters, 335(1), 58-65 (2013-02-09)
Prostate cancer is the most common malignancy among men. Prostate cancer-related deaths are largely attributable to the development of hormone resistance in the tumor. No effective chemotherapy has yet been developed for advanced prostate cancer. It is desirable if a
C Wang et al.
Cancer gene therapy, 19(11), 796-801 (2012-09-29)
In our previous works, we demonstrated that human neural stem cells (NSCs) transduced with the cytosine deaminase (CD) gene showed remarkable 'bystander killer effect' on glioma and medulloblastoma cells after administration of the prodrug 5-fluorocytosine (5-FC). In addition, herpes simplex
Johanna K Kaufmann et al.
The Journal of investigative dermatology, 133(4), 1034-1042 (2012-12-12)
Effective treatment modalities for advanced melanoma are desperately needed. An innovative approach is virotherapy, in which viruses are engineered to infect cancer cells, resulting in tumor cell lysis and an amplification effect by viral replication and spread. Ideally, tumor selectivity
A Vermes et al.
The Journal of antimicrobial chemotherapy, 46(2), 171-179 (2000-08-10)
Flucytosine (5-FC) is a synthetic antimycotic compound, first synthesized in 1957. It has no intrinsic antifungal capacity, but after it has been taken up by susceptible fungal cells, it is converted into 5-fluorouracil (5-FU), which is further converted to metabolites
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