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Key Documents

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F7129

Sigma-Aldrich

5-Fluorocytosine

nucleoside analog

Sinónimos:

4-amino-5-fluoro-2(1H)-pyrimidinone, Flucytosine

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About This Item

Fórmula empírica (notación de Hill):
C4H4FN3O
Número de CAS:
2022-85-7
Peso molecular:
129.09
Beilstein/REAXYS Number:
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

signalword

Warning

hcodes

H361

pcodes

P281

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Annemarie E Brouwer et al.
Antimicrobial agents and chemotherapy, 51(3), 1038-1042 (2006-12-30)
In a randomized controlled trial of amphotericin B-based therapy for human immunodeficiency virus (HIV)-associated cryptococcal meningitis in Thailand, we also compared the mycological efficacy, toxicity, and pharmacokinetics of oral versus intravenous flucytosine at 100 mg/kg of body weight/day for the
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
Francesco Imperi et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(18), 7458-7463 (2013-04-10)
Although antibiotic resistance represents a public health emergency, the pipeline of new antibiotics is running dry. Repurposing of old drugs for new clinical applications is an attractive strategy for drug development. We used the bacterial pathogen Pseudomonas aeruginosa as a
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
P Francis et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 15(6), 1003-1018 (1992-12-01)
Flucytosine is an antifungal agent useful in combination with amphotericin B in the treatment of several deeply invasive mycoses. The potentially dose-limiting, hematologic, gastrointestinal, and hepatic toxicities of flucytosine lead to a reluctance to use it in myelosuppressed patients. To
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