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F7129

Sigma-Aldrich

5-Fluorocytosine

nucleoside analog

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C4H4FN3O
Número CAS:
2022-85-7
Peso molecular:
129.09
Beilstein:
127285
Número CE:
217-968-7
Número MDL:
MFCD00006035
Código UNSPSC:
41116107
ID de substância PubChem:
24894928
NACRES:
NA.32

Ensaio

≥99% (TLC)

pf

298-300 °C (dec.) (lit.)

espectro de atividade do antibiótico

fungi

Modo de ação

DNA synthesis | interferes
protein synthesis | interferes

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

NC1=NC(=O)NC=C1F

InChI

1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)

chave InChI

XRECTZIEBJDKEO-UHFFFAOYSA-N

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Descrição geral

Chemical structure: nucleoside

Aplicação

Used in studies on TMP biosynthesis.

Ações bioquímicas/fisiológicas

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.

Pictogramas

Health hazard
GHS08

Palavra indicadora

Warning

Frases de perigo

H361

Declarações de precaução

P281

Classificações de perigo

Repr. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

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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
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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
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
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
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