F7129

5-Fluorocytosine

Name: 5-Fluorocytosine
Brand: SIGMA

nucleoside analog

Synonym(s):

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

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All Photos(3)

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

Product Name

5-Fluorocytosine, nucleoside analog

InChI key

XRECTZIEBJDKEO-UHFFFAOYSA-N

InChI

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

SMILES string

NC1=NC(=O)NC=C1F

assay

≥99% (TLC)

Quality Level

200

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

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Related Categories

Antibiotics

Biochemicals

Cell Culture Supplements & Reagents

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.

General description

Chemical structure: nucleoside

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

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000505355

0000505356

0000492803

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Oral versus intravenous flucytosine in patients with human immunodeficiency virus-associated cryptococcal meningitis.

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

Repurposing the antimycotic drug flucytosine for suppression of Pseudomonas aeruginosa pathogenicity.

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

Cytosine deaminase-expressing human neural stem cells inhibit tumor growth in prostate cancer-bearing mice.

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

Evolving role of flucytosine in immunocompromised patients: new insights into safety, pharmacokinetics, and antifungal therapy.

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

Prevalence and susceptibility profile of Candida metapsilosis and Candida orthopsilosis: results from population-based surveillance of candidemia in Spain.

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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