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Merck
CN

F7129

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
UNSPSC Code:
41116107
NACRES:
NA.32
PubChem Substance ID:
24894928
EC Number:
217-968-7
Beilstein/REAXYS Number:
127285
MDL number:
MFCD00006035

Key Documents

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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

λmax

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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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

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
0000505355
0000505356
0000505356
0000492803

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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
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
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
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
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
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Product Information Sheet - F7129

Product Information Sheet

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