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Chemical Structure| 2022-85-7 Chemical Structure| 2022-85-7

Structure of 5-Fluorocytosine
CAS No.: 2022-85-7

Chemical Structure| 2022-85-7

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5-Fluorocytosine is an antimycotic prodrug which can be converted to 5-fluorouracil, working by inhibiting DNA and RNA synthesis and interfering with ribosomal protein synthesis. It shows both antifungal and antitumor activity.

Synonyms: Flucytosine; NSC 103805; Flucytosine, 5-fluorocytosine, Flucytosin, Ancobon, Ancotil

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Product Details of 5-Fluorocytosine

CAS No. :2022-85-7
Formula : C4H4FN3O
M.W : 129.09
SMILES Code : O=C1NC(=C(F)C=N1)N
Synonyms :
Flucytosine; NSC 103805; Flucytosine, 5-fluorocytosine, Flucytosin, Ancobon, Ancotil
MDL No. :MFCD00006035
InChI Key :XRECTZIEBJDKEO-UHFFFAOYSA-N
Pubchem ID :3366

Safety of 5-Fluorocytosine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
H9 human embryonic stem cells 50 µM 36 h To verify the cytotoxic effect of 5-FC on H9 human embryonic stem cells, results showed no significant toxicity at 50 µM concentration Exp Mol Med. 2019 Jul 19;51(7):1-12
293T cells 50 µM 48 h To verify the cytotoxic effect of 5-FC on 293T cells, results showed no significant toxicity at 50 µM concentration Exp Mol Med. 2019 Jul 19;51(7):1-12
R3327-AT cells 100 µg/ml 24 h To evaluate the cytotoxicity of 5-FC and 5-FU on R3327-AT cells. Results showed that CDUPRT-expressing cells were more sensitive to 5-FC and 5-FU than CD-expressing cells. Radiother Oncol. 2009 Sep;92(3):345-52
T24 bladder epithelial cells 10 µg/mL 30 min To evaluate the effect of 5-FC on KTE223 strain adhesion to bladder epithelial cells. Results showed that 5-FC reduced adhesion in a dose-dependent manner and slightly increased epithelial cell survival. Antimicrob Agents Chemother. 2025 Apr 3;69(5):e0028025
KTE223 UPEC strain 2.5 µg/mL 24 h To assess the effect of 5-FC on virulence factor expression in the KTE223 strain. Results showed that 5-FC significantly inhibited the expression of csgB and csgD genes, indicating its impact on biofilm formation through pyrimidine starvation. Antimicrob Agents Chemother. 2025 Apr 3;69(5):e0028025
Uropathogenic Escherichia coli (UPEC) clinical isolates 2.5 µg/mL 24 h To evaluate the effect of 5-FC on biofilm formation and adhesion in UPEC strains. Results showed that 5-FC significantly reduced biofilm adhesion of UPEC clinical isolates at both 30°C and 37°C. Antimicrob Agents Chemother. 2025 Apr 3;69(5):e0028025
HB1.F3.CD cells 1, 10, 100 µg/mL 4 days To evaluate the effect of 5-FC on CD-expressing stem cell growth, results showed significant inhibition of HB1.F3.CD cell growth Cancer Sci. 2010 Apr;101(4):955-62
SKOV-3 cells 1, 10, 100 µg/mL 4 days To evaluate the effect of 5-FC on ovarian cancer cell growth, results showed no significant inhibition of SKOV-3 cell growth at tested concentrations Cancer Sci. 2010 Apr;101(4):955-62
MCF-7 human breast cancer cells 2 mM 72 h To investigate the cytotoxicity of 5-FC in the presence of UC-ACD on MCF-7 cells. ACS Nano. 2022 Oct 25;16(10):15873-15883
Caco-2 human colorectal cancer cells 2 mM 72 h To investigate the cytotoxicity of 5-FC in the presence of UC-ACD (conjugates of upconversion nanoparticles and anti-EGFR affibody-cytosine deaminase fusion proteins) on Caco-2 cells. ACS Nano. 2022 Oct 25;16(10):15873-15883
Human prostate carcinoma cells DU145 0–30mM 6 days To evaluate the sensitivity of DU145 cells transfected with wild-type and mutant bCD to 5FC, results showed that mutant bCD-transfected cells were 2.1–5-fold more sensitive to 5FC than wild-type. Cancer Res. 2009 Jun 1;69(11):4791-9
Human colorectal carcinoma cells HCT116 0–30mM 6 days To evaluate the sensitivity of HCT116 cells transfected with wild-type and mutant bCD to 5FC, results showed that mutant bCD-transfected cells were 2.4–17-fold more sensitive to 5FC than wild-type. Cancer Res. 2009 Jun 1;69(11):4791-9
Rat C6 glioma cells 0–30mM 6 days To evaluate the sensitivity of C6 cells transfected with wild-type and mutant bCD to 5FC, results showed that mutant bCD-transfected cells were 1.3–2.7-fold more sensitive to 5FC than wild-type. Cancer Res. 2009 Jun 1;69(11):4791-9
Cryptococcus gattii VGII 300 mg/mL To evaluate the adaptation of VGII strains to 5-fluorocytosine, finding that some VGII strains exhibited high adaptation to 5-fluorocytosine Innovation (Camb). 2024 Jul 31;5(5):100681

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Male athymic nu/nu mice Subcutaneous tumor model Intravenous injection 150 mg/kg Single dose, monitored for 2 hours To monitor the metabolism of 5-FC and 5-FU using 19F MRS. Results showed that CDUPRT expression led to enhanced accumulation of fluorine nucleotide (FNuc) in vivo. Radiother Oncol. 2009 Sep;92(3):345-52
C57BL/6 mice Intracerebral infection with Cryptococcus neoformans Intraperitoneal injection 100 mg/kg Every other day for 28 days Evaluate the efficacy of 5-FC combined with Amphotericin B. Results showed that all mice treated with AmpB + 5-FC survived until the end of the experiment, whereas only 33% of mice in the AmpB + PEA group survived. Antimicrob Agents Chemother. 2023 Oct 18;67(10):e0045923
BALB/c athymic nude mice Caco-2 tumor model Oral gavage 10 mg/mL Evaluate the tumor targeting and 5-FC conversion efficacy of UC-ACD in vivo. Results showed significantly slower tumor growth (2.2±0.04 - 2.5±0.16-fold) in UC-ACD (+)IR treated tumors, with median survival increasing from 28 to 35 days. ACS Nano. 2022 Oct 25;16(10):15873-15883
Nude mice HCT116 xenograft tumor model Intraperitoneal injection 375mg/kg Twice daily for 21 days To evaluate the tumor growth inhibition of mutant bCD (1525) in vivo, results showed that 1525-expressing tumors were significantly restricted in growth under 5FC treatment, while wild-type bCD-expressing tumors were unresponsive to the same dose of 5FC. Cancer Res. 2009 Jun 1;69(11):4791-9

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

7.75mL

1.55mL

0.77mL

38.73mL

7.75mL

3.87mL

77.47mL

15.49mL

7.75mL

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