Structure of 5-Fluorocytosine
CAS No.: 2022-85-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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| 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 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302 |
| Precautionary Statements: | P280-P305+P351+P338 |
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 |
| 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 |
|
Tags: Flucytosine | 5-Fluorocytosine | NSC 103805 | Ro 2-9915 | NSC103805 | NSC 103805 | NSC-103805 | Fungal | Antibiotic | 5-FC | 5-FU | MKN45 | CD-hMSC | 2022-85-7 |
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