Flucytosine

For research use only. Not for therapeutic Use.

  • CAT Number: A000838
  • CAS Number: 2022-85-7
  • Molecular Formula: C4H4FN3O
  • Molecular Weight: 129.10
  • Purity: ≥95%
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Flucytosine(Cat No.:A000838)is a fluorinated pyrimidine analog with potent antifungal activity, commonly used in research and clinical applications. It targets fungal cells by converting into 5-fluorouracil, disrupting RNA and DNA synthesis. Effective against Candida, Cryptococcus, and certain molds, Flucytosine is often combined with other antifungal agents, such as amphotericin B, to enhance efficacy and reduce resistance. Its unique mechanism and selective toxicity to fungal cells make it a valuable tool in antifungal drug development. Research focuses on optimizing dosing and managing resistance for improved therapeutic outcomes.


Catalog Number A000838
CAS Number 2022-85-7
Synonyms

5-Fluorocytosine; Flucytosine; 2022-85-7; Ancotil; Ancobon; Flucytosin

Molecular Formula C4H4FN3O
Purity ≥95%
Target Antibiotic
Solubility >6.4mg/mL in DMSO
Storage -20°C
IUPAC Name 6-amino-5-fluoro-1H-pyrimidin-2-one
InChI InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
InChIKey XRECTZIEBJDKEO-UHFFFAOYSA-N
SMILES C1=NC(=O)NC(=C1F)N
Reference

1: Fang XF, Li D, Tangadanchu VKR, Gopala L, Gao WW, Zhou CH. Novel potentially
antifungal hybrids of 5-flucytosine and fluconazole: Design, synthesis and
bioactive evaluation. Bioorg Med Chem Lett. 2017 Nov 15;27(22):4964-4969. doi:
10.1016/j.bmcl.2017.10.020. Epub 2017 Oct 13. PubMed PMID: 29050784.

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2: Folk A, Balta C, Herman H, Ivan A, Boldura OM, Paiusan L, Ardelean A,
Hermenean A. Flucytosine and Amphotericin B Coadministration Induces Dose-Related
Renal Injury. Dose Response. 2017 Jun 5;15(2):1559325817703461. doi:
10.1177/1559325817703461. eCollection 2017 Apr-Jun. PubMed PMID: 28620270; PubMed
Central PMCID: PMC5464384.
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3: Asadzadeh M, Ahmad S, Al-Sweih N, Khan Z. Population structure and molecular
genetic characterization of 5-flucytosine-susceptible and -resistant clinical
Candida dubliniensis isolates from Kuwait. PLoS One. 2017 Apr 5;12(4):e0175269.
doi: 10.1371/journal.pone.0175269. eCollection 2017. PubMed PMID: 28380072;
PubMed Central PMCID: PMC5381908.
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4: Wani MY, Ahmad A, Kumar S, Sobral AJ. Flucytosine analogues obtained through
Biginelli reaction as efficient combinative antifungal agents. Microb Pathog.
2017 Apr;105:57-62. doi: 10.1016/j.micpath.2017.02.006. Epub 2017 Feb 9. PubMed
PMID: 28189732.
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5: Husseini F, Delord JP, Fournel-Federico C, Guitton J, Erbs P, Homerin M,
Halluard C, Jemming C, Orange C, Limacher JM, Kurtz JE. Vectorized gene therapy
of liver tumors: proof-of-concept of TG4023 (MVA-FCU1) in combination with
flucytosine. Ann Oncol. 2017 Jan 1;28(1):169-174. doi: 10.1093/annonc/mdw440.
PubMed PMID: 28177438.
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6: Pais P, Pires C, Costa C, Okamoto M, Chibana H, Teixeira MC. Membrane
Proteomics Analysis of the Candida glabrata Response to 5-Flucytosine: Unveiling
the Role and Regulation of the Drug Efflux Transporters CgFlr1 and CgFlr2. Front
Microbiol. 2016 Dec 21;7:2045. doi: 10.3389/fmicb.2016.02045. eCollection 2016.
PubMed PMID: 28066366; PubMed Central PMCID: PMC5174090.
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7: Berger AG, Restaino SM, White IM. Vertical-flow paper SERS system for
therapeutic drug monitoring of flucytosine in serum. Anal Chim Acta. 2017 Jan
1;949:59-66. doi: 10.1016/j.aca.2016.10.035. Epub 2016 Nov 2. PubMed PMID:
27876146.
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8: Tsuji G, Matsuda T, Shigyo A, Matsuda T, Furue M. Primary cutaneous
cryptococcosis successfully managed by surgical debridement and liposomal
amphotericin B/flucytosine therapy. Eur J Dermatol. 2017 Feb 1;27(1):96-97. doi:
10.1684/ejd.2016.2910. PubMed PMID: 27758760.
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9: Costabile G, d/’Angelo I, d/’Emmanuele di Villa Bianca R, Mitidieri E, Pompili
B, Del Porto P, Leoni L, Visca P, Miro A, Quaglia F, Imperi F, Sorrentino R,
Ungaro F. Development of inhalable hyaluronan/mannitol composite dry powders for
flucytosine repositioning in local therapy of lung infections. J Control Release.
2016 Sep 28;238:80-91. doi: 10.1016/j.jconrel.2016.07.029. Epub 2016 Jul 19.
PubMed PMID: 27449745.
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10: Claustre J, Brion JP, Quétant S, Bedouch P, Pison C, Camara B. Favorable
Evolution of Cryptococcal Meningitis in the Context of Flucytosine Resistance.
Exp Clin Transplant. 2016 Apr 26. doi: 10.6002/ect.2015.0217. [Epub ahead of
print] PubMed PMID: 27143150.

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