Flucytosine

Base Information

• Chemical Name: Flucytosine
• CAS No.: 2022-85-7
• Molecular Formula: C4H4FN3O
• Molecular Weight: 129.094
• Hs Code.: 29335990
• European Community (EC) Number: 217-968-7
• NSC Number: 759130,103805
• UNII: D83282DT06
• DSSTox Substance ID: DTXSID3023059
• Nikkaji Number: J3.695A
• Wikipedia: Flucytosine
• Wikidata: Q238490
• NCI Thesaurus Code: C501
• RXCUI: 4451
• Metabolomics Workbench ID: 43329
• ChEMBL ID: CHEMBL1463
• Mol file: 2022-85-7.mol

Synonyms:5-Fluorocytosine;Alcobon;Ancobon;Ancotil;Flucytosine

Chemical Property of Flucytosine

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0.0492mmHg at 25°C
• Melting Point: 298-300 °C (dec.)(lit.)
• Refractive Index: 1.613
• Boiling Point: 298oC
• PKA: 3.26(at 25℃)
• Flash Point: 96.4°C
• PSA: 71.77000
• Density: 1.73 g/cm³
• LogP: 0.07240
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Sparingly soluble in water, slightly soluble in ethanol (96 per cent)
• Water Solubility.: 1.5g/100mL (25 ºC)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 129.03383992
• Heavy Atom Count: 9
• Complexity: 208

Purity/Quality:

99% ^*data from raw suppliers

5-Fluorocytosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T, Xi
• Hazard Codes: Xn,T,Xi
• Statements: 40-36/37/38-63
• Safety Statements: 22-24/25-45-36/37-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antifungal Agents
• Canonical SMILES: C1=NC(=O)NC(=C1F)N
• Recent ClinicalTrials: Clinical Study of ABCD in the Treatment of Cryptococcal Meningitis
• Recent EU Clinical Trials: A dose escalation and phase IIa study of TG6002 plus flucytosine in patients with unresectable colorectal cancer with liver metastases
• General Description: Fluorocytosine, also known as 5-fluorocytosine (5-FC), is an antifungal and antineoplastic agent that has been explored for its therapeutic potential, particularly in the development of derivatives with enhanced antitumor activity and reduced toxicity. The study highlights its role as a precursor in synthesizing novel compounds, such as 5′-deoxy-N-alkyloxycarbonyl-5-fluorocytosine-5′-carboxylic acid, aimed at improving chemotherapeutic efficacy while minimizing adverse effects compared to existing treatments like 5-fluorouracil (5-FU) and capecitabine.

Technology Process of Flucytosine

There total 21 articles about Flucytosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.1%

2,5-difluoro-4-chloro-pyrimidine (99429-06-8) → Flucytosine (2022-85-7)

Guidance literature:

With ammonia; In hydrogenchloride; ethanol; water;

Reference yield: 98.0%

→ Flucytosine (2022-85-7)

Guidance literature:

Reference yield: 95.7%

Cytosine (71-30-7) → Flucytosine (2022-85-7)

Guidance literature:

Cytosine; With hydrogen fluoride; at -15 - 0 ℃; Inert atmosphere;

at -20 ℃; for 4h; Further stages; Inert atmosphere;

upstream raw materials:

2-ethylsulfanyl-5-fluoro-pyrimidin-4-ylamine

Cytosine

β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine

2,5-difluoro-4-chloro-pyrimidine

Downstream raw materials:

N¹-(4-benzoyl-2-butyn-1-yl)-5-fluorocytosine

1-(3,5-O-dibenzoyl-2-fluoro-β-D-arabinofuranosyl)-5-fluorocytosine

4-amino-5-fluoro-1-<<2-(benzoyloxy)-1-<(benzoyloxy)methyl>ethoxy>methyl>cytosine

5-fluorouracil

Refernces

Synthesis and biological activity of the new 5-fluorocytosine derivatives, 5′-deoxy-N-alkyloxycarbonyl-5-fluorocytosine-5′-carboxylic acid

10.1016/S0960-894X(01)00782-X

The study focuses on the synthesis and biological activity of new 5-fluorocytosine derivatives, specifically 50-deoxy-N-alkyloxycarbonyl-5-fluorocytosine-50-carboxylic acid 6, which were designed to possess potent antitumor activity and low toxicity. The chemicals used in the study include 5-fluorocytosine, 1,1,1,3,3,3-hexamethyldisilazane, ammonium sulfate, b-dribofuranose 1,2,3,5-tetraacetate, N,N-diisopropylethylamine, alkyl chloroformate, sodium methoxide, and platinum oxide. These chemicals served various purposes in the synthetic route to produce the new derivatives, such as coupling agents, catalysts, and reagents for alkyloxycarbonylation, hydrolysis, and oxidation steps. The purpose of these chemicals was to create new compounds that could potentially replace or improve upon existing chemotherapeutic agents like 5-fluorouracil (5-FU) and capecitabine, offering more effective cancer treatment with fewer side effects.