5-Fluorouridine

Base Information

• Chemical Name: 5-Fluorouridine
• CAS No.: 316-46-1
• Molecular Formula: C9H11FN2O6
• Molecular Weight: 262.195
• Hs Code.: 29349990
• European Community (EC) Number: 206-260-3
• UNII: 4K0M952561
• DSSTox Substance ID: DTXSID4040397
• Nikkaji Number: J36.572F
• Wikidata: Q27073979
• Metabolomics Workbench ID: 52243
• ChEMBL ID: CHEMBL54918
• Mol file: 316-46-1.mol

Synonyms:5-fluorouridine;5-fluorouridine, 18F-labeled

Chemical Property of 5-Fluorouridine

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 182-184 °C
• Refractive Index: 18 ° (C=1, H2O)
• PKA: 7.63±0.10(Predicted)
• PSA: 124.78000
• Density: 1.77 g/cm³
• LogP: -2.71280
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 50 mg/ml), in Water (up to 50 mg/ml), or in Ethanol (up to 6 mg/ml with warming)
• Water Solubility.: soluble
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 262.06011424
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

99% ^*data from raw suppliers

5-Fluorouridine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 40-68-36/37/38
• Safety Statements: 22-26-36/37-36/37/39-27-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)F
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)F
• Recent ClinicalTrials: A Phase II Study of Envofolimab and BD0801 With/Without Chemotherapy in Patients With Advanced Solid Tumors
• Description: 5-Fluorouridine (316-46-1) is an inhibitor of ribozyme self-cleavage in mammalian cells.1? Induces apoptosis in HCT-116 colorectal carcinoma cells causing diverse gene expression patterns suggesting that mechanisms besides global inhibition of RNA synthesis and processing contribute to 5-fluorouridine cytotoxicity.2 Cell permeable and active in vivo.
• Uses: 5-Fluoro Uridine is an active metabolite of Doxifluridine (D556750). Antihypertensive 5-Fluorouridine exhibits anticancer activity. It is often used in chemical and biochemical comparison studies with fluorouracil and thymine analogs. It is an active metabolite of Doxifluridine.

Technology Process of 5-Fluorouridine

There total 41 articles about 5-Fluorouridine 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: 79.0%

uridine (58-96-8) → 5-fluorouridine (316-46-1)

Guidance literature:

With caesium fluoroxysulphate; triethylamine; In methanol; water; Ambient temperature;

DOI:10.1039/c39830000563

Reference yield: 76.0%

5-fluorouracil (51-21-8) + 7-methylguanosine hydroiodide (81100-62-1) → 5-fluorouridine (316-46-1)

Guidance literature:

With potassium dihydrogenphosphate; E_. coli purine nucleoside phosphorylase; E_. coli uridine phosphorylase; In aq. buffer; at 20 ℃; for 20h; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.bbapap.2019.140292

Reference yield: 46.6%

CYTIDINE (65-46-3) → 5-fluorouridine (316-46-1)

Guidance literature:

upstream raw materials:

1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-fluoro-uracil

Acetic acid (4R,5S)-3-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-fluoro-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

Acetic acid (4S,5R)-3-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-fluoro-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

acetyl hypofluorite

Downstream raw materials:

5-fluoro-5'-O-trityl-2',3'-secouridine

choline

Octadecanoic acid (S)-2-{[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-1-octadecanoyloxymethyl-ethyl ester

2',3'-O-isopropylidene-5-fluorouridine

Refernces

• 1、 Yung et al.. "-". . p. 4060,4063. Retrieved 1961.
• 2、 Birmingham, William R.,Burke, Ashleigh J.,Charnock, Simon J.,Crawshaw, Rebecca,Finnigan, James D.,Green, Anthony P.,Holgate, Gregory M.,Lovelock, Sarah L.,Muldowney, Mark P.,Rowles, Ian,Thorpe, Thomas W.,Turner, Nicholas J.,Young, Carl,Zhuo, Ying,Zucoloto Da Costa, Bruna. "An Engineered Cytidine Deaminase for Biocatalytic Production of a Key Intermediate of the Covid-19 Antiviral Molnupiravir". supporting information. p. 3761 - 3765. Retrieved 2022/03/15.
• 3、 Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "Thermodynamic Reaction Control of Nucleoside Phosphorolysis". . p. 867 - 876. Retrieved 2020/01/24.