F5130
5-Fluorouridine
≥99% (HPLC), synthetic (organic), powder
Synonym(s):
5-Fluorouracil 1β-D-ribofuranoside, FUrd
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About This Item
Empirical Formula (Hill Notation):
C9H11FN2O6
CAS Number:
Molecular Weight:
262.19
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
206-260-3
MDL number:
Beilstein/REAXYS Number:
33662
Assay:
≥99% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
Product Name
5-Fluorouridine, proapoptotic anitproliferative plant growth regulator
biological source
synthetic (organic)
Quality Level
assay
≥99% (HPLC)
form
powder
solubility
water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
SMILES string
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=C(F)C(=O)NC2=O
InChI
1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
InChI key
FHIDNBAQOFJWCA-UAKXSSHOSA-N
General description
5-Fluorouridine (FUrd) is a fluoropyrimidine nucleoside analog and a cell-permeable modified RNA precursor.
Application
5-Fluorouridine has been used for labeling active transcription sites in the porcine fetal fibroblasts and human cell lines for immunocytochemistry analysis. It has also been used to monitor apoptosis during drug sensitivity assay in esophageal squamous cell carcinoma (ESCC) cells.
Biochem/physiol Actions
5-Fluorouridine (FUrd) is cytotoxic towards cancer cells. FUrd is often used in chemical and biochemical comparison studies with fluorouracil and thymine analogs.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
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Inhibition of RNA synthesis by 5-fluorouridine accounts for its cyto toxicity on colorectal cancer cells in vitro
Subbarayan PR, et al.
Cancer research, 65(9) (2005)
P V Sahasrabudhe et al.
Nucleic acids research, 23(19), 3916-3921 (1995-10-11)
The effects of 5-fluorouridine (FUrd) and 5-fluorodeoxyuridine (FdUrd) substitution on the stabilities of duplex RNA and DNA have been studied to determine how FUrd substitution in nucleic acids may alter the efficiency of biochemical processes that require complementary base pairing
Angelica M Bello et al.
Journal of medicinal chemistry, 52(6), 1648-1658 (2009-03-06)
A series of 6-substituted and 5-fluoro-6-substituted uridine derivatives were synthesized and evaluated for their potential as anticancer agents. The designed molecules were synthesized from either fully protected uridine or the corresponding 5-fluorouridine derivatives. The mononucleotide derivatives were used for enzyme