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Merck
CN

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:
316-46-1
Molecular Weight:
262.19
NACRES:
NA.51
PubChem Substance ID:
24894883
UNSPSC Code:
41106305
EC Number:
206-260-3
MDL number:
MFCD00036832
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

Key Documents

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Product Name

5-Fluorouridine, proapoptotic anitproliferative plant growth regulator

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

biological source

synthetic (organic)

assay

≥99% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

Quality Level

100

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW8681
MKCV4635
MKCT2114
MKCN6639
MKCQ7684

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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
P M Ellery et al.
Placenta, 30(4), 329-334 (2009-02-14)
The aim was to test for evidence of transcriptional activity within the nuclei of the syncytiotrophoblast of the human placenta. The syncytiotrophoblast forms the epithelial covering of the villous tree, and is a multinucleated, terminally-differentiated syncytium generated through fusion of
Nikolaos Tsesmetzis et al.
Cancers, 10(7) (2018-07-26)
Antimetabolites, in particular nucleobase and nucleoside analogues, are cytotoxic drugs that, starting from the small field of paediatric oncology, in combination with other chemotherapeutics, have revolutionised clinical oncology and transformed cancer into a curable disease. However, even though combination chemotherapy
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