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543020

Sigma-Aldrich

5-Fluorocytidine

97%

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About This Item

Empirical Formula (Hill Notation):
C9H12FN3O5
CAS Number:
2341-22-2
Molecular Weight:
261.21
MDL number:
MFCD00210953
UNSPSC Code:
12352200
PubChem Substance ID:
24878655
NACRES:
NA.22

assay

97%

form

solid

optical activity

[α]20/D +55°, c = 1% in methanol

mp

196-200 °C (lit.)

SMILES string

NC1=NC(=O)N(C=C1F)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O

InChI

1S/C9H12FN3O5/c10-3-1-13(9(17)12-7(3)11)8-6(16)5(15)4(2-14)18-8/h1,4-6,8,14-16H,2H2,(H2,11,12,17)/t4-,5-,6-,8-/m1/s1

InChI key

STRZQWQNZQMHQR-UAKXSSHOSA-N

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
11917TH
00931TO

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Xian-Run Luo et al.
Asian Pacific journal of cancer prevention : APJCP, 13(3), 781-784 (2012-05-29)
The aim of this study was to evaluate the effect of the adenovirus-mediated double suicide gene (CD/TK) for selective killing of gastric cancer cells. Gastric cancer cells SCG7901 and normal gastric epithelial cell lines were infected by adenoviruses Ad-survivin/GFP and
K Randerath et al.
Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer, 84, 283-297 (1983-01-01)
5-Fluoropyrimidines and 5-azapyrimidines were found in our laboratory to be specific inhibitors of modification reactions taking place at the 5 position of pyrimidines in nucleic acids. Thus, 5-fluorouracil and 5-fluorouridine specifically inhibit the formation of 5-methyluracil, pseudouridine, and 5,6-dihydrouracil in
K A Watanabe et al.
Journal of medicinal chemistry, 24(7), 893-897 (1981-07-01)
5'-O-Glucuronides of anticancer nucleosides, 5-fluorouridine and 5-fluorocytidine, were synthesized by three different methods. The best preparative procedure was the one starting from benzyl 5-O-(methyl 2', 3', 4'-tri-O-acetyl-beta-D-glucopyranosyluronate)-2,3-O-isopropylidene-beta-D-ribof uranoside (15) that was obtained almost quantitatively by condensation of benzyl 2,3-O-isopropylidene-beta-D-ribofuranoside (8)
I I Kaiser et al.
Biochimica et biophysica acta, 825(1), 12-20 (1985-05-24)
RNAs isolated from Escherichia coli B grown in the presence of 5-fluorouracil have high levels of the analog replacing uridine and uridine-derived modified nucleosides. Cytidine has also been shown to be replaced in these RNAs by 5-fluorocytidine, a metabolic product
L E Grosso et al.
Biochemistry, 23(12), 2651-2656 (1984-06-05)
The effects of 5-fluorocytidine on ribosomal RNA maturation and structure in Novikoff hepatoma cells were investigated. Like other nucleic acid base analogues that are incorporated into RNA, this compound inhibits maturation of the 45S ribosomal RNA precursor. The 45S RNA
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