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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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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)
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
Mode of action of 5-fluorocytidine and 5-fluoro-2'-deoxycytidine in L5178Y cells in vitro.
M Yoshida et al.
Chemical & pharmaceutical bulletin, 30(3), 1018-1023 (1982-03-01)
Gottfried K Schroeder et al.
Biochemistry, 51(32), 6476-6486 (2012-07-11)
Cytidine deaminase (CDA) binds the inhibitor zebularine as its 3,4-hydrate (K(d) ~ 10(-12) M), capturing all but ~5.6 kcal/mol of the free energy of binding expected of an ideal transition state analogue (K(tx) ~ 10(-16) M). On the basis of
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