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543020

Sigma-Aldrich

5-Fluorocytidine

97%

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About This Item

Empirical Formula (Hill Notation):
C9H12FN3O5
CAS Number:
Molecular Weight:
261.21
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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

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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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
J E Kurtz et al.
Current genetics, 36(3), 130-136 (1999-09-29)
Cytidine metabolism in the yeast Saccharomyces cerevisiae was analyzed by genetic and biochemical approaches. Disruption of a unique ORF (Genbank accession No. U 20865) bearing homology with eucaryotic or bacterial cytidine deaminases abolished cytidine deaminase activity and resulted in 5-fluorocytidine
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
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)
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

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