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F8423

Sigma-Aldrich

Fluorouracil

meets USP testing specifications

Synonym(s):

5-Fluorouracil, 2,4-Dihydroxy-5-fluoropyrimidine, 5-FU, 5-Fluoro-2,4(1H,3H)-pyrimidinedione

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About This Item

Empirical Formula (Hill Notation):
C4H3FN2O2
CAS Number:
51-21-8
Molecular Weight:
130.08
Beilstein:
127172
EC Number:
200-085-6
MDL number:
MFCD00006018
UNSPSC Code:
12352207
PubChem Substance ID:
24894963
NACRES:
NA.71

Agency

USP/NF
meets USP testing specifications

mp

282-286 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

SMILES string

FC1=CNC(=O)NC1=O

InChI

1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

InChI key

GHASVSINZRGABV-UHFFFAOYSA-N

Gene Information

human ... TYMS(7298)

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Related Categories

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Certificates of Analysis (COA)

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Aurélien Montagu et al.
European journal of medicinal chemistry, 46(2), 778-786 (2011-01-15)
The synthesis and antiviral evaluation of a series of C5-(1,4- and 1,5-disubstituted-1,2,3-triazolo)-nucleoside derivatives is described. The key steps of this synthesis are regioselective Huisgen's 1,3-dipolar cycloaddition, using either copper-catalyzed azide-alkyne cycloaddition (CuAAC) or ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) under microwave activation.
Julia K J Ahlskog et al.
Bioorganic & medicinal chemistry letters, 19(16), 4851-4856 (2009-07-21)
We describe the synthesis and characterization of two acetazolamide derivatives containing either a charged fluorophore or an albumin-binding moiety, which restrict binding to carbonic anhydrase IX and XII present on tumor cells. In vivo studies showed the preferentially targeting of
Zhiyang Chen et al.
Nature communications, 6, 6808-6808 (2015-04-17)
Wild-type p53-induced phosphatase 1 (Wip1) negatively regulates several tumour suppressor and DNA damage response pathways. However, the impact of Wip1 on haematopoietic stem cell (HSC) homeostasis and aging remains unknown. Here we show that Wip1 is highly expressed in HSCs
Umashankar Das et al.
European journal of medicinal chemistry, 42(1), 71-80 (2006-09-26)
The 3,5-bis(arylidene)-4-piperidones 1 contain the 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore which is considered to interact at a complementary binding site in susceptible neoplasms. The hypothesis was formulated that the presence of an acyl group attached to the piperidyl nitrogen atom in series 1
Umashankar Das et al.
Journal of medicinal chemistry, 54(9), 3445-3449 (2011-04-01)
Novel 3,5-bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones (3a-e) display potent cytotoxicity and a preferential lethality toward various neoplasms compared to some normal cells. The corresponding sulfonic acid analogues 5a-e and an isostere 4 demonstrated substantially lower activity. The leads 3d and 3e possess very high
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