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F0503

Sigma-Aldrich

5-Fluoro-2′-deoxyuridine

thymidylate synthase inhibitor

Synonym(s):

floxuridine, 2′-Deoxy-5-fluorouridine, FUDR, Floxuridine

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About This Item

Empirical Formula (Hill Notation):
C9H11FN2O5
CAS Number:
50-91-9
Molecular Weight:
246.19
Beilstein/REAXYS Number:
90221
EC Number:
200-072-5
MDL number:
MFCD00006530
UNSPSC Code:
12352202
PubChem Substance ID:
24894724
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

assay

≥99% (HPLC)

form

powder

mp

148 °C (lit.)

solubility

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

storage temp.

room temp

SMILES string

OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(F)C(=O)NC2=O

InChI

1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

InChI key

ODKNJVUHOIMIIZ-RRKCRQDMSA-N

Gene Information

human ... TYMS(7298)
mouse ... Tyms(22171)

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General description

5-Fluoro-2′-deoxyuridine, also called floxuridine elicits DNA-directed cytotoxicity in cancer cells. Floxuridine is effective for treating liver cancer and eliminating virulence of Staphylococcus aureus. Dipeptide prodrugs combination of floxuridine with gemcitabine are more cell permeable and display enhanced anti-proliferative activity. Floxuridine is effective on solid tumours and advanced stage cancers.

Application

5-Fluoro-2′-deoxyuridine has been used as a mitotic inhibitor in schwann cell proliferation, glia proliferation and nonneuronal cells in dorsal root ganglion cultures.

Biochem/physiol Actions

Antineoplastic drug that acts as a potent inhibitor of thymidylate synthetase Resistance to FUdR can develop in cancer cell cultures, among other means, by low-level Mycoplasma infection.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The FDA-approved anti-cancer drugs, streptozotocin and floxuridine, reduce the virulence of Staphylococcus aureus
Yeo WS, et al.
Scientific Reports, 8(1), 2521-2521 (2018)
Palmitoylation enables MAPK-dependent proteostasis of axon survival factors
Summers DW, et al.
Proceedings of the National Academy of Sciences of the USA, 115(37), E8746-E8754 (2018)
Enhanced absorption and growth inhibition with amino acid monoester prodrugs of floxuridine by targeting hPEPT1 transporters
Tsume Y, et al.
Molecules (Basel), 13(7), 1441-1454 (2008)
Cheng Shi et al.
Science (New York, N.Y.), 343(6170), 536-540 (2013-12-21)
Interactions between the germ line and the soma help optimize reproductive success. We discovered a phenomenon linking reproductive status to longevity: In both hermaphroditic and gonochoristic Caenorhabditis, mating leads to female shrinking and death, compressing postreproductive life span. Male sperm
The Dipeptide Monoester Prodrugs of Floxuridine and Gemcitabine?Feasibility of Orally Administrable Nucleoside Analogs
Tsume Y, et al.
Pharmaceuticals (Basel, Switzerland), 7(2), 169-191 (2014)
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