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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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC6160
SLCB5571
SLBS1345V
SLBQ4116V
SLBL9184V

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Elite Possik et al.
PLoS genetics, 10(4), e1004273-e1004273 (2014-04-26)
Dysregulation of AMPK signaling has been implicated in many human diseases, which emphasizes the importance of characterizing AMPK regulators. The tumor suppressor FLCN, responsible for the Birt-Hogg Dubé renal neoplasia syndrome (BHD), is an AMPK-binding partner but the genetic and
S G Louie et al.
British journal of cancer, 109(7), 1744-1749 (2013-09-12)
The aging process is accompanied by physiological changes including reduced glomerular filtration and hepatic function, as well as changes in gastric secretions. To investigate what effect would aging have on the disposition of capecitabine and its metabolites, the pharmacokinetics between
Diana Andrea Fernandes de Abreu et al.
PLoS genetics, 10(3), e1004225-e1004225 (2014-03-29)
Insulin-like peptides (ILPs) play highly conserved roles in development and physiology. Most animal genomes encode multiple ILPs. Here we identify mechanisms for how the forty Caenorhabditis elegans ILPs coordinate diverse processes, including development, reproduction, longevity and several specific stress responses.
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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Articles

Nucleotide Synthesis in Cancer Cells

Neoplastic cells are highly dependent on the de novo synthesis of nucleotides to maintain sufficient pools to support DNA replication and the production of RNA.

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