Product Name

Floxuridine

CAS Number

50-91-9

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Product Name:
Floxuridine
CAS Number:
50-91-9
Indication:
For palliative management of gastrointestinal adenocarcinoma metastatic to the liver, when given by continuous regional intra-arterial infusion in carefully selected patients who are considered incurable by surgery or other means. Also for the palliative management of liver cancer (usually administered by hepatic intra-arterial infusion).
Mode of Action:

Floxuridine is rapidly catabolized to 5-fluorouracil, which is the active form of the drug. The primary effect is interference with DNA synthesis and to a lesser extent, inhibition of RNA formation through the drug's incorporation into RNA, thus leading to the production of fraudulent RNA. Fluorouracil also inhibits uracil riboside phophorylase, which prevents the utilization of preformed uracil in RNA synthesis. As well, the monophosphate of floxuridine, 5-fluoro-2'-deoxyuridine-5'-phosphate (FUDR-MP) inhibits the enzyme thymidylate synthetase. This leads to the inhibition of methylation of deoxyuridylic acid to thymidylic acid, thus interfering with DNA synthesis.

Pharmacodynamics:

Floxuridine is a pyrimidine analog that acts as an inhibitor of the S-phase of cell division. This selectively kills rapidly dividing cells. Floxuridine is an anti-metabolite. Anti-metabolites masquerade as pyramidine-like molecules which prevents normal pyrimidines from being incorporated into DNA during the S phase of the cell cycle. Flurouracil (the end-product of catabolism of floxuridine) blocks an enzyme which converts cytosine nucleosides into the deoxy derivative. In addition, DNA synthesis is further inhibited because fluoruracil blocks the incorporation of the thymdine nucleotide into the DNA strand.

Metabolism:

Hepatic.

Toxicity:

Oral, rat LD50: 215 mg/kg. Signs of overdose include nausea, vomiting, diarrhea, gastrointestinal ulceration and bleeding, and bone marrow depression (including thrombocytopenia, leukopenia and agranulocytosis).

IUPAC:
5-fluoro-1-[(2R, 4S, 5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1, 2, 3, 4-tetrahydropyrimidine-2, 4-dione
PubChem:
5790
DrugBank:
DB00322 (APRD00692)
Formula:
C24H30F2O6
Molecular Mass:
246.1924
Synonyms:
5 Fluorodeoxyuridine 5FDU Deoxyfluorouridine FDUR FDURD Floxiridina [INN-Spanish] Floxuridin Floxuridinum [INN-Latin] Fluorodeoxyuridine Fluoruridine Deoxyribose
SMILES:
OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O
InChi:
ODKNJVUHOIMIIZ-RRKCRQDMSA-N

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