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floxuridine

Structure via PubChem · Public domain (PubChem)

EntityQ5462356· pop 12· linked from 280 articles

floxuridine

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Also known as 5-fluoro-2'-deoxyuridine, floxidine, FUDR®, FdU, Floxuridin, beta-5-Fluoro-2'-deoxyuridine, Fluoruridine deoxyribose, 5-Fluoro-2-desoxyuridine

Floxuridine (also 5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites. Specifically, floxuridine is a pyrimidine analog, classified as a deoxyuridine. The drug is usually administered via an artery, and most often used in the treatment of colorectal cancer. The quality of life and survival rates of individuals that receive continuous hepatic artery infusion of floxuridine for colorectal cancer metastases is significantly higher than control groups. Floxuridine can also be prescribed for the treatment of kidney and stomach cancers. In vitro uses of floxu

Chemical data

Formula
C9H11FN2O5
Molecular weight
246.19 g/mol
IUPAC name
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
SMILES
C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)F)CO)O
InChIKey
ODKNJVUHOIMIIZ-RRKCRQDMSA-N
XLogP
-1.2
Polar surface area
99.1 Ų
H-bond donors
3
H-bond acceptors
6
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
First approval
1970
Admin. routes
parenteral
Indications
hepatocellular carcinoma, colorectal adenocarcinoma, gastric adenocarcinoma, colorectal neoplasm

via ChEMBL · EBI

Research

3,715 papers

via PubMed

Wikidata facts

Subclass of
deoxyuridine
Mass
246.0652
Has use
medication
Show 10 more facts
chemical formula
C₉H₁₁FN₂O₅
medical condition treated
stomach cancer
isomeric SMILES
C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)F)CO)O
canonical SMILES
C1C(C(OC1N2C=C(C(=O)NC2=O)F)CO)O
World Health Organisation international non-proprietary name
floxuridine
subject has role
bactericide
Commons category
Floxuridine
melting point
150
legal status (medicine)
boxed warning
found in taxon
Streptomyces
Sources (5)

via Wikidata · CC0

~7 min read

Encyclopedic overview

15 sections
Contents
  • Biosynthesis
  • Pharmacology
  • Pharmacodynamics
  • Mechanism of action
  • Route of elimination
  • Side effects
  • Common (30% of patients)
  • Less common (10–29% of patients)
  • Contact your health provider immediately
  • Contact your health provider
  • Other
  • Use in research
  • History
  • Alternative names
  • References

Floxuridine (also 5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites. Specifically, floxuridine is a pyrimidine analog, classified as a deoxyuridine. The drug is usually administered via an artery, and most often used in the treatment of colorectal cancer. The quality of life and survival rates of individuals that receive continuous hepatic artery infusion of floxuridine for colorectal cancer metastases is significantly higher than control groups. Floxuridine can also be prescribed for the treatment of kidney and stomach cancers. In vitro uses of floxuridine include 5-minute treatments of fluorouracil, floxuridine, and mitomycin to increase cell proliferation in Tenon's capsule fibroblasts.

==Biosynthesis == thumb|400px|Biosynthesis of floxuridine Immobilized Aeromonas salmonicida ATCC 27013, when exposed to thymidine and 5-fluorouracil in phosphate buffer at room temperature for one hour, can synthesize floxuridine and thymine.

Excerpted from Wikipedia’s “floxuridine” article, available under the CC BY-SA 4.0 licence.

Gallery (2)

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