floxuridine   Click here for help

GtoPdb Ligand ID: 4801

Synonyms: 5-fluoro-2'-deoxyuridine | floxidine | FUDR®
Approved drug
floxuridine is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: Floxuridine is metabolized to 5-fluorouracil when given by rapid injection, but is converted to floxuridine monophosphate when given as continuous infusion. 5-fluorouracil is considered the active drug.

floxuridine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 104.55
Molecular weight 246.07
XLogP -0.66
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCC1OC(CC1O)n1cc(F)c(=O)[nH]c1=O
Isomeric SMILES OC[C@H]1O[C@H](C[C@@H]1O)n1cc(F)c(=O)[nH]c1=O
InChI 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
Bioactivity Comments
We have been unable to find publicly available bioactivity data for this drug at its proposed molecular target (thymidylate synthase) to substantiate its MMOA, and have therefore not tagged a primary drug target.
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Solute carrier family 28 member 3
Equilibrative nucleoside transporter 1
Equilibrative nucleoside transporter 3 1