Identification

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Name
5-fluorouridine
Accession Number
DB01629  (EXPT00263)
Type
Small Molecule
Groups
Experimental
Description

5-fluorouridine is also known as FUrd, 5-Fluorouracil 1-beta-D-ribofuranoside, 5-Fur, or 5-Fluoro-uridine. 5-fluorouridine is a solid. This compound belongs to the pyrimidine nucleosides and analogues. These are compounds comprising a pyrimidine base attached to a sugar. 5-fluorouridine is known to target uridine phosphorylase. FUrd is often used in chemical and biochemical comparison studies with fluorouracil and thymine analogs.

Structure
Thumb
Synonyms
  • 5-Fluoro-uridine
  • 5-Fluorouracil 1beta-D-ribofuranoside
  • 5-Fur
Categories
UNII
4K0M952561
CAS number
316-46-1
Weight
Average: 262.1918
Monoisotopic: 262.060114299
Chemical Formula
C9H11FN2O6
InChI Key
FHIDNBAQOFJWCA-UAKXSSHOSA-N
InChI
InChI=1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(F)C(=O)NC1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUridine phosphorylaseNot AvailableEscherichia coli (strain K12)
USuperoxide dismutase [Cu-Zn]Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(6R)-Folinic acidThe risk or severity of adverse effects can be increased when (6R)-Folinic acid is combined with 5-fluorouridine.
(6S)-5,6,7,8-tetrahydrofolateThe risk or severity of adverse effects can be increased when (6S)-5,6,7,8-tetrahydrofolate is combined with 5-fluorouridine.
(R)-warfarinThe risk or severity of bleeding can be increased when 5-fluorouridine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when 5-fluorouridine is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when 5-fluorouridine is combined with 4-hydroxycoumarin.
5-methyltetrahydrofolic acidThe risk or severity of adverse effects can be increased when 5-methyltetrahydrofolic acid is combined with 5-fluorouridine.
AcenocoumarolThe risk or severity of bleeding can be increased when 5-fluorouridine is combined with Acenocoumarol.
CarbamazepineThe therapeutic efficacy of Carbamazepine can be decreased when used in combination with 5-fluorouridine.
CimetidineThe serum concentration of 5-fluorouridine can be increased when it is combined with Cimetidine.
ClorindioneThe risk or severity of bleeding can be increased when 5-fluorouridine is combined with Clorindione.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

References

Synthesis Reference

Setsuro Fujii, Eiichi Sakakibara, "2'-Deoxy-5-fluorouridine derivative and a process for producing the same and an antitumor agent comprising the same." U.S. Patent US4490366, issued October, 1977.

US4490366
General References
  1. Miracco EJ, Mueller EG: The products of 5-fluorouridine by the action of the pseudouridine synthase TruB disfavor one mechanism and suggest another. J Am Chem Soc. 2011 Aug 10;133(31):11826-9. doi: 10.1021/ja201179f. Epub 2011 Jul 15. [PubMed:21744792]
  2. Arbos P, Campanero MA, Irache JM: RP-LC determination of 5-fluorouridine in nanoparticulate formulations. J Pharm Biomed Anal. 2002 Jun 1;28(5):857-66. [PubMed:12039627]
External Links
Human Metabolome Database
HMDB0060396
KEGG Compound
C16633
PubChem Compound
9427
PubChem Substance
46504520
ChemSpider
9056
BindingDB
50132299
ChEBI
40154
ChEMBL
CHEMBL54918
HET
5UD
PDB Entries
1rxc / 1tgv / 4a7s / 4pb2
MSDS
Download (54.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)182 °CMSDS
Predicted Properties
PropertyValueSource
Water Solubility60.7 mg/mLALOGPS
logP-1.4ALOGPS
logP-2.2ChemAxon
logS-0.64ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area119.33 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.77 m3·mol-1ChemAxon
Polarizability21.9 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8632
Blood Brain Barrier+0.7942
Caco-2 permeable-0.8975
P-glycoprotein substrateNon-substrate0.777
P-glycoprotein inhibitor INon-inhibitor0.9316
P-glycoprotein inhibitor IINon-inhibitor0.9126
Renal organic cation transporterNon-inhibitor0.9424
CYP450 2C9 substrateNon-substrate0.7769
CYP450 2D6 substrateNon-substrate0.8695
CYP450 3A4 substrateNon-substrate0.6119
CYP450 1A2 substrateNon-inhibitor0.8802
CYP450 2C9 inhibitorNon-inhibitor0.9434
CYP450 2D6 inhibitorNon-inhibitor0.897
CYP450 2C19 inhibitorNon-inhibitor0.9158
CYP450 3A4 inhibitorNon-inhibitor0.9241
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9388
Ames testNon AMES toxic0.6664
CarcinogenicityNon-carcinogens0.869
BiodegradationNot ready biodegradable0.9304
Rat acute toxicity2.1401 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9707
hERG inhibition (predictor II)Non-inhibitor0.7555
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (164 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Not Available
Direct Parent
Pyrimidine nucleosides
Alternative Parents
Glycosylamines / Pentoses / Pyrimidones / Halopyrimidines / Aryl fluorides / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas
show 10 more
Substituents
Pyrimidine nucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Halopyrimidine / Pyrimidone / Aryl fluoride / Aryl halide / Hydropyrimidine / Monosaccharide
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, uridines (CHEBI:40154)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Uridine phosphorylase activity
Specific Function
Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources ...
Gene Name
udp
Uniprot ID
P12758
Uniprot Name
Uridine phosphorylase
Molecular Weight
27158.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name
SOD1
Uniprot ID
P00441
Uniprot Name
Superoxide dismutase [Cu-Zn]
Molecular Weight
15935.685 Da
References
  1. Wright GS, Antonyuk SV, Kershaw NM, Strange RW, Samar Hasnain S: Ligand binding and aggregation of pathogenic SOD1. Nat Commun. 2013;4:1758. doi: 10.1038/ncomms2750. [PubMed:23612299]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Serine-type endopeptidase inhibitor activity
Specific Function
Major thyroid hormone transport protein in serum.
Gene Name
SERPINA7
Uniprot ID
P05543
Uniprot Name
Thyroxine-binding globulin
Molecular Weight
46324.12 Da

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:20