5-fluorouridine

Identification

Generic Name
5-fluorouridine
DrugBank Accession Number
DB01629
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 262.1918
Monoisotopic: 262.060114299
Chemical Formula
C9H11FN2O6
Synonyms
  • 5-Fluoro-uridine
  • 5-Fluorouracil 1beta-D-ribofuranoside
  • 5-Fur

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USuperoxide dismutase [Cu-Zn]Not AvailableHumans
UUridine phosphorylaseNot AvailableEscherichia coli (strain K12)
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when 5-fluorouridine is combined with Acenocoumarol.
AllantoinThe therapeutic efficacy of Allantoin can be decreased when used in combination with 5-fluorouridine.
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.
DantroleneThe therapeutic efficacy of Dantrolene can be decreased when used in combination with 5-fluorouridine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Glycosyl compound / Halopyrimidine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, uridines (CHEBI:40154)
Affected organisms
Not Available

Chemical Identifiers

UNII
4K0M952561
CAS number
316-46-1
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

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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0060396
KEGG Compound
C16633
PubChem Compound
9427
PubChem Substance
46504520
ChemSpider
9056
BindingDB
50132299
ChEBI
40154
ChEMBL
CHEMBL54918
ZINC
ZINC000001078624
PDBe Ligand
5UD
PDB Entries
1rxc / 1tgv / 4a7s / 4pb2 / 7r9f
MSDS
Download (54.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentAdvanced Solid Tumors1

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)8.07Chemaxon
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
Polarizability21.92 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-MSsplash10-0536-9440000000-95cd5ad111dfa003f286
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0920000000-2c17462e21480c5a2cfc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-4910000000-f06b62938cf5fed1cdde
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-6900000000-2b684873a6d54ec1251f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-9600000000-e65e962d08316dbcb220
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-7900000000-5d494c8c09298e0acadf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9810000000-150b6a6a211000c01dfa
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-161.7367571
predicted
DarkChem Lite v0.1.0
[M-H]-159.76476
predicted
DeepCCS 1.0 (2019)
[M+H]+164.7120571
predicted
DarkChem Lite v0.1.0
[M+H]+162.16086
predicted
DeepCCS 1.0 (2019)
[M+Na]+162.1592571
predicted
DarkChem Lite v0.1.0
[M+Na]+168.67719
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
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. [Article]
  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. [Article]

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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:51