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

3D

Download

MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for 5-fluorouridine (DB01629)

×

Close

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

Reduce drug development failure rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

See how

Build, train, & validate predictive machine-learning models with structured datasets.

See how

Contraindications & Blackbox Warnings

Avoid life-threatening adverse drug events

Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Learn more

Avoid life-threatening adverse drug events & improve clinical decision support.

Learn more

Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
USuperoxide dismutase [Cu-Zn]	Not Available	Humans
UUridine phosphorylase	Not Available	Escherichia 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

Improve decision support & research outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.

Learn more

Improve decision support & research outcomes with our structured adverse effects data.

Learn more

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Integrate drug-drug interactions in your software
Acenocoumarol	The risk or severity of bleeding can be increased when 5-fluorouridine is combined with Acenocoumarol.
Allantoin	The therapeutic efficacy of Allantoin can be decreased when used in combination with 5-fluorouridine.
Carbamazepine	The therapeutic efficacy of Carbamazepine can be decreased when used in combination with 5-fluorouridine.
Cimetidine	The serum concentration of 5-fluorouridine can be increased when it is combined with Cimetidine.
Dantrolene	The therapeutic efficacy of Dantrolene can be decreased when used in combination with 5-fluorouridine.
Dicoumarol	The risk or severity of bleeding can be increased when 5-fluorouridine is combined with Dicoumarol.
Ethotoin	The therapeutic efficacy of Ethotoin can be decreased when used in combination with 5-fluorouridine.
Fluindione	The risk or severity of bleeding can be increased when 5-fluorouridine is combined with Fluindione.
Folic acid	The risk or severity of adverse effects can be increased when Folic acid is combined with 5-fluorouridine.
Fosphenytoin	The serum concentration of Fosphenytoin can be increased when it is combined with 5-fluorouridine.

Identify potential medication risks

Easily compare up to 40 drugs with our drug interaction checker.

Get severity rating, description, and management advice.

Learn more

Food Interactions

Not Available

Categories

Drug Categories

• Fluorouracil and prodrugs
• Nucleic Acids, Nucleotides, and Nucleosides
• Nucleosides
• Pyrimidine Nucleosides
• Pyrimidines
• Ribonucleosides
• Thyroxine-binding globulin inducers

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 / Secondary alcohols / Lactams / Oxacyclic compounds / Azacyclic compounds / Hydrocarbon derivatives / Organic oxides / Organofluorides / Organonitrogen compounds / Organopnictogen compounds / Primary alcohols

show 10 more

Substituents

Alcohol / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Glycosyl compound / Halopyrimidine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Monosaccharide / N-glycosyl compound / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organofluoride / Organohalogen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Pentose monosaccharide / Primary alcohol / Pyrimidine / Pyrimidine nucleoside / Pyrimidone / Secondary alcohol / Tetrahydrofuran / Urea / Vinylogous amide

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]

External Links

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

Phase	Status	Purpose	Conditions	Count
2	Recruiting	Treatment	Advanced Solid Tumors	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	182 °C	MSDS

Predicted Properties

Property	Value	Source
Water Solubility	60.7 mg/mL	ALOGPS
logP	-1.4	ALOGPS
logP	-2.2	Chemaxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	8.07	Chemaxon
pKa (Strongest Basic)	-3	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	119.33 Å2	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	52.77 m3·mol-1	Chemaxon
Polarizability	21.92 Å3	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.8632
Blood Brain Barrier	+	0.7942
Caco-2 permeable	-	0.8975
P-glycoprotein substrate	Non-substrate	0.777
P-glycoprotein inhibitor I	Non-inhibitor	0.9316
P-glycoprotein inhibitor II	Non-inhibitor	0.9126
Renal organic cation transporter	Non-inhibitor	0.9424
CYP450 2C9 substrate	Non-substrate	0.7769
CYP450 2D6 substrate	Non-substrate	0.8695
CYP450 3A4 substrate	Non-substrate	0.6119
CYP450 1A2 substrate	Non-inhibitor	0.8802
CYP450 2C9 inhibitor	Non-inhibitor	0.9434
CYP450 2D6 inhibitor	Non-inhibitor	0.897
CYP450 2C19 inhibitor	Non-inhibitor	0.9158
CYP450 3A4 inhibitor	Non-inhibitor	0.9241
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9388
Ames test	Non AMES toxic	0.6664
Carcinogenicity	Non-carcinogens	0.869
Biodegradation	Not ready biodegradable	0.9304
Rat acute toxicity	2.1401 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9707
hERG inhibition (predictor II)	Non-inhibitor	0.7555

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (164 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Learn more

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Learn more

Details1. Superoxide dismutase [Cu-Zn]

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]

Details2. Uridine phosphorylase

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]

×

Identify potential medication risks

Easily compare up to 40 drugs with our drug interaction checker.

Get severity rating, description, and management advice.

Learn more

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