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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- 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol 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 risksEasily 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
- 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
- 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]
- 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
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

- 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
- 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
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