Trifluridine (CED0005296)

Record Information

Version

1.0

Creation Date

2016-05-22 05:50:04 UTC

Update Date

2026-08-17 22:14:46 UTC

SynCED ID

CED0005296

Secondary Accession Numbers

CHEM019116

Identification

Common Name

Trifluridine

Class

Small Molecule

Description

Trifluridine is an organic compound with the formula C10H11F3N2O5 and an average molecular weight of 296.20 g/mol. Trifluridine belongs to the pyrimidine 2'-deoxyribonucleosides, a subclass of pyrimidine nucleosides within the organic compounds. This compound is recorded as being released from healthcare, pharmaceuticals, and veterinary products, specifically acting as an antiinfective and an antineoplastic agent. Recorded exposure routes for the substance include oral and ophthalmic administration. In terms of biological activity, trifluridine interacts with two recorded protein targets, acting as an inhibitor of thymidylate synthase (TYMS) and targeting thymidylate synthase (TMP1).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-(Trifluoromethyl)deoxyuridine	ChEBI
5-Trifluoromethyl-2-deoxyuridine	ChEBI
Trifluoromethyldeoxyuridine	ChEBI
Trifluorothymidine	ChEBI
Trifluorothymine deoxyriboside	ChEBI
Trifluridina	ChEBI
Trifluridinum	ChEBI
Viroptic	ChEBI
Elcon brand OF trifluridine	HMDB
Viromidin	HMDB
5-Trifluoromethyl-2'-deoxyuridine	HMDB
Allergan brand OF trifluridine	HMDB
Mann brand OF trifluridine	HMDB
Monarch brand OF trifluridine	HMDB
Tramedico brand OF trifluridine	HMDB
Trifluoridine	HMDB
2'-Deoxy-5-(trifluoromethyl)uridine	HMDB
5 Trifluoromethyl 2' deoxyuridine	HMDB
TFT Ophtiole	HMDB
Triflumann	HMDB
Virophta	HMDB

Chemical Formula

C₁₀H₁₁F₃N₂O₅

Average Molecular Mass

296.200 g/mol

Monoisotopic Mass

296.062 g/mol

CAS Registry Number

70-00-8

IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

trifluridine

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(C(=O)NC1=O)C(F)(F)F

InChI Identifier

InChI=1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1

InChI Key

VSQQQLOSPVPRAZ-RRKCRQDMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
Pyrimidone
Hydroxypyrimidine
Hydropyrimidine
Pyrimidine
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Alkyl halide
Alkyl fluoride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:75179 )
nucleoside analogue (CHEBI:75179 )
pyrimidine 2'-deoxyribonucleoside (CHEBI:75179 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.69 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-0.75	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.34 m³·mol⁻¹	ChemAxon
Polarizability	23.07 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-002f-9070000000-5b0bc8f23d4e75143939	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0v70-9845200000-37084cd9faa19fab8cdd	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-98b3bdac019c141f7f2b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0910000000-88c39b37d01c15092d5b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001r-1900000000-6af805305211581c822e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0w2a-1490000000-06d5a9ab5df20c112030	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6r-0790000000-aca1588a5498c0e36172	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-5900000000-3142b258f9393903ca54	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002b-0090000000-9941fbdce182b1697ae3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ufr-1920000000-0b7d290fcb81239751b5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9500000000-c59f899250e30f03cf63	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0290000000-d2c6f13535b38e719f66	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0910000000-2f204a289423b2c2048d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-053r-2960000000-d74ea6cb75e5abd92cdb	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2083.0 Log mg/kg [1200:3700]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000358	Antineoplastic agents?Antineoplastic agents are a class of synthetic chemicals used primarily in the treatment of cancer.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000395	Antiinfectives?Anti-infectives are a class of synthetic chemicals designed to combat infections caused by bacteria, viruses, fungi, and parasites.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	Not Available
CEDs000673	Unmanned Aerial Vehicles?Unmanned Aerial Vehicles (UAVs), commonly known as drones, utilize various synthetic chemicals in their manufacturing, operation, and maintenance processes.	Aviation & Aerospace	Not Available
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	Not Available
CEDs000684	Cements?Cements are a composite material primarily used as a binding agent in construction applications, formed by the calcination of limestone and clay minerals at high temperatures.	Building & Construction	Not Available
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	Not Available
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	Not Available
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	Not Available
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	Not Available

Pathways

2 pathwaysPathway Source: PathBank

Trifluridine Action Pathway

Trifluridine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Thymidine kinase, cytosolic	P04183	Humans	Predicted (SEA)	Prediction Confidence Score 0.632 Applicability Domain 0.688 Statistical Significance 1.00e-05 Supporting Reference Compounds 11 E-value 0.0778492
Click to view 3D structure	Thymidine kinase	A3RLP8	Macacine herpesvirus 1	Predicted (SEA)	Prediction Confidence Score 0.55 Applicability Domain 0.688 Statistical Significance 1.00e-05 Supporting Reference Compounds 4 E-value 0.0778492
Click to view 3D structure	Thymidine kinase	P06479	Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)	Predicted (SEA)	Prediction Confidence Score 0.533 Applicability Domain 0.688 Statistical Significance 1.00e-05 Supporting Reference Compounds 10 E-value 0.0778492
Click to view 3D structure	Thymidylate synthase ThyA	P9WFR9	Mycobacterium tuberculosis	Predicted (SEA)	Prediction Confidence Score 0.508 Applicability Domain 0.508 Statistical Significance 4.00e-05 Supporting Reference Compounds 1 E-value 0.311397
Click to view 3D structure	Thymidylate kinase	P9WKE1	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	Prediction Confidence Score 0.485 Applicability Domain 0.688 Statistical Significance 5.00e-05 Supporting Reference Compounds 6 E-value 0.389246
Click to view 3D structure	Thymidylate synthase	P00469	Lactobacillus casei	Predicted (SEA)	Prediction Confidence Score 0.477 Applicability Domain 0.5 Statistical Significance 4.80e-04 Supporting Reference Compounds 33 E-value 3.73676
Click to view 3D structure	Thymidine kinase 2	D3ZGQ2	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.444 Applicability Domain 0.444 Statistical Significance 9.00e-05 Supporting Reference Compounds 1 E-value 0.700643
Click to view 3D structure	Thymidylate synthase	P07607	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.441 Applicability Domain 0.723 Statistical Significance 5.90e-04 Supporting Reference Compounds 24 E-value 4.5931
Click to view 3D structure	Flavin-dependent thymidylate synthase	P9WG57	Mycobacterium tuberculosis	Predicted (SEA)	Prediction Confidence Score 0.438 Applicability Domain 0.508 Statistical Significance 5.00e-05 Supporting Reference Compounds 2 E-value 0.389246
Click to view 3D structure	Thymidine kinase, cytosolic	P27158	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.421 Applicability Domain 0.547 Statistical Significance 1.60e-04 Supporting Reference Compounds 2 E-value 1.24559
Click to view 3D structure	Thymidylate synthase	Q2TA32	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.415 Applicability Domain 0.417 Statistical Significance 8.00e-05 Supporting Reference Compounds 2 E-value 0.622794
Click to view 3D structure	Reverse transcriptase/RNaseH	Q72547	Human immunodeficiency virus 1	Predicted (SEA)	Prediction Confidence Score 0.388 Applicability Domain 0.467 Statistical Significance 0.0017 Supporting Reference Compounds 79 E-value 13.2344
Click to view 3D structure	Thymidine kinase	Q9QNF7	HHV-1	Predicted (SEA)	Prediction Confidence Score 0.379 Applicability Domain 0.623 Statistical Significance 2.00e-05 Supporting Reference Compounds 11 E-value 0.155698
Click to view 3D structure	Thymidine kinase	P09250	HHV-3	Predicted (SEA)	Prediction Confidence Score 0.364 Applicability Domain 0.377 Statistical Significance 6.00e-05 Supporting Reference Compounds 3 E-value 0.467095
Click to view 3D structure	Thymidine kinase 2, mitochondrial	O00142	Humans	Predicted (SEA)	Prediction Confidence Score 0.348 Applicability Domain 0.466 Statistical Significance 1.10e-04 Supporting Reference Compounds 7 E-value 0.856341
Click to view 3D structure	DNA polymerase delta catalytic subunit	P28340	Humans	Predicted (SEA)	Prediction Confidence Score 0.338 Applicability Domain 0.338 Statistical Significance 4.30e-04 Supporting Reference Compounds 1 E-value 3.34752
Click to view 3D structure	Ribonuclease pancreatic	P61823	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.323 Statistical Significance 5.80e-04 Supporting Reference Compounds 1 E-value 4.51525
Click to view 3D structure	Thymidylate synthase	P04818	Humans	Predicted (SEA)	Prediction Confidence Score 0.322 Applicability Domain 0.484 Statistical Significance 0.0015 Supporting Reference Compounds 51 E-value 11.9888
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.353 Statistical Significance 0.0335 Supporting Reference Compounds 472 E-value 260.873
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.353 Statistical Significance 0.0154 Supporting Reference Compounds 242 E-value 119.81
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.353 Statistical Significance 0.0233 Supporting Reference Compounds 332 E-value 181.311
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.353 Statistical Significance 0.0284 Supporting Reference Compounds 407 E-value 220.78
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.353 Statistical Significance 0.0121 Supporting Reference Compounds 165 E-value 94.2754
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	Prediction Confidence Score 0.309 Applicability Domain 0.353 Statistical Significance 0.0106 Supporting Reference Compounds 157 E-value 82.8316
Click to view 3D structure	Ribonuclease pancreatic	P07998	Humans	Predicted (SEA)	Prediction Confidence Score 0.308 Applicability Domain 0.308 Statistical Significance 0.0022 Supporting Reference Compounds 1 E-value 17.049