trifluridine   Click here for help

GtoPdb Ligand ID: 8697

Synonyms: TFT | trifluorothymidine
Approved drug
trifluridine is an approved drug (Japan, FDA (2015), EMA (2016))
Compound class: Synthetic organic
Comment: Trifluridine was originally approved by the US FDA in 1980, and was used for its antiviral effects (marketed as Vitroptic®). The drug is now being investigated for its antineoplastic (cytotoxic) effect.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 104.55
Molecular weight 296.06
XLogP 0.1
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OCC1OC(CC1O)n1cc(c(=O)[nH]c1=O)C(F)(F)F
Isomeric SMILES OC[C@H]1O[C@H](C[C@@H]1O)n1cc(c(=O)[nH]c1=O)C(F)(F)F
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (Japan, FDA (2015), EMA (2016))
IUPAC Name Click here for help
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
4146 trifluridine
Synonyms Click here for help
TFT | trifluorothymidine
Database Links Click here for help
ChEMBL Ligand CHEMBL1129
DrugBank Ligand DB00432
DrugCentral Ligand 2743
GtoPdb PubChem SID 252166897
PubChem CID 6256
Search Google for chemical match using the InChIKey VSQQQLOSPVPRAZ-RRKCRQDMSA-N
Search Google for chemicals with the same backbone VSQQQLOSPVPRAZ
Search PubMed clinical trials trifluridine
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Search PubMed titles/abstracts trifluridine
UniChem Compound Search for chemical match using the InChIKey VSQQQLOSPVPRAZ-RRKCRQDMSA-N
UniChem Connectivity Search for chemical match using the InChIKey VSQQQLOSPVPRAZ-RRKCRQDMSA-N