Trifluridine

Trifluridine

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Systematic (IUPAC) name
1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5- (trifluoromethyl) pyrimidine-2,4-dione
Clinical data
Trade names	Viroptic
AHFS/Drugs.com	monograph
Pregnancy category	US: C (Risk not ruled out)
Legal status	CA: ℞-only US: ℞-only
Routes of administration	Eye drops
Pharmacokinetic data
Biological half-life	12 minutes
Identifiers
CAS Number	70-00-8 Y
ATC code	S01AD02 (WHO)
PubChem	CID: 6256
DrugBank	DB00432 Y
ChemSpider	6020 Y
UNII	RMW9V5RW38 Y
KEGG	D00391 Y
ChEBI	CHEBI:75179 N
ChEMBL	CHEMBL1129 Y
Chemical data
Formula	C10H11F3N2O5
Molecular mass	296.2 g/mol
SMILES FC(F)(F)C=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)C2)CO
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 Y Key:VSQQQLOSPVPRAZ-RRKCRQDMSA-N Y
NY (what is this?)  (verify)

Trifluridine (also called trifluorothymidine or TFT) is an anti-herpesvirus antiviral drug, used primarily on the eye. It was sold under the trade name, Viroptic, by Glaxo Wellcome, now merged into GlaxoSmithKline. The brand is now owned by Monarch Pharmaceuticals, which is wholly owned by King Pharmaceuticals.

It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into viral DNA replication, but the -CF₃ group added to the uracil component blocks base pairing, thus interfering with DNA replication.

It is a component of the experimental anti-cancer drug TAS-102.

A Cochrane Systematic Review showed that trifluridine was a more effective treatment than idoxuridine or vidarabine, significantly increasing the relative number of successfully healed eyes in 14 days.

Synthesis

File:Trifluridine synthesis.png

Trifluridine synthesis: U.S. Patent 3,531,464 U.S. Patent 3,201,387