Trifluridine

Trifluridine

Clinical data
Trade names	Viroptic; Lonsurf (+tipiracil)
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Eye drops; tablets (+tipiracil)
ATC code	S01AD02 (WHO)
Legal status
Legal status	CA: ℞-only US: ℞-only
Pharmacokinetic data
Bioavailability	Negligible (eye drops); ≥57% (oral)
Protein binding	>96%
Metabolism	Thymidine phosphorylase
Biological half-life	12 minutes (eye drops); 1.4–2.1 hrs (combination with tipiracil)
Excretion	Mostly via urine
Identifiers
IUPAC name 1-[4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)-(1H,3H)-pyrimidine-2,4-dione
Synonyms	α,α,α-trifluorothymidine; 5-trifluromethyl-2′-deoxyuridine; FTD5-trifluoro-2′-deoxythymidine; TFT; CF3dUrd; FTD; F3TDR; F3Thd
CAS Number	70-00-8 Y
PubChem CID	6256
DrugBank	DB00432 Y
ChemSpider	6020 Y
UNII	RMW9V5RW38
KEGG	D00391 Y
ChEBI	CHEBI:75179 N
ChEMBL	CHEMBL1129 Y
ECHA InfoCard	100.000.657
Chemical and physical data
Formula	C10H11F3N2O5
Molar mass	296.2 g/mol
3D model (Jmol)	Interactive image
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?)

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.

Trifluridine was approved for medical use in 1980. It is also a component of the anti-cancer drug trifluridine/tipiracil, which is taken by mouth.

Trifluridine eye drops are used for the treatment of keratitis and caused by the herpes simplex virus types 1 and 2, as well as for prevention and treatment of vaccinia virus infections of the eye.

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.

For cancer treatment, the combination trifluridine/tipiracil is used.

Common side effects of trifluridine eye drops include transient burning, stinging, local irritation, and edema of the eyelids.

Adverse effects of the anti-cancer formulation have only been evaluated for the combination trifluridine/tipiracil, not for the individual components.

Only in vitro interaction studies are available. In these, trifluridine used the concentrative nucleoside transporter 1 (CNT1) and equilibrative nucleoside transporters 1 (ENT1) and 2 (ENT2). Drugs that interact with these transporters could influence blood plasma concentrations of trifluridine. Being a thymidine phosphorylase inhibitor, trifluridine could also interact with substrates of this enzyme such as zidovudine.