Trifluridine

Trifluridine

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)
Routes of administration	Eye drops
Legal status
Legal status	CA: ℞-only US: ℞-only
Pharmacokinetic data
Biological half-life	12 minutes
Identifiers
CAS Number	70-00-8
ATC code	S01AD02 (WHO)
PubChem	CID 6256
DrugBank	DB00432
ChemSpider	6020
UNII	RMW9V5RW38
KEGG	D00391
ChEBI	CHEBI:75179
ChEMBL	CHEMBL1129
Chemical data
Formula	C10H11F3N2O5
Molar 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 Key:VSQQQLOSPVPRAZ-RRKCRQDMSA-N
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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.^[1]

Synthesis

Trifluridine synthesis: U.S. Patent 3,531,464 U.S. Patent 3,201,387 ^[2][3]

References

1. Wilhelmus KR (2010). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". Cochrane Database Syst Rev 12: CD002898. doi:10.1002/14651858.CD002898.pub4. PMID 21154352.
2. Heidelberger, C.; Parsons, D.; Remy, D. C. (1962). "Syntheses of 5-Trifluoromethyluracil and 5-Trifluoromethyl-2″-Deoxyuridine". Journal of the American Chemical Society 84 (18): 3597. doi:10.1021/ja00877a046.
3. Heidelberger, C.; Parsons, D. G.; Remy, D. C. (1964). "Syntheses of 5-Trifluoromethyluracil and 5-Trifluoromethyl-2'-deoxyuridine1,2". Journal of Medicinal Chemistry 7: 1. doi:10.1021/jm00331a001.

External links

• Costin D, Dogaru M, Popa A, Cijevschi I (2004). "Trifluridine therapy in herpetic in keratitis". Rev Med Chir Soc Med Nat Iasi 108 (2): 409–12. PMID 15688823.
• Kuster P, Taravella M, Gelinas M, Stepp P (1998). "Delivery of trifluridine to human cornea and aqueous using collagen shields.". CLAO J 24 (2): 122–4. PMID 9571274.
• O'Brien W, Taylor J (1991). "Therapeutic response of herpes simplex virus-induced corneal edema to trifluridine in combination with immunosuppressive agents.". Invest Ophthalmol Vis Sci 32 (9): 2455–61. PMID 1907950.
• "Trifluridine Ophthalmic Solution, 1%" (PDF). Retrieved 2007-03-24.