Trifluridine , 三氟胸苷

Trifluorothymidine is a derivative of thymidine that exhibits antiviral and anticancer activity by inhibiting thymidylate synthase, thereby blocking nucleic acid synthesis, and by incorporating into DNA, which leads to DNA damage and apoptosis.

Trifluorothymidine is an inhibitor of TS (thymidylate synthase). It is also a substrate used to study the specificity and kinetics of thymidine kinases. Acts as an anti-herpesvirus drug by blocking viral DNA replication. Decreases CRISPR-mediated HDR (homology-directed repair) efficiency.

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Trifluridine is a fluorinated thymidine analog with potential antineoplastic activity. Trifluridine is incorporated into DNA and inhibits thymidylate synthase, resulting in inhibition of DNA synthesis, inhibition of protein synthesis, and apoptosis. This agent also exhibits antiviral activity. (NCI04)

Trifluridine/tipiracil is the combination of an antineoplastic pyrimidine analogue (trifluridine) with an inhibitor of its metabolism (tipiracil) that is used in the therapy of refractory, metastatic colorectal cancer. Trifluridine/tipiracil is associated with a low rate of transient serum enzyme elevations during therapy, but has not been implicated in cases of clinically apparent acute liver injury with jaundice.

Trifluridine is a pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis. It has a role as an antiviral drug, an antimetabolite, an EC 2.1.1.45 (thymidylate synthase) inhibitor and an antineoplastic agent. It is a nucleoside analogue, an organofluorine compound and a pyrimidine 2'-deoxyribonucleoside.

Title: Trifluridine

CAS Registry Number: 70-00-8

CAS Name: a,a,a-Trifluorothymidine

Additional Names: 2'-deoxy-5-(trifluoromethyl)uridine; 5-(trifluoromethyl)-2'-deoxyuridine; F3TDR

Manufacturers' Codes: NSC-75520

Trademarks: TFT Thilo (Alcon-Thilo); Virophta (Dulcis); Viroptic (Burroughs Wellcome)

Molecular Formula: C10H11F3N2O5

Molecular Weight: 296.20

Percent Composition: C 40.55%, H 3.74%, F 19.24%, N 9.46%, O 27.01%

Literature References: Prepn: C. Heidelberger et al., J. Am. Chem. Soc. 84, 3597 (1962); eidem, J. Med. Chem. 7, 1 (1964); C. Heidelberger, US 3201387 (1965 to U.S. Dept. HEW). Crystal structure: A. H. Tench, Diss. Abstr. Int. B 33, 3587 (1973). NMR study: R. J. Cushley et al., J. Am. Chem. Soc. 90, 709 (1968). Metabolism: D. L. Dexter et al., Cancer Res. 32, 247 (1972); W. J. O'Brien, H. F. Edelhauser, Invest. Ophthalmol. Visual Sci. 16, 1093 (1977). Pharmacodynamics: B. L. Wigdahl, J. R. Parkhurst, Antimicrob. Agents Chemother. 14, 470 (1978); G. J. Smith et al., Biochem. Biophys. Res. Commun. 83, 1538 (1978). Teratogenicity study: M. Itoi et al., Arch. Ophthalmol. 93, 46 (1975). Cytotoxicity and mutagenicity study: E. Huberman, C. Heidelberger, Mutat. Res. 14, 130 (1972). Clinical studies: H. E. Kaufman, Invest. Ophthalmol. Visual Sci. 17, 941 (1978); R. A. Hyndiuk et al., Arch. Ophthalmol. 96, 1839 (1978). Review of mechanism of antiviral activity: C. Heidelberger, Ann. N.Y. Acad. Sci. 255, 317 (1975). Review of pharmacology and therapeutic use: A. A. Carmine et al., Drugs 23, 329-353 (1982).

Properties: Cryst from ethyl acetate, mp 186-189°. uv max (0.1N HCl): 260 nm (e 9960); (0.1N NaOH): 260 nm (e 6590).

Melting point: mp 186-189°

Absorption maximum: uv max (0.1N HCl): 260 nm (e 9960); (0.1N NaOH): 260 nm (e 6590)

Therap-Cat: Antiviral (ophthalmic).

Keywords: Antiviral; Purines/Pyrimidinones.