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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/13 13:45:22」(JST)

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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

^ 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.
^ 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.
^ 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.

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UpToDate Contents

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1. 単純ヘルペス性角膜炎 herpes simplex keratitis
2. 新生児単純ヘルペスウイルス感染：管理および予防 neonatal herpes simplex virus infection management and prevention
3. 中毒性結膜炎 toxic conjunctivitis

English Journal

Exposure-dependent incorporation of trifluridine into DNA of tumors and white blood cells in tumor-bearing mouse.

Yamashita F1, Komoto I, Oka H, Kuwata K, Takeuchi M, Nakagawa F, Yoshisue K, Chiba M.
Cancer chemotherapy and pharmacology.Cancer Chemother Pharmacol.2015 Jun 18. [Epub ahead of print]
PURPOSE: Trifluridine (TFT) is an antitumor component of a novel nucleoside antitumor agent, TAS-102, which consists of TFT and tipiracil hydrochloride (thymidine phosphorylase inhibitor). Incorporation of TFT into DNA is a probable mechanism of antitumor activity and hematological toxicity. The obj
PMID 26084259

Crucial roles of thymidine kinase 1 and deoxyUTPase in incorporating the antineoplastic nucleosides trifluridine and 2'-deoxy-5-fluorouridine into DNA.

Sakamoto K1, Yokogawa T1, Ueno H1, Oguchi K1, Kazuno H1, Ishida K1, Tanaka N1, Osada A1, Yamada Y1, Okabe H1, Matsuo K1.
International journal of oncology.Int J Oncol.2015 Jun;46(6):2327-34. doi: 10.3892/ijo.2015.2974. Epub 2015 Apr 20.
Trifluridine (FTD) and 2'-deoxy-5-fluorouridine (FdUrd), a derivative of 5-fluorouracil (5-FU), are antitumor agents that inhibit thymidylate synthase activity and their nucleotides are incorporated into DNA. However, it is evident that several differences occur in the underlying antitumor mechanism
PMID 25901475

Randomized trial of TAS-102 for refractory metastatic colorectal cancer.

Mayer RJ, Van Cutsem E, Falcone A, Yoshino T, Garcia-Carbonero R, Mizunuma N, Yamazaki K, Shimada Y, Tabernero J, Komatsu Y, Sobrero A, Boucher E, Peeters M, Tran B, Lenz HJ, Zaniboni A, Hochster H, Cleary JM, Prenen H, Benedetti F, Mizuguchi H, Makris L, Ito M, Ohtsu A; RECOURSE Study Group.
The New England journal of medicine.N Engl J Med.2015 May 14;372(20):1909-19. doi: 10.1056/NEJMoa1414325.
BACKGROUND: Early clinical trials conducted primarily in Japan have shown that TAS-102, an oral agent that combines trifluridine and tipiracil hydrochloride, was effective in the treatment of refractory colorectal cancer. We conducted a phase 3 trial to further assess the efficacy and safety of TAS-
PMID 25970050

Japanese Journal

Delivery of trifluridine to human cornea and aqueous using collagen shields

CLAO J 24, 122-124, 1998
NAID 10009310201

A prospective, masked clinical trial of trifluridine, dexamethasone, and artificial tears in the treatment of epidemic keratoconjunctivitis

Cornea 12, 216-221, 1993
NAID 30018747718

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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); ;
Legal status	CA: ℞-only; US: ℞-only;
Routes of; administration	Eye drops
Pharmacokinetic data
Biological half-life	12 minutes
Identifiers
CAS Number	70-00-8
ATC code	S01AD02
PubChem	CID: 6256
DrugBank	DB00432
ChemSpider	6020
UNII	RMW9V5RW38
KEGG	D00391
ChEBI	CHEBI:75179
ChEMBL	CHEMBL1129
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 ; Key:VSQQQLOSPVPRAZ-RRKCRQDMSA-N ;
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英: trifluridine
商: ロンサーフ配合

[Wilhelmus-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.

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trifluridine