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70-00-8-Trifluorothymidine Trifluorothymidine

Trifluorothymidine

For research use only. Not for therapeutic Use.

  • CAT Number: A000501
  • CAS Number: 70-00-8
  • Molecular Formula: C₁₀H₁₁F₃N₂O₅
  • Molecular Weight: 296.2
  • Purity: ≥95%
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Related Small Molecules: Citicoline     Pyrroloquinoline quinone     Spermidine    
Research Areas: Antiviral     Infection Disease Research     Viral Entry    

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


Catalog Number A000501
CAS Number 70-00-8
Synonyms

TRIFLUOROTHYMIDINE; 70-00-8; Viroptic; 5-Trifluorothymidine; Trifluridina

Molecular Formula C₁₀H₁₁F₃N₂O₅
Purity ≥95%
Target Anti-infection
Solubility >14.5mg/mL in DMSO
Storage -20°C
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
InChIKey VSQQQLOSPVPRAZ-RRKCRQDMSA-N
SMILES C1C(C(OC1N2C=C(C(=O)NC2=O)C(F)(F)F)CO)O
Reference

1: Suzuki N, Tsukihara H, Nakagawa F, Kobunai T, Takechi T. Synergistic
anticancer activity of a novel oral chemotherapeutic agent containing
trifluridine and tipiracil in combination with anti-PD-1 blockade in
microsatellite stable-type murine colorectal cancer cells. Am J Cancer Res. 2017
Oct 1;7(10):2032-2040. eCollection 2017. PubMed PMID: 29119052; PubMed Central
PMCID: PMC5665850.
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2: Bullement A, Underhill S, Fougeray R, Hatswell AJ. Cost-effectiveness of
Trifluridine/tipiracil for Previously Treated Metastatic Colorectal Cancer in
England and Wales. Clin Colorectal Cancer. 2017 Sep 28. pii:
S1533-0028(16)30287-0. doi: 10.1016/j.clcc.2017.09.001. [Epub ahead of print]
PubMed PMID: 29110922.
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3: Puthiamadathil JM, Weinberg BA. Emerging combination therapies for metastatic
colorectal cancer – impact of trifluridine/tipiracil. Cancer Manag Res. 2017 Oct
3;9:461-469. doi: 10.2147/CMAR.S113320. eCollection 2017. Review. PubMed PMID:
29056855; PubMed Central PMCID: PMC5635852.
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4: Takahashi K, Yoshisue K, Chiba M, Nakanishi T, Tamai I. Contribution of
Equilibrative Nucleoside Transporter(s) to Intestinal Basolateral and Apical
Transports of Anticancer Trifluridine. Biopharm Drug Dispos. 2017 Oct 20. doi:
10.1002/bdd.2110. [Epub ahead of print] PubMed PMID: 29055025.
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5: Kim SY, Jung JH, Lee HJ, Soh H, Lee SJ, Oh SJ, Chae SY, Lee JH, Lee SJ, Hong
YS, Kim TW, Moon DH. [(18)F]fluorothymidine positron emission tomography informs
the synergistic efficacy of capecitabine and trifluridine/tipiracil in colon
cancer. Cancer Res. 2017 Oct 20. pii: canres.1406.2017. doi:
10.1158/0008-5472.CAN-17-1406. [Epub ahead of print] PubMed PMID: 29055019.
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6: Matsuoka K, Kobunai T, Nukatsuka M, Takechi T. Improved chemoradiation
treatment using trifluridine in human colorectal cancer cells in vitro. Biochem
Biophys Res Commun. 2017 Dec 9;494(1-2):249-255. doi: 10.1016/j.bbrc.2017.10.044.
Epub 2017 Oct 9. PubMed PMID: 29024630.
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7: Sforza V, Martinelli E, Cardone C, Martini G, Napolitano S, Vitiello PP,
Vitale P, Zanaletti N, Reginelli A, Bisceglie MD, Latiano TP, Bochicchio AM,
Cecere F, Selvaggi F, Ciardiello F, Troiani T. Clinical outcome of patients with
chemorefractory metastatic colorectal cancer treated with trifluridine/tipiracil
(TAS-102): a single Italian institution compassionate use programme. ESMO Open.
2017 Sep 21;2(4):e000229. doi: 10.1136/esmoopen-2017-000229. eCollection 2017.
PubMed PMID: 29018575; PubMed Central PMCID: PMC5623320.
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8: Sunakawa Y, Izawa N, Mizukami T, Horie Y, Hirakawa M, Arai H, Ogura T, Tsuda
T, Nakajima TE. Profile of trifluridine/tipiracil hydrochloride in the treatment
of metastatic colorectal cancer: efficacy, safety, and place in therapy. Onco
Targets Ther. 2017 Sep 15;10:4599-4605. doi: 10.2147/OTT.S106101. eCollection
2017. Review. PubMed PMID: 28979148; PubMed Central PMCID: PMC5608085.

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9: Moriwaki T, Fukuoka S, Taniguchi H, Takashima A, Kumekawa Y, Kajiwara T,
Yamazaki K, Esaki T, Makiyama C, Denda T, Satake H, Suto T, Sugimoto N, Enomoto
M, Ishikawa T, Kashiwada T, Sugiyama M, Komatsu Y, Okuyama H, Baba E, Sakai D,
Watanabe T, Tamura T, Yamashita K, Gosho M, Shimada Y. Propensity Score Analysis
of Regorafenib Versus Trifluridine/Tipiracil in Patients with Metastatic
Colorectal Cancer Refractory to Standard Chemotherapy (REGOTAS): A Japanese
Society for Cancer of the Colon and Rectum Multicenter Observational Study.
Oncologist. 2017 Sep 11. pii: theoncologist.2017-0275. doi:
10.1634/theoncologist.2017-0275. [Epub ahead of print] PubMed PMID: 28894015.
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10: Tsunekuni K, Konno M, Asai A, Koseki J, Kobunai T, Takechi T, Doki Y, Mori M,
Ishii H. MicroRNA profiles involved in trifluridine resistance. Oncotarget. 2017
May 23;8(32):53017-53027. doi: 10.18632/oncotarget.18078. eCollection 2017 Aug 8.
PubMed PMID: 28881790; PubMed Central PMCID: PMC5581089.

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