Trifluridine
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MedKoo CAT#: 206038

CAS#: 70-00-8

Description: 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.


Chemical Structure

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Trifluridine
CAS# 70-00-8

Theoretical Analysis

MedKoo Cat#: 206038
Name: Trifluridine
CAS#: 70-00-8
Chemical Formula: C10H11F3N2O5
Exact Mass: 296.06201
Molecular Weight: 296.2
Elemental Analysis: C, 40.55; H, 3.74; F, 19.24; N, 9.46; O, 27.01

Price and Availability

Size Price Availability Quantity
100.0mg USD 150.0 Same day
500.0mg USD 550.0 Same day
1.0g USD 950.0 Same day
5.0g USD 2950.0 Same day
10.0g USD 3950.0 Same day
50.0g USD 8950.0 2 Weeks
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Synonym: FTD ; NSC 529182; NSC-529182; NSC529182; NSC 75520; NSC-75520; NSC75520; Trifluorothymidine; Viroptic; 2-Deoxy-5-trifluoromethyluridine; Trifluridine; 5-Trifluorothymidine;

IUPAC/Chemical Name: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione.

InChi Key: VSQQQLOSPVPRAZ-RRKCRQDMSA-N

InChi Code: 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

SMILES Code: O=C1NC(C(C(F)(F)F)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 296.2 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548483/ PubMed PMID: 31643802.

2: Kang C, Dhillon S, Deeks ED. Trifluridine/Tipiracil: A Review in Metastatic Gastric Cancer. Drugs. 2019 Sep;79(14):1583-1590. doi: 10.1007/s40265-019-01195-w. Review. Erratum in: Drugs. 2019 Sep 18;:. PubMed PMID: 31489588; PubMed Central PMCID: PMC6751145.

3: Trifluridine/tipiracil for colorectal cancer. Aust Prescr. 2018 Oct;41(5):171. doi: 10.18773/austprescr.2018.053. Epub 2018 Sep 11. Review. PubMed PMID: 30410217; PubMed Central PMCID: PMC6202293.

4: Vaflard P, Ederhy S, Torregrosa C, André T, Cohen R, Lopez-Trabada D. [Fluoropyrimidines cardiac toxicity: 5-fluorouracil, capecitabine, compound S-1 and trifluridine/tipiracil]. Bull Cancer. 2018 Jul - Aug;105(7-8):707-719. doi: 10.1016/j.bulcan.2018.05.005. Epub 2018 Jun 28. Review. French. PubMed PMID: 29960638.

5: Martinez-Perez J, Riesco-Martinez MC, Garcia-Carbonero R. The safety of trifluridine and tipiracil for the treatment of metastatic colorectal cancer. Expert Opin Drug Saf. 2018 Jun;17(6):643-650. doi: 10.1080/14740338.2018.1475557. Epub 2018 May 23. Review. PubMed PMID: 29745737.

6: Peeters M, Cervantes A, Moreno Vera S, Taieb J. Trifluridine/tipiracil: an emerging strategy for the management of gastrointestinal cancers. Future Oncol. 2018 Jul;14(16):1629-1645. doi: 10.2217/fon-2018-0147. Epub 2018 Apr 27. Review. PubMed PMID: 29701076.

7: Ramaekers BLT, Wolff R, van Giessen A, Pouwels X, Fayter D, Lang S, Armstrong N, Worthy G, Duffy S, Kleijnen J, Joore MA. Trifluridine-Tipiracil for Previously Treated Metastatic Colorectal Cancer: An Evidence Review Group Perspective of a NICE Single Technology Appraisal. Pharmacoeconomics. 2018 Mar;36(3):285-288. doi: 10.1007/s40273-017-0591-4. Review. PubMed PMID: 29177842; PubMed Central PMCID: PMC5834593.

8: 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.

9: 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.

10: White T, Larson H, Minnella A, Hochster HS. Metastatic Colorectal Cancer: Management With Trifluridine/Tipiracil
. Clin J Oncol Nurs. 2017 Apr 1;21(2):E30-E37. doi: 10.1188/17.CJON.E30-E37. Review. PubMed PMID: 28315543.

11: Lee JJ, Chu E. Adherence, Dosing, and Managing Toxicities With Trifluridine/Tipiracil (TAS-102). Clin Colorectal Cancer. 2017 Jun;16(2):85-92. doi: 10.1016/j.clcc.2017.01.003. Epub 2017 Jan 25. Review. PubMed PMID: 28242161; PubMed Central PMCID: PMC5743195.

12: Burness CB, Duggan ST. Trifluridine/Tipiracil: A Review in Metastatic Colorectal Cancer. Drugs. 2016 Sep;76(14):1393-402. doi: 10.1007/s40265-016-0633-9. Review. PubMed PMID: 27568360.

13: Weinberg BA, Marshall JL, Salem ME. Trifluridine/tipiracil and regorafenib: new weapons in the war against metastatic colorectal cancer. Clin Adv Hematol Oncol. 2016 Aug;14(8):630-8. Review. PubMed PMID: 27487107.

14: Jeffers KD. Trifluridine/Tipiracil: Old Drug, New Tricks. J Adv Pract Oncol. 2016 May-Jun;7(4):449-453. Epub 2016 May 1. Review. PubMed PMID: 29226002; PubMed Central PMCID: PMC5679033.

15: Kitao H, Matsuoka K, Iimori M, Tokunaga E, Saeki H, Oki E, Miyamoto Y, Baba H, Maehara Y. [Antitumor Molecular Mechanism of Trifluridine and Tipiracil Hydrochloride (TAS-102: TFTD)]. Gan To Kagaku Ryoho. 2016 Jan;43(1):8-14. Review. Japanese. PubMed PMID: 26809521.

16: Carmine AA, Brogden RN, Heel RC, Speight TM, Avery GS. Trifluridine: a review of its antiviral activity and therapeutic use in the topical treatment of viral eye infections. Drugs. 1982 May;23(5):329-53. Review. PubMed PMID: 6284470.



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