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Merck
CN

T2255

Trifluorothymidine

≥99% (HPLC), synthetic, powder

Synonym(s):

α,α,α-Trifluorothymidine, 2′-Deoxy-5-trifluoromethyluridine, Trifluorothymine deoxyriboside, Trifluridine

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About This Item

Empirical Formula (Hill Notation):
C10H11F3N2O5
CAS Number:
70-00-8
Molecular Weight:
296.20
NACRES:
NA.51
PubChem Substance ID:
24900027
UNSPSC Code:
41106305
EC Number:
200-722-8
MDL number:
MFCD00006534

Key Documents

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Product Name

Trifluorothymidine, ≥99% (HPLC)

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

InChI key

VSQQQLOSPVPRAZ-RRKCRQDMSA-N

SMILES string

OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(C(=O)NC2=O)C(F)(F)F

biological source

synthetic

assay

≥99% (HPLC)

form

powder

mp

190-193 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

100

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Application

Trifluorothymidine has been used as a component of selection medium to screen thymidine kinase (TK) mutants in lymphoma cells, human lymphoblastoid TK6 cells, and L5178Y mouse lymphoma cells.

Biochem/physiol Actions

Trifluorothymidine is a thymidine analog and is light sensitive. TFT serves as a thymidine kinase substrate to study enzyme specificity and kinetics. Incorporation of phosphorylated TFT into DNA induces damage, making it useful for DNA repair studies. TFT may also be used in the inhibition of thymidylate synthase and in screening mutant thymidine kinase gene.. It elicits antitumor activity in gastrointestinal (GI) cancers and has therapeutic potential to treat herpetic keratitis.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Health hazard
GHS08

signalword

Warning

Hazard Classifications

Carc. 2 - Muta. 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9251
BCCK8225
BCCJ6756
BCCG7691
BCCD9525

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Julien Massonneau et al.
Mutation research, 849, 503128-503128 (2020-02-24)
A physiological decrease in extracellular pH (pHe) alters the efficiency of DNA repair and increases formation of DNA double-strand breaks (DSBs). Whether this could translate into genetic instability and variations, was investigated using the TK6 cell model, in which positive
Norihiko Suzuki et al.
International journal of oncology, 39(1), 263-270 (2011-04-15)
Trifluorothymidine (TFT) is well known to be converted to TFT-monophosphate by thymidine kinase and to inhibit thymidylate synthase. In addition, TFT-triphosphate (TFT-TP) is also incorporated into DNA, resulting in cytocidal effects. However, the precise mechanism of TFT-induced DNA damage is
Methods for using the mouse lymphoma assay to screen for chemical mutagenicity and photo-mutagenicity
Optimization in Drug Discovery: In Vitro Methods, 561-592 (2014)
Novel cell death mechanisms of trifluorothymidine.
Bijnsdorp IV, Kruyt F, et al.
Nucleic Acids Symposium Series, 52, 649-649 (2008)
Connie Kang et al.
Drugs, 79(14), 1583-1590 (2019-09-07)
Trifluridine/tipiracil (Lonsurf®) is a fixed-dose combination tablet comprising trifluridine, an antineoplastic nucleoside analogue, and tipiracil, a thymidine phosphorylase inhibitor. Trifluridine/tipiracil has recently been granted an additional indication in the USA for the treatment of metastatic gastric cancer, including gastroesophageal junction
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