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Merck
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Key Documents

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T2255

Sigma-Aldrich

Trifluorothymidine

≥99% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H11F3N2O5
Número de CAS:
70-00-8
Peso molecular:
296.20
EC Number:
200-722-8
MDL number:
MFCD00006534
UNSPSC Code:
41106305
PubChem Substance ID:
24900027
NACRES:
NA.51

biological source

synthetic

Quality Level

100

assay

≥99% (HPLC)

form

powder

mp

190-193 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

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

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

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Categorías relacionadas

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Marc Peeters et al.
Future oncology (London, England), 14(16), 1629-1645 (2018-04-28)
Fluoropyrimidines are currently the backbone of treatment for gastrointestinal (GI) cancers but development of resistance to these agents remains a major problem. Trifluridine/tipiracil is an oral chemotherapeutic agent recently approved for third-line treatment of chemorefractory metastatic colorectal cancer. This article
A A Carmine et al.
Drugs, 23(5), 329-353 (1982-05-01)
Trifluridine (trifluorothymidine) is an antiviral agent for topical use in the eye, and is structurally related to idoxuridine. In vitro studies have shown that it effectively inhibits the replication of herpes simplex virus type 1, which causes primary keratoconjunctivitis and
Olaf H Temmink et al.
Molecular cancer therapeutics, 9(4), 1047-1057 (2010-04-08)
Trifluorothymidine (TFT) is part of the novel oral formulation TAS-102, which is currently evaluated in phase II studies. Drug resistance is an important limitation of cancer therapy. The aim of the present study was to induce resistance to TFT in
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
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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