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T2255

Sigma-Aldrich

Trifluorothymidine

≥99% (HPLC)

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
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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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

Signal Word

Warning

Hazard Statements

H341,H351,H361d

Hazard Classifications

Carc. 2 - Muta. 2 - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
I V Bijnsdorp et al.
Nucleosides, nucleotides & nucleic acids, 27(6), 699-703 (2008-07-05)
Trifluorothymidine (TFT), a potent anticancer agent, inhibits thymidylate synthase (TS) and is incorporated into the DNA, both events resulting in cell death. Cell death induction related to DNA damage often involves activation of p53. We determined the role of p53
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
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