trifluridine

Ligand id: 8697

Name: trifluridine

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 99.1
Molecular weight 296.06
XLogP -0.08
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

No information available.
Summary of Clinical Use
Trifluridine is a component of the anticancer therapeutic Lonsurf® (code-named TAS-102), was first approved in Japan for the treatment of metastatic/unresectable colorectal cancer. The other component of TAS-102 is tipiracil [1]. In September 2015, the US FDA approved Lonsurf® for the treatment of patients with RAS wild type, metastatic colorectal cancer who have already received chemotherapy, anti-VEGF, and anti-EGFR therapies. TAS-102 is being assessed in Phase III clinical trial for metastatic gastric cancer (NCT02500043).
Mechanism Of Action and Pharmacodynamic Effects
Trifluridine is a modified form of deoxyuridine (nucleoside analogue). Trifluridine is metabolised to its monophosphate-derivative and this inhibits thymidylate synthase, one of the rate-limiting enzymes in pyrimidine de novo deoxynucleotide synthesis. Thymidylate synthase is therefore crucial for DNA synthesis. In addition, if trifluridine is incorporated directly in to DNA during replication, the -CF3 group of trifluridine blocks base pairing. These actions underly the compound's cytotoxic effect [2].
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