Description: TAS-102 is an investigational drug candidate for metastatic colorectal cancer. It contains trifluridine (TFT) and Tipiracil hydrochloride (TTP) in a molar ratio of 1;0.5. Trifluridine is a nucleoside analog, and tipiracil hydrochloride is a thymidine phosphorylase inhibitor, which prevents rapid metabolism of trifluiridine, increasing the bioavailability of trifluiridine. After oral administration of TAS-102, TFT is phosphorylated to the active monophosphate form TF-TMP, which binds covalently to the active site of thymidylate synthase, thereby reducing the nucleotide pool levels required for DNA replication. Furthermore, the triphosphate form TF-TTP can be incorporated into DNA, which induces DNA fragmentation and leads to the inhibition of tumor growth. TPI exhibits a dual effect: 1) an anti-angiogenic effect mediated through the inhibition of thymidine phosphorylase, which plays an important role in nucleotide metabolism and a variety of development processes, including angiogenesis, 2) increased bioavailability of the normally short-lived antimetabolite TFT by preventing its degradation into the inactive form trifluorothymine (TF-Thy). The synergistic effect of the components in TAS-102 may demonstrate antitumor activity in 5-FU-resistant cancer cells.

Name: TAS-102 (Trifluridine/Tipiracil HCl)
CAS#: 733030-01-8
Chemical Formula: C19H23Cl2F3N6O7
Exact Mass:
Molecular Weight: 575.3232
Elemental Analysis: C, 39.67; H, 4.03; Cl, 12.32; F, 9.91; N, 14.61; O, 19.47

Synonym: TAS102, TAS-102, TAS 102, Trifluridine/tipiracil hydrochloride

IUPAC/Chemical Name: 4-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(trifluoromethyl)pyrimidin-2(1H)-one compound with 5-chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4-diol (1:1) hydrochloride

InChi Key: PLIXOHWIPDGJEI-OJSHLMAWSA-N

InChi Code: InChI=1S/C10H11F3N2O5.C9H11ClN4O2.ClH/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7;10-7-5(12-9(16)13-8(7)15)4-14-3-1-2-6(14)11;/h2,5-7,16-17H,1,3H2,(H,14,18,19);11H,1-4H2,(H2,12,13,15,16);1H/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.O=C3NC(C(Cl)=C(CN4C(CCC4)=N)N3)=O.[H]Cl

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