Tecarfarin

• CAT Number: R029004
• CAS Number: 867257-26-9
• Molecular Formula: C21H14F6O5
• Molecular Weight: 460.328
• Purity: ≥95%
• Synonyms: 4-[(4-Hydroxy-2-oxo-2H-1-benzopyran-3-yl)methyl]benzoic Acid 2,2,2-Trifluoro-1-methyl-1-(trifluoromethyl)ethyl Ester; ATI 5923
• Target: vitamin K epoxide reductase inhibitor
• Storage: -20°C
• IUPAC Name: (1,1,1,3,3,3-hexafluoro-2-methylpropan-2-yl) 4-[(4-hydroxy-2-oxochromen-3-yl)methyl]benzoate
• InChI: InChI=1S/C21H14F6O5/c1-19(20(22,23)24,21(25,26)27)32-17(29)12-8-6-11(7-9-12)10-14-16(28)13-4-2-3-5-15(13)31-18(14)30/h2-9,28H,10H2,1H3
• InChIKey: QFLNTQDOVCLQKW-UHFFFAOYSA-N
• SMILES: CC(C(F)(F)F)(C(F)(F)F)OC(=O)C1=CC=C(C=C1)CC2=C(C3=CC=CC=C3OC2=O)O

Tecarfarin, also known as ATI-5923, is a potent and orally active vitamin K epoxide reductase inhibitor with antithrombotic activity. Like warfarin, tecarfarin attenuates venous and arterial thrombus formation in animal models by reducing the levels of the vitamin K-dependent coagulation factors. ecarfarin, via a vitamin K-dependent mechanism, causes changes in key parameters of haemostasis in beagle dogs that are consistent with effective anticoagulation. Compared to warfarin it has a decreased potential to interact metabolically with drugs that inhibit CYP450 enzymes and, therefore, may offer an improved safety profile for patients.

Reference

1:Pharmacokinetics and pharmacodynamics of tecarfarin, a novel vitamin K antagonist oral anticoagulant. Albrecht D, Ellis D, Canafax DM, Combs D, Druzgala P, Milner PG, Midei MG.Thromb Haemost. 2017 Apr 3;117(4):706-717. doi: 10.1160/TH16-08-0623. Epub 2017 Feb 9. PMID: 28180234 2:A randomised, double blind comparison of tecarfarin, a novel vitamin K antagonist, with warfarin. The EmbraceAC Trial. Whitlock RP, Fordyce CB, Midei MG, Ellis D, Garcia D, Weitz JI, Canafax DM, Albrecht D, Milner PG.Thromb Haemost. 2016 Aug 1;116(2):241-50. doi: 10.1160/TH15-11-0910. Epub 2016 May 12. PMID: 27173100 3:Identification of VKORC1 genotype leading to resistance to tecarfarin. Matagrin B, Montagut-Romans A, Damin M, Lemaire M, Popowycz F, Benoit E, Lattard V.J Clin Pharmacol. 2014 Aug;54(8):896-900. doi: 10.1002/jcph.332. No abstract available. PMID: 24838629 4:Antithrombotic activity of the novel oral anticoagulant, Tecarfarin [Sodium 3-[4-((1,1,1,3,3,3-hexafluoro-2-methylpropan-2-yloxy) carbonyl) benzyl]-2-oxo-2H-chromen-4-olate] in animal models. Bowersox SS, Canafax D, Druzgala P, Milner P, Weitz JI.Thromb Res. 2010 Nov;126(5):e383-8. doi: 10.1016/j.thromres.2010.08.025. PMID: 20869102 5:Tecarfarin, a novel vitamin K reductase antagonist, is not affected by CYP2C9 and CYP3A4 inhibition following concomitant administration of fluconazole in healthy participants. Bavisotto LM, Ellis DJ, Milner PG, Combs DL, Irwin I, Canafax DM.J Clin Pharmacol. 2011 Apr;51(4):561-74. doi: 10.1177/0091270010370588. Epub 2010 Jul 9. PMID: 20622200 6:Effect of tecarfarin, a novel vitamin K epoxide reductase inhibitor, on coagulation in beagle dogs. Choppin A, Irwin I, Lach L, McDonald MG, Rettie AE, Shao L, Becker C, Palme MP, Paliard X, Bowersox S, Dennis DM, Druzgala P.Br J Pharmacol. 2009 Nov;158(6):1536-47. doi: 10.1111/j.1476-5381.2009.00420.x. Epub 2009 Oct 20. PMID: 19845677 Free PMC Article7:The first evaluation of a novel vitamin K antagonist, tecarfarin (ATI-5923), in patients with atrial fibrillation. Ellis DJ, Usman MH, Milner PG, Canafax DM, Ezekowitz MD.Circulation. 2009 Sep 22;120(12):1029-35, 2 p following 1035. doi: 10.1161/CIRCULATIONAHA.109.856120. Epub 2009 Sep 8. PMID: 19738136 Free Article