4-Desfluoro Sitagliptin

• CAT Number: R015062
• CAS Number: 1345822-87-8
• Molecular Formula: C₁₆H₁₉F₅N₅O₅P
• Molecular Weight: 487.32
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (3R)-3-amino-4-(2,5-difluorophenyl)-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]butan-1-one;phosphoric acid
• InChI: InChI=1S/C16H16F5N5O.H3O4P/c17-10-1-2-12(18)9(5-10)6-11(22)7-14(27)25-3-4-26-13(8-25)23-24-15(26)16(19,20)21;1-5(2,3)4/h1-2,5,11H,3-4,6-8,22H2;(H3,1,2,3,4)/t11-;/m1./s1
• InChIKey: UOKMPNRCGWVMBY-RFVHGSKJSA-N
• SMILES: C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=C(C=CC(=C3)F)F)N.OP(=O)(O)O

4-Desfluoro Sitagliptin (CAS 1345822-87-8) is a metabolite of Sitagliptin phosphate. Sitagliptin is a trizolopyrazine dipeptidyl peptidase IV inhibitor. Sitagliptin has recently been approved for the therapy of type II diabetes.

Reference

1.Kim, Dooseop, et al. "(2 R)-4-Oxo-4-[3-(trifluoromethyl)-5, 6-dihydro [1, 2, 4] triazolo [4, 3-a] pyrazin-7 (8 H)-yl]-1-(2, 4, 5-trifluorophenyl) butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes." Journal of medicinal chemistry 48.1 (2005): 141-151.
2.Ahrén, Bo, et al. "Beta-cell expression of a dominant-negative HNF-1α compromises the ability of inhibition of dipeptidyl peptidase-4 to elicit a long-term augmentation of insulin secretion in mice." European journal of pharmacology 521.1-3 (2005): 164-168.
3.Bergman, Arthur J., et al. "Pharmacokinetic and pharmacodynamic properties of multiple oral doses of sitagliptin, a dipeptidyl peptidase-IV inhibitor: a double-blind, randomized, placebo-controlled study in healthy male volunteers." Clinical therapeutics 28.1 (2006): 55-72.