3-amino-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

• ChemBase ID: 177780
• Molecular Formular: C16H15F6N5O
• Molecular Mass: 407.3136192
• Monoisotopic Mass: 407.11807945
• SMILES: c1(cc(c(cc1F)CC(CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)N)F)F
• Canonical SMILES: NC(Cc1cc(F)c(cc1F)F)CC(=O)N1CCn2c(C1)nnc2C(F)(F)F
• InChI: InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2
• InChIKey: MFFMDFFZMYYVKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
• IUPAC Traditional name: sitagliptin
• Synonyms: 7-[3-Amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine; rac-SitagliptinSee: S491000

Database IDs

• CAS Number: 823817-56-7
• PubChem SID: 164233690
• PubChem CID: 11306691

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.583009
• LogD (pH = 7.4): -0.13560155
• Log P: 1.2572163
• Molar Refractivity: 87.4946 cm^3
• Polarizability: 31.48081 Å^3
• Polar Surface Area: 77.04 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Light Brown Syrup

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - S490990

A trizolopyrazine dipeptidyl peptidase IV inhibitor. It has recently been approved for the therapy of type II diabetes.

REFERENCES

• Kim, D., et al.: J. Med. Chem., 48, 141 (2005)
• Ahren, B., et al.: Eur. J. Pharmacol., 521 164 (2005)
• Bergman, A., et al: Clin. Ther., 28, 55 (2006)