2-({6-[(3R)-3-aminopiperidin-1-yl]-3-(2H3)methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl}methyl)benzonitrile

• ChemBase ID: 159715
• Molecular Formular: C18H21N5O2
• Molecular Mass: 339.39164
• Monoisotopic Mass: 339.16952494
• SMILES: c1c(=O)n(c(=O)n(c1N1C[C@@H](CCC1)N)Cc1ccccc1C#N)C
• Canonical SMILES: N#Cc1ccccc1Cn1c(cc(=O)n(c1=O)C)N1CCC[C@H](C1)N
• InChI: InChI=1S/C18H21N5O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3/t15-/m1/s1
• InChIKey: ZSBOMTDTBDDKMP-OAHLLOKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({6-[(3R)-3-aminopiperidin-1-yl]-3-(^2H₃)methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl}methyl)benzonitrile
• IUPAC Traditional name: 2-({6-[(3R)-3-aminopiperidin-1-yl]-3-(^2H₃)methyl-2,4-dioxopyrimidin-1-yl}methyl)benzonitrile
• Synonyms: 2-[[6-[(3R)-3-Amino-1-piperidinyl]-3,4-dihydro-3-(methyl-d3)-2,4-dioxo-1(2H)-pyrimidinyl]methyl]benzonitrile; Alogliptin-d3

Database IDs

• CAS Number: 1133421-35-8
• PubChem SID: 162253850
• PubChem CID: 71313111

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.830191
• LogD (pH = 7.4): -0.86919
• Log P: 1.1556401
• Molar Refractivity: 104.2632 cm^3
• Polarizability: 35.805405 Å^3
• Polar Surface Area: 93.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 126-128°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A575427

Labelled Alogliptin (A575425). It is an oral antihyperglycemic agent that is a selective inhibitor of the enzyme dipeptidyl peptidase-4 (DPP-4). Antidiabetic agent.

REFERENCES

• Lynn, F., et al.: Diabetes, 50, 1004 (2001)
• Trumper, A., et al.: J. Endocrinol., 174, 233 (2001)
• Vollmer, K., et al.: J. Clin. Endocrinol. Metab., 94, 1379 (2001)