(1R,3R,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl](1,2-13C2)acetyl](6-13C)-2-azabicyclo[3.1.0]hexane-3-carbonitrile

• ChemBase ID: 177696
• Molecular Formular: C18H25N3O2
• Molecular Mass: 318.38796451
• Monoisotopic Mass: 318.20474157
• SMILES: N1([13C](=O)[13C@@H](N)[C@@]23C[C@H]4C[C@@H](C2)C[C@@](C3)(C4)O)[C@H](C[C@H]2[C@@H]1[13CH2]2)C#N
• Canonical SMILES: N#C[C@H]1C[C@H]2[C@@H](N1[13C](=O)[13C@H]([C@]13C[C@@H]4C[C@H](C1)C[C@](C3)(C4)O)N)[13CH2]2
• InChI: InChI=1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10-,11+,12-,13-,14+,15-,17+,18-/m1/s1/i3+1,15+1,16+1
• InChIKey: QGJUIPDUBHWZPV-KBDLEKJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl](1,2-^1^3C₂)acetyl](6-^1^3C)-2-azabicyclo[3.1.0]hexane-3-carbonitrile
• IUPAC Traditional name: (1R,3R,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl](1,2-^1^3C₂)acetyl](6-^1^3C)-2-azabicyclo[3.1.0]hexane-3-carbonitrile
• Synonyms: (1S,3S,5S)-2-[(2S)-2-Amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile-13C3; BMS 477118-13C3; BMS 477118-11-13C3; Onglyza-13C3; Saxagliptin-13C3

Database IDs

• PubChem SID: 164233606
• PubChem CID: 71752158

CALCULATED PROPERTIES

• Acid pKa: 14.743205
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.388905
• LogD (pH = 7.4): -0.6962074
• Log P: -0.079534434
• Molar Refractivity: 83.9913 cm^3
• Polarizability: 33.454536 Å^3
• Polar Surface Area: 90.35 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S143502

Labelled Saxagliptin. It is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible

REFERENCES

• Feng, J., et al.: J. Med. Chem., 50, 2297 (2007)
• Rosenstock, J., et al.: Diabetes Obes. Metab., 10, 376 (2007)
• Thomas, L., et al.: J. Pharmacol. Exp. Ther., 325, 175 (2007)