(2S)-1-(2-{[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]amino}acetyl)(2,5,5-2H3)pyrrolidine-2-carbonitrile

• ChemBase ID: 179495
• Molecular Formular: C17H25N3O2
• Molecular Mass: 303.3993
• Monoisotopic Mass: 303.19467706
• SMILES: C1[C@]2(C[C@]3(C[C@@H]1C[C@@H](C2)C3)NCC(=O)N1CCC[C@H]1C#N)O
• Canonical SMILES: N#C[C@@H]1CCCN1C(=O)CN[C@]12C[C@@H]3C[C@H](C1)C[C@](C2)(C3)O
• InChI: InChI=1S/C17H25N3O2/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16/h12-14,19,22H,1-8,10-11H2/t12-,13+,14-,16+,17-/m0/s1
• InChIKey: SYOKIDBDQMKNDQ-NHMCJKAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-(2-{[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]amino}acetyl)(2,5,5-^2H₃)pyrrolidine-2-carbonitrile
• IUPAC Traditional name: (2S)-1-(2-{[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]amino}acetyl)(2,5,5-^2H₃)pyrrolidine-2-carbonitrile
• Synonyms: (2S)-1-[2-[(3-Hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-2-(pyrrolidine-d3)carbonitrile; LAF 237-d3; NVP-LAF 237-d3; Galvus-d3; Vildagliptin-d3

Database IDs

• CAS Number: 1217546-82-1
• PubChem SID: 164235405
• PubChem CID: 71752939

CALCULATED PROPERTIES

• Acid pKa: 14.705235
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.2804537
• LogD (pH = 7.4): -1.8509002
• Log P: -0.21739453
• Molar Refractivity: 81.9991 cm^3
• Polarizability: 32.339184 Å^3
• Polar Surface Area: 76.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V305002

Labelled Vildagliptin. It is a new oral anti-hyperglycemic agent of a new dipeptidyl peptidase-IV (DPP-IV) inhibitor class of drugs. Antidiabetic.

REFERENCES

• Ahren, B., et al.: Diabetes Care, 27, 2874 (2004)
• Barlocco, D., et al.: Curr. Opin. Invest. Drugs, 5, 1094 (2004)
• Ahren, B., et al.: J. Clin. Endocrinol. Metab., 89, 2078 (2004)