10394. Saxagliptin
Nomenclature
CAS number: 361442-04-8
(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; (S)-3-hydroxyadamantylglycine-l-cis-4,5-methanoprolinenitrile; BMS-477118. C18H25N3O2; mol wt 315.41.
C 68.54%, H 7.99%, N 13.32%, O 10.15%.
Description and references
Dipeptidyl peptidase-IV (DPP-IV) inhibitor. Prepn: J. A. Robl et al., WO 0168603; eidem, US 6395767 (2001, 2002 both to Bristol-Myers Squibb). Synthesis and pharmacology: D. J. Augeri et al., J. Med. Chem. 48, 5025 (2005) DOI PubMed. Mechanism of action: Y. B. Kim et al., Arch. Biochem. Biophys. 445, 9 (2006) DOI PubMed. Crystal structure of complex with DPP-IV variants: W. J. Metzler et al., Protein Sci. 17, 240 (2008) DOI PubMed. Clinical experience in treatment-naive type 2 diabetes: J. Rosenstock et al., Diabetes Obes. Metab. 10, 376 (2008) DOI PubMed. Review of discovery and development: B. Gallwitz, IDrugs 11, 906-917 (2008) PubMed.
Derivative
Monohydrate.Nomenclature
CAS number: 945667-22-1
BMS-477118-11; Onglyza (BMS). C18H25N3O2.H2O; mol wt 333.43.
C 64.84%, H 8.16%, N 12.60%, O 14.40%.
Therapeutic Category
Antidiabetic.
Keywords
Antidiabetic; Dipeptidyl Peptidase IV Inhibitor