Saxagliptin
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Molecular Identity
Saxagliptin
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
PubChem CID: 11243969
Saxagliptin is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2S)-amino(3-hydroxyadamantan-1-yl)acetic acid with the amino group of (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile. Used in its monohydrate form for the treatment of Type II diabetes. It has a role as a hypoglycemic agent and an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor. It is a nitrile, a tertiary alcohol, a monocarboxylic acid amide, an azabicycloalkane and a member of adamantanes.
2D Structure
Properties
C18H25N3O2
Molecular Formula
315.40
Molecular Weight
g/mol
315.1947
Exact Mass
Da
0.7
XLogP
Drug-like (Lipinski: < 5)
90.4
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
4
H-Bond Acceptors
609
Complexity
SMILES
Canonical SMILES
SMILES: C1C2CC2N(C1C#N)C(=O)C(C34CC5CC(C3)CC(C5)(C4)O)NIsomeric SMILES
SMILES: C1[C@@H]2C[C@@H]2N([C@@H]1C#N)C(=O)[C@H](C34CC5CC(C3)CC(C5)(C4)O)NSynonyms(20)
Saxagliptin361442-04-8BMS-477118Saxagliptin anhydrousBMS 477118SaxagliptineDTXSID70485808I7IO46IVQ(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrileDTXCID3028506BMS477118CHEBI:71272SaxagliptinaNSC760407(1S,3S,5S)-2-((2S)-Amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl)-2-azabicyclo(3.1.0)hexane-3-carbonitrile
Data from PubChem (NCBI)
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