Compound: Saxagliptin
SMILES: O=C(N1[C@H](C#N)C[C@H]2[C@@H]1C2)[C@@H](N)C34CC5(O)CC(C3)CC(C4)C5
InChIKey: QGJUIPDUBHWZPV-SGTAVMJGSA-N
Synonyms: Saxagliptin, 361442-04-8, BMS-477118, Saxagliptin anhydrous, BMS 477118, Saxagliptine, 8I7IO46IVQ, DTXSID7048580, DTXCID3028506, BMS477118, CHEBI:71272, Saxagliptina, NSC760407, (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, (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile, (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile, NSC-760407, (1S,3S,5S)-2-((2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetyl)-2-azabicyclo[3.1.0]hexane-3-carbonitrile, 3-hydroxyadamantylglycine-4,5-methanoprolinenitrile hydrate, QTERNMET COMPONENT SAXAGLIPTIN, saxagliptinum, (1S,3S,5S)-2-((2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl)-2-azabicyclo(3.1.0)hexane-3-carbonitrile, (1S,3S,5S)-2-((2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl)-2-azabicyclo(3.1.0)hexane-3-carbonitrile, RefChem:931331, A10BH03, (1S,3S,5S)-2-((2S)-2-Amino-2-(3-hydroxyadamantan-1-yl) acetyl)-2-azabicyclo(3.1.0)hexane-3-carbonitrile hydrate, 9GB927LAJW, BMS-477118-11, Saxagliptin Monohydrate, Onglyza, Saxagliptin [INN], OPC-262, CHEMBL385517, UNII-8I7IO46IVQ, Saxagliptin?, HSDB 8199, OPC 262, NCGC00242597-01, SAXAGLIPTIN [MI], Saxagliptin (USAN/INN), SCHEMBL17168, SAXAGLIPTIN [WHO-DD], MLS006011223, GTPL6316, BDBM11542, QGJUIPDUBHWZPV-SGTAVMJGSA-N, HMS3264P11, Pharmakon1600-01502500, MSK10924, SBMS-477118, Tox21_112908, BDBM50225074, EBC-02059, s1540, Saxagliptin (BMS-477118,Onglyza), AKOS015896547, Saxagliptin for system suitability CRS, AC-6008, CCG-213084, CCG-267647, CS-0650, DB06335, EX-7795, FA29598, NCGC00242597-02, NCGC00242597-10, HY-10285, SMR004702984, SY022234, CAS-361442-04-8, D08996, EN300-761487, AB01562984_01, AB01562984_02, Q3121121, BRD-A81513827-001-03-6, Z2235802036, (S)-3-Hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt, (1S,6S)-2-(2-adamantan-1-yl-2-amino-acetyl)-2-aza-bicyclo[3.1.0]hexane-3-carbonitrile, (1S,3S,5S)-2-((2S)-AMINO(3-HYDROXYTRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YL)ACETYL)-2-AZABICYCLO(3.1.0)HEXANE-3-CARBONITRILE, (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile; 2,2,2-trifluoroacetic acid, (1S,3S,5S)-2-[(2S)-2-Amino-2-(3-hydroxytricyclo[3.3.1.1(3,7)]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile, (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile, (1S,3S,5S)-2-[(S)-2-amino-2-(3-hydroxy-adamantan-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carbonitrile, (1S,3S,5S)-2-[2-Amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile, 2-AZABICYCLO(3.1.0)HEXANE-3-CARBONITRILE, 2-((2S)-AMINO(3-HYDROXYTRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YL)ACETYL), (1S,3S,5S)-, 2-Azabicyclo(3.1.0)hexane-3-carbonitrile, 2-((2S)-amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl) , (1S,3S,5S)-
Theoretical properties:
molecular_formula: C18H25N3O2
molecular_weight: 315.4 g/mol
exact_mass: 315.19467705 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 23
topological_polar_surface_area: 90.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: Sparingly soluble
Descriptions:
pubchem: 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.
chebi: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2<i>S</i>)-amino(3-hydroxyadamantan-1-yl)acetic acid with the amino group of (1<i>S</i>,3<i>S</i>,5<i>S</i>)-2-azabicyclo[3.1.0]hexane-3-carbonitrile. Used in its monohydrate form for the treatment of Type II diabetes.
chembl: SAXAGLIPTIN ANHYDROUS is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Saxagliptin, sold under the brand name Onglyza, is an oral hypoglycemic (anti-diabetic drug) of the dipeptidyl peptidase-4 (DPP-4) inhibitor class. Early development was solely by Bristol-Myers Squibb; in 2007 AstraZeneca joined with Bristol-Myers Squibb to co-develop the final compound and collaborate on the marketing of the drug.
In April 2016, the U.S. FDA added a warning about increased risk of heart failure. This was based on data in an article that concluded "DPP-4 inhibition with saxagliptin did not increase or decrease the rate of ischemic events, though the rate of hospitalization for heart failure was increased. Although saxagliptin improves glycemic control, other approaches are necessary to reduce cardiovascular risk in patients with diabetes."