| Identification | Back Directory | [Name]
Saxagliptin hydrate | [CAS]
945667-22-1 | [Synonyms]
CS-1180
Onglyza hydrate
BMS477118 hydrate
BMS-477118 hydrate
BMS 477118 hydrate
Saxagliptin hydrate
Saxagliptin hydrate
Unii-9gb927lajw
Saxagliptin hydrate (BMS-477118 hydrate)
BMS-477118 HYDRATE;BMS 477118 HYDRATE;BMS477118 HYDRATE
(1S,3S,5S)-2-((2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl)-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrate
(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 hydrate
2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, hydrate (1:1), (1S,3S,5S)-
Saxagliptin hydrate
(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 hydrate | [EINECS(EC#)]
641-082-3 | [Molecular Formula]
C18H27N3O3 | [MOL File]
945667-22-1.mol | [Molecular Weight]
333.43 |
| Chemical Properties | Back Directory | [Melting point ]
106-108°C | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO (Slightly), Methanol (Sparingly) | [form ]
Solid | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Description]
While liraglutide targets the incretin system as a GLP-1 analog for
therapeutic intervention in T2DM, saxagliptin enhances GLP-1 plasma concentrations by inhibiting the DPP-4 enzyme responsible for degradation of
GLP-1 by cleavage of the two N-terminal amino acids adjacent to alanine (or
proline), thereby rendering the hormone inactive.
Similarto vildagliptin,
saxagliptin is a cyanopyrrolidine substrate-based inhibitor. The proline
mimetic occupies the small S1-pocket while the nitrile’s trajectory aligns
with the scissile bond of the substrate. The slow dissociation kinetics of
saxagliptin is attributed to a reversible, covalent reaction between the nitrile
and the catalytically active serine hydroxyl (Ser630).
The steric bulk provided by the adamantyl moiety and the constrained cyclopropyl ring stabilizes the trans-rotamer of the amide, thereby preventing the problematic
intramolecular cyclization, via the amino group attacking the nitrile, which
is favored in the cis-conformation.
Since metabolism of saxagliptin is primarily mediated by CYP3A4/5, there is a potential for drug interactions with concomitant administration of strong inducers or inhibitors of these cytochrome P450 enzymes. The most common adverse events (>5% of patients) included upper respiratory tract infection, urinary tract infection, and headache. | [Originator]
Bristol-Myers-Squibb (US) | [Uses]
Saxagliptin Hydrate is a selective and reversible dipeptidyl peptidase-4 (DPP4) inhibitor that may be used to develop treatment for type 2 diabetes. | [Definition]
ChEBI: A hydrate that is the monohydrate form of anhydrous saxagliptin. Used for the treatment of Type II diabetes. | [Brand name]
Onglyza |
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