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SML2302

Sigma-Aldrich

Vildagliptin

≥98% (HPLC)

Synonym(s):

Vildagliptin, (2S)-1-[[(3-Hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-2-pyrrolidinecarbonitrile, LAF-237, NVP-LAF237, (S)-1-(((1R,3R,5R,7S)-3-hydroxyadamantan-1-yl)glycyl)pyrrolidine-2-carbonitrile

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About This Item

Empirical Formula (Hill Notation):
C17H25N3O2
CAS Number:
274901-16-5
Molecular Weight:
303.40
MDL number:
MFCD08275142
UNSPSC Code:
12352200

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -81 to -91°, c = 0.1 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

N#C[C@H]1N(CCC1)C(CN[C@@](C[C@]2([H])C3)(C[C@@](C2)([H])C4)C[C@@]34O)=O

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

InChI key

SYOKIDBDQMKNDQ-NHMCJKAESA-N

Application

Vildagliptin has been used:
  • as a dipeptidyl peptidase-4 (DPP4) inhibitor to study its effects on endoplasmic reticulum (ER) pathway under diabetic conditions
  • in pharmacological inhibition to investigate the kinetics of transposable element (TE) desilencing and confirm its dependence on DPF-3 (a P-granule-localized N-terminal dipeptidase) enzymatic activity
  • to study its electrochemical properties and determination in biological fluid and drug forms

Biochem/physiol Actions

Vildagliptin ia a selective inhibitor of dipeptidyl peptidase 4 (DPP4). This enzyme breaks down the incretins GLP-1 and GIP, gastrointestinal hormones that are released in response to a meal. By preventing GLP-1 and GIP inactivation, GLP-1 and GIP are able to potentiate the secretion of insulin and suppress the release of glucagon by the pancreas.
Vildagliptin may participate in lipid metabolism. It plays a key role in attenuating postprandial hypertriglyceridemia, reducing serum triglycerides, apolipoprotein B, and blood total cholesterol levels. Vildagliptin is used in diabetes mellitus type 2 (DM2) therapy and may also possess vasculoprotective properties. Vildagliptin also helps to improve mitochondrial dysfunction caused by diabetes.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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