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Vildagliptin

Item № 14705
CAS № 274901-16-5
Purity ≥98%
product image
                (CAS 274901-16-5)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     10 mg $25.00 0.00
     50 mg $75.00 0.00
     100 mg $113.00 0.00
     1 g $250.00 0.00

Pricing updated 2019-07-23. Prices are subject to change without notice.

Description

Glyptins are a class of oral antihyperglycemic agents that inhibit dipeptidyl peptidase 4 (DPP-4), which can act as a serine exopeptidase.1 In addition to having use in type 2 diabetes, gliptins have positive cardiovascular and anti-inflammatory effects.1,2,3 Vildagliptin is an inhibitor of DPP-4 (IC50 = 3.5-34 nM).4,5 It also inhibits DPP-8 and DPP-9 (Ki = 810 and 95 nM, respectively) but not DPP-2 or the related fibroblast activation protein α.6 Through its effects on DPP-4, it blocks the degradation of several circulating peptides, including incretins (stimulators of insulin secretion) like glucose-dependent insulinotropic polypeptide and glucagon-like peptide-1.7,8 Vildagliptin reduces fasting and postprandial glucose levels and decreases inflammatory and oxidative stress in diverse animal models of disease.1,3

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Technical Information
Formal Name
1-[2-[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-2S-pyrrolidinecarbonitrile
CAS Number
274901-16-5
Molecular Formula
C17H25N3O2
Formula Weight
303.4
Purity
≥98%
Formulation
A crystalline solid
SMILES
O=C(CN[C@@]1(CC(C2)C3)CC3C[C@]2(O)C1)N4[C@H](C#N)CCC4
InChI Code
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-
InChI Key
SYOKIDBDQMKNDQ-QWJLZPNVSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Scheen, A.J. Cardiovascular effects of gliptins Nat.Rev.Cardiol. 10(2), 73-84 (2013).

2. Doupis, J., and Veves, A. DPP4 inhibitors: A new approach in diabetes treatment Advances in Therapy 25(7), 627-643 (2008).

3. Strain, W.D., Lukashevich, V., Kothny, W., et al. Individualised treatment targets for elderly patients with type 2 diabetes using vildagliptin add-on or lone therapy (INTERVAL): A 24 week, randomised, double-blind, placebo-controlled study Langmuir 382(9890), 409-416 (2013).

4. Weber, A.E. Dipeptidyl peptidase IV inhibitors for the treatment of diabetes Journal of Medicinal Chemistry 47(17), 4135-4141 (2004).

5. Parmee, E.R., He, J., Mastracchio, A., et al. 4-amino cyclohexylglycine analogues as potent dipeptidyl peptidase IV inhibitors Bioorganic & Medicinal Chemistry Letters 14(1), 43-46 (2004).

6. Ikuma, Y., Hochigai, H., Kimura, H., et al. Discovery of 3H-imidazol[4,5-c]quinolin-4(5H)-ones as potent and selective dipeptidyl peptidase IV (DPP-4) inhibitors Bioorganic & Medicinal Chemistry 20(19), 5864-5883 (2012).

7. Mari, A., Sallas, W.M., He, Y.L., et al. Vildagliptin, a dipeptidyl peptidase-IV inhibitor, improves model-assessed β-cell function in patients with type 2 diabetes Journal of Clinical Endocrinology and Metabolism 90(8), 4888-4894 (2005).

8. Burkey, B.F., Li, X., Bolognese, L., et al. Acute and chronic effects of the incretin enhancer vildagliptin in insulin-resistant rats Journal of Pharmacology and Experimental Therapeutics 315(2), 688-695 (2005).

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