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SML2302

Sigma-Aldrich

Vildagliptin

≥98% (HPLC)

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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
Empirical Formula (Hill Notation):
C17H25N3O2
CAS Number:
Molecular Weight:
303.40
MDL number:

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

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SML2257SML1037SML0723
Vildagliptin ≥98% (HPLC)

Sigma-Aldrich

SML2302

Vildagliptin

IBR2 ≥98% (HPLC)

Sigma-Aldrich

SML2257

IBR2

UNC0642 ≥98% (HPLC)

Sigma-Aldrich

SML1037

UNC0642

Sigma-Aldrich

Sigma-Aldrich

SML0723

ML252

form

powder

form

powder

form

powder

form

powder

color

white to beige

color

white to beige

color

white to beige

color

, light to dark purple

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 5 mg/mL, clear (warmed)

solubility

DMSO: 25 mg/mL, clear

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

optical activity

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

optical activity

-

optical activity

-

optical activity

-

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Michał Wiciński et al.
International journal of molecular sciences, 21(7) (2020-03-29)
Vildagliptin is a representative of Dipeptidyl Peptidase-4 (DPP-4) inhibitors, antihyperglycemic drugs, approved for use as monotherapy and combination therapy in type 2 diabetes mellitus. By inhibiting enzymatic decomposition, DPP-4 inhibitors increase the half-life of incretins such as GLP-1 (Glucagon-like peptide-1)
Alberto Palazzuoli et al.
Heart failure reviews, 23(3), 325-335 (2018-01-24)
Heart failure (HF) is a common complication in patients with type 2 diabetes and it is closely associated with high morbidity and mortality rate. The incidence of cardiovascular events in patients with diabetes is related to high levels of glycemia
Rajani Kanth Gudipati et al.
Molecular cell, 81(11), 2388-2402 (2021-04-15)
Small RNA pathways defend the germlines of animals against selfish genetic elements, yet pathway activities need to be contained to prevent silencing of self genes. Here, we reveal a proteolytic mechanism that controls endogenous small interfering (22G) RNA activity in
Pongpan Tanajak et al.
The Journal of endocrinology, 236(2), 69-84 (2017-11-17)
Sodium-glucose cotransporter 2 inhibitor (SGLT2-i) effects on cardiac ischemia/reperfusion (I/R) injury are unclear. Unlike SGLT2-i, dipeptidyl peptidase 4 inhibitors (DPP4-i) have shown effective cardioprotection in cardiac I/R injury. We aimed to investigate whether SGLT2-i reduces myocardial dysfunction and myocardial injury
Roberto Trevisan
Diabetes therapy : research, treatment and education of diabetes and related disorders, 8(6), 1215-1226 (2017-10-07)
Diabetes is the leading cause of chronic kidney disease, and even in the absence of albuminuria, decreased renal function in type 2 diabetes mellitus (T2DM) patients increases the risk for major adverse cardiovascular events and death. The evidence derived from

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