Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H25N3O2 |
| Molecular Weight | 303.3993 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 1 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N4CCC[C@H]4C#N
InChI
InChIKey=SYOKIDBDQMKNDQ-XWTIBIIYSA-N
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
| Molecular Formula | C17H25N3O2 |
| Molecular Weight | 303.3993 |
| Charge | 0 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04876
Curator's Comment: Description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04876
Vildagliptin, previously identified as LAF237, is a new oral anti-hyperglycemic agent (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Vildagliptin inhibits the inactivation of GLP-1 and GIP by DPP-4, allowing GLP-1 and GIP to potentiate the secretion of insulin in the beta cells and suppress glucaon release by the alpha cells of the islets of Langerhans in the pancreas. It is currently in clinical trials in the U.S. and has been shown to reduce hyperglycemia in type 2 diabetes mellitus. While the drug is still not approved for use in the US, it was approved in Feb 2008 by European Medicines Agency for use within the EU and is listed on the Australian PBS with certain restrictions. Vildagliptin is marketed under the trade names Galvus, Zomelis.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| New therapeutic strategies for the treatment of type 2 diabetes mellitus based on incretins. | 2005 Summer |
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| Exenatide: a novel approach for treatment of type 2 diabetes. | 2006 Nov |
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| The absolute oral bioavailability and population-based pharmacokinetic modelling of a novel dipeptidylpeptidase-IV inhibitor, vildagliptin, in healthy volunteers. | 2007 |
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| Pharmacokinetics and pharmacodynamics of vildagliptin in patients with type 2 diabetes mellitus. | 2007 |
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| Review of sitagliptin phosphate: a novel treatment for type 2 diabetes. | 2007 |
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| Dipeptidyl peptidase-4 inhibitors and the management of type 2 diabetes mellitus. | 2007 Apr |
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| [Glucagon-like peptide-1 (GLP-1), new target for the treatment of type 2 diabetes]. | 2007 Apr |
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| Inhibition of DPP-4: a new therapeutic approach for the treatment of type 2 diabetes. | 2007 Apr |
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| beta-cell failure in diabetes and preservation by clinical treatment. | 2007 Apr |
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| Effects of vildagliptin on glucose control over 24 weeks in patients with type 2 diabetes inadequately controlled with metformin. | 2007 Apr |
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| The dipeptidyl peptidase IV inhibitor vildagliptin suppresses endogenous glucose production and enhances islet function after single-dose administration in type 2 diabetic patients. | 2007 Apr |
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| Efficacy and tolerability of vildagliptin monotherapy in drug-naïve patients with type 2 diabetes. | 2007 Apr |
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| [Incretin enhancers, incretin mimetics: from therapeutic concept to clinical application]. | 2007 Apr 1 |
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| Evaluation of pharmacokinetic interactions between vildagliptin and digoxin in healthy volunteers. | 2007 Aug |
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| Dipeptidyl peptidase IV inhibitors and the incretin system in type 2 diabetes mellitus. | 2007 Aug |
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| Dipeptidyl peptidase 4 inhibition and vildagliptin therapy for type 2 diabetes. | 2007 Aug |
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| Antihyperglycaemic therapy in elderly patients with type 2 diabetes: potential role of incretin mimetics and DPP-4 inhibitors. | 2007 Aug |
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| Antidiabetic medications in overweight/obese patients with type 2 diabetes: drawbacks of current drugs and potential advantages of incretin-based treatment on body weight. | 2007 Aug |
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| Evaluation of the potential for steady-state pharmacokinetic interaction between vildagliptin and simvastatin in healthy subjects. | 2007 Dec |
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| Management of type 2 diabetes in treatment-naive elderly patients: benefits and risks of vildagliptin monotherapy. | 2007 Dec |
|
| Incretin receptors for glucagon-like peptide 1 and glucose-dependent insulinotropic polypeptide are essential for the sustained metabolic actions of vildagliptin in mice. | 2007 Dec |
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| Incretins: a new treatment option for type 2 diabetes? | 2007 Feb |
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| Comparison of vildagliptin and rosiglitazone monotherapy in patients with type 2 diabetes: a 24-week, double-blind, randomized trial. | 2007 Feb |
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| Vildagliptin does not affect C-peptide clearance in patients with type 2 diabetes. | 2007 Jan |
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| The physiology of incretin hormones and the basis for DPP-4 inhibitors. | 2007 Jan-Feb |
|
| A review of the effects of antihyperglycaemic agents on body weight: the potential of incretin targeted therapies. | 2007 Jul |
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| The influence of hepatic impairment on the pharmacokinetics of the dipeptidyl peptidase IV (DPP-4) inhibitor vildagliptin. | 2007 Jul |
|
| Efficacy and safety of incretin therapy in type 2 diabetes: systematic review and meta-analysis. | 2007 Jul 11 |
|
| Dipeptidyl peptidase 4 (DPP-4) inhibitors and their role in Type 2 diabetes management. | 2007 Jul-Aug |
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| Vildagliptin: a novel oral therapy for type 2 diabetes mellitus. | 2007 Jun |
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| Which patients are candidates for dipeptidyl peptidase IV inhibitors? | 2007 Jun |
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| Addition of vildagliptin to insulin improves glycaemic control in type 2 diabetes. | 2007 Jun |
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| Vildagliptin in drug-naïve patients with type 2 diabetes: a 24-week, double-blind, randomized, placebo-controlled, multiple-dose study. | 2007 Mar |
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| Efficacy and tolerability of initial combination therapy with vildagliptin and pioglitazone compared with component monotherapy in patients with type 2 diabetes. | 2007 Mar |
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| Vildagliptin in combination with pioglitazone improves glycaemic control in patients with type 2 diabetes failing thiazolidinedione monotherapy: a randomized, placebo-controlled study. | 2007 Mar |
|
| 3-[2-((2S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-3-methyl-butyramide analogues as selective DPP-IV inhibitors for the treatment of type-II diabetes. | 2007 Mar 1 |
|
| The role of vildagliptin in the management of type 2 diabetes mellitus. | 2007 May |
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| Pharmacodynamics of vildagliptin in patients with type 2 diabetes during OGTT. | 2007 May |
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| Dipeptidyl peptidase 8/9-like activity in human leukocytes. | 2007 May |
|
| Vildagliptin was noninferior to rosiglitazone for glycemic control in type 2 diabetes but caused less weight gain. | 2007 May-Jun |
|
| The dipeptidyl peptidase 4 inhibitor vildagliptin does not accentuate glibenclamide-induced hypoglycemia but reduces glucose-induced glucagon-like peptide 1 and gastric inhibitory polypeptide secretion. | 2007 Nov |
|
| The DPP-4 inhibitor vildagliptin: robust glycaemic control in type 2 diabetes and beyond. | 2007 Sep |
|
| Incretin-based treatment of type 2 diabetes: glucagon-like peptide-1 receptor agonists and dipeptidyl peptidase-4 inhibitors. | 2007 Sep |
|
| Dose proportionality and the effect of food on vildagliptin, a novel dipeptidyl peptidase IV inhibitor, in healthy volunteers. | 2007 Sep |
|
| Comparison between vildagliptin and metformin to sustain reductions in HbA(1c) over 1 year in drug-naïve patients with Type 2 diabetes. | 2007 Sep |
|
| Vildagliptin was effective as add-on therapy in type 2 diabetes inadequately controlled with metformin monotherapy. | 2007 Sep-Oct |
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| Effects of the dipeptidyl peptidase-IV inhibitor vildagliptin on incretin hormones, islet function, and postprandial glycemia in subjects with impaired glucose tolerance. | 2008 Jan |
|
| Characterization of the influence of vildagliptin on model-assessed -cell function in patients with type 2 diabetes and mild hyperglycemia. | 2008 Jan |
|
| The dipeptidyl peptidase-4 inhibitor vildagliptin improves beta-cell function and insulin sensitivity in subjects with impaired fasting glucose. | 2008 Jan |
|
| The effect of age, gender, and body mass index on the pharmacokinetics and pharmacodynamics of vildagliptin in healthy volunteers. | 2008 Mar |
Sample Use Guides
When used as monotherapy, in combination with metformin, in combination with thiazolidinedione, in combination with metformin and a sulphonylurea, or in combination with insulin (with or without
metformin), the recommended daily dose of vildagliptin is 100 mg, administered as one dose of 50 mg in the morning and one dose of 50 mg in the evening. When used in dual combination with a sulphonylurea, the recommended dose of vildagliptin is 50 mg
once daily administered in the morning. In this patient population, vildagliptin 100 mg daily was no more effective than vildagliptin 50 mg once daily.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
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Wed Jul 05 23:01:13 UTC 2023
by
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on
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| Record UNII |
I6B4B2U96P
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Validated (UNII)
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C98086
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A10BD08
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RR-71
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596554
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DB04876
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DTXSID80881091
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I6B4B2U96P
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CHEMBL142703
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274901-16-5
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C66653
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3642
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SUB25199
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8399
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VILDAGLIPTIN
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6310
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C502012
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M11447
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100000089156
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6918537
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EXCRETED UNCHANGED |
FECAL
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BINDER->LIGAND |
The mean plasma protein binding of vildagliptin in humans was low (9.3%) and also independent of concentration.
BINDING
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SALT/SOLVATE -> PARENT |
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EXCRETED UNCHANGED |
URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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