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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H25N3O2.ClH
Molecular Weight 339.86
Optical Activity ( - )
Defined Stereocenters 1 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Vildagliptin hydrochloride

SMILES

Cl.OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N4CCC[C@H]4C#N

InChI

InChIKey=RZUUYWHYKBKAGN-DNSMMRBLSA-N
InChI=1S/C17H25N3O2.ClH/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;1H/t12?,13?,14-,16?,17?;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Description
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.

CNS Activity

Curator's Comment: Vildagliptin does not cross the blood-brain barrier

Originator

Curator's Comment: # Novartis

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Galvus

Approved Use

Vildagliptin is indicated in the treatment of type 2 diabetes mellitus in adults

Launch Date

1.19067836E12
PubMed

PubMed

TitleDatePubMed
Vildagliptin.
2006
Vildagliptin: a novel DPP-4 inhibitor with pancreatic islet enhancement activity for treatment of patients with type 2 diabetes.
2006 Aug
American Diabetes Association--66th scientific sessions. 9-13 June 2006, Washington, DC, USA.
2006 Aug
Dipeptidyl peptidase IV (DPP IV) inhibitors: A newly emerging drug class for the treatment of type 2 diabetes.
2006 Dec
7-But-2-ynyl-9-(6-methoxy-pyridin-3-yl)-6-piperazin-1-yl-7,9-dihydro-purin-8-one is a novel competitive and selective inhibitor of dipeptidyl peptidase IV with an antihyperglycemic activity.
2006 Dec
Exenatide: a novel approach for treatment of type 2 diabetes.
2006 Nov
DPP-4 inhibitors and their potential role in the management of type 2 diabetes.
2006 Nov
Oral agents for type 2 diabetes reduce HbA1c, are weight neutral.
2006 Sep
The absolute oral bioavailability and population-based pharmacokinetic modelling of a novel dipeptidylpeptidase-IV inhibitor, vildagliptin, in healthy volunteers.
2007
Pharmacokinetics and pharmacodynamics of vildagliptin in patients with type 2 diabetes mellitus.
2007
Review of sitagliptin phosphate: a novel treatment for type 2 diabetes.
2007
Dipeptidyl peptidase-4 inhibitors and the management of type 2 diabetes mellitus.
2007 Apr
[Glucagon-like peptide-1 (GLP-1), new target for the treatment of type 2 diabetes].
2007 Apr
Gateways to clinical trials.
2007 Apr
Inhibition of DPP-4: a new therapeutic approach for the treatment of type 2 diabetes.
2007 Apr
Effects of vildagliptin on glucose control over 24 weeks in patients with type 2 diabetes inadequately controlled with metformin.
2007 Apr
Evaluation of pharmacokinetic interactions between vildagliptin and digoxin in healthy volunteers.
2007 Aug
Dipeptidyl peptidase 4 inhibition and vildagliptin therapy for type 2 diabetes.
2007 Aug
Antihyperglycaemic therapy in elderly patients with type 2 diabetes: potential role of incretin mimetics and DPP-4 inhibitors.
2007 Aug
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
Evaluation of the potential for steady-state pharmacokinetic interaction between vildagliptin and simvastatin in healthy subjects.
2007 Dec
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
Comparison of vildagliptin and rosiglitazone monotherapy in patients with type 2 diabetes: a 24-week, double-blind, randomized trial.
2007 Feb
Vildagliptin does not affect C-peptide clearance in patients with type 2 diabetes.
2007 Jan
Liraglutide, a long-acting glucagon-like peptide-1 analog, reduces body weight and food intake in obese candy-fed rats, whereas a dipeptidyl peptidase-IV inhibitor, vildagliptin, does not.
2007 Jan
Gliptins.
2007 Jan 27
The physiology of incretin hormones and the basis for DPP-4 inhibitors.
2007 Jan-Feb
[New concepts in the treatment of type 2 diabetes].
2007 Jul
The influence of hepatic impairment on the pharmacokinetics of the dipeptidyl peptidase IV (DPP-4) inhibitor vildagliptin.
2007 Jul
Dipeptidyl peptidase 4 (DPP-4) inhibitors and their role in Type 2 diabetes management.
2007 Jul-Aug
Vildagliptin: a novel oral therapy for type 2 diabetes mellitus.
2007 Jun
Dipeptidyl peptidase-4 inhibitors: clinical data and clinical implications.
2007 Jun
Efficacy and tolerability of initial combination therapy with vildagliptin and pioglitazone compared with component monotherapy in patients with type 2 diabetes.
2007 Mar
Vildagliptin in combination with pioglitazone improves glycaemic control in patients with type 2 diabetes failing thiazolidinedione monotherapy: a randomized, placebo-controlled study.
2007 Mar
Dipeptidyl peptidase-IV inhibitors: a major new class of oral antidiabetic drug.
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
Effects of dipeptidyl peptidase-4 inhibition on gastrointestinal function, meal appearance, and glucose metabolism in type 2 diabetes.
2007 May
Dipeptidyl peptidase 8/9-like activity in human leukocytes.
2007 May
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
DPP-4 inhibition improves glucose tolerance and increases insulin and GLP-1 responses to gastric glucose in association with normalized islet topography in mice with beta-cell-specific overexpression of human islet amyloid polypeptide.
2007 Oct 4
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
Vildagliptin was effective as add-on therapy in type 2 diabetes inadequately controlled with metformin monotherapy.
2007 Sep-Oct
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
Patents

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
Vildagliptin inhibited rat plasma DPP-IV activity in vitro with an IC(50) value of 2.12 nmol/l
Substance Class Chemical
Created
by admin
on Fri Jul 07 00:16:23 UTC 2023
Edited
by admin
on Fri Jul 07 00:16:23 UTC 2023
Record UNII
9KND64V2AA
Record Status Validated (UNII)
Record Version
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Name Type Language
Vildagliptin hydrochloride
Common Name English
Vildagliptin hydrochloride [WHO-DD]
Common Name English
2-Pyrrolidinecarbonitrile, 1-[2-[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-, hydrochloride (1:1), (2S)-
Systematic Name English
(2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile hydrochloride
Systematic Name English
Code System Code Type Description
PUBCHEM
16070539
Created by admin on Fri Jul 07 00:16:23 UTC 2023 , Edited by admin on Fri Jul 07 00:16:23 UTC 2023
PRIMARY
CAS
924914-75-0
Created by admin on Fri Jul 07 00:16:23 UTC 2023 , Edited by admin on Fri Jul 07 00:16:23 UTC 2023
PRIMARY
FDA UNII
9KND64V2AA
Created by admin on Fri Jul 07 00:16:23 UTC 2023 , Edited by admin on Fri Jul 07 00:16:23 UTC 2023
PRIMARY
Related Record Type Details
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