Vildagliptin

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

Structure Search

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

HIDE SMILES / InChI

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
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000771/WC500020327.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dipeptidyl peptidase IV 37 Target ID: CHEMBL284 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000771/WC500020327.pdf	Inhibitor 8297		62.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000771/WC500020327.pdf	Primary		Approved 8429	Galvus Approved Use Vildagliptin is indicated in the treatment of type 2 diabetes mellitus in adults Launch Date 2007

PubMed

Title	Date	PubMed
Glucagon-like peptide-1-based therapies for the treatment of type 2 diabetes mellitus.	2005	16318402
Incretins: what does the future hold?	2005 Oct	16241889
New therapeutic strategies for the treatment of type 2 diabetes mellitus based on incretins.	2005 Summer	17491680
T-cell activation via CD26 and caveolin-1 in rheumatoid synovium.	2006	16622717
Gateways to clinical trials.	2006 Apr	16810345
Newer therapeutic options for children with diabetes mellitus: theoretical and practical considerations.	2006 Apr	16629719
Vildagliptin: an inhibitor of dipeptidyl peptidase-4 with antidiabetic properties.	2006 Apr	16548792
Diabetes: assessing the pipeline.	2006 Apr	16504599
Dipeptidyl peptidase IV (DPP IV) inhibitors: A newly emerging drug class for the treatment of type 2 diabetes.	2006 Dec	17160910
Dipeptidyl-peptidase IV converts intact B-type natriuretic peptide into its des-SerPro form.	2006 Jan	16254193
Therapeutic options in development for management of diabetes: pharmacologic agents and new technologies.	2006 Jan-Feb	16627399
Gateways to clinical trials.	2006 Jan-Feb	16541195
Therapies for the treatment of type 2 diabetes mellitus based on incretin action.	2006 Jun	16682937
[Dipeptidylpeptidase IV inhibitors and dual action PPAR-agonists].	2006 Mar	16550882
Molecule of the month. Vildagilptin.	2006 May	16823497
DPP-4 inhibitors and their potential role in the management of type 2 diabetes.	2006 Nov	17073841
The incretin system: glucagon-like peptide-1 receptor agonists and dipeptidyl peptidase-4 inhibitors in type 2 diabetes.	2006 Nov 11	17098089
Oral agents for type 2 diabetes reduce HbA1c, are weight neutral.	2006 Sep	16998999
Vildagliptin therapy reduces postprandial intestinal triglyceride-rich lipoprotein particles in patients with type 2 diabetes.	2006 Sep	16816950
Review of sitagliptin phosphate: a novel treatment for type 2 diabetes.	2007	17580730
Inhibition of DPP-4: a new therapeutic approach for the treatment of type 2 diabetes.	2007 Apr	17407649
beta-cell failure in diabetes and preservation by clinical treatment.	2007 Apr	17353295
Effects of vildagliptin on glucose control over 24 weeks in patients with type 2 diabetes inadequately controlled with metformin.	2007 Apr	17277036
[Incretin enhancers, incretin mimetics: from therapeutic concept to clinical application].	2007 Apr 1	17383951
Dipeptidyl peptidase IV inhibitors and the incretin system in type 2 diabetes mellitus.	2007 Aug	17655515
Does addition of vildagliptin to metformin monotherapy improve glycemic control in patients with type 2 diabetes mellitus?	2007 Aug	17549095
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	17717280
Incretins: a new treatment option for type 2 diabetes?	2007 Feb	17379930
Comparison of vildagliptin and rosiglitazone monotherapy in patients with type 2 diabetes: a 24-week, double-blind, randomized trial.	2007 Feb	17259484
Vildagliptin does not affect C-peptide clearance in patients with type 2 diabetes.	2007 Jan	17192511
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	17192459
Gliptins.	2007 Jan 27	17258657
Gateways to clinical trials.	2007 Jan-Feb	17344945
The physiology of incretin hormones and the basis for DPP-4 inhibitors.	2007 Jan-Feb	17272793
A review of the effects of antihyperglycaemic agents on body weight: the potential of incretin targeted therapies.	2007 Jul	17559747
[New concepts in the treatment of type 2 diabetes].	2007 Jul	17541529
Efficacy and safety of incretin therapy in type 2 diabetes: systematic review and meta-analysis.	2007 Jul 11	17622601
Which patients are candidates for dipeptidyl peptidase IV inhibitors?	2007 Jun	17563046
Addition of vildagliptin to insulin improves glycaemic control in type 2 diabetes.	2007 Jun	17387446
Dipeptidyl peptidase-4 inhibitors: clinical data and clinical implications.	2007 Jun	17337494
Vildagliptin in drug-naïve patients with type 2 diabetes: a 24-week, double-blind, randomized, placebo-controlled, multiple-dose study.	2007 Mar	17373638
Dipeptidyl peptidase-IV inhibitors: a major new class of oral antidiabetic drug.	2007 Mar	17300591
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	17194587
The role of vildagliptin in the management of type 2 diabetes mellitus.	2007 May	17456545
New treatments for diabetes.	2007 May 24	17522409
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	17698900
Incretin-based treatment of type 2 diabetes: glucagon-like peptide-1 receptor agonists and dipeptidyl peptidase-4 inhibitors.	2007 Sep	17877544
Effects of the dipeptidyl peptidase-IV inhibitor vildagliptin on incretin hormones, islet function, and postprandial glycemia in subjects with impaired glucose tolerance.	2008 Jan	17947341
The dipeptidyl peptidase-4 inhibitor vildagliptin improves beta-cell function and insulin sensitivity in subjects with impaired fasting glucose.	2008 Jan	17909087
The effect of age, gender, and body mass index on the pharmacokinetics and pharmacodynamics of vildagliptin in healthy volunteers.	2008 Mar	17961192

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 Dec 15 15:31:32 GMT 2023` Edited by `admin` on `Fri Dec 15 15:31:32 GMT 2023`
Record UNII	I6B4B2U96P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Vildagliptin

Official Name

English

VILDAGLIPTIN [USAN]

Common Name

English

LAF-237

Code

English

2-PYRROLIDINECARBONITRILE, 1-(((3-HYDROXYTRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YL)AMINO)ACETYL)-, (2S)-

Systematic Name

English

EQUA

Brand Name

English

VILDAGLIPTIN [EMA EPAR]

Common Name

English

NVP-LAF237

Code

English

VITAGLIPTIN

Common Name

English

VILDAGLIPTIN [MART.]

Common Name

English

LAF237

Code

English

VILDAGLIPTIN [MI]

Common Name

English

(-)-(2S)-1-(((3-HYDROXYTRICYCLO(3.3.1.1(SUP(3,7))DEC-1-YL)AMINO)ACETYL)PYRROLIDINE-2-CARBONITRILE

Systematic Name

English

vildagliptin [INN]

Common Name

English

GALVUS

Brand Name

English

Vildagliptin [WHO-DD]

Common Name

English

VILDAGLIPTIN [JAN]

Common Name

English

(2S)-1-(((3-HYDROXYTRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YL)AMINO)ACETYL)PYRROLIDINE-2-CARBONITRILE

Systematic Name

English

NVP-LAF 237

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C98086