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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 of Vildagliptin

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
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

2007
PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2004 Dec
Gateways to clinical trials.
2004 Nov
American Diabetes Association - 65th Scientific Sessions. DDP-IV inhibitors.
2005 Aug
Improved meal-related beta-cell function and insulin sensitivity by the dipeptidyl peptidase-IV inhibitor vildagliptin in metformin-treated patients with type 2 diabetes over 1 year.
2005 Aug
Gateways to clinical trials.
2005 Jun
Alpha cell function in health and disease: influence of glucagon-like peptide-1.
2005 Sep
Vildagliptin.
2006
Gateways to clinical trials.
2006 Apr
Vildagliptin: an inhibitor of dipeptidyl peptidase-4 with antidiabetic properties.
2006 Apr
Dipeptidyl peptidase IV (DPP IV) inhibitors: A newly emerging drug class for the treatment of type 2 diabetes.
2006 Dec
Twelve-week monotherapy with the DPP-4 inhibitor vildagliptin improves glycemic control in subjects with type 2 diabetes.
2006 Jun
Therapies for the treatment of type 2 diabetes mellitus based on incretin action.
2006 Jun
[Dipeptidylpeptidase IV inhibitors and dual action PPAR-agonists].
2006 Mar
The incretin system: glucagon-like peptide-1 receptor agonists and dipeptidyl peptidase-4 inhibitors in type 2 diabetes.
2006 Nov 11
Vildagliptin therapy reduces postprandial intestinal triglyceride-rich lipoprotein particles in patients with type 2 diabetes.
2006 Sep
Dipeptidyl peptidase-4 inhibitors and the management of type 2 diabetes mellitus.
2007 Apr
beta-cell failure in diabetes and preservation by clinical treatment.
2007 Apr
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
Antihyperglycaemic therapy in elderly patients with type 2 diabetes: potential role of incretin mimetics and DPP-4 inhibitors.
2007 Aug
Evaluation of the potential for steady-state pharmacokinetic interaction between vildagliptin and simvastatin in healthy subjects.
2007 Dec
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
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
Vildagliptin: a novel oral therapy for type 2 diabetes mellitus.
2007 Jun
Which patients are candidates for dipeptidyl peptidase IV inhibitors?
2007 Jun
Vildagliptin in combination with pioglitazone improves glycaemic control in patients with type 2 diabetes failing thiazolidinedione monotherapy: a randomized, placebo-controlled study.
2007 Mar
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
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
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 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
  • Download
Name Type Language
Vildagliptin
EMA EPAR   INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
WHO-ATC A10BD08
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
WHO-VATC QA10BD08
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
WHO-VATC QA10BH02
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
WHO-ATC A10BH02
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
Code System Code Type Description
USAN
RR-71
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
RXCUI
596554
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB04876
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID80881091
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
FDA UNII
I6B4B2U96P
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
ChEMBL
CHEMBL142703
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
CAS
274901-16-5
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
NCI_THESAURUS
C66653
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
DRUG CENTRAL
3642
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
EVMPD
SUB25199
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
INN
8399
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
WIKIPEDIA
VILDAGLIPTIN
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
IUPHAR
6310
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
MESH
C502012
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
MERCK INDEX
m11447
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY Merck Index
SMS_ID
100000089156
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
PUBCHEM
6918537
Created by admin on Fri Dec 15 15:31:32 GMT 2023 , Edited by admin on Fri Dec 15 15:31:32 GMT 2023
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
FECAL
BINDER->LIGAND
The mean plasma protein binding of vildagliptin in humans was low (9.3%) and also independent of concentration.
BINDING
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
URINE
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
PLASMA
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
PLASMA
METABOLITE -> PARENT
URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION