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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

CNS Non-penetrant
1014
Curator's Comment: Vildagliptin does not cross the blood-brain barrier

Originator

Novartis
173
Curator's Comment: # Novartis

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 62.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Galvus

Approved Use

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

Launch Date

2007
PubMed

PubMed

TitleDatePubMed
Glucagon-like peptide-1-based therapies for the treatment of type 2 diabetes mellitus.
2005
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
Vildagliptin, a dipeptidyl peptidase-IV inhibitor, improves model-assessed beta-cell function in patients with type 2 diabetes.
2005 Aug
Inhibition of dipeptidyl-peptidase IV catalyzed peptide truncation by Vildagliptin ((2S)-{[(3-hydroxyadamantan-1-yl)amino]acetyl}-pyrrolidine-2-carbonitrile).
2005 Jul 1
Acute and chronic effects of the incretin enhancer vildagliptin in insulin-resistant rats.
2005 Nov
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
Dipeptidyl-peptidase IV converts intact B-type natriuretic peptide into its des-SerPro form.
2006 Jan
Gateways to clinical trials.
2006 Jan-Feb
Therapies for the treatment of type 2 diabetes mellitus based on incretin action.
2006 Jun
Exenatide: a novel approach for treatment of type 2 diabetes.
2006 Nov
Oral agents for type 2 diabetes reduce HbA1c, are weight neutral.
2006 Sep
Targeting postprandial hyperglycemia.
2006 Sep
Review of sitagliptin phosphate: a novel treatment for type 2 diabetes.
2007
11 Years of cyanopyrrolidines as DPP-IV inhibitors.
2007
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
Gateways to clinical trials.
2007 Jan-Feb
Dipeptidyl peptidase 4 (DPP-4) inhibitors and their role in Type 2 diabetes management.
2007 Jul-Aug
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
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
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
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
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 effect of age, gender, and body mass index on the pharmacokinetics and pharmacodynamics of vildagliptin in healthy volunteers.
2008 Mar
Patents

Patents

JP2007509898A
2
JP2010043002A
4
JP2011509922A
12
JP2011510067A
57
JP2011529945A
21
JP2012500190A
22
JP2013241429A
2
JP4806628B2
2

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
  • 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
Structure of Vildagliptin
EXCRETED UNCHANGED
FECAL
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
The mean plasma protein binding of vildagliptin in humans was low (9.3%) and also independent of concentration.
BINDING
Structure of Vildagliptin hydrochloride
SALT/SOLVATE -> PARENT
Structure of Vildagliptin
EXCRETED UNCHANGED
URINE
DIPEPTIDYL PEPTIDASE 4 MEMBRANE FORM
TARGET -> INHIBITOR
Related Record Type Details
Structure of 2-((3-HYDROXYADAMANTAN-1-YL)AMINO)ACETIC ACID
METABOLITE -> PARENT
PLASMA
Structure of L-PROLINE, N-(3-HYDROXYTRICYCLO(3.3.1.13,7)DEC-1-YL)GLYCYL-
METABOLITE -> PARENT
FECAL
Structure of L-PROLINE, N-(3-HYDROXYTRICYCLO(3.3.1.13,7)DEC-1-YL)GLYCYL-
METABOLITE -> PARENT
MAJOR
URINE
Structure of 4-((2-((3-HYDROXYTRICYCLO(3.3.1.13,7)DEC-1-YL)AMINO)ACETYL)AMINO)BUTANOIC ACID
METABOLITE -> PARENT
URINE
Structure of 2-((3-HYDROXYADAMANTAN-1-YL)AMINO)ACETIC ACID
METABOLITE -> PARENT
FECAL
Structure of .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 3-((2-((2S)-2-CYANO-1-PYRROLIDINYL)-2-OXOETHYL)AMINO)TRICYCLO(3.3.1.13,7)DEC-1-YL
METABOLITE -> PARENT
URINE
Structure of L-PROLINE, N-(3-HYDROXYTRICYCLO(3.3.1.13,7)DEC-1-YL)GLYCYL-
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 3-((2-((2S)-2-CYANO-1-PYRROLIDINYL)-2-OXOETHYL)AMINO)TRICYCLO(3.3.1.13,7)DEC-1-YL
METABOLITE -> PARENT
URINE
Structure of 4-((2-((3-HYDROXYTRICYCLO(3.3.1.13,7)DEC-1-YL)AMINO)ACETYL)AMINO)BUTANOIC ACID
METABOLITE -> PARENT
PLASMA
Structure of 2-((3-HYDROXYADAMANTAN-1-YL)AMINO)ACETIC ACID
METABOLITE -> PARENT
URINE
Related Record Type Details
Structure of Vildagliptin
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

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