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 |
DescriptionSources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000771/WC500020327.pdfCurator's Comment: Description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04876
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19088168
Curator's Comment: Vildagliptin does not cross the blood-brain barrier
Originator
Sources: http://adisinsight.springer.com/drugs/800017333
Curator's Comment: # Novartis
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19904014
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
Edited
Fri Dec 15 15:31:32 GMT 2023
by
admin
on
Fri Dec 15 15:31:32 GMT 2023
|
Record UNII |
I6B4B2U96P
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 |
|
||