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Compound Detail

CHEMBL142703

VILDAGLIPTIN
💊 Approved Drug
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💊 Approved Drug
N#C[C@@H]1CCCN1C(=O)CNC12CC3CC(CC(O)(C3)C1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL142703
Name VILDAGLIPTIN
Phase Approved
Structure Type MOL
InChI Key SYOKIDBDQMKNDQ-XWTIBIIYSA-N
Therapeutic ✓ Yes

Known Names

Equa Galvus Jalra LAF 237 LAF-237 LAF237 NVP-LAF 237 NVP-LAF237 Vildagliptin Vildagliptina Vildagliptine Vitagliptin +1 more
10
Targets
100
Activities
3
Assay Types
17
PK Parameters
20
Publications
13
Known Names
8
Indications
1
Mechanisms

Molecular Properties

303.4
MW (Da)
1.17
ALogP
4
HBA
2
HBD
76.4
PSA (Ų)
0.82
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2007
Availability Unknown
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -gliptin
USAN Year 2005

Extended Properties

Molecular Formula C17H25N3O2
MW 303.41
Aromatic Rings 0
Heavy Atoms 22
NP-Likeness -0.50

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dipeptidyl peptidase IV inhibitor INHIBITOR Dipeptidyl peptidase 4 ✓ ✓

Indications

Diabetes Mellitus Diabetes Mellitus, Type 2 Diabetes Mellitus, Type 1 Prediabetic State Breast Neoplasms Diabetes, Gestational Glucose Intolerance Depressive Disorder, Major

ATC Classification

A10BH02
vildagliptin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES

Activity Summary

IC50 85 meas. best 9.92
Ki 13 meas. best 8.52
Kd 2 meas. best 8.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dipeptidyl peptidase 9
CHEMBL4793
 IC50 9.92 6.8623 0.1 13
Dipeptidyl peptidase 4
CHEMBL284
 IC50 9.24 7.5636 0.6 39
Dipeptidyl peptidase 8
CHEMBL4657
 IC50 8.73 5.4526 1.9 19
Dipeptidyl peptidase 4
CHEMBL284
 Kd 8.62 8.295 2.4 2
Dipeptidyl peptidase 4
CHEMBL284
 Ki 8.52 7.395 3.0 4
Caco-2
CHEMBL614058
 IC50 8.46 8.46 3.5 1
Dipeptidyl peptidase IV
CHEMBL4295559
 Ki 7.77 7.77 17.0 1
Dipeptidyl peptidase 4
CHEMBL3883
 IC50 7.58 7.58 26.0 1
Dipeptidyl peptidase 9
CHEMBL4793
 Ki 7.17 7.0575 68.0 4
Dipeptidyl peptidase 9
CHEMBL4295538
 IC50 6.17 6.17 680.0 1
Unchecked
CHEMBL612545
 IC50 6.17 6.17 680.0 1
Dipeptidyl peptidase 8
CHEMBL4657
 Ki 6.09 6.035 810.0 4
Dipeptidyl peptidase IV
CHEMBL4295559
 IC50 5.89 5.89 1300.0 1
Prolyl endopeptidase FAP
CHEMBL4683
 IC50 5.43 4.5867 3720.0 6
Prolyl endopeptidase FAP
CHEMBL5769
 IC50 4.28 4.28 52000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 35.8 ng.hr.mL-1 Mus musculus
AUC 41.7 ng.hr.mL-1 Mus musculus
AUC 51.4 ng.hr.mL-1 Mus musculus
AUC 7384999.4 ng.hr.mL-1 Mus musculus
AUC 4954685.3 ng.hr.mL-1 Mus musculus
AUC 5145833.6 ng.hr.mL-1 Mus musculus
AUC 5458345.9 ng.hr.mL-1 Mus musculus
AUC 4571882.01 ng.hr.mL-1 Mus musculus
AUC 16329019.51 ng.hr.mL-1 Mus musculus
AUC 4571882.01 ng.hr.mL-1 Mus musculus
CL 40.6 L/hr Homo sapiens
F 90.0 % Macaca fascicularis
F 90.0 % Macaca fascicularis
T1/2 2.0 hr Homo sapiens
T1/2 1.5 hr Homo sapiens
T1/2 1.5 hr Macaca fascicularis
T1/2 0.05833 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dipeptidyl peptidase 9 IC50 = 0.12 nM 9.92 Inhibition of human recombinant DPP9 using Gly-Pro-AMC as substrate preincubated... 34399391
Dipeptidyl peptidase 4 IC50 = 0.58 nM 9.24 Inhibition of DPP4 in human plasma assessed as formation of 7-amino-4-methylcoum... 21865048
Dipeptidyl peptidase 8 IC50 = 1.85 nM 8.73 Inhibition of human recombinant DPP8 using Gly-Pro-AMC as substrate preincubated... 34399391
Dipeptidyl peptidase 4 Kd = 2.4 nM 8.62 Binding affinity to human recombinant DPP4 (39 to 766 residues) by surface plasm... 27438064
Dipeptidyl peptidase 4 IC50 = 3.0 nM 8.52 Inhibition of human recombinant DPP4 by fluorescence assay 19482472
Dipeptidyl peptidase 4 Ki = 3.0 nM 8.52 Inhibition of DPP4 in human plasma using Gly-Pro-AMC as substrate by fluorimetri... 22938786
Dipeptidyl peptidase 4 IC50 = 3.0 nM 8.52 Inhibition of human purified His-tagged DPP-4 assessed as cleavage of substrate ... 23938053
Dipeptidyl peptidase 4 IC50 = 3.2 nM 8.49 Inhibition of human DPP4 expressed in baculovirus expression system using Gly-Pr... 22503246
Dipeptidyl peptidase 4 IC50 = 3.5 nM 8.46 Inhibitory concentration against dipeptidylpeptidase IV 15293982
Caco-2 IC50 = 3.5 nM 8.46 Antiproliferative activity against human Caco-2 cells assessed as reduction in c... 38704940
Dipeptidyl peptidase 4 IC50 = 3.5 nM 8.46 Inhibition of DPP4 (unknown origin) 24099035
Dipeptidyl peptidase 4 IC50 = 3.5 nM 8.46 Inhibition of DPP4 19375196
Dipeptidyl peptidase 4 IC50 = 3.5 nM 8.46 Inhibition of DPP-4 in human Caco-2 cells using H-Ala-Pro-pNA as substrate prein... 37647598
Dipeptidyl peptidase 4 Ki = 4.0 nM 8.4 Inhibition of human DPP4 expressed in Caco-2 cells 17034148
Dipeptidyl peptidase 4 IC50 = 9.0 nM 8.05 Inhibition of DPP4 20488702
Dipeptidyl peptidase 4 IC50 = 10.0 nM 8.0 Inhibition of DPP4 (unknown origin) 37721854
Dipeptidyl peptidase 4 IC50 = 10.0 nM 8.0 Inhibition of DPP4 (unknown origin) 24439847
Dipeptidyl peptidase 4 Kd = 10.7 nM 7.97 Binding affinity to human recombinant DPP4 (39 to 766 residues) at 5 uM by isoth... 27438064
Dipeptidyl peptidase 4 Ki = 13.0 nM 7.89 Binding affinity to human DPP-4 using gly-pro-pNA as substrate assessed as inhib... 37647598
Dipeptidyl peptidase 4 IC50 = 15.0 nM 7.82 Inhibition of DPP4 in human serum assessed as decrease in p-nitroaniline formati... 31683103

Literature References

PubMed DOI Target Context # Activities
24153396 10.1016/j.bmc.2013.09.048 Mus musculus 21
28666735 10.1016/j.bmcl.2017.06.051 Dipeptidyl peptidase 4 15
37647598 10.1021/acs.jmedchem.3c00412 Dipeptidyl peptidase 4 10
25164763 10.1016/j.ejmech.2014.08.059 Mus musculus 8
27438064 10.1021/acs.jmedchem.6b00475 Dipeptidyl peptidase 4 7
24531224 10.1016/j.ejmech.2014.01.021 Mus musculus 6
28826083 10.1016/j.ejmech.2017.08.024 Dipeptidyl peptidase IV 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
31683103 10.1016/j.ejmech.2019.111808 NON-PROTEIN TARGET 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
19482472 10.1016/j.bmcl.2009.05.048 Unchecked 3
20483603 10.1016/j.bmcl.2010.04.124 Dipeptidyl peptidase 4 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
30642693 10.1016/j.bmc.2019.01.001 Dipeptidyl peptidase 4 3
20488702 10.1016/j.bmcl.2010.04.120 Mus musculus 3
16392822 10.1021/jm0507781 Dipeptidyl peptidase 4 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
34428715 10.1016/j.bmc.2021.116354 Mus musculus 3

Data from ChEMBL 36 via Core Engine