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Compound Detail

CHEMBL1422

SITAGLIPTIN
💊 Approved Drug
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💊 Approved Drug
N[C@@H](CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1422
Name SITAGLIPTIN
Phase Approved
Structure Type MOL
InChI Key MFFMDFFZMYYVKS-SECBINFHSA-N
Therapeutic ✓ Yes

Known Names

LEZ-763 LEZ763 Sitagliptin Sitagliptin component of zituvimet Sitagliptina Sitagliptine Zituvio
9
Targets
111
Activities
3
Assay Types
30
PK Parameters
20
Publications
7
Known Names
20
Indications

Molecular Properties

407.3
MW (Da)
2.02
ALogP
5
HBA
1
HBD
77.0
PSA (Ų)
0.62
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2006
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -gliptin
USAN Year 2005

Extended Properties

Molecular Formula C16H15F6N5O
MW 407.32
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -1.40

Indications

Diabetes Mellitus Diabetes Mellitus, Type 2 Diabetic Foot Graft vs Host Disease Graft vs Host Disease Myocardial Infarction Renal Insufficiency, Chronic Severe Acute Respiratory Syndrome Carcinoma, Pancreatic Ductal Cystic Fibrosis Diabetes Mellitus, Type 1 Glucose Intolerance Glucose Intolerance HIV Infections Hyperlipidemias Non-alcoholic Fatty Liver Disease Non-alcoholic Fatty Liver Disease Obesity Polycystic Ovary Syndrome Prediabetic State

ATC Classification

A10BH01
sitagliptin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES

Activity Summary

IC50 106 meas. best 9.06
Kd 4 meas. best 8.28
Ki 1 meas. best 7.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dipeptidyl peptidase 4
CHEMBL284
 IC50 9.06 7.753 0.9 61
Dipeptidyl peptidase 4
CHEMBL284
 Kd 8.28 7.9875 5.3 4
Dipeptidyl peptidase 4
CHEMBL3883
 IC50 7.83 7.6233 14.7 3
Dipeptidyl peptidase 4
CHEMBL284
 Ki 7.75 7.75 18.0 1
Dipeptidyl peptidase 4
CHEMBL4653
 IC50 7.48 7.48 33.0 1
Dipeptidyl peptidase 8
CHEMBL4657
 IC50 5.74 4.4854 1820.0 13
Dipeptidyl peptidase 9
CHEMBL4793
 IC50 5.51 4.37 3060.0 6
Prolyl endopeptidase FAP
CHEMBL4683
 IC50 5.23 4.6067 5830.0 3
Angiotensin-converting enzyme
CHEMBL1808
 IC50 4.96 4.96 11000.0 1
Dipeptidyl peptidase IV
CHEMBL4295559
 IC50 4.75 4.75 18000.0 1
Dipeptidyl peptidase 2
CHEMBL3976
 IC50 4.22 4.22 59830.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 0.523 uM.hr.Kg/mg Rattus norvegicus
AUC 1.0 uM.hr.Kg/mg Macaca mulatta
AUC 8.3 uM.hr.Kg/mg Canis lupus familiaris
AUC 0.523 uM.hr.Kg/mg Rattus norvegicus
AUC 560.0 ng.hr.mL-1 Mus musculus
AUC 740.0 ng.hr.mL-1 Mus musculus
CL 60.0 mL.min-1.kg-1 Rattus norvegicus
CL 60.0 mL.min-1.kg-1 Rattus norvegicus
CL 6.0 mL.min-1.kg-1 Canis lupus familiaris
CL 28.0 mL.min-1.kg-1 Macaca mulatta
CL 60.0 mL.min-1.kg-1 Rattus norvegicus
CL 6.0 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 6.0 mL.min-1.kg-1 Homo sapiens
CL 6.0 mL.min-1.kg-1 Homo sapiens
Cmax 330.0 nM Rattus norvegicus
Cmax 761.07 nM Mus musculus
F 76.0 % Rattus norvegicus
F 76.0 % Rattus norvegicus
F 100.0 % Canis lupus familiaris
F 68.0 % Macaca mulatta
F 76.0 % Rattus norvegicus
F 75.7 % Mus musculus
F 76.0 % Rattus norvegicus
Fu 0.62 - Homo sapiens
Fu 0.62 - Homo sapiens
MRT 7.78 hr Homo sapiens
T1/2 1.7 hr Rattus norvegicus
T1/2 1.7 hr Rattus norvegicus
T1/2 4.9 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dipeptidyl peptidase 4 IC50 = 0.87 nM 9.06 Inhibition of human DPP-4 expressed in human Caco-2 cells using H-Gly-Pro-AMC as... 34428715
Dipeptidyl peptidase 4 IC50 = 3.5 nM 8.46 Inhibition of DPP4 in human plasma assessed as formation of 7-amino-4-methylcoum... 21865048
Dipeptidyl peptidase 4 Kd = 5.3 nM 8.28 Binding affinity to human recombinant DPP4 (39 to 766 residues) by surface plasm... 27438064
Dipeptidyl peptidase 4 IC50 = 6.24 nM 8.21 Inhibition of DPP4 (unknown origin) expressed in Sf9 cells using Gly-Pro-AMC sub... 27396490
Dipeptidyl peptidase 4 IC50 = 6.9 nM 8.16 Inhibition of recombinant human DPP4 expressed in baculovirus infected Sf9 insec... 30642693
Dipeptidyl peptidase 4 IC50 = 7.0 nM 8.15 Inhibition of DPP4 (unknown origin) 24439847
Dipeptidyl peptidase 4 IC50 = 7.8 nM 8.11 Inhibition of recombinant human DPP4 using Gly-Pro-AMC as substrate after 1 hr b... 29609120
Dipeptidyl peptidase 4 IC50 = 7.8 nM 8.11 Inhibition of recombinant human DPP4 using Gly-Pro-AMC as substrate incubated fo... 33214038
Dipeptidyl peptidase 4 IC50 = 8.0 nM 8.1 Inhibition of human DPP4 using Gly-Pro-NA as substrate incubated for 30 mins by ... 37393789
Dipeptidyl peptidase 4 IC50 = 8.4 nM 8.08 Inhibition of DPP4 (unknown origin) using Gly-Pro-p-nitroanilide as substrate in... 31926470
Dipeptidyl peptidase 4 IC50 = 8.8 nM 8.06 Inhibition of human recombinant DPP4 using H-Gly-Pro-AMC as substrate incubated ... 36201615
Dipeptidyl peptidase 4 IC50 = 10.0 nM 8.0 Inhibition of human recombinant DPP4 (39 to 766) 24439847
Dipeptidyl peptidase 4 IC50 = 12.0 nM 7.92 Inhibition of human DPP4 -
Dipeptidyl peptidase 4 Kd = 12.7 nM 7.9 Binding affinity to DPP4 (unknown origin) assessed as dissociation constant by S... 27396490
Dipeptidyl peptidase 4 Kd = 12.7 nM 7.9 Binding affinity to DPP4 (unknown origin) expressed in baculovirus expressing sy... 30694668
Dipeptidyl peptidase 4 Kd = 13.5 nM 7.87 Binding affinity to human recombinant DPP4 (39 to 766 residues) at 5 uM by isoth... 27438064
Dipeptidyl peptidase 4 IC50 = 14.0 nM 7.85 Inhibition Activity Assay: Screening Method:Name of method: Activity Evaluation ... -
Dipeptidyl peptidase 4 IC50 = 14.7 nM 7.83 Inhibition of DPP4 in C57BL/6 mouse serum pre-incubated for 5 mins followed by G... 31747282
Dipeptidyl peptidase 4 IC50 = 16.0 nM 7.8 Inhibition of DPP4 (unknown origin) pre-incubated for 1 hr before Gly-Pro-pNA su... 25838146
Dipeptidyl peptidase 4 IC50 = 16.0 nM 7.8 Inhibition of human recombinant DPP-4 in Caco-2 cells using GP-AMC as substrate ... 37647598

Literature References

PubMed DOI Target Context # Activities
37647598 10.1021/acs.jmedchem.3c00412 Dipeptidyl peptidase 4 11
24675378 10.1016/j.bmcl.2014.03.009 Mus musculus 11
20070106 10.1021/jm901371v Homo sapiens 8
27438064 10.1021/acs.jmedchem.6b00475 Dipeptidyl peptidase 4 6
36029562 10.1016/j.ejmech.2022.114697 Unchecked 5
18570365 10.1021/jm800219f Rattus norvegicus 4
17827003 10.1016/j.bmcl.2007.07.100 Canis familiaris 4
17827003 10.1016/j.bmcl.2007.07.100 Rattus norvegicus 4
17827003 10.1016/j.bmcl.2007.07.100 Rhesus monkey 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
38665828 10.1039/d3md00455d PC-12 4
25147615 10.1021/ml5001905 Mus musculus 4
27396490 10.1021/acs.jmedchem.6b00505 Dipeptidyl peptidase 4 4
17434732 10.1016/j.bmcl.2007.03.098 Rattus norvegicus 4
38665828 10.1039/d3md00455d HT-22 4
18426954 10.1124/dmd.108.020479 ADMET 4
31747282 10.1021/acs.jmedchem.9b01649 Mus musculus 4
28442252 10.1016/j.bmcl.2017.04.036 Plasma 3
28666735 10.1016/j.bmcl.2017.06.051 Dipeptidyl peptidase 4 3
- 10.6019/CHEMBL3301361 ADMET 3

Data from ChEMBL 36 via Core Engine