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Compound Detail

CHEMBL385517

SAXAGLIPTIN ANHYDROUS
💊 Approved Drug
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💊 Approved Drug
N#C[C@@H]1C[C@@H]2C[C@@H]2N1C(=O)[C@@H](N)C12CC3CC(CC(O)(C3)C1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL385517
Name SAXAGLIPTIN ANHYDROUS
Phase Approved
Structure Type MOL
InChI Key QGJUIPDUBHWZPV-SGTAVMJGSA-N
Therapeutic ✓ Yes

Known Names

BMS-477118 Saxagliptin anhydrous SBMS-477118
5
Targets
29
Activities
3
Assay Types
12
PK Parameters
20
Publications
3
Known Names

Molecular Properties

315.4
MW (Da)
1.16
ALogP
4
HBA
2
HBD
90.3
PSA (Ų)
0.80
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -gliptin
USAN Year 2007

Extended Properties

Molecular Formula C18H25N3O2
MW 315.42
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness 0.17

Activity Summary

IC50 17 meas. best 9.22
Ki 10 meas. best 9.22
Kd 2 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dipeptidyl peptidase 4
CHEMBL284
 Kd 9.52 8.66 0.3 2
Dipeptidyl peptidase 4
CHEMBL284
 IC50 9.22 8.174 0.6 10
Dipeptidyl peptidase 4
CHEMBL284
 Ki 9.22 9.165 0.6 6
Dipeptidyl peptidase 4
CHEMBL3883
 IC50 8.72 8.72 1.9 1
Dipeptidyl peptidase 9
CHEMBL4793
 Ki 7.15 7.08 71.0 2
Dipeptidyl peptidase 9
CHEMBL4793
 IC50 7.0 6.99 100.0 2
Dipeptidyl peptidase 8
CHEMBL4657
 Ki 6.89 6.59 130.0 2
Dipeptidyl peptidase 8
CHEMBL4657
 IC50 6.62 6.615 240.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 845.0 ng.hr.mL-1 Homo sapiens
CL 234.0 ml/min Homo sapiens
Cmax 884.53 nM Homo sapiens
F 75.0 % Rattus norvegicus
F 51.0 % Macaca mulatta
F 76.0 % Canis lupus familiaris
F 75.0 % Rattus norvegicus
T1/2 2.1 hr Rattus norvegicus
T1/2 2.45 hr Homo sapiens
T1/2 2.5 hr Homo sapiens
T1/2 0.8333 hr Homo sapiens
Tmax 0.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dipeptidyl peptidase 4 Kd = 0.3 nM 9.52 Binding affinity to human recombinant DPP4 (39 to 766 residues) by surface plasm... 27438064
Dipeptidyl peptidase 4 Ki = 0.6 nM 9.22 Inhibition of human DPP4 17937986
Dipeptidyl peptidase 4 Ki = 0.6 nM 9.22 Inhibition of human DPP4 expressed in Caco-2 cells 17034148
Dipeptidyl peptidase 4 Ki = 0.6 nM 9.22 In vitro inhibition constant against human Dipeptidyl peptidase IV 16033281
Dipeptidyl peptidase 4 Ki = 0.6 nM 9.22 Inhibition of human DPP4 19217790
Dipeptidyl peptidase 4 IC50 = 0.6 nM 9.22 Inhibition of DPP4 21711053
Dipeptidyl peptidase 4 Ki = 0.6 nM 9.22 Inhibition of DPP4 19375196
Dipeptidyl peptidase 4 Ki = 1.3 nM 8.89 Binding affinity to human DPP-4 using gly-pro-pNA as substrate assessed as inhib... 37647598
Dipeptidyl peptidase 4 IC50 = 1.5 nM 8.82 Inhibition of human DPP4 using Gly-Pro-AMC as substrate incubated for 30 mins by... 36209967
Dipeptidyl peptidase 4 IC50 = 1.5 nM 8.82 Inhibition of human recombinant DPP-4 (1 to 530 residues) using Gly-Pro-AMC as s... 37647598
Dipeptidyl peptidase 4 IC50 = 1.9 nM 8.72 Inhibition of mouse DPP-4 using Gly-Pro-AMC as substrate measured after 5 mins b... 37647598
Dipeptidyl peptidase 4 IC50 = 3.0 nM 8.52 Inhibition of human recombinant DPP4 by fluorescence assay 19482472
Dipeptidyl peptidase 4 IC50 = 3.37 nM 8.47 Inhibition of DPP4 in human plasma using Gly-Pro-AMC as substrate by fluorimetri... 22938786
Dipeptidyl peptidase 4 IC50 = 3.4 nM 8.47 Inhibition of DPP4 20483603
Dipeptidyl peptidase 4 Kd = 15.9 nM 7.8 Binding affinity to human recombinant DPP4 (39 to 766 residues) at 5 uM by isoth... 27438064
Dipeptidyl peptidase 4 IC50 = 30.3 nM 7.52 Inhibition of human recombinant DPP-4 using H-Gly-Pro-AMC as substrate after 10 ... 24457090
Dipeptidyl peptidase 4 IC50 = 50.0 nM 7.3 Inhibition of DPP4 (unknown origin) 24099035
Dipeptidyl peptidase 4 IC50 = 50.0 nM 7.3 Inhibition of human recombinant DPP-4 expressed in human Caco-2 cells using H-Al... 37647598
Dipeptidyl peptidase 4 IC50 = 50.0 nM 7.3 Inhibition of DPP4 in human Caco2 cells using H-Ala-Pro-7-amido-4-trifluoromethy... 23623674
Dipeptidyl peptidase 9 Ki = 71.0 nM 7.15 Inhibition of DPP9 17034148

Literature References

PubMed DOI Target Context # Activities
28666735 10.1016/j.bmcl.2017.06.051 Dipeptidyl peptidase 4 11
37647598 10.1021/acs.jmedchem.3c00412 Dipeptidyl peptidase 4 8
22496391 10.1124/dmd.112.045450 Cytochrome P450 3A4 8
16033281 10.1021/jm050261p Dipeptidyl peptidase 4 7
27438064 10.1021/acs.jmedchem.6b00475 Dipeptidyl peptidase 4 6
22496391 10.1124/dmd.112.045450 ADMET 6
22496391 10.1124/dmd.112.045450 Hepatocyte 5
22496391 10.1124/dmd.112.045450 Homo sapiens 5
22496391 10.1124/dmd.112.045450 Cytochrome P450 3A5 4
19482472 10.1016/j.bmcl.2009.05.048 Unchecked 3
22496391 10.1124/dmd.112.045450 Liver microsome 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
22496391 10.1124/dmd.112.045450 Cytochrome P450 2C8 2
22496391 10.1124/dmd.112.045450 Cytochrome P450 2D6 2
22496391 10.1124/dmd.112.045450 Cytochrome P450 2C19 2
22496391 10.1124/dmd.112.045450 Cytochrome P450 2E1 2
22496391 10.1124/dmd.112.045450 Cytochrome P450 2C9 2
22496391 10.1124/dmd.112.045450 Cytochrome P450 2A6 2
22496391 10.1124/dmd.112.045450 Cytochrome P450 1A2 2
16033281 10.1021/jm050261p ADMET 2

Data from ChEMBL 36 via Core Engine