ALOGLIPTIN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC A10BH04
UNII JHC049LO86
EPA CompTox DTXSID90234130

Structure

InChI Key ZSBOMTDTBDDKMP-OAHLLOKOSA-N
Smiles Cn1c(=O)cc(N2CCC[C@@H](N)C2)n(Cc2ccccc2C#N)c1=O
InChI
InChI=1S/C18H21N5O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3/t15-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H21N5O2
Molecular Weight 339.4
AlogP 0.39
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 97.05
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 25.0
Assay Description Organism Bioactivity Reference
Inhibition of human DPP4 by fluorimetry Homo sapiens 10.0 nM
Inhibition of human DPP4 Homo sapiens 7.0 nM
Inhibition of DPP4 after 20 mins by fluorescence assay None 3.4 nM
Inhibition of DPP4 in human plasma assessed as formation of 7-amino-4-methylcoumarin from glycyl-L-proline 4-methylcoumaryl-7-amide by fluorescence assay Homo sapiens 1.0 nM
Inhibition of human DPP4 after 10 mins Homo sapiens 3.4 nM
Inhibition of DPP4 in human plasma using Gly-Pro-AMC as substrate by fluorimetric analysis Homo sapiens 4.0 nM
Inhibition of DPP4 in human Caco2 cells using H-Ala-Pro-7-amido-4-trifluoromethylcoumarin as substrate after 1 hr by fluorescence assay Homo sapiens 24.0 nM
In vivo inhibition of DPP-4 in ICR mouse assessed as cleavage rate of Gly-Pro-AMC in plasma at 1 mg/kg, po measured at 24 hrs by fluorescence assay relative to control Mus musculus 0.5 %
In vivo inhibition of DPP-4 in ICR mouse assessed as cleavage rate of Gly-Pro-AMC in plasma at 1 mg/kg, po measured at 7 hrs by fluorescence assay relative to control Mus musculus 27.6 %
In vivo inhibition of DPP-4 in ICR mouse assessed as cleavage rate of Gly-Pro-AMC in plasma at 1 mg/kg, po measured at 4.5 hrs by fluorescence assay relative to control Mus musculus 49.4 %
In vivo inhibition of DPP-4 in ICR mouse assessed as cleavage rate of Gly-Pro-AMC in plasma at 1 mg/kg, po measured at 0.5 hrs by fluorescence assay relative to control Mus musculus 72.6 %
In vivo inhibition of DPP-4 in ICR mouse assessed as cleavage rate of Gly-Pro-AMC in plasma at 3 mg/kg, po measured at 24 hrs by fluorescence assay relative to control Mus musculus 0.8 %
In vivo inhibition of DPP-4 in ICR mouse assessed as cleavage rate of Gly-Pro-AMC in plasma at 3 mg/kg, po measured at 7 hrs by fluorescence assay relative to control Mus musculus 50.9 %
In vivo inhibition of DPP-4 in ICR mouse assessed as cleavage rate of Gly-Pro-AMC in plasma at 3 mg/kg, po measured at 4.5 hrs by fluorescence assay relative to control Mus musculus 71.5 %
In vivo inhibition of DPP-4 in ICR mouse assessed as cleavage rate of Gly-Pro-AMC in plasma at 3 mg/kg, po measured at 0.5 hrs by fluorescence assay relative to control Mus musculus 83.8 %
Inhibition of human DPP-4 using Gly-pro-AMC as substrate preincubated for 10 mins followed by substrate addition measured after 10 mins Homo sapiens 1.5 nM
Inhibition of plasma DPP4 (unknown origin) after 24 hrs Homo sapiens 70.0 %
Inhibition of human recombinant DPP4 pre-incubated with compound for 15 mins before substrate addition by luminescence assay Homo sapiens 7.0 nM
Inhibition of human DPP4 Homo sapiens 6.9 nM
Inhibition of human DPP4 preincubated for 30 mins followed by Gly-Pro-AMC addition measured for 50 mins by continuous fluorescence assay Homo sapiens 7.6 nM
Inhibition of human recombinant DPP4 using Gly-Pro-7-amido-4-methyl-coumarin as substrate incubated for 15 mins by fluorescence assay Homo sapiens 5.3 nM
Inhibition of human DPP4 using A-P-7-amido-4-trifluoromethylcoumarin as substrate pretreated for 10 mins followed by substrate addition measured after 10 mins Homo sapiens 4.0 nM
Inhibition of recombinant human DPP4 expressed in baculovirus infected Sf9 insect cells using Gly-Pro-AMC as substrate preincubated for 15 mins followed by substrate addition measured at 60 secs interval for 20 mins by fluorometic method Homo sapiens 4.46 nM
Anti-diabetic activity in Sprague-Dawley rat assessed as redcution in DPP4 inhibition in plasma at 10 mg/kg, po via gavage administered as single dose measured up to 12 hrs post dose by fluorometric assay relative to control Rattus norvegicus 80.0 %
Inhibition of recombinant human DPP4 expressed in baculovirus infected Sf9 insect cells at 200 nM using Gly-Pro-AMC as substrate measured at 60 secs interval for 20 mins by fluorescence assay relative to control Homo sapiens 96.7 %
Inhibition of recombinant human DPP4 expressed in baculovirus infected Sf9 insect cells at 40 nM using Gly-Pro-AMC as substrate measured at 60 secs interval for 20 mins by fluorescence assay relative to control Homo sapiens 85.1 %
Inhibition of recombinant human DPP4 expressed in baculovirus infected Sf9 insect cells using Gly-Pro-AMC as substrate measured at 60 secs interval for 20 mins by fluorescence assay Homo sapiens 2.7 nM
Inhibition of human recombinant DPP4 (39 to 766 residues) using Ala-Pro-AFC as substrate incubated for 1 hr by fluorescence assay Homo sapiens 7.0 nM
Binding affinity to human recombinant DPP4 (39 to 766 residues) by surface plasmon resonance analysis Homo sapiens 2.4 nM
Binding affinity to human recombinant DPP4 (39 to 766 residues) at 5 uM by isothermal titration calorimetry Homo sapiens 28.5 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.53 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.14 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.14 %
Inhibition of DPP4 in human Caco-2 cells using AP-AFC as substrate preincubated with enzyme for 10 mins followed by substrate addition and measured after 10 mins by fluorescence based analysis Homo sapiens 4.0 nM
Anti-Hyperglycemic activity in high fat diet-fed/streptozotocin-induced type 2 diabetic mellitus C57BL/6 mouse model assessed as reduction in AUC(0 to 120 mins) of blood glucose level at 10 mg/kg, ip administered 30 mins prior to glucose challenge and measured after 120 mins by IGTT Mus musculus 30.0 %
Anti-Hyperglycemic activity in high fat diet-fed/streptozotocin-induced type 2 diabetic mellitus C57BL/6 mouse model assessed as reduction in blood glucose level at 10 mg/kg/day for 14 days and measured on day 14 Mus musculus 57.0 %
Inhibition of human recombinant DPP9 using Gly-Pro-AMC as substrate preincubated for 15 mins followed by substrate addition and measured for 20 mins by fluorescence based microplate reader assay Homo sapiens 100.0 nM
Inhibition of human recombinant DPP8 using Gly-Pro-AMC as substrate preincubated for 15 mins followed by substrate addition and measured for 20 mins by fluorescence based microplate reader assay Homo sapiens 100.0 nM
Inhibition of human recombinant DPP4 using Gly-Pro-AMC as substrate preincubated for 15 mins followed by substrate addition and measured for 20 mins by fluorescence based microplate reader assay Homo sapiens 3.1 nM
Inhibition of human recombinant DPP4 at 40 nM using Gly-Pro-AMC as substrate preincubated for 15 mins followed by substrate addition and measured for 20 mins by fluorescence based microplate reader assay relative to control Homo sapiens 85.1 %
Inhibition of human recombinant DPP4 at 200 nM using Gly-Pro-AMC as substrate preincubated for 15 mins followed by substrate addition and measured for 20 mins by fluorescence based microplate reader assay relative to control Homo sapiens 96.7 %
In vivo inhibition of DPP4 in Sprague-Dawley rat plasma at 10 mg/kg, po via gavage using Gly-Pro-AMC as substrate measured after 24 hrs relative to control Rattus norvegicus 45.0 %

Related Entries

Cross References

Resources Reference
ChEBI 72323
ChEMBL CHEMBL376359
DrugBank DB06203
DrugCentral 4340
FDA SRS JHC049LO86
Guide to Pharmacology 6319
PDB T22
PubChem 11450633
SureChEMBL SCHEMBL121028
ZINC ZINC000014961096
CONTENTS