SITAGLIPTIN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC A10BH01
UNII QFP0P1DV7Z
EPA CompTox DTXSID70197572

Structure

InChI Key MFFMDFFZMYYVKS-SECBINFHSA-N
Smiles N[C@@H](CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F
InChI
InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H15F6N5O
Molecular Weight 407.32
AlogP 2.02
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 77.04
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 28.0
Assay Description Organism Bioactivity Reference
In vitro inhibition of human DPP-4 activity Homo sapiens 18.0 nM
Inhibition of DPP4 None 18.0 nM
Inhibition of DPP4 activity Homo sapiens 18.0 nM
Inhibition of DPP4 None 18.0 nM
Inhibition of DPP4 None 18.0 nM
Inhibition of DPP4 None 18.0 nM
Inhibition of DPP4 None 40.0 nM
Inhibition of human DPP4 expressed in baculovirus system Homo sapiens 18.0 nM
Inhibition of DPP4 in human Caco-2 cells after 60 mins by fluorimetry assay Homo sapiens 110.0 nM
Inhibition of human DPP4 Homo sapiens 30.0 nM
Inhibition of DPP4 None 30.0 nM
Inhibition of DPP4 None 18.0 nM
Inhibition of DPP4 None 30.0 nM
Ex vivo inhibition of DPP4 in rat plasma at 3 mg/kg, po after 30 mins Rattus norvegicus 30.0 %
Ex vivo inhibition of DPP4 in rat plasma at 3 mg/kg, po after 8 hrs Rattus norvegicus 20.0 %
Inhibition of DPP4 in presence of 50% human serum None 18.0 nM
Inhibition of DPP4 in presence of 50% rat serum None 46.0 nM
Inhibition of human recombinant His-tagged DPP4 expressed in insect cells Homo sapiens 23.0 nM
Inhibition of human seminal fluid DPP4 Homo sapiens 11.0 %
Inhibition of human recombinant DPP4 after 60 mins by fluorescence plate reader Homo sapiens 20.0 nM
Inhibition of DPP4 None 18.0 nM
Inhibition of human DPP4 assessed as hydrolytic reaction of Ala-Pro-AMC Homo sapiens 19.4 nM
Inhibition of DPP4 None 40.0 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 3.5 nM
Inhibition of human seminal plasma DPP4 assessed as pNA release from Gly-Pro-p-nitroanilide substrate pre-incubated with enzyme for 15 min prior to substrate addition by fluorescence technique Homo sapiens 40.0 nM
Inhibition of DPP4 in human plasma using Gly-Pro-AMC as substrate by fluorimetric analysis Homo sapiens 18.0 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 19.0 nM
Inhibition of human purified His-tagged DPP-4 assessed as cleavage of substrate using Gly-Pro-AMC chromogenic substrate after 60 mins by fluorescence spectrophotometry Homo sapiens 24.83 nM
Ex vivo inhibition of DPP4 in Sprague-Dawley rat plasma at 3 mg/kg, po after 8 hrs Rattus norvegicus 30.0 %
Ex vivo inhibition of DPP4 in Sprague-Dawley rat plasma at 3 mg/kg, po after 1 to 2 hrs Rattus norvegicus 82.0 %
Inhibition of human recombinant DPP4 (39 to 766) Homo sapiens 10.0 nM
Inhibition of DPP4 (unknown origin) Homo sapiens 7.0 nM
Inhibition of recombinant his6-tagged DPP4 (unknown origin) expressed in baculovirus expression system using Ala-pro-AMC as substrate by fluorometric analysis Homo sapiens 20.0 nM
Inhibition of DPP4 (unknown origin) Homo sapiens 19.0 nM
Inhibition of plasma DPP4 (unknown origin) after 24 hrs Homo sapiens 70.0 %
Inhibition of human DPP-4 expressed in baculovirus expression system using H-Gly-Pro-AMC as substrate after 30 mins by fluorometric analysis Homo sapiens 18.0 nM
Competitive reversible inhibition of DPP4 (unknown origin) Homo sapiens 18.0 nM
Inhibition of human recombinant his6-tagged DPP4 using Ala-Pro-AMC as substrate by continuous fluorometric method Homo sapiens 20.0 nM
Inhibition of human DPP-4 using H-Gly-Pro-para-Nitroanilide as substrate incubated for 20 mins prior to substrate addition measured after 30 mins by spectrophotometry Homo sapiens 18.0 nM
Inhibition of human recombinant DPP4 pre-incubated with compound for 15 mins before substrate addition by luminescence assay Homo sapiens 29.0 nM
Inhibition of DPP4 activity in C57BL/6 mouse at 3 mg/kg, po administered as single dose 30 mins before orally glucose challenge and measured 20 mins post oral glucose challenge by luminescence assay Mus musculus 59.5 %
Antidiabetic activity in C57BL/6 mouse assessed as reduction in plasma glucose AUC (0 to 120 mins) at 3 mg/kg, po administered as single dose 30 mins before orally glucose challenge by oral glucose tolerance test Mus musculus 59.0 %
Inhibition of human recombinant DPP4 expressed in baculovirus expression system using Ala-Pro-AMC as substrate by continuous fluorometric assay Homo sapiens 20.0 nM
Inhibition of DPP4 (unknown origin) at 1 uM pre-incubated for 1 hr before Gly-Pro-pNA substrate addition and measured 2 hrs post substrate addition Homo sapiens 101.9 %
Inhibition of DPP4 (unknown origin) pre-incubated for 1 hr before Gly-Pro-pNA substrate addition and measured 2 hrs post substrate addition Homo sapiens 16.0 nM
Inhibition of human recombinant DPP4 using H-Gly-Pro-AMC substrate incubated for 15 mins by fluorescent AMC release assay Homo sapiens 22.0 nM
Inhibition of DPP4 extracted from human Caco2 cells using H-Gly-Pro-AMC substrate after 10 mins by fluorescence assay Homo sapiens 19.0 nM
Anti-diabetic effect in ICR mouse assessed as plasma glucose lowering effect at 10 mg/kg, po treated 1 hr before 2.5 mg/kg, po glucose load by Oral glucose tolerance test relative to control Mus musculus 40.0 %
Anti-diabetic effect in ICR mouse assessed as plasma glucose lowering effect at 10 mg/kg, po treated 1 hr before 2.5 mg/kg, po glucose load measured after 8 hrs by Oral glucose tolerance test relative to control Mus musculus 24.0 %
Inhibition of human DPP4 Homo sapiens 12.0 nM
Inhibition of human recombinant DPP-4 using Gly-pro-p-nitroanilide as substrate assessed as formation of p-nitroaniline after 30 mins by colorimetric assay Homo sapiens 18.0 nM
Inhibition of DPP-4 (unknown origin) Homo sapiens 18.0 nM
Inhibition of DPP4 (unknown origin) expressed in Sf9 cells using Gly-Pro-AMC substrate Homo sapiens 6.24 nM
Binding affinity to DPP4 (unknown origin) assessed as dissociation constant by SPR assay Homo sapiens 12.7 nM
Inhibition of DPP4 (unknown origin) using Gly-Pro-p-nitroanilide as substrate at 10 uM incubated for 1 hr Homo sapiens 99.0 %
Inhibition of DPP4 (unknown origin) using Gly-Pro-p-nitroanilide as substrate incubated for 1 hr Homo sapiens 17.0 nM
Inhibition of Wistar rat plasma DPP4 Rattus norvegicus 33.0 nM
Inhibition of ob/ob mouse plasma DPP4 Mus musculus 46.0 nM
Inhibition of human plasma DPP4 Homo sapiens 20.0 nM
Inhibition of human recombinant C-terminal 6His-tagged DPP-4 expressed in insect cells incubated for 30 mins by TPE-KFPE fluorescent probe-based assay Homo sapiens 37.96 nM
Inhibition of human recombinant C-terminal 6His-tagged DPP-4 expressed in insect cells at 100 nM to 10 uM incubated for 30 mins by TPE-KFPE fluorescent probe-based assay Homo sapiens 100.49 %
Inhibition of Porphyromonas gingivalis N-terminal His-tagged DPP4 expressed in Escherichia coli at 10 uM using Gly-Pro-p-nitroanilide as substrate relative to control Porphyromonas gingivalis 50.0 %
Inhibition of Porphyromonas gingivalis N-terminal His-tagged DPP4 expressed in Escherichia coli at 100 uM using Gly-Pro-p-nitroanilide as substrate relative to control Porphyromonas gingivalis 50.0 %
Inhibition of human DPP4 Homo sapiens 40.0 nM
Inhibition of recombinant human DPP4 using Gly-Pro-AMC as substrate after 1 hr by fluorescence assay Homo sapiens 7.8 nM
Inhibition of human DPP-4 using Ala-Pro-AMC as substrate preincubated for 10 mins followed by substrate addition and measured after 5 to 10 mins by fluorescence assay Homo sapiens 120.0 nM
Inhibition of ADP-induced platelet aggregation in human platelet-rich plasma at 0.1 mM preincubated for 5 mins followed by ADP-stimulation and measured within 5 mins by Born's turbidimetric analysis relative to control Homo sapiens 4.24 %
Inhibition of DPP4 in C57BL/6 mouse serum pre-incubated for 5 mins followed by Gly-Pro-7-AMC substrate addition by fluorescence based assay Mus musculus 14.7 nM
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 82.7 %
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 73.5 %
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 6.9 nM
Binding affinity to human recombinant DPP4 (39 to 766 residues) by surface plasmon resonance analysis Homo sapiens 5.3 nM
Binding affinity to human recombinant DPP4 (39 to 766 residues) at 5 uM by isothermal titration calorimetry Homo sapiens 13.5 nM
Binding affinity to DPP4 (unknown origin) expressed in baculovirus expressing system Homo sapiens 12.7 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 6.08 %
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 -0.01 % 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 -0.01 %
Inhibition of human SET7 overexpressed in Escherichia coli BL21 (DE3) cells at 25 uM preincubated for 15 mins followed by addition of SAM as substrate and biotinylated Histone H3 (1-50) peptide measured after 30 mins by AlphaLISA assay relative to control Homo sapiens 6.0 %
Inhibition of DPP4 (unknown origin) at 10 uM using Gly-Pro-p-nitroanilide as substrate incubated for 1 hr relative to control Homo sapiens 99.0 %
Inhibition of DPP4 (unknown origin) using Gly-Pro-p-nitroanilide as substrate incubated for 1 hr Homo sapiens 8.4 nM
Inhibition of recombinant human DPP4 using Gly-Pro-AMC as substrate incubated for 1 hr by fluorogenic assay Homo sapiens 7.8 nM

Environmental Exposure

Environmental Exposure Map
Countries
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Cross References

Resources Reference
ChEBI 40237
ChEMBL CHEMBL1422
DrugBank DB01261
DrugCentral 2448
FDA SRS QFP0P1DV7Z
Human Metabolome Database HMDB0015390
Guide to Pharmacology 6286
PDB 715
PharmGKB PA164748978
PubChem 4369359
SureChEMBL SCHEMBL17783
ZINC ZINC000001489478
CONTENTS