OMARIGLIPTIN

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Search structure


Synonyms	MK-3102 Omarigliptin
Status
Molecule Category	UNKNOWN
UNII	CVP59Q4JE1
EPA CompTox	DTXSID70153678


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	MKMPWKUAHLTIBJ-ISTRZQFTSA-N
Smiles	CS(=O)(=O)n1cc2c(n1)CN([C@H]1CO[C@H](c3cc(F)ccc3F)[C@@H](N)C1)C2
InChI	InChI=1S/C17H20F2N4O3S/c1-27(24,25)23-7-10-6-22(8-16(10)21-23)12-5-15(20)17(26-9-12)13-4-11(18)2-3-14(13)19/h2-4,7,12,15,17H,5-6,8-9,20H2,1H3/t12-,15+,17-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C17H20F2N4O3S
Molecular Weight	398.44
AlogP	1.14
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	3.0
Polar Surface Area	90.45
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	27.0

Bioactivity

Mechanism of Action	Action	Reference
Dipeptidyl peptidase IV inhibitor	INHIBITOR	PubMed


Protein: Dipeptidyl peptidase IV Description: Dipeptidyl peptidase 4 Organism : Homo sapiens P27487 ENSG00000197635

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Protease Serine protease Serine protease SC clan Serine protease S9B subfamily	-	2-3	3-3	1	-
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel	-	39000	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antidiabetic activity in lean mouse assessed as reduction in blood glucose AUC at 0.01 mg/kg, po after 1 hr by oral glucose tolerance test	Mus musculus	7.0 %
Antidiabetic activity in lean mouse assessed as reduction in blood glucose AUC at 0.3 mg/kg, po after 1 hr by oral glucose tolerance test	Mus musculus	51.0 %
In vivo inhibition of DPP4 in mouse plasma at 0.3 mg/kg, po	Mus musculus	85.0 %
Inhibition of DPP4 in mouse plasma	Mus musculus	43.9 nM
Competitive reversible inhibition of DPP4 (unknown origin)	Homo sapiens	1.6 nM		Competitive reversible inhibition of DPP4 (unknown origin)	Homo sapiens	0.8 nM
Inhibition of recombinant human DPP4 expressed in Sf9 cells using Gly-Pro-AMC substrate after 30 mins by plate reader analysis	Homo sapiens	2.6 nM
Inhibition of DPP4 (unknown origin) expressed in Sf9 cells using Gly-Pro-AMC substrate	Homo sapiens	2.22 nM
Binding affinity to DPP4 (unknown origin) assessed as dissociation constant by SPR assay	Homo sapiens	2.75 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	4.78 %
Binding affinity to DPP4 (unknown origin) expressed in baculovirus expressing system	Homo sapiens	2.75 nM
Anti-diabetic activity in 8 hrs-fasted ICR mouse assessed as reduction in blood glucose AUC (0 to 120 mins)at 0.3 mg/kg, po pretreated for 60 mins followed by glucose challenge and measured after 120 mins post glucose challenge by OGTT relative to control	Mus musculus	14.6 %
Anti-diabetic activity in 8 hrs-fasted ICR mouse assessed as reduction in blood glucose AUC (0 to 120 mins) at 3 mg/kg, po pretre at ed for 60 mins followed by glucose challenge and measured after 120 mins post glucose challenge by OGTT rel at ive to control	Mus musculus	22.1 %
Anti-diabetic activity in 8 hrs-fasted ICR mouse assessed as reduction in blood glucose AUC (0 to 120 mins) at 10 mg/kg, po pretre at ed for 60 mins followed by glucose challenge and measured after 120 mins post glucose challenge by OGTT rel at ive to control	Mus musculus	8.3 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	1.15 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	12.82 %
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	-0.1 %		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	-0.04 %		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	-0.04 %		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	-0.1 %
Inhibition of human recombinant DPP4 incubated for 15 mins using Gly-Pro-7-AMC substrate	Homo sapiens	3.1 nM

Cross References

Resources	Reference
ChEBI	134735
ChEMBL	CHEMBL2105762
DrugBank	DB11992
DrugCentral	5054
FDA SRS	CVP59Q4JE1
Guide to Pharmacology	8402
PubChem	46209133
SureChEMBL	SCHEMBL827590
ZINC	ZINC000084758480

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).