IPRAGLIFLOZIN

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Search structure


Synonyms	ASP-1941 Ipragliflozin
Status
Molecule Category	UNKNOWN
ATC	A10BK05
UNII	3N2N8OOR7X


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

Structure


InChI Key	AHFWIQIYAXSLBA-RQXATKFSSA-N
Smiles	OC[C@H]1O[C@@H](c2ccc(F)c(Cc3cc4ccccc4s3)c2)[C@H](O)[C@@H](O)[C@@H]1O
InChI	InChI=1S/C21H21FO5S/c22-15-6-5-12(21-20(26)19(25)18(24)16(10-23)27-21)7-13(15)9-14-8-11-3-1-2-4-17(11)28-14/h1-8,16,18-21,23-26H,9-10H2/t16-,18-,19+,20-,21+/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H21FO5S
Molecular Weight	404.46
AlogP	2.15
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	4.0
Polar Surface Area	90.15
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	28.0

Bioactivity

Mechanism of Action	Action	Reference
Sodium/glucose cotransporter 2 inhibitor	INHIBITOR	PubMed PMDA


Protein: Sodium/glucose cotransporter 2 Description: Sodium/glucose cotransporter 2 Organism : Homo sapiens P31639 ENSG00000140675

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC05 family of sodium-dependent glucose transporters	1900	7-8	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of human SGLT2 expressed in CHO cells assessed as [14C]AMG accumulation after 2 hrs by scintillation counting	Homo sapiens	7.4 nM
Inhibition of SGLT2 (unknown origin)	Homo sapiens	8.4 nM
Inhibition of recombinant human full-length SGLT2 expressed in CHO cells assessed as decrease in [14C]-AMG uptake measured after 2 hrs by topcount scintillation counting method	Homo sapiens	7.4 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	7.57 %
Inhibition of human SGLT2	Homo sapiens	7.38 nM
Inhibition of SGLT2 (unknown origin)	Homo sapiens	7.4 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	10.83 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	2.969 %
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	0.0 %		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	-0.06 %		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	-0.06 %		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	0.0 %

Cross References

Resources	Reference
ChEBI	134724
ChEMBL	CHEMBL2018096
DrugBank	DB11698
DrugCentral	4890
FDA SRS	3N2N8OOR7X
Guide to Pharmacology	9394
PubChem	10453870
SureChEMBL	SCHEMBL337645
ZINC	ZINC000038897728

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).