SOTAGLIFLOZIN

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Synonyms
Status
Molecule Category Free-form
ATC A10BK06
UNII 6B4ZBS263Y
EPA CompTox DTXSID20144314

Structure

InChI Key QKDRXGFQVGOQKS-CRSSMBPESA-N
Smiles CCOc1ccc(Cc2cc([C@@H]3O[C@H](SC)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)cc1
InChI
InChI=1S/C21H25ClO5S/c1-3-26-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(27-20)28-2/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H25ClO5S
Molecular Weight 424.95
AlogP 3.17
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 6.0
Polar Surface Area 79.15
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 28.0

Bioactivity

Mechanism of Action Action Reference
Sodium/glucose cotransporter 1 inhibitor INHIBITOR PubMed
Protein: Sodium/glucose cotransporter 1
Description: Sodium/glucose cotransporter 1
Organism : Homo sapiens
P13866 ENSG00000100170
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
- 2-2 - - -
Assay Description Organism Bioactivity Reference
Inhibition of human HA-tagged SGLT1 expressed in HEK293 cells assessed as decrease in [14C]-AMG uptake measured after 1 to 2 hrs by scintillation counting method Homo sapiens 36.2 nM
Inhibition of human HA-tagged SGLT2 expressed in HEK293 cells assessed as decrease in [14C]-AMG uptake measured after 1 to 2 hrs by scintillation counting method Homo sapiens 1.8 nM
Inhibition of human SGLT2 expressed in CHO cells assessed as decrease in uptake of [14C]AMG after 120 mins by TopCount method Homo sapiens 1.5 nM
Inhibition of human SGLT1 expressed in CHO cells assessed as decrease in uptake of [14C]AMG after 120 mins by TopCount method Homo sapiens 34.6 nM
Inhibition of human SGLT2 Homo sapiens 1.5 nM
Inhibition of human SGLT1 Homo sapiens 34.6 nM
Inhibition of SGLT2 (unknown origin) Homo sapiens 1.8 nM
Inhibition of SGLT1 (unknown origin) Homo sapiens 36.0 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 3.93 %
Inhibition of human SGLT1 Homo sapiens 34.6 nM
Inhibition of human SGLT2 Homo sapiens 1.5 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 24.11 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.112 %
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 -0.17 % 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 0.13 % 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 0.13 % 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 -0.17 %
Inhibition of SGLT1 (unknown origin) Homo sapiens 36.0 nM
Inhibition of SGLT2 (unknown origin) Homo sapiens 1.8 nM

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL3039507
DrugBank DB12713
DrugCentral 5339
FDA SRS 6B4ZBS263Y
Guide to Pharmacology 8312
PubChem 24831714
SureChEMBL SCHEMBL1038287
ZINC ZINC000095641922
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