CANAGLIFLOZIN

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Trade Names
Synonyms
Status
Molecule Category Mixture
ATC A10BK02
UNII 6S49DGR869

Structure

InChI Key XTNGUQKDFGDXSJ-ZXGKGEBGSA-N
Smiles Cc1ccc([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1Cc1ccc(-c2ccc(F)cc2)s1
InChI
InChI=1S/C24H25FO5S/c1-13-2-3-15(24-23(29)22(28)21(27)19(12-26)30-24)10-16(13)11-18-8-9-20(31-18)14-4-6-17(25)7-5-14/h2-10,19,21-24,26-29H,11-12H2,1H3/t19-,21-,22+,23-,24+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H27FO6S
Molecular Weight 462.54
AlogP 2.97
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 5.0
Polar Surface Area 90.15
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 31.0

Bioactivity

Mechanism of Action Action Reference
Sodium/glucose cotransporter 2 inhibitor INHIBITOR DailyMed
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 2-7 - - -
Assay Description Organism Bioactivity Reference
Inhibition of human SGLT2 expressed in CHO-K1 cells by [14C]AMG uptake assay Homo sapiens 6.7 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 2.2 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 265.0 nM
Inhibition of SGLT2 (unknown origin) Homo sapiens 2.2 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 7.31 %
Inhibition of human SGLT1 Homo sapiens 684.0 nM
Inhibition of human SGLT2 Homo sapiens 4.4 nM
Inhibition of SGLT1 (unknown origin) Homo sapiens 910.0 nM
Inhibition of SGLT2 (unknown origin) Homo sapiens 2.2 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 13.64 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 16.16 %
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 0.05 % 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 0.05 % 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 %

Cross References

Resources Reference
ChEBI 73274
ChEMBL CHEMBL2048484
DrugBank DB08907
DrugCentral 4758
FDA SRS 6S49DGR869
Guide to Pharmacology 4582
SureChEMBL SCHEMBL157162
ZINC ZINC000043207238
ChEMBL CHEMBL4594217
FDA SRS B2L6AES9XQ
SureChEMBL SCHEMBL322059
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