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Compound Detail

CHEMBL2048484

CANAGLIFLOZIN ANHYDROUS
💊 Approved Drug
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💊 Approved Drug
Cc1ccc([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1Cc1ccc(-c2ccc(F)cc2)s1

Basic Information

ChEMBL ID CHEMBL2048484
Name CANAGLIFLOZIN ANHYDROUS
Phase Approved
Structure Type MOL
InChI Key XTNGUQKDFGDXSJ-ZXGKGEBGSA-N
Therapeutic ✓ Yes

Known Names

Canagliflozin anhydrous JNJ-28431754 TA-7284
2
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
3
Known Names

Molecular Properties

444.5
MW (Da)
2.97
ALogP
6
HBA
4
HBD
90.2
PSA (Ų)
0.49
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning First in Class
USAN Stem -gliflozin
USAN Year 2009

Extended Properties

Molecular Formula C24H25FO5S
MW 444.52
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness 0.27

Activity Summary

IC50 12 meas. best 8.66
EC50 2 meas. best 8.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium/glucose cotransporter 2
CHEMBL3884
EC50 8.66 8.66 2.2 1
Sodium/glucose cotransporter 2
CHEMBL3884
IC50 8.66 8.4914 2.2 7
Sodium/glucose cotransporter 1
CHEMBL4979
IC50 6.58 6.176 265.0 5
Sodium/glucose cotransporter 1
CHEMBL4979
EC50 6.04 6.04 910.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium/glucose cotransporter 2 EC50 = 2.2 nM 8.66 Inhibition of SGLT2 (unknown origin) 31930920
Sodium/glucose cotransporter 2 IC50 = 2.2 nM 8.66 Inhibition of human SGLT2 expressed in CHO cells assessed as decrease in uptake ... 28447791
Sodium/glucose cotransporter 2 IC50 = 2.2 nM 8.66 Inhibition of SGLT2 (unknown origin) 29954682
Sodium/glucose cotransporter 2 IC50 = 2.2 nM 8.66 Inhibition of human SGLT2 by liquid scintillation counter analysis 36584305
Sodium/glucose cotransporter 2 IC50 = 2.4 nM 8.62 Inhibition of SGLT2 (unknown origin) 37608596
Sodium/glucose cotransporter 2 IC50 = 4.4 nM 8.36 Inhibition of human SGLT2 31630053
Sodium/glucose cotransporter 2 IC50 = 4.9 nM 8.31 SGLT1/2 in-vitro assay: To analyze a sodium-dependent glucose transport, cells f... -
Sodium/glucose cotransporter 2 IC50 = 6.7 nM 8.17 Inhibition of human SGLT2 expressed in CHO-K1 cells by [14C]AMG uptake assay 22652255
Sodium/glucose cotransporter 1 IC50 = 265.0 nM 6.58 Inhibition of human SGLT1 expressed in CHO cells assessed as decrease in uptake ... 28447791
Sodium/glucose cotransporter 1 IC50 = 550.0 nM 6.26 SGLT1/2 in-vitro assay: To analyze a sodium-dependent glucose transport, cells f... -
Sodium/glucose cotransporter 1 IC50 = 684.0 nM 6.17 Inhibition of human SGLT1 31630053
Sodium/glucose cotransporter 1 IC50 = 710.0 nM 6.15 Inhibition of SGLT1 (unknown origin) 37608596
Sodium/glucose cotransporter 1 EC50 = 910.0 nM 6.04 Inhibition of SGLT1 (unknown origin) 31930920
Sodium/glucose cotransporter 1 IC50 = 1900.0 nM 5.72 Inhibition of human SGLT1 expressed in CHO-K1 cells by [14C]AMG uptake assay 22652255

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
22652255 10.1016/j.bmc.2012.04.053 Cytochrome P450 3A4 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37608596 10.1021/acs.jmedchem.3c01138 Sodium/glucose cotransporter 2 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
31630053 10.1016/j.ejmech.2019.111773 Sodium/glucose cotransporter 2 1
31630053 10.1016/j.ejmech.2019.111773 Sodium/glucose cotransporter 1 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
22652255 10.1016/j.bmc.2012.04.053 Sodium/glucose cotransporter 2 1
28447791 10.1021/acs.jmedchem.6b01818 Rattus norvegicus 1
28447791 10.1021/acs.jmedchem.6b01818 Unchecked 1
28447791 10.1021/acs.jmedchem.6b01818 Sodium/glucose cotransporter 2 1
28447791 10.1021/acs.jmedchem.6b01818 Rhesus monkey 1
37608596 10.1021/acs.jmedchem.3c01138 Unchecked 1

Data from ChEMBL 36 via Core Engine