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Compound Detail

CHEMBL429910

DAPAGLIFLOZIN
💊 Approved Drug
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💊 Approved Drug
CCOc1ccc(Cc2cc([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)cc1

Basic Information

ChEMBL ID CHEMBL429910
Name DAPAGLIFLOZIN
Phase Approved
Structure Type MOL
InChI Key JVHXJTBJCFBINQ-ADAARDCZSA-N
Therapeutic ✓ Yes

Known Names

BMS-512148 Dapagliflozin Dapagliflozin component of br1019 Dapagliflozin component of qtern Dapagliflozin component of qternmet Dapagliflozin component of qternmet dapaglifozin Dapagliflozin component of qternmet xr Dapagliflozin viatris Dapagliflozina Dapagliflozine LYN-045
4
Targets
70
Activities
2
Assay Types
30
PK Parameters
20
Publications
11
Known Names
20
Indications
1
Mechanisms

Molecular Properties

408.9
MW (Da)
1.84
ALogP
6
HBA
4
HBD
99.4
PSA (Ų)
0.58
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2012
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -gliflozin
USAN Year 2007

Extended Properties

Molecular Formula C21H25ClO6
MW 408.88
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 0.61

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium/glucose cotransporter 2 inhibitor INHIBITOR Sodium/glucose cotransporter 2

Indications

Diabetes Mellitus Diabetes Mellitus, Type 2 Heart Failure Renal Insufficiency, Chronic Acute Kidney Injury Atrial Fibrillation Coronary Disease Diabetes Mellitus, Type 1 Diabetic Retinopathy Fatty Liver Glomerulonephritis, IGA Insulin Resistance Kidney Failure, Chronic Non-alcoholic Fatty Liver Disease Polycystic Ovary Syndrome Renal Insufficiency Severe Acute Respiratory Syndrome ST Elevation Myocardial Infarction Albuminuria Amyloidosis, Familial

ATC Classification

A10BK01
dapagliflozin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES

Activity Summary

IC50 57 meas. best 9.31
EC50 13 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium/glucose cotransporter 2
CHEMBL3884
IC50 9.31 8.7997 0.5 36
Sodium/glucose cotransporter 2
CHEMBL3884
EC50 8.96 8.7867 1.1 6
Sodium/glucose cotransporter 2
CHEMBL4316
EC50 8.52 8.52 3.0 2
Sodium/glucose cotransporter 1
CHEMBL4979
IC50 6.43 5.9375 370.0 20
Sodium/myo-inositol cotransporter 2
CHEMBL1744524
IC50 6.42 6.42 380.0 1
Sodium/glucose cotransporter 1
CHEMBL4979
EC50 6.37 6.076 428.5 5

Pharmacokinetic Data

Parameter Value Units Species
AUC 11658.0 ng.hr.mL-1 Rattus norvegicus
AUC 3011.2 ng.hr.mL-1 Rattus norvegicus
AUC 13313.3 ng.hr.mL-1 Rattus norvegicus
CL 4.8 mL.min-1.kg-1 Rattus norvegicus
CL 6.0 ml/min Homo sapiens
CL 10.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.5 mL.min-1.kg-1 Canis lupus familiaris
CL 0.08 mL.min-1.kg-1 Rattus norvegicus
Cmax 1467.42 nM Rattus norvegicus
Cmax 26169.05 nM Canis lupus familiaris
Cmax 6114.26 nM Rattus norvegicus
Cmax 6114.26 nM Rattus norvegicus
Cmax 3920.47 nM Rattus norvegicus
Cmax 3186.75 nM Rattus norvegicus
Cmax 6114.26 nM Rattus norvegicus
F 84.0 % Rattus norvegicus
F 100.0 % Rattus norvegicus
F 83.0 % Canis lupus familiaris
F 88.42 % Rattus norvegicus
F 88.0 % Rattus norvegicus
F 88.4 % Rattus norvegicus
Fu 0.04 - Homo sapiens
Fu 0.03 - Rattus norvegicus
Fu 0.085 - Homo sapiens
T1/2 4.6 hr Rattus norvegicus
T1/2 7.4 hr Canis lupus familiaris
T1/2 3.0 hr Macaca mulatta
T1/2 15.0 hr Homo sapiens
T1/2 4.4 hr Rattus norvegicus
T1/2 7.4 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human recombinant SGLT2 expressed in CHO cells by liquid scintilla... 20181486
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human SGLT2 expressed in CHO cells by methyl-alpha-D-glucopyranosi... 34813882
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human SGLT2 expressed in CHO cells assessed as [14C]-alpha-methyl-... 21906953
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human SGLT2 expressed in CHO cells assessed as [14C]-alpha-methyl-... 21514014
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human SGLT2 expressed in CHO cells assessed as [14C]-alpha-methyl-... 24900297
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of [14C]... 21193308
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human SGLT2 assessed as inhibition of methyl-alpha-D-glucopyranosi... 20952196
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human SGLT2 20637636
Sodium/glucose cotransporter 2 IC50 = 0.49 nM 9.31 Inhibition of human SGLT2 expressed in CHO cells assessed as [14C]alpha-methyl-D... 20434909
Sodium/glucose cotransporter 2 IC50 = 0.8 nM 9.1 Inhibition of human SGLT2 expressed in HEK293 cells assessed as reduction in 2-d... 28098449
Sodium/glucose cotransporter 2 IC50 = 1.0 nM 9.0 Inhibition of human SGLT2 expressed in CHOK1 cells assessed as inhibition of [14... 24842618
Sodium/glucose cotransporter 2 IC50 = 1.05 nM 8.98 Inhibition of full-length human SGLT2 expressed in CHO cells assessed as decreas... 29764742
Sodium/glucose cotransporter 2 IC50 = 1.1 nM 8.96 Inhibition of SGLT2 (unknown origin) 29954682
Sodium/glucose cotransporter 2 EC50 = 1.1 nM 8.96 Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of [14C]... 18260618
Sodium/glucose cotransporter 2 EC50 = 1.1 nM 8.96 Inhibition of SGLT2 (unknown origin) 31930920
Sodium/glucose cotransporter 2 EC50 = 1.1 nM 8.96 Inhibition of human kidney SGLT2 assessed as renal glucose reabsorption 19243175
Sodium/glucose cotransporter 2 IC50 = 1.12 nM 8.95 Inhibition of human SGLT2 31630053
Sodium/glucose cotransporter 2 IC50 = 1.16 nM 8.94 Inhibition of human SGLT2 24556379
Sodium/glucose cotransporter 2 IC50 = 1.2 nM 8.92 Inhibition of SGLT2 (unknown origin) 37608596
Sodium/glucose cotransporter 2 IC50 = 1.3 nM 8.89 Inhibition of human SGLT2 expressed in CHO-K1 cells by [14C]AMG uptake assay 22652255

Literature References

PubMed DOI Target Context # Activities
19243175 10.1021/jm8013019 Homo sapiens 33
33626870 10.1021/acs.jmedchem.0c00627 Rattus norvegicus 20
19243175 10.1021/jm8013019 Rattus norvegicus 16
18260618 10.1021/jm701272q Rattus norvegicus 12
34813882 10.1016/j.bmcl.2021.128466 ADMET 9
24456245 10.1021/jm401780b Rattus norvegicus 7
20302302 10.1021/jm901893x Canis familiaris 6
20434909 10.1016/j.bmcl.2010.04.006 Rattus norvegicus 6
29954682 10.1016/j.bmc.2018.06.017 Mus musculus 5
20149653 10.1016/j.bmcl.2010.01.075 Rattus norvegicus 5
24900297 10.1021/ml100256c Rattus norvegicus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
22652255 10.1016/j.bmc.2012.04.053 Cytochrome P450 3A4 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
19700318 10.1016/j.bmcl.2009.08.030 Sodium/glucose cotransporter 2 2
28098449 10.1021/acs.jmedchem.6b01134 Sodium/glucose cotransporter 1 2

Data from ChEMBL 36 via Core Engine