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Compound Detail

CHEMBL1770248

ERTUGLIFLOZIN
💊 Approved Drug
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💊 Approved Drug
CCOc1ccc(Cc2cc([C@]34OC[C@](CO)(O3)[C@@H](O)[C@H](O)[C@H]4O)ccc2Cl)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1770248
Name ERTUGLIFLOZIN
Phase Approved
Structure Type MOL
InChI Key MCIACXAZCBVDEE-CUUWFGFTSA-N
Therapeutic ✓ Yes

Known Names

Ertugliflozin Ertugliflozina Ertugliflozine MK-8835 Pf-04971729 PF-04971729-00 PF04971729
4
Targets
11
Activities
1
Assay Types
22
PK Parameters
20
Publications
7
Known Names
4
Indications
1
Mechanisms

Molecular Properties

436.9
MW (Da)
1.36
ALogP
7
HBA
4
HBD
108.6
PSA (Ų)
0.54
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2017
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product Chemical Probe
USAN Stem -gliflozin
USAN Year 2011

Extended Properties

Molecular Formula C22H25ClO7
MW 436.89
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness 0.78

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 Mitral Valve Insufficiency Heart Failure

ATC Classification

A10BK04
ertugliflozin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES

Activity Summary

IC50 11 meas. best 9.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium/glucose cotransporter 2
CHEMBL3884
 IC50 9.06 8.972 0.9 5
Sodium/glucose cotransporter 2
CHEMBL4316
 IC50 8.94 8.94 1.1 1
Rattus norvegicus
CHEMBL376
 IC50 8.74 8.74 1.8 1
Sodium/glucose cotransporter 1
CHEMBL4979
 IC50 6.41 5.8825 392.0 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 2787.0 ng.hr.mL-1 Homo sapiens
AUC 2802.0 ng.hr.mL-1 Homo sapiens
CL 4.04 mL.min-1.kg-1 Rattus norvegicus
CL 4.5 uL.min-1.(10^6cells)-1 Homo sapiens
CL 12.0 mL.min-1.g-1 Homo sapiens
Cmax 4440.48 nM Rattus norvegicus
Cmax 1122.02 nM Homo sapiens
F 69.0 % Rattus norvegicus
F 69.0 % Rattus norvegicus
F 94.0 % Canis lupus familiaris
F 94.0 % Canis lupus familiaris
F 69.0 % Rattus norvegicus
Fu 0.0004 - Rattus norvegicus
Fu 0.00064 - Homo sapiens
T1/2 4.1 hr Rattus norvegicus
T1/2 11.0 hr Homo sapiens
T1/2 16.87 hr Homo sapiens
T1/2 4.1 hr Rattus norvegicus
T1/2 7.6 hr Canis lupus familiaris
Tmax 1.0 hr Rattus norvegicus
Tmax 1.0 hr Homo sapiens
Tmax 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium/glucose cotransporter 2 IC50 = 0.877 nM 9.06 Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of methy... 21449606
Sodium/glucose cotransporter 2 IC50 = 0.87 nM 9.06 Inhibition of SGLT2 (unknown origin) 30151080
Sodium/glucose cotransporter 2 IC50 = 0.877 nM 9.06 Inhibition of human SGLT2 31630053
Sodium/glucose cotransporter 2 IC50 = 0.88 nM 9.06 Inhibition of human SGLT2 34213340
Sodium/glucose cotransporter 2 IC50 = 1.15 nM 8.94 Inhibition of rat SGLT2 21449606
Rattus norvegicus IC50 = 1.8 nM 8.74 Inhibition of SGLT2 in po dosed Sprague-Dawley rat after 24 hrs 21449606
Sodium/glucose cotransporter 2 IC50 = 2.4 nM 8.62 Inhibition of human SGLT2 expressed in CHO cells assessed as decrease in uptake ... 28447791
Sodium/glucose cotransporter 1 IC50 = 392.0 nM 6.41 Inhibition of human SGLT1 expressed in CHO cells assessed as decrease in uptake ... 28447791
Sodium/glucose cotransporter 1 IC50 = 1960.0 nM 5.71 Inhibition of human SGLT1 expressed in CHO cells assessed as inhibition of methy... 21449606
Sodium/glucose cotransporter 1 IC50 = 1960.0 nM 5.71 Inhibition of human SGLT1 31630053
Sodium/glucose cotransporter 1 IC50 = 2000.0 nM 5.7 Inhibition of human SGLT1 34213340

Literature References

PubMed DOI Target Context # Activities
21449606 10.1021/jm200049r Rattus norvegicus 11
23169609 10.1124/dmd.112.049551 Homo sapiens 7
23169609 10.1124/dmd.112.049551 ADMET 5
34213340 10.1021/acs.jmedchem.1c00790 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
21449606 10.1021/jm200049r Unchecked 4
31630053 10.1016/j.ejmech.2019.111773 ADMET 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
21449606 10.1021/jm200049r Solute carrier family 22 member 2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
23169609 10.1124/dmd.112.049551 Canis familiaris 2
21449606 10.1021/jm200049r Plasma 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
21449606 10.1021/jm200049r Sodium/glucose cotransporter 2 2
21449606 10.1021/jm200049r Solute carrier family 22 member 6 1
21449606 10.1021/jm200049r Hepatocyte 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
21449606 10.1021/jm200049r No relevant target 1
21449606 10.1021/jm200049r Solute carrier family 22 member 3 1
23169609 10.1124/dmd.112.049551 Plasma 1

Data from ChEMBL 36 via Core Engine