EMPAGLIFLOZIN

Search structure
Trade Names:
Synonyms:
Status: Approved (2014)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A10BK03
UNII: HDC1R2M35U

Structure
InChI Key OBWASQILIWPZMG-QZMOQZSNSA-N
Smile OC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(O[C@H]4CCOC4)cc3)c2)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChI=1S/C23H27ClO7/c24-18-6-3-14(23-22(28)21(27)20(26)19(11-25)31-23)10-15(18)9-13-1-4-16(5-2-13)30-17-7-8-29-12-17/h1-6,10,17,19-23,25-28H,7-9,11-12H2/t17-,19+,20+,21-,22+,23-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H27ClO7
Molecular Weight 450.92
AlogP 1.61
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 6.0
Polar Surface Area 108.61
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 31.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Sodium/glucose cotransporter 2 inhibitor
Primary Target
Sodium/glucose cotransporter 2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Transferase
- - - - 8.726-13.29
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -4.11-17.84
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC05 family of sodium-dependent glucose transporters
3 3.1-3.1 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Diabetes, Gestational 3 D016640 ClinicalTrials
Diabetic Nephropathies 3 D003928 ClinicalTrials
Non-alcoholic Fatty Liver Disease 3 D065626 ClinicalTrials
Insulin Resistance 3 D007333 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Cardiotoxicity 3 D066126 ClinicalTrials
Diabetes Mellitus, Type 1 3 D003922 ClinicalTrials
Metabolic Syndrome 3 D024821 ClinicalTrials
Shock 3 D012769 ClinicalTrials
Kidney Calculi 2 D007669 ClinicalTrials
Polycystic Kidney, Autosomal Dominant 2 D016891 ClinicalTrials
Inappropriate ADH Syndrome 2 D007177 ClinicalTrials
Glycogen Storage Disease Type I 2 D005953 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Depressive Disorder, Major 2 D003865 ClinicalTrials
Hypertension, Portal 2 D006975 ClinicalTrials
Kidney Diseases 2 D007674 ClinicalTrials
Colitis, Ulcerative 2 D003093 ClinicalTrials
ST Elevation Myocardial Infarction 2 D000072657 ClinicalTrials
Ascites 2 D001201 ClinicalTrials
Hypoglycemia 2 D007003 ClinicalTrials
Kidney Failure, Chronic 2 D007676 ClinicalTrials
Polycystic Ovary Syndrome 2 D011085 ClinicalTrials
Familial Primary Pulmonary Hypertension 2 D065627 ClinicalTrials
Prediabetic State 2 D011236 ClinicalTrials
Hyponatremia 2 D007010 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Epilepsy 1 D004827 ClinicalTrials
Acute Kidney Injury 1 D058186 ClinicalTrials
Inflammatory Bowel Diseases 1 D015212 ClinicalTrials
Diabetic Neuropathies 1 D003929 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Neuropathy peripheral 16.0
Infections and infestations Urinary tract infection 9.3
Eye disorders Retinal disorder 8.0
Infections and infestations Urinary tract infection
Infections and infestations Urinary tract infection 7.6
Endocrine disorders Diabetic nephropathy 7.0
Infections and infestations Genital infection fungal 6.4
Infections and infestations Genital infection fungal 5.4
Infections and infestations Upper respiratory tract infection 4.0
Metabolism and nutrition disorders Dyslipidaemia 3.9
Infections and infestations Upper respiratory tract infection
Metabolism and nutrition disorders Dyslipidaemia
Infections and infestations Genital infection fungal 3.1
Infections and infestations Upper respiratory tract infection 3.1
Metabolism and nutrition disorders Dyslipidaemia 2.9
Musculoskeletal and connective tissue disorders Arthralgia 2.4
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.4
Musculoskeletal and connective tissue disorders Arthralgia 2.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.3
Gastrointestinal disorders Nausea 2.3
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Infections and infestations Genital infection fungal 1.6
Infections and infestations Genital infection fungal
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 1.1
Infections and infestations Genital infection fungal

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Metabolism and nutrition disorders
13.68
Investigations
9.29
Infections and infestations
7.87
Gastrointestinal disorders
7.8
Endocrine disorders
7.08
General disorders and administration site conditions
7.0
Renal and urinary disorders
6.94
Nervous system disorders
6.56
Vascular disorders
5.77
Cardiac disorders
4.79
Skin and subcutaneous tissue disorders
3.86
Respiratory, thoracic and mediastinal disorders
3.23
Musculoskeletal and connective tissue disorders
3.13
Reproductive system and breast disorders
2.76
Injury, poisoning and procedural complications
2.63
Psychiatric disorders
2.26

Cross References

Resources Reference
CAS NUMBER 864070-44-0
ChEBI 82720
ChEMBL CHEMBL2107830
DrugBank DB09038
DrugCentral 4830
FDA SRS HDC1R2M35U
Guide to Pharmacology 4754
PDB 7R3
PharmGKB PA166163327
PubChem 11949646
SureChEMBL SCHEMBL899986
ZINC ZINC000036520252
CONTENTS