empagliflozin   Click here for help

GtoPdb Ligand ID: 4754

Synonyms: BI 10773 | Jardiance®
Approved drug PDB Ligand
empagliflozin is an approved drug (FDA & EMA (2014))
Comment: Empagliflozin is a member of the 'gliflozin' class of drugs which inhibit reabsorption of glucose in the kidney to lower blood sugar.
It is the first glucose-lowering, antidiabetes therapy to be granted approval to reduce the risk of cardiovascular (CV) death in type 2 diabetes patients with CV disease.

SARS-CoV-2 and COVID-19: Empagliflozin was added to the RECOVERY trial (NCT04381936) in July 2021, to determine if using empagliflozin to correct metabolic dysregulation caused by SARS-CoV-2 infection can protect against organ damage and improve recovery in COVID-19 patients. This was predicated by results of a study exploring dapagliflozin-mediated organ protection, which found that the drug elicited a non-significant reduction in the risk of organ failure or death in COVID-19 patients [4].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: empagliflozin

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 108.61
Molecular weight 450.14
XLogP 2.51
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES OCC1OC(c2ccc(c(c2)Cc2ccc(cc2)OC2COCC2)Cl)C(C(C1O)O)O
Isomeric SMILES OC[C@H]1O[C@@H](c2ccc(c(c2)Cc2ccc(cc2)O[C@@H]2COCC2)Cl)[C@@H]([C@H]([C@@H]1O)O)O
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
InChI Key OBWASQILIWPZMG-QZMOQZSNSA-N
No information available.
Summary of Clinical Use Click here for help
After being assessed in clinical trials for the treatment of type 2 diabetes mellitus (T2DM) [1], either as mono- or combination therapy (with linagliptin or metformin for example), empagliflozin was approved in August 2014 for the improvement of glycemic control in adult patients alongside diet and exercise.
In February 2015 the US FDA approved the fixed dose formulation Glyxambi® (empagliflozin and linagliptin) for the treatment of T2DM. The EMA has granted marketing authorisation for the fixed-dose combination of empagliflozin plus metformin (Synjardy®) for the treatment of T2DM.
A postmarket clinical trial of more than 7,000 patients with T2DM and CV disease showed that empagliflozin reduces the risk of CV death (compared to placebo) as an add-on to standard of care diabetes and atherosclerotic CV disease therapies [7]. These findings led to FDA approval in Dec 2016 for empagliflozin to be used to reduce the risk of CV death in T2DM patients with CV disease.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Empagliflozin is an inhibitor of the sodium glucose co-transporter-2 (gene symbol SLC5A2), a protein responsible for renal reabsorption of blood glucose. Inhibition of the transporter promotes urinary excretion of glucose [2,5].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04381936 Randomised Evaluation of COVID-19 Therapy Phase 2/Phase 3 Interventional University of Oxford Empagliflozin was added to this trial in July 2021. The intention is to recruit 2500 patients who will be randomly allocated to receive empagliflozin (10mg tablet once daily) plus usual standard-of-care, to be compared against at least 2500 patients who receive usual standard-of-care. The primary outcome will be reduction in risk of death in hospitalised COVID-19 patients. Secondary evaluations will determine if empagliflozin treatment shortens the length of hospital stay or reduces the number of patients progressing to mechanical ventilation. 6
External links Click here for help