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))
Compound class: Synthetic organic
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].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: empagliflozin

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA & EMA (2014))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2S,3R,4R,5S,6R)-2-[4-chloro-3-({4-[(3S)-oxolan-3-yloxy]phenyl}methyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
International Nonproprietary Names Click here for help
INN number INN
9398 empagliflozin
Synonyms Click here for help
BI 10773 | Jardiance®
Database Links Click here for help
CAS Registry No. 864070-44-0 (source: Scifinder)
ChEBI CHEBI:82720
ChEMBL Ligand CHEMBL2107830
DrugCentral Ligand 4830
GtoPdb PubChem SID 178101464
PubChem CID 11949646
RCSB PDB Ligand 7R3
Search Google for chemical match using the InChIKey OBWASQILIWPZMG-QZMOQZSNSA-N
Search Google for chemicals with the same backbone OBWASQILIWPZMG
Search PubMed clinical trials empagliflozin
Search PubMed titles empagliflozin
Search PubMed titles/abstracts empagliflozin
UniChem Compound Search for chemical match using the InChIKey OBWASQILIWPZMG-QZMOQZSNSA-N
UniChem Connectivity Search for chemical match using the InChIKey OBWASQILIWPZMG-QZMOQZSNSA-N
Wikipedia Empagliflozin