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].
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2D Structure
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Physico-chemical Properties
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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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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 Natural product or derivative
Approved drug? Yes (FDA & EMA (2014))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). 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
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Wikipedia Empagliflozin