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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View more information in the IUPHAR Pharmacology Education Project: empagliflozin

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
References
1. Abdul-Ghani MA, DeFronzo RA. (2008)
Inhibition of renal glucose reabsorption: a novel strategy for achieving glucose control in type 2 diabetes mellitus.
Endocr Pract, 14 (6): 782-90. [PMID:18996802]
2. Bays H. (2009)
From victim to ally: the kidney as an emerging target for the treatment of diabetes mellitus.
Curr Med Res Opin, 25 (3): 671-81. [PMID:19232040]
3. Grempler R, Thomas L, Eckhardt M, Himmelsbach F, Sauer A, Sharp DE, Bakker RA, Mark M, Klein T, Eickelmann P. (2012)
Empagliflozin, a novel selective sodium glucose cotransporter-2 (SGLT-2) inhibitor: characterisation and comparison with other SGLT-2 inhibitors.
Diabetes Obes Metab, 14 (1): 83-90. [PMID:21985634]
4. Kosiborod MN, Esterline R, Furtado RHM, Oscarsson J, Gasparyan SB, Koch GG, Martinez F, Mukhtar O, Verma S, Chopra V et al.. (2021)
Dapagliflozin in patients with cardiometabolic risk factors hospitalised with COVID-19 (DARE-19): a randomised, double-blind, placebo-controlled, phase 3 trial.
Lancet Diabetes Endocrinol, [Epub ahead of print]. DOI: 10.1016/S2213-8587(21)00180-7 [PMID:34302745]
5. Nair S, Wilding JP. (2010)
Sodium glucose cotransporter 2 inhibitors as a new treatment for diabetes mellitus.
J Clin Endocrinol Metab, 95 (1): 34-42. [PMID:19892839]
6. RECOVERY Trial team. 
Empagliflozin to be investigated as a possible treatment for COVID-19 in the RECOVERY trial.
Accessed on 28/07/2021. Modified on 28/07/2021. recoverytrial.net, https://www.recoverytrial.net/news/empagliflozin-to-be-investigated-as-a-possible-treatment-for-covid-19-in-the-recovery-trial
7. Zinman B, Wanner C, Lachin JM, Fitchett D, Bluhmki E, Hantel S, Mattheus M, Devins T, Johansen OE, Woerle HJ et al.. (2015)
Empagliflozin, Cardiovascular Outcomes, and Mortality in Type 2 Diabetes.
N Engl J Med, 373 (22): 2117-28. [PMID:26378978]