Empagliflozin (BI 10773)

Modify Date: 2024-01-02 19:32:11

Empagliflozin (BI 10773) Structure
Empagliflozin (BI 10773) structure
 Common Name Empagliflozin (BI 10773)
CAS Number 864070-44-0 Molecular Weight 450.909
Density 1.4±0.1 g/cm3 Boiling Point 664.5±55.0 °C at 760 mmHg
Molecular Formula C23H27ClO7 Melting Point N/A
MSDS N/A Flash Point 355.7±31.5 °C

 Use of Empagliflozin (BI 10773)


Empagliflozin is a selective sodium glucose cotransporter-2 (SGLT-2) inhibitor with an IC50 of 3.1 nM for human SGLT-2.

 Names

Name empagliflozin
Synonym More Synonyms

 Empagliflozin (BI 10773) Biological Activity

Description Empagliflozin is a selective sodium glucose cotransporter-2 (SGLT-2) inhibitor with an IC50 of 3.1 nM for human SGLT-2.
Related Catalog
Target

IC50: 3.1 nM (SGLT-2), 1.1 μM (SGLT-5), 2 μM (SGLT-6), 8.3 μM (SGLT-1), 11 μM (SGLT-4)[1]
In Vitro Empagliflozin is a potent and competitive SGLT-2 inhibitor with an excellent selectivity profile and the highest selectivity window of the tested SGLT-2 inhibitors over hSGLT-1. Empagliflozin inhibits the uptake of [14C]-alpha-methyl glucopyranoside (AMG) via hSGLT-2 in a dose-dependent manner with an IC50 of 3.1 nM, but is less potent for other SGLTs (IC50 range: 1100-11000 nM). [3H]-Empagliflozin displays a high affinity for SGLT-2 with a mean Kd of 57±37 nM in the absence of glucose in kinetic binding experiments[1].
In Vivo Glucose intolerance is significantly improved after 8 days of Empagliflozin treatment at either dose (3mg/kg Empagliflozin 3058±180 vs 10mg/kg Empagliflozin 3090±219). Therefore, acute treatment with Empagliflozin has a beneficial effect on hyperglycemia and glucose intolerance. Since there are no significant differences in blood glucose homeostasis with the two different doses of Empagliflozin, and random blood glucose levels of T1DM mice are significantly improved by 3mg/kg of Empagliflozin, the effect of the lower dose of Empagliflozin (3mg/kg) is investigated on preserving β-cell mass and function[2].
Kinase Assay Membranes (60 μg/well) are assayed in a 10 mM 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) buffer (pH 7.4) containing 137 mM NaCl in the presence or absence of 20 mM glucose and indicated concentrations of [3H]-Empagliflozin in 96-well plates at room temperature for 2 h. Incubations are stopped by rapid filtration through GF/B Filterplates impregnated with polyethyleneimine 0.5% and prewetted with 0.9% NaCl solution, and washed four times with 0.9% NaCl solution (4°C) using a Harvester Filtermate 96. Filterplates are dried for 2 h and 50 μL of Microscint 20 is added to each well. Radioactivity retained on the filters is measured using the TopCount NXT. In parallel, the actual amount of activity used in the assays is determined by adding the same amount of [3H]-Empagliflozin that is added per well in the radioligand binding studies and 4 mL Ultima Gold Scintilator into 5 mL vials and measuring using a Tricarb 2900TR. Non-specific [3H]-Empagliflozin-binding is determined in the presence of 30 μM dapagliflozin[1].
Animal Admin Mice[2] Male C57BL/6J mice (10 weeks of age) are used. Empagliflozin is dissolved in hydroxy ethyl cellulose (HEC) and administered to mice in the experimental group (3 or 10 mg/kg) by oral gavage once daily for 8 days, whereas the vehicle group is given same volume of HEC alone.
References

[1]. Grempler R, et al. Empagliflozin, a novel selective sodium glucose cotransporter-2 (SGLT-2) inhibitor: characterisation and comparison with other SGLT-2 inhibitors. Diabetes Obes Metab. 2012 Jan;14(1):83-90.

[2]. Cheng ST, et al. The Effects of Empagliflozin, an SGLT2 Inhibitor, on Pancreatic β-Cell Mass and Glucose Homeostasis in Type 1 Diabetes. PLoS One. 2016 Jan 25;11(1):e0147391.

[3]. Nikole J.ByrneBSc, et al. Empagliflozin Prevents Worsening of Cardiac Function in an Experimental Model of Pressure Overload-Induced Heart Failure. JACC Basic Transl Sci. 2017 Aug;2(4):347-354.

[4]. Sakaeda T, et al. Susceptibility to serious skin and subcutaneous tissue disorders and skin tissue distribution of sodium-dependent glucose co-transporter type 2 (SGLT2) inhibitors. Int J Med Sci. 2018 Jun 13;15(9):937-943.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 664.5±55.0 °C at 760 mmHg
Molecular Formula C23H27ClO7
Molecular Weight 450.909
Flash Point 355.7±31.5 °C
Exact Mass 450.144531
PSA 108.61000
LogP 3.38
Vapour Pressure 0.0±2.1 mmHg at 25°C
Index of Refraction 1.628

 Synthetic Route

Methyl 1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-alpha-D-glucopyranoside structure

Methyl 1-C-[4-c...

CAS#:1279691-36-9

~74%

Empagliflozin (BI 10773) Structure

Empagliflozin (...

CAS#:864070-44-0
Literature: BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WEBER, Dirk; RENNER, Svenja; FIEDLER, Tobias; ORLICH, Simone Patent: WO2011/39107 A1, 2011 ; Location in patent: Page/Page column 21-23 ;
(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan structure

(3S)-3-[4-[(2-C...

CAS#:915095-94-2
(3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one structure

(3R,4S,5R,6R)-3...

CAS#:32469-28-6

~74%

Empagliflozin (BI 10773) Structure

Empagliflozin (...

CAS#:864070-44-0
Literature: BOEHRINGER INGELHEIM INTERNATIONAL GMBH Patent: US2011/237526 A1, 2011 ; Location in patent: Page/Page column 8 ;
1-chloro-4-(1-methoxy-D-glucopyranos-1-yl)-2-(4-(S)-tetrahydrofuran-3-yloxy-benzyl)-benzene structure

1-chloro-4-(1-m...

CAS#:915095-96-4

~%

Empagliflozin (BI 10773) Structure

Empagliflozin (...

CAS#:864070-44-0
Literature: US2006/258749 A1, ; Page/Page column 29-30 ;
Fluorobenzene structure

Fluorobenzene

CAS#:462-06-6

~%

Empagliflozin (BI 10773) Structure

Empagliflozin (...

CAS#:864070-44-0
Literature: US2011/237789 A1, ;
2-Chloro-5-iodobenzoic acid structure

2-Chloro-5-iodo...

CAS#:19094-56-5

~%

Empagliflozin (BI 10773) Structure

Empagliflozin (...

CAS#:864070-44-0
Literature: US2011/237789 A1, ;
2-Chloro-4'-fluoro-5-iodobenzophenone structure

2-Chloro-4'-flu...

CAS#:915095-86-2

~%

Empagliflozin (BI 10773) Structure

Empagliflozin (...

CAS#:864070-44-0
Literature: US2011/237789 A1, ;
(2-CHLORO-5-IODOPHENYL)[4-[[(3S)-TETRAHYDRO-3-FURANYL)OXY]PHENYL]METHANONE structure

(2-CHLORO-5-IOD...

CAS#:915095-87-3

~%

Empagliflozin (BI 10773) Structure

Empagliflozin (...

CAS#:864070-44-0
Literature: US2011/237789 A1, ;

 Synonyms

X5927
Empagliflozin
(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-, (1S)-
Jardiance
CS-0940
BI10773
(1S)-1,5-Anhydro-1-(4-chloro-3-{4-[(3S)-tetrahydro-3-furanyloxy]benzyl}phenyl)-D-glucitol
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1800196-46-6
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2452301-12-9
Empagliflozin Impurity D
1620758-26-0
Empagliflozin Impurity 22
2452301-22-1
Empagliflozin Impurity 82
2452301-16-3
Empagliflozin Impurity 89
2452301-32-3
Empagliflozin Impurity 7
864070-37-1
Empagliflozin Impurity POE
2452301-14-1
(Z)-bi(4,4-dimethyl-3-oxothiolan-2-ylidene)
16292-00-5
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