Empagliflozin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Empagliflozin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Empagliflozin?

The molecule Empagliflozin presents a molecular formula of C23H27ClO7 and its IUPAC name is (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol.

Empagliflozin is a molecule of the class of drugs known as sodium-glucose cotransporter 2 (SGLT2) inhibitors. Empagliflozin works by inhibiting the reabsorption of glucose in the kidney, leading to increased urinary glucose excretion and lowered blood glucose levels..

Empagliflozin was approved by the U.S. Food and Drug Administration (FDA) in 2014, and is marketed under the brand name Jardiance. Empagliflozin is also approved in the European Union (EU) and other countries..

Empagliflozin is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus..

A common side effect of empagliflozin is genital mycotic infections (e.g., candidiasis). Other potential side effects include hypoglycemia, urinary tract infections, and increased urination..

Empagliflozin is contraindicated in patients with severe renal impairment (eGFR <30 mL/min/1.73 m2) or end-stage renal disease on dialysis..

Empagliflozin should be used with caution in patients at risk for volume depletion, such as those with congestive heart failure..

3D structure

Cartesian coordinates

Geometry of Empagliflozin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Empagliflozin OBWASQILIWPZMG-QZMOQZSNSA-N chemical compound 2D structure molecule svg
Empagliflozin

 

Molecule descriptors

 
IUPAC name(2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
InChI codeInChI=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 KeyOBWASQILIWPZMG-QZMOQZSNSA-N
SMILESOC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(O[C@H]4CCOC4)cc3)c2)[C@H](O)[C@@H](O)[C@@H]1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (1S)-1,5-ANHYDRO-1-C-(4-CHLORO-3-((4-(((3S)-OXAN-3-YL)OXY)PHENYL)METHYL)PHENYL)-D-GLUCITOL
  • (1S)-1,5-Anhydro-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucitol
  • (1S)-1,5-anhydro-1-(4-chloro-3-{4-[(3S)-tetrahydrofuran-3-yloxy]benzyl}phenyl)-D-glucitol
  • (1S)-1,5-anhydro-1-C-{4-chloro-3-((4-{((3S)-oxolan-3-yl)oxy}phenyl)methyl)phenyl}-D-glucitol
  • (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
  • (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  • (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
  • (2S,3R,4R,5S,6R)-2-[4-CHLORO-3-[[4-[(3S)-OXOLAN-3-YL]OXYPHENYL]METHYL]PHENYL]-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL
  • (2S,3R,4R,5S,6R)-2-[4-Chloro-3-[[4-[(3S)-tetrahydrofuran-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
  • (2S,3R,4R,5S,6R)-2-[4-chloranyl-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  • (2S,3R,4R,5S,6R)-2-[4-chloro-3-({4-[(3S)-oxolan-3-yloxy]phenyl}methyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  • (S)-Empagliflozin D4
  • 1,5-anhydro-1-{4-chloro-3-[4-(tetrahydro-3-furanyloxy)benzyl]phenyl}hexitol
  • 1-chloro-4-(glucopyranos-1-yl)-2-(4-(tetrahydrofuran-3-yloxy)benzyl)benzene
  • 7R3
  • 864070-44-0
  • A852380
  • AC-27643
  • AMY1858
  • AU-004/43508285
  • BBL104150
  • BDBM150162
  • BI 10773
  • BI-10773
  • BI-10773;Empagliflozin
  • BI10773
  • C22194
  • CCG-269242
  • CS-0940
  • D-Glucitol, 1,5-anhydro-1-C-(4-chloro-3-((4-(((3S)-tetrahydro-3-furanyl)oxy)phenyl)methyl)phenyl)-, (1S)-
  • D10459
  • DB09038
  • DS-9824
  • EMPAGLIFLOZIN COMPONENT OF GLYXAMBI
  • EMPAGLIFLOZIN COMPONENT OF SYNJARDY
  • EMPAGLIFLOZIN COMPONENT OF TRIJARDY XR
  • EX-A414
  • Empagliflozin
  • Empagliflozin (BI-10773;BI 10773;BI10773)
  • Empagliflozin (BI 10773)
  • Empagliflozin (BI10773)
  • Empagliflozin (JAN/USAN/INN)
  • GLYXAMBI COMPONENT EMPAGLIFLOZIN
  • GTPL4754
  • HDC1R2M35U
  • HY-15409
  • JARDIANCE
  • MFCD22566222
  • PB23119
  • Q5373824
  • STL557964
  • SW219120-1
  • TRIJARDY XR COMPONENT EMPAGLIFLOZIN
  • US8980829, EMPAGLIFLOZIN
  • s8022

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC36520252
  • UNII-HDC1R2M35U
  • AKOS024464680
  • DTXSID601026093
  • CHEMBL2107830
  • CHEBI:82720
  • SCHEMBL899986

Physico-Chemical properties

IUPAC name(2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC23H27ClO7
Molecular weight450.909
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity113.41
LogP1.6
Topological polar surface area108.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.