Saxagliptin

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

What is the Saxagliptin?

The molecule Saxagliptin presents a molecular formula of C18H25N3O2 and its IUPAC name is (1S,3S,5S)-2-[(2S)-2-amino-2-[(5S,7R)-3-hydroxy-1-adamantyl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile.

Saxagliptin (Onglyza) is a dipeptidyl peptidase-4 (DPP-4) inhibitor used to treat type 2 diabetes. It works by increasing levels of natural substances called incretins, which help to control blood sugar..

Saxagliptin was approved by the FDA in 2009. It exists as a tablet and is taken by mouth..

Common side effects of saxagliptin include headache, upper respiratory tract infection, and runny nose..

Saxagliptin is a prescription medication used to treat type 2 diabetes. It belongs to a class of drugs called DPP-4 inhibitors..

DPP-4 inhibitors work by increasing levels of natural substances called incretins. Incretins help to control blood sugar by increasing insulin release from the pancreas and decreasing sugar production by the liver..

Saxagliptin was approved by the FDA in 2009 and exists as a tablet. It is usually taken once daily with or without food..

Common side effects of saxagliptin include headache, upper respiratory tract infection, and runny nose..

Saxagliptin is a safe and effective medication when used as directed. Talk to your doctor about the risks and benefits of treatment with saxagliptin..

3D structure

Cartesian coordinates

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

2D drawing

 

Saxagliptin QGJUIPDUBHWZPV-KFHUQKARSA-N chemical compound 2D structure molecule svg
Saxagliptin

 

Molecule descriptors

 
IUPAC name(1S,3S,5S)-2-[(2S)-2-amino-2-[(5S,7R)-3-hydroxy-1-adamantyl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
InChI codeInChI=1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10-,11+,12-,13+,14+,15-,17?,18?/m1/s1
InChI KeyQGJUIPDUBHWZPV-KFHUQKARSA-N
SMILESN#C[C@@H]1C[C@@H]2C[C@@H]2N1C(=O)[C@@H](N)C12C[C@@H]3C[C@@H](CC(O)(C3)C1)C2

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,3S,5S)-2-[(2S)-2-Amino-2-[(5S,7R)-3-hydroxy-1-adamantyl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
  • (1s,3s,5s)-2-{(2s)-2-Amino-2-[(1r,3s,5r,7s)-3-Hydroxytricyclo[3.3.1.1~3,7~]dec-1-Yl]acetyl}-2-Azabicyclo[3.1.0]hexane-3-Carbonitrile
  • 361442-04-8
  • 442S048
  • AS-35207
  • BDBM50489025
  • BMS-477118;BMS 477118;BMS477118
  • DB07465
  • J-524237
  • Q27096685
  • Saxagliptin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13648755
  • ZINC100035546
  • AKOS037643762
  • CHEMBL2298396
  • SCHEMBL2742680

Physico-Chemical properties

IUPAC name(1S,3S,5S)-2-[(2S)-2-amino-2-[(5S,7R)-3-hydroxy-1-adamantyl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Molecular formulaC18H25N3O2
Molecular weight315.41
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity88.48
LogP1.8
Topological polar surface area90.4

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.