Selexipag

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

What is the Selexipag?

The molecule Selexipag presents a molecular formula of C26H32N4O4S and its IUPAC name is 2-[4-[(5,6-diphenylpyrazin-2-yl)-propan-2-ylamino]butoxy]-N-methylsulfonylacetamide.

Selexipag is an investigational, orally-active prostacyclin receptor agonist being studied for the treatment of pulmonary arterial hypertension (PAH). It is a selective, potent and long-acting prostacyclin receptor agonist with a half-life of approximately 24 hours. In animal models of PAH, selexipag has shown efficacy in reducing pulmonary vascular resistance and right ventricular hypertrophy, and has also been shown to improve exercise tolerance..

In clinical trials, selexipag has been well tolerated, with the most common adverse effects being headache, diarrhea, nausea and fatigue. Selexipag is currently being studied in Phase III clinical trials for the treatment of PAH..

3D structure

Cartesian coordinates

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

2D drawing

 

Selexipag QXWZQTURMXZVHJ-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Selexipag

 

Molecule descriptors

 
IUPAC name2-[4-[(5,6-diphenylpyrazin-2-yl)-propan-2-ylamino]butoxy]-N-methylsulfonylacetamide
InChI codeInChI=1S/C26H32N4O4S/c1-20(2)30(16-10-11-17-34-19-24(31)29-35(3,32)33)23-18-27-25(21-12-6-4-7-13-21)26(28-23)22-14-8-5-9-15-22/h4-9,12-15,18,20H,10-11,16-17,19H2,1-3H3,(H,29,31)
InChI KeyQXWZQTURMXZVHJ-UHFFFAOYSA-N
SMILESCC(C)N(CCCCOCC(=O)NS(C)(=O)=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1

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.

  • 2-(4-((5,6-DIPHENYLPYRAZIN-2-YL)(PROPAN-2-YL)AMINO)BUTOXY)-N-(METHANESULFONYL)ACETAMIDE
  • 2-(4-((5,6-Diphenylpyrazin-2-yl)(propan-2-yl)amino)butoxy}-n-(methanesulfonyl)acetamide
  • 2-(4-((5,6-diphenyl-2-pyrazinyl)(isopropyl)amino)butoxy)-n-(methylsulfonyl)acetamide
  • 2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)-N-(methylsulfonyl)acetamide
  • 2-[4-[(5,6-Diphenyl-2-pyrazinyl)(1-methylethyl)amino]butoxy]-N-(methylsulfonyl)acetamide
  • 2-[4-[(5,6-diphenylpyrazin-2-yl)-propan-2-ylamino]butoxy]-N-methylsulfonylacetamide
  • 2-[4-[[5,6-di(phenyl)pyrazin-2-yl]-propan-2-ylamino]butoxy]-N-methylsulfonylacetamide
  • 2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}-N-(methanesulfonyl)acetamide
  • 2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}-N-methanesulfonylacetamide
  • 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}-N-(methylsulfonyl)acetamide
  • 475086-01-2
  • 5EXC0E384L
  • A857156
  • AC-30209
  • ACT 293987
  • ACT-293987
  • ACT293987
  • AMY10851
  • B7378
  • BCP09146
  • BDBM50235383
  • BS-16872
  • CCG-269668
  • CS-3774
  • D09994
  • DB-119997
  • DB11362
  • FT-0776043
  • GTPL7552
  • HY-14870
  • MFCD10567093
  • NCGC00370833-01
  • NCGC00370833-02
  • NS 304
  • NS-304
  • NS-304(Selexipag)
  • NS-304;ACT-293987
  • Q15424759
  • SB17055
  • Selexipag
  • Selexipag (JAN/USAN/INN)
  • Selexipag(NS-304)
  • Uptravi
  • s3726

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3990451
  • UNII-5EXC0E384L
  • AKOS024457572
  • DTXSID301027959
  • CHEMBL238804
  • CHEBI:90844
  • SCHEMBL674122

Physico-Chemical properties

IUPAC name2-[4-[(5,6-diphenylpyrazin-2-yl)-propan-2-ylamino]butoxy]-N-methylsulfonylacetamide
Molecular formulaC26H32N4O4S
Molecular weight496.622
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity138.62
LogP5.4
Topological polar surface area109.9

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.