Apremilast

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

What is the Apremilast?

The molecule Apremilast presents a molecular formula of C22H24N2O7S and its IUPAC name is N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide.

Apremilast is a molecule that was first synthesized in the laboratory of Dr. Ronald R. Emkey at Emory University. It is a member of a class of compounds called phosphodiesterase 4 (PDE4) inhibitors. PDE4 inhibitors are drugs that block the action of an enzyme called phosphodiesterase 4. This enzyme belongs in many body tissues, including the skin, lungs, and blood vessels. PDE4 participes in the regulation of many cellular processes, including inflammation and cell proliferation..

Apremilast was originally developed as a treatment for psoriasis, a chronic inflammatory skin disease. However, it has also been shown to be effective in the treatment of other inflammatory diseases, such as Crohn's disease, ulcerative colitis, and psoriatic arthritis. In addition, apremilast has been shown to be effective in the treatment of plaque psoriasis, a type of psoriasis that is characterized by the formation of thick, scaly patches on the skin..

The exact mechanism of action of apremilast is not fully understood. However, it is thought to work by inhibiting the action of PDE4, which leads to the decrease of inflammatory mediators. In addition, apremilast is thought to modulate the activity of certain immune cells, which leads to the reduction of inflammation..

Apremilast exists in the form of an oral tablet. It is generally well-tolerated, with the most common side effects being nausea, diarrhea, headache, and fatigue..

3D structure

Cartesian coordinates

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

2D drawing

 

Apremilast IMOZEMNVLZVGJZ-QGZVFWFLSA-N chemical compound 2D structure molecule svg
Apremilast

 

Molecule descriptors

 
IUPAC nameN-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
InChI codeInChI=1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1
InChI KeyIMOZEMNVLZVGJZ-QGZVFWFLSA-N
SMILESCCOc1cc([C@@H](CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC

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.

  • (+)-N-(2-((1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxo- 2,3-dihydro-1H-isoindol-4-yl)acetamide
  • (S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione
  • (S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione(Apremilast)
  • (S)-N-(2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide
  • (S)-N-{2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide
  • 4-[[5 pound not7-dihydroxy-2 pound not2-dimethyl-8-(2-methylpropanoyl)chromen-6-yl]methy l]-3 pound not5-dihydroxy-6 pound not6-dimethyl-2-(2-methylpropanoyl)cyclohexa-2 pound not4-dien- 1-one
  • 608141-41-9
  • 608141-44-2
  • A9L
  • AC-27650
  • AMY371
  • Acetamide, N-(2-((1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)- 2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl)-
  • Acetamide, N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]-
  • Apremilast
  • Apremilast (CC-10004)
  • Apremilast (JAN/USAN)
  • Apremilast- Bio-X
  • BA164215
  • BCP03783
  • BCP0726000109
  • BCP25283
  • BCP9000311
  • BDBM50248919
  • CC 10004
  • CC-10004
  • CC10004
  • CCG-269336
  • CS-0671
  • D08860
  • DB05676
  • EX-A336
  • FK-0727
  • GTPL7372
  • HSDB 8221
  • HY-12085
  • MFCD18782607
  • N-[2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide
  • N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
  • N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide
  • N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide
  • OTEZLA
  • Q2858961
  • SW219856-1
  • UP7QBP99PN
  • apremilastum
  • cas:608141-41-9;Apremilast
  • s8034

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC30691736
  • UNII-UP7QBP99PN
  • AKOS016339660
  • DTXSID30976289
  • CHEMBL514800
  • CHEBI:78540
  • SCHEMBL302992

Physico-Chemical properties

IUPAC nameN-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
Molecular formulaC22H24N2O7S
Molecular weight460.5
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity121.89
LogP3.5
Topological polar surface area127.5

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.