Acitretin

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

What is the Acitretin?

The molecule Acitretin presents a molecular formula of C21H26O3 and its IUPAC name is (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid.

Acitretin (brand name Soriatane) is a molecule of the retinoid class. It is a metabolite of etretinate, which is itself an analog of retinoic acid. Acitretin is used to treat psoriasis and other disorders of keratinization. It is a second-line treatment, after other treatments such as topical corticosteroids and phototherapy have failed..

Acitretin is a retinoid, meaning it is related to vitamin A and retinoic acid. It works by affecting the growth of skin cells. Acitretin slows down the production of new skin cells, and also decreases the size of the cells that are produced. This leads to a reduction in the thickness of the skin, and also to a reduction in the scale that is characteristic of psoriasis..

Acitretin is typically taken as a pill once or twice a day. It is important to take acitretin with food, as this increases its absorption. Acitretin can be absorbed through the skin, so it is important to avoid sun exposure and to use sunscreen when outdoors..

Acitretin can cause a number of side effects, including dry skin, itching, and redness. These side effects are typically mild and go away with time. More serious side effects can occur, but are rare. These include liver damage, changes in cholesterol levels, and birth defects..

Acitretin is a effective treatment for psoriasis, but it is important to be aware of the potential side effects. If you experience any side effects, be sure to talk to your doctor..

3D structure

Cartesian coordinates

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

2D drawing

 

Acitretin IHUNBGSDBOWDMA-AQFIFDHZSA-N chemical compound 2D structure molecule svg
Acitretin

 

Molecule descriptors

 
IUPAC name(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
InChI codeInChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
InChI KeyIHUNBGSDBOWDMA-AQFIFDHZSA-N
SMILESCOc1cc(C)c(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)c(C)c1C

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.

  • (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(methyloxy)phenyl]nona-2,4,6,8-tetraenoic acid
  • (2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid
  • (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid
  • (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
  • (all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid
  • 079A839
  • 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-, (all-E)-
  • 2,4,6,8-Nonatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-
  • 2,4,6,8-Nonatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (2E,4E,6E,8E)-
  • 2,4,6,8-Nonatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (all-E)-
  • 419534-31-9
  • 54757-46-9
  • 55079-83-9
  • 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid
  • 9-cis Acitretin
  • A830475
  • AB00698376-08
  • AB00698376_09
  • AC-4702
  • AS-12644
  • Acetretin
  • Acitretin
  • Acitretin (USP/INN)
  • Acitretin,(S)
  • Acitretin- Bio-X
  • Acitretina
  • Acitretine
  • Acitretinum
  • BA164136
  • BCP9000229
  • BCPP000437
  • BDBM50088429
  • BIDD:GT0617
  • C75579
  • CCG-220668
  • CCRIS 5534
  • CS-0368934
  • CS-1855
  • D02754
  • DB00459
  • DSSTox_CID_2553
  • DSSTox_GSID_22553
  • DSSTox_RID_76624
  • Etretin
  • GTPL7598
  • HMS2234L17
  • HMS3259J12
  • HMS3714E17
  • HSDB 7187
  • HY-B0107
  • KS-5246
  • LCH760E9T7
  • MFCD00866632
  • MLS001076667
  • NCGC00163127-01
  • NCGC00163127-02
  • NCGC00163127-03
  • Neotigason
  • Q341500
  • Retinoid etretin
  • Ro 10-1670
  • Ro 10-1670/000
  • Ro-10-1670
  • Ro-10-1670/000
  • Ro-101670000
  • SMR000499573
  • SR-01000763200
  • SR-01000763200-3
  • STL565770
  • SW199134-2
  • Soriatane
  • Soriatane CK
  • TMMP
  • U0279
  • all-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoic acid
  • all-trans-Acitretin
  • all-trans-Etretin
  • s1368

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3798734
  • CAS-55079-83-9
  • UNII-LCH760E9T7
  • AKOS015889991
  • BRD-K90699611-001-01-4
  • DTXSID6022553
  • CHEMBL1131
  • CHEBI:50173
  • CHEBI:50172
  • Tox21_112012
  • EINECS 259-474-4
  • SCHEMBL3759
  • Spectrum5_002065

Physico-Chemical properties

IUPAC name(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Molecular formulaC21H26O3
Molecular weight326.429
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity101.54
LogP5.2
Topological polar surface area46.5

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.