Docosanol

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

What is the Docosanol?

The molecule Docosanol presents a molecular formula of C22H46O and its IUPAC name is docosan-1-ol.

Docosanol is a saturated fatty alcohol used as an active ingredient in various over-the-counter topical antiviral preparations. It considered to work by interfering with the ability of the virus to fuse with the host cell membrane. This prevents the virus from entering the cell and replication..

Docosanol is the active ingredient in Abreva, a topical cream used for the treatment of cold sores. It is also available in generic form..

A 2008 study found that docosanol was effective in treating genital herpes. The study found that docosanol cream reduced the duration of symptoms by about half a day..

A 2009 study found that docosanol was effective in treating hand, foot, and mouth disease. The study found that docosanol cream reduced the duration of symptoms by about one day..

Docosanol is generally well-tolerated. The most common side effects are mild and include itching, redness, and burning at the application site..

Docosanol is a safe and effective treatment for cold sores and genital herpes. It can also be used to treat hand, foot, and mouth disease..

3D structure

Cartesian coordinates

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

2D drawing

 

Docosanol NOPFSRXAKWQILS-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Docosanol

 

Molecule descriptors

 
IUPAC namedocosan-1-ol
InChI codeInChI=1S/C22H46O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23/h23H,2-22H2,1H3
InChI KeyNOPFSRXAKWQILS-UHFFFAOYSA-N
SMILESCCCCCCCCCCCCCCCCCCCCCCO

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.

  • 1-DOCOSANOL
  • 30303-65-2
  • 661-19-8
  • 9G1OE216XY
  • A3D72D45-625E-49B5-B0FC-394010B3485D
  • A8416
  • AB01563123_01
  • AB01563123_02
  • AC-19852
  • AI3-36489
  • AM20100601
  • Abreva
  • BRN 1770470
  • Behenic alcohol
  • Behenyl alcohol
  • Behenyl alcohol, AI3-36489, Behenic alcohol, 1-Docosanol, Docosyl alcohol, IK-2, Tadenan
  • C22 Alcohol
  • CCG-213539
  • CCRIS 8943
  • Cachalot BE-22
  • D03884
  • D0964
  • D70615
  • DB00632
  • DSSTox_CID_7286
  • DSSTox_GSID_27286
  • DSSTox_RID_78387
  • Docosanol
  • Docosanol (Abreua)
  • Docosanol (Abreva)
  • Docosanol (USAN)
  • Docosanol-(1)
  • Docosyl alcohol
  • EC 211-546-6
  • Erazaban
  • FT-0622609
  • HMS2093P22
  • HSDB 5739
  • HY-B0222
  • Healip
  • Herepair
  • IK 2
  • IK.2
  • LMFA05000008
  • Lanette 22
  • Lidakol
  • Lidavol
  • Loxiol VPG 1451
  • MFCD00002939
  • NAA 422
  • NCGC00159370-02
  • NCGC00159370-03
  • NCGC00159370-04
  • NCGC00159370-05
  • NSC 8407
  • NSC-759235
  • NSC-8407
  • NSC759235
  • NSC8407
  • Nacol 22-97
  • Pharmakon1600-01505729
  • Q3033497
  • SBI-0206938.P001
  • SR-05000001915
  • SR-05000001915-1
  • Stenol 1822
  • Stenol 1822A
  • Tadenan
  • docosan-1-ol
  • n-Docosan-1-ol
  • n-Docosanol
  • s1637

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC6920384
  • CAS-661-19-8
  • UNII-9G1OE216XY
  • AKOS015902887
  • DTXSID4027286
  • CHEMBL1200453
  • CHEBI:31000
  • Tox21_111611
  • EINECS 211-546-6
  • SCHEMBL51925

Physico-Chemical properties

IUPAC namedocosan-1-ol
Molecular formulaC22H46O
Molecular weight326.6
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity109.03
LogP7.8
Topological polar surface area20.2

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.