U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H46O
Molecular Weight 326.6
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOCOSANOL

SMILES

CCCCCCCCCCCCCCCCCCCCCCO

InChI

InChIKey=NOPFSRXAKWQILS-UHFFFAOYSA-N
InChI=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

HIDE SMILES / InChI

Description

Docosanol is a saturated 22-carbon aliphatic alcohol which exhibits antiviral activity against many lipid enveloped viruses including herpes simplex virus (HSV). Docosanol speeds the healing of cold sores and fever blisters on the face or lips. It also relieves the accompanying symptoms, including tingling, pain, burning, and itching. Docosanol works by inhibiting fusion between the human cell plasma membrane and the herpes simplex virus (HSV) envelope, thereby preventing viral entry into cells and subsequent viral replication. Unlike other cold-sore antivirals, docosanol does not act directly on the virus, and as such it is unlikely it will produce drug resistant mutants of HSV. Used for the topical treatment of recurrent oral-facial herpes simplex episodes (cold sores or fever blisters).

Approval Year

PubMed

PubMed

TitleDatePubMed
n-Docosanol inhibits in vitro replication of HIV and other retroviruses.
1996 Jan 1
Effect of combinations of antiviral drugs on herpes simplex encephalitis.
2009 Dec 29
Policosanol, alpha-tocopherol, and moisture content as a function of timing of harvest of Switchgrass (Panicum virgatum L.).
2009 May 13
[Study on the chemical constituents from Clematis brevicaudata].
2009 Oct
Topical n-docosanol for management of recurrent herpes labialis.
2010 Apr
Soybean metabolites regulated in root hairs in response to the symbiotic bacterium Bradyrhizobium japonicum.
2010 Aug
An ethnobotanical survey of medicinal plants in Babungo, Northwest Region, Cameroon.
2010 Feb 15
Nutritional bioactive components of wheat straw as affected by genotype and environment.
2010 Jan
LAP5 and LAP6 encode anther-specific proteins with similarity to chalcone synthase essential for pollen exine development in Arabidopsis.
2010 Jul
Rapid sampling of molecules via skin for diagnostic and forensic applications.
2010 Jul
A Potent, Broad-Spectrum Antiviral Agent that Targets Viral Membranes.
2010 May
Nongenital herpes simplex virus.
2010 Nov 1
Patents

Sample Use Guides

In Vivo Use Guide
Apply docosanol topical in a quantity sufficient to cover the affected lesions and immediately surrounding skin five times a day until the lesions are healed.
Route of Administration: Topical
In Vitro Use Guide
31 mM docosanol inhibited HIV-1 replication up to 82%
Name Type Language
DOCOSANOL
HSDB   II   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
NSC-8407
Code English
1-DOCOSANOL
Systematic Name English
N-DOCOSANOL
MI  
Common Name English
DOCOSANOL [ORANGE BOOK]
Common Name English
BEHENIC ALCOHOL
Common Name English
DOCOSANOL [MART.]
Common Name English
DOCOSANOL [VANDF]
Common Name English
BEHENYL ALCOHOL [INCI]
Common Name English
DOCOSANOL [HSDB]
Common Name English
DOCOSANOL [WHO-DD]
Common Name English
N-DOCOSANOL [MI]
Common Name English
STENOL 1822
Brand Name English
ABREVA
Brand Name English
BEHENYL ALCOHOL
INCI  
INCI  
Official Name English
DOCOSANOL [USAN]
Common Name English
DOCOSANOL [II]
Common Name English
Classification Tree Code System Code
WHO-ATC D06BB11
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
WHO-VATC QD06BB11
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
Code System Code Type Description
CAS
661-19-8
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY
EPA CompTox
661-19-8
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY
MERCK INDEX
M4714
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL1200453
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY
NCI_THESAURUS
C47498
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY
RXCUI
594680
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY RxNorm
PUBCHEM
12620
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY SWITZERF
HSDB
661-19-8
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY
EVMPD
SUB21986
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY
WIKIPEDIA
DOCOSANOL
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY
ECHA (EC/EINECS)
211-546-6
Created by admin on Tue Mar 06 12:15:48 UTC 2018 , Edited by admin on Tue Mar 06 12:15:48 UTC 2018
PRIMARY