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Details

Stereochemistry ACHIRAL
Molecular Formula C22H46O
Molecular Weight 326.6009
Optical Activity NONE
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
Curator's Comment:: Description was created based on several sources, including

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: HIV-1 replication
10 mM [EC50]
Target ID: P03200
Gene ID: 3783713
Gene Symbol: NA
Target Organism: Epstein-Barr virus (strain B95-8) (HHV-4) (Human herpesvirus 4)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Abreva

Approved Use

Herpes Labialis Topical treatment of recurrent herpes labialis (perioral herpes, cold sores, fever blisters)

Launch Date

964396800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.007 ng × eq/g
25 mg/kg single, topical
dose: 25 mg/kg
route of administration: Topical
experiment type: SINGLE
co-administered:
DOCOSANOL plasma
Oryctolagus cuniculus
population: UNKNOWN
age: ADULT
sex: MALE
food status: UNKNOWN
318 ng/mL
5 g single, oral
dose: 5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DOCOSANOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.02 μg × eq × h/g
25 mg/kg single, topical
dose: 25 mg/kg
route of administration: Topical
experiment type: SINGLE
co-administered:
DOCOSANOL plasma
Oryctolagus cuniculus
population: UNKNOWN
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 % 5 times / day steady, topical
Recommended
Dose: 10 %, 5 times / day
Route: topical
Route: steady
Dose: 10 %, 5 times / day
Sources:
unhealthy, 18-77 years
Health Status: unhealthy
Age Group: 18-77 years
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim
PubMed

PubMed

TitleDatePubMed
Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex.
1991 Dec 1
n-Docosanol inhibits in vitro replication of HIV and other retroviruses.
1996 Jan 1
The effect of Pygeum africanum on fibroblast growth factor (FGF) and transforming growth factor beta (TGF beta 1/LAP) expression in animal model.
2001
The antiviral drug docosanol as a treatment for Kaposi's sarcoma lesions in HIV type 1-infected patients: a pilot clinical study.
2001 Jan 1
Herpes simplex virus: clinical presentation and treatment.
2001 May
Effect of oral Tadenan treatment on rabbit bladder structure and function after partial outlet obstruction.
2002 May
Inhibition of type 1 and type 2 5alpha-reductase activity by free fatty acids, active ingredients of Permixon.
2002 Oct
Effect of Pygeum africanum tadenan on micturition and prostate growth of the rat secondary to coadministered treatment and post-treatment with dihydrotestosterone.
2003 Feb
Docosanol: a topical antiviral for herpes labialis.
2004 Dec
Therapeutic options for herpes labialis, II: Topical agents.
2004 Jul
Low-dose tadenan protects the rabbit bladder from bilateral ischemia/ reperfusion-induced contractile dysfunction.
2005 Jan
[Modern pharmacotherapy of benign prostatic hyperplasia].
2005 Nov
New antiviral agents.
2006 Apr
Self-assembled two-dimensional ordered arrays of tripod-type molecules on graphite.
2006 Jul 4
Structure and performance of cationic assembly dispersed in amphoteric surfactants solution as a shampoo for hair damaged by coloring.
2007
Management and prevention of recurrent herpes labialis in immunocompetent patients.
2007 Dec
[Studies on the chemical constituents of the aerial parts of Seseli mairei].
2007 Jan
Management of recurrent oral herpes simplex infections.
2007 Mar
Alpha-glucosidase inhibitors from Millettia conraui.
2007 Sep
Expression of transforming growth factor beta1 gene, basic fibroblast growth factor gene and hydroxyproline in diabetes-induced bladder dysfunction in a rat model.
2008
[Efficacy of tadenan in chronic prostatitis complicated by sterility].
2008 Jul-Aug
Phytotherapy for lower urinary tract symptoms secondary to benign prostatic hyperplasia.
2008 Jun
Effect of combinations of antiviral drugs on herpes simplex encephalitis.
2009 Dec 29
Docosanol: new drug. Herpes labialis: barely more effective than an excipient.
2009 Jun
[Tadenan treatment of prostatic adenoma].
2009 Mar-Apr
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
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
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
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

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 Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
WHO-VATC QD06BB11
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
NCI_THESAURUS C281
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
Code System Code Type Description
CAS
661-19-8
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
EPA CompTox
661-19-8
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
FDA UNII
9G1OE216XY
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
MERCK INDEX
M4714
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00632
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200453
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
DRUG CENTRAL
940
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
NCI_THESAURUS
C47498
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
RXCUI
594680
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY RxNorm
PUBCHEM
12620
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
HSDB
5739
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
EVMPD
SUB21986
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
WIKIPEDIA
DOCOSANOL
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-546-6
Created by admin on Sat Jun 26 07:15:14 UTC 2021 , Edited by admin on Sat Jun 26 07:15:14 UTC 2021
PRIMARY