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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

Molecular Formula C22H46O
Molecular Weight 326.6009
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
10.0 mM [EC50]
Target ID: P03200
Gene ID: 3783713.0
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

9.6439678E11
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: Page: 1
unhealthy, 18-77 years
n = 370
Health Status: unhealthy
Condition: Recurrent herpes simplex labialis
Age Group: 18-77 years
Sex: M+F
Population Size: 370
Sources: Page: 1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Clinical efficacy of topical docosanol 10% cream for herpes simplex labialis: A multicenter, randomized, placebo-controlled trial.
2001 Aug
Identification of Mycobacterium xenopi by gas chromatography.
2001 Jan
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
A review of antiviral therapy for herpes labialis.
2001 Sep
Comparison of new topical treatments for herpes labialis: efficacy of penciclovir cream, acyclovir cream, and n-docosanol cream against experimental cutaneous herpes simplex virus type 1 infection.
2001 Sep
The toxicity of behenyl alcohol. I. Genotoxicity and subchronic toxicity in rats and dogs.
2002 Aug
Effect of oral Tadenan treatment on rabbit bladder structure and function after partial outlet obstruction.
2002 May
Synergistic inhibition of herpesvirus replication by docosanol and antiviral nucleoside analogs.
2002 Nov
Inhibition of type 1 and type 2 5alpha-reductase activity by free fatty acids, active ingredients of Permixon.
2002 Oct
N-docosanol (Abreva) for herpes labialis: problems and questions.
2002 Sep
Study of detrusor dysfunction due to outlet obstruction: link between analysis of uroflows of men with benign prostatic hyperplasia and animal studies.
2003
Constituents of Hypericum laricifolium and their cyclooxygenase (COX) enzyme activities.
2003 Dec
Docosanol: a topical antiviral for herpes labialis.
2004 Dec
Molecular transfer and transport in noncovalent microcontact printing.
2004 Feb 3
Therapeutic options for herpes labialis, II: Topical agents.
2004 Jul
[Tadenan (Pygeum africanum extract) in the treatment of patients with benign prostatic hyperplasia].
2004 Sep-Oct
Low-dose tadenan protects the rabbit bladder from bilateral ischemia/ reperfusion-induced contractile dysfunction.
2005 Jan
New antiviral agents.
2006 Apr
The lipid polyester composition of Arabidopsis thaliana and Brassica napus seeds.
2006 Dec
Structure and performance of cationic assembly dispersed in amphoteric surfactants solution as a shampoo for hair damaged by coloring.
2007
Management of recurrent oral herpes simplex infections.
2007 Mar
Single-day treatment for orolabial and genital herpes: a brief review of pathogenesis and pharmacology.
2008 Apr
[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
Comments on study of paw pad lesions in dogs.
2009 Sep 15
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

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%
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:15:14 UTC 2021
Edited
by admin
on Sat Jun 26 07:15:14 UTC 2021
Record UNII
9G1OE216XY
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ACTIVE MOIETY