DOCOSANOL

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 Search

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
Sources: http://www.drugbank.ca/drugs/DB00632
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).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Target ID: HIV-1 replication Sources: https://www.ncbi.nlm.nih.gov/pubmed/8825621	Inhibitor 7701		10 mM [EC50]
Envelope glycoprotein GP350 1 Target ID: P03200 Gene ID: 3783713 Gene Symbol: NA Target Organism: Epstein-Barr virus (strain B95-8) (HHV-4) (Human herpesvirus 4) Sources: http://www.drugbank.ca/drugs/DB00632	Inhibitor 7701	Herpes labialis
Envelope glycoprotein 1 Target ID: CHEMBL2364696 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9864049	Inhibitor 7701	Herpes labialis

Conditions

Condition	Modality	Targets	Highest Phase	Product
Herpes labialis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-941_Abreva_prntlbl.pdf	Primary	Envelope glycoprotein Envelope glycoprotein GP350	Approved 7997	Abreva Approved Use Herpes Labialis Topical treatment of recurrent herpes labialis (perioral herpes, cold sores, fever blisters) Launch Date 964396800000

C_max

Value	Dose	Co-administered	Analyte	Population
0.007 ng × eq/g REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/020941s000_PharmR.pdf	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 REVIEW https://mri.cts-mrp.eu/human/downloads/AT_H_0985_001_PAR.pdf	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

Value	Dose	Co-administered	Analyte	Population
1.02 μg × eq × h/g REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/020941s000_PharmR.pdf	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

Dose	Population	Adverse events
10 % 5 times / day steady, topical Recommended Dose: 10 %, 5 times / day Route: topical Route: steady Dose: 10 %, 5 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11464183/	unhealthy, 18-77 years Health Status: unhealthy Age Group: 18-77 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11464183/	Sources: https://pubmed.ncbi.nlm.nih.gov/11464183/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT 160

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 160	substrate 2752 Sources: https://www.epa.gov/sites/production/files/2019-08/documents/support_document_for_proposed_designation_of_1-docosanol.pdf#page=23 Page: 23	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00301Q
AK Scientific	K949
APExBIO	A8416
AbovChem LLC	HY-B0222
Acros Organics	17372
Angene	AGN-PC-0WH8OC
BLDpharm	BD22073
BOC Sciences	661-19-8
BOC Sciences	67905-30-0
Bide Pharmatech	BD22073
BlocksMatrix Scientific	98867
Capot Chemical	35298
Chem Scene	CS-4300
ChemShuttle	141420
Compound Cloud	12620
Fluorochem	240559
Fluorochem	323656
Frontier Scientific Services	500055561
Hairui	HR123407
Hairui	HR140184
Hangzhou APIChem Technology	AC-19852
Hangzhou Yuhao Chemical Technology	LT4022
Indofine	40-2200
Lab Network	LN00196449
Lab Seeker	SC-15883
MolPort	MolPort-003-666-887
Molnova	M15518
MuseChem	A000652
NCI Plated 2007	8407
Nanjing Pope Bio-tech	NSTH-B06089
Norris Pharm	NSTH-B06089
Ryan Scientific	Riboflavin
Sigma Aldrich	169102
Sigma Aldrich	169102\|ALDRICH
Sigma Aldrich	43960
Sigma Aldrich	43960\|SIAL
StruChem	SC-15883
TargetMol	T0884
Tetrahedron	TS63446
TimTec	SBB060170
TimTec	ST51046404
Wonderchem	WD06JBM
ZINC	ZINC000006920384	http://zinc15.docking.org/substances/ZINC000006920384
eMolecules	484978
mcule	MCULE-3239333381

PubMed

Title	Date	PubMed
Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex.	1991 Dec 1	1660151
n-Docosanol inhibits in vitro replication of HIV and other retroviruses.	1996 Jan 1	8825621
The effect of Pygeum africanum on fibroblast growth factor (FGF) and transforming growth factor beta (TGF beta 1/LAP) expression in animal model.	2001	11233693
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	11177381
Herpes simplex virus: clinical presentation and treatment.	2001 May	11443814
Effect of oral Tadenan treatment on rabbit bladder structure and function after partial outlet obstruction.	2002 May	11956488
Inhibition of type 1 and type 2 5alpha-reductase activity by free fatty acids, active ingredients of Permixon.	2002 Oct	12477490
Effect of Pygeum africanum tadenan on micturition and prostate growth of the rat secondary to coadministered treatment and post-treatment with dihydrotestosterone.	2003 Feb	12597984
Docosanol: a topical antiviral for herpes labialis.	2004 Dec	15571473
Therapeutic options for herpes labialis, II: Topical agents.	2004 Jul	15293698
Low-dose tadenan protects the rabbit bladder from bilateral ischemia/ reperfusion-induced contractile dysfunction.	2005 Jan	15693703
[Modern pharmacotherapy of benign prostatic hyperplasia].	2005 Nov	16498818
New antiviral agents.	2006 Apr	16816493
Self-assembled two-dimensional ordered arrays of tripod-type molecules on graphite.	2006 Jul 4	16800659
Structure and performance of cationic assembly dispersed in amphoteric surfactants solution as a shampoo for hair damaged by coloring.	2007	17898494
Management and prevention of recurrent herpes labialis in immunocompetent patients.	2007 Dec	18371287
[Studies on the chemical constituents of the aerial parts of Seseli mairei].	2007 Jan	17539301
Management of recurrent oral herpes simplex infections.	2007 Mar	17379150
Alpha-glucosidase inhibitors from Millettia conraui.	2007 Sep	17827772
Expression of transforming growth factor beta1 gene, basic fibroblast growth factor gene and hydroxyproline in diabetes-induced bladder dysfunction in a rat model.	2008	17763394
[Efficacy of tadenan in chronic prostatitis complicated by sterility].	2008 Jul-Aug	19054994
Phytotherapy for lower urinary tract symptoms secondary to benign prostatic hyperplasia.	2008 Jun	18423748
Effect of combinations of antiviral drugs on herpes simplex encephalitis.	2009 Dec 29	20054446
Docosanol: new drug. Herpes labialis: barely more effective than an excipient.	2009 Jun	19637417
[Tadenan treatment of prostatic adenoma].	2009 Mar-Apr	19526878
Policosanol, alpha-tocopherol, and moisture content as a function of timing of harvest of Switchgrass (Panicum virgatum L.).	2009 May 13	19415924
[Study on the chemical constituents from Clematis brevicaudata].	2009 Oct	20112713
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
Topical n-docosanol for management of recurrent herpes labialis.	2010 Apr	20210688
Soybean metabolites regulated in root hairs in response to the symbiotic bacterium Bradyrhizobium japonicum.	2010 Aug	20534735
An ethnobotanical survey of medicinal plants in Babungo, Northwest Region, Cameroon.	2010 Feb 15	20156356
LAP5 and LAP6 encode anther-specific proteins with similarity to chalcone synthase essential for pollen exine development in Arabidopsis.	2010 Jul	20442277
Rapid sampling of molecules via skin for diagnostic and forensic applications.	2010 Jul	20238151
A Potent, Broad-Spectrum Antiviral Agent that Targets Viral Membranes.	2010 May	21994673
Nongenital herpes simplex virus.	2010 Nov 1	21121552

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

Official Name

English

NSC-8407

Code

English

1-DOCOSANOL

Systematic Name

English

N-DOCOSANOL

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

Official Name

English

DOCOSANOL [USAN]

Common Name

English

DOCOSANOL [II]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D06BB11