DOCOSANOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H46O
Molecular Weight	326.6
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	Potency
Target ID: HIV-1 replication Sources: https://www.ncbi.nlm.nih.gov/pubmed/8825621	Inhibitor 8228	10.0 mM [EC50]
Envelope glycoprotein GP350 1 Target ID: P03200 Gene ID: 3783713.0 Gene Symbol: NA Target Organism: Epstein-Barr virus (strain B95-8) (HHV-4) (Human herpesvirus 4) Sources: http://www.drugbank.ca/drugs/DB00632	Inhibitor 8228
Envelope glycoprotein 1 Target ID: CHEMBL2364696 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9864049	Inhibitor 8228

Conditions

Condition	Modality	Targets	Highest Phase	Product
Herpes labialis 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-941_Abreva_prntlbl.pdf	Primary		Approved 8360	Abreva Approved Use Herpes Labialis Topical treatment of recurrent herpes labialis (perioral herpes, cold sores, fever blisters) Launch Date 9.6439678E11

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/ 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: https://pubmed.ncbi.nlm.nih.gov/11464183/ Page: 1	Sources: https://pubmed.ncbi.nlm.nih.gov/11464183/ Page: 1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT 187

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 187	substrate 3326 Sources: https://www.epa.gov/sites/production/files/2019-08/documents/support_document_for_proposed_designation_of_1-docosanol.pdf#page=23 Page: 23.0	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY565990	https://www.001chemical.com/chem/661-19-8
3B Scientific (Wuhan) Corp	3B3-032978	http://www.3bsc.com/index/pro_info.php?id=54242
AHH Chemical co.,ltd	MT-28428	http://www.ahhchemical.com/product/MT-28428.html
AK Scientific, Inc. (AKSCI)	K949	http://www.aksci.com/item_detail.php?cat=K949
Achemica	ACMC-1CMUG	http://www.achemica.com/prodinfo/?id=117994
Acros Organics	AC173720250	https://www.fishersci.com/shop/products/1-docosanol-98-acros-organics/AC173720250
Acros Organics	AC173721000	https://www.fishersci.com/shop/products/1-docosanol-98-acros-organics/AC173721000
Adooq BioScience	A10327	https://www.adooq.com/docosanol.html
Alfa Chemistry	ACM661198	https://lipids.alfa-chemistry.com/product/docosanol-cas-661-19-8-304978.html
Alichem	490019133	http://www.alichem.com/en/products/661-19-8.html
Ambeed	A762512	https://www.ambeed.com/products/661-19-8.html
Angene	AGN-PC-0WH8OC	http://www.angenechemical.com/productshow/AGN-PC-0WH8OC.html
Anward	ANW-35147	http://www.anward.com/pro_result/2410
ApexBio Technology	A8416	http://www.apexbt.com/docosanol-abreua.html
Ark Pharm	AK113719	http://www.arkpharminc.com/products/661-19-8.html
Avantor Inc	EM8.22047.0100	https://us.vwr.com/store/product/15143036/1-docosanol-for-synthesis
Avantor Inc	TCD0964-025G	https://us.vwr.com/store/product/4541677/1-docosanol-98-0
Avantor Inc	TCD0964-500G	https://us.vwr.com/store/product/4541677/1-docosanol-98-0
Avantor Inc	700002-742	https://us.vwr.com/store/product/7829092/1-docosanol
Avantor Inc	700002-744	https://us.vwr.com/store/product/7829092/1-docosanol
BLD Pharm	BD22073	http://www.bldpharm.com/products/661-19-8.html
BioCrick	BCC3769	http://www.biocrick.com/Docosanol-Abreua-BCC3769.html
CSNpharm	CSN12875	https://www.csnpharm.com/products/1-docosanol.html
Chem Scene	CS-4300	http://www.chemscene.com/661-19-8.html
ChemMol	30107535	http://www.chemmol.com/chemmol/30107535.html
ChemMol	44005380	http://www.chemmol.com/chemmol/44005380.html
ChemMol	49413354	http://www.chemmol.com/chemmol/49413354.html
ChemMol	99086466	http://www.chemmol.com/chemmol/99086466.html
Chemspace	CSSB00000066819	https://chem-space.com/CSSB00000066819
DC Chemicals	DCAPI1299	http://www.dcchemicals.com//product_show-Docosanol_Abreva_.html
Finetech	FT-0622609	http://www.finetechnology-ind.com/prod/detail/pub/661-19-8.html
Glentham Life Sciences	GL7672	http://www.glentham.com/products/product/GL7672/
Hairui	HR140184	http://www.hairuichem.com/en/product/30303-65-2.html
Hairui	HR123407	http://www.hairuichem.com/en/product/661-19-8.html
LGC Standards	DRE-C13058000	https://www.lgcstandards.com/US/en/p/DRE-C13058000
Lab Network	LN00196449	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00196449
Matrix Scientific	98867	https://www.matrixscientific.com/098867.html
MedChem Express	HY-B0222	https://www.medchemexpress.com/1-Docosanol.html
Molcore	MC565990	https://www.molcore.com/product/661-19-8
Oakwood	240559	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=121558&ExtHyperLink=1
Parchem	1620	http://www.parchem.com/chemical-supplier-distributor/Behenyl-Alcohol-002999.aspx
Selleck Chemicals	S1637	http://www.selleckchem.com/products/Docosanol(Abreva).html
Sigma-Aldrich	169102_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/169102?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	43960_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/43960?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S526479	http://www.smolecule.com/products/s526479
TCI (Tokyo Chemical Industry)	D0964	http://www.tcichemicals.com/eshop/en/us/commodity/D0964/index.html
THE BioTek	bt-266139	https://www.thebiotek.com/product/inhibitors/bt-266139
Yuhao Chemical	LT4022	http://www.chemyuhao.com/661-19-8.html
abcr GmbH	AB142921	http://www.abcr.com/shop/en/AB142921
eNovation Chemicals	D676418	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676418
iChemical	EBD35098	http://www.ichemical.com/chemicals/cas-661-19-8
mcule	MCULE-3239333381	https://mcule.com/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
Clinical efficacy of topical docosanol 10% cream for herpes simplex labialis: A multicenter, randomized, placebo-controlled trial.	2001 Aug	11464183
New drug approvals in 2000.	2001 Jul-Aug	12016673
Herpes simplex virus: clinical presentation and treatment.	2001 May	11443814
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	11559210
N-docosanol (Abreva) for herpes labialis: problems and questions.	2002 Sep	12196766
Study of detrusor dysfunction due to outlet obstruction: link between analysis of uroflows of men with benign prostatic hyperplasia and animal studies.	2003	15088913
Constituents of Hypericum laricifolium and their cyclooxygenase (COX) enzyme activities.	2003 Dec	14646327
Efficacy of docosanol.	2003 Sep	12963936
Docosanol: a topical antiviral for herpes labialis.	2004 Dec	15571473
Molecular transfer and transport in noncovalent microcontact printing.	2004 Feb 3	15773108
Therapeutic options for herpes labialis, II: Topical agents.	2004 Jul	15293698
[Tadenan (Pygeum africanum extract) in the treatment of patients with benign prostatic hyperplasia].	2004 Sep-Oct	15560171
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
The lipid polyester composition of Arabidopsis thaliana and Brassica napus seeds.	2006 Dec	17055542
Two-dimensional miscibility studies--the analysis of interaction between long-chain alcohols and semifluorinated alkanes.	2006 Feb 23	16494312
Self-assembled two-dimensional ordered arrays of tripod-type molecules on graphite.	2006 Jul 4	16800659
Weak first-order tilting transition in monolayers of mono- and bipolar docosanol derivatives.	2006 Nov 9	17078664
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
Single-day treatment for orolabial and genital herpes: a brief review of pathogenesis and pharmacology.	2008 Apr	18728852
[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
Comments on study of paw pad lesions in dogs.	2009 Sep 15	19751157
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
Nutritional bioactive components of wheat straw as affected by genotype and environment.	2010 Jan	19716291
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

Docosanol [WHO-DD]

Common Name

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

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