DrugBank: Docosanol (DB00632)

targets (2)

Identification

Name

Docosanol

Accession Number

DB00632 (APRD00933)

Type

small molecule

Groups

approved

Description

Docosanol is a drug used for topical treatment for recurrent herpes simplex labialis episodes (episodes of cold sores or fever blisters). A saturated 22-carbon aliphatic alcohol, docosanol exhibits antiviral activity against many lipid enveloped viruses including herpes simplex virus (HSV). Docosanol inhibits fusion between the plasma membrane and the herpes simplex virus (HSV) envelope, thereby preventing viral entry into cells and subsequent viral replication.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Behenyl alcohol

Salts

Not Available

Brand names

Name	Company
Abreva

Brand mixtures

Not Available

Categories

Antiviral Agents
Dermatologicals

CAS number

30303-65-2

Weight

Average: 326.6
Monoisotopic: 326.354866094

Chemical Formula

C₂₂H₄₆O

InChI Key

InChIKey=NOPFSRXAKWQILS-UHFFFAOYSA-N

InChI

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

Plain Text

IUPAC Name

docosan-1-ol

SMILES

CCCCCCCCCCCCCCCCCCCCCCO

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Alcohols and Polyols

Substructures

Hydroxy Compounds
Alcohols and Polyols

Pharmacology

Indication

For the topical treatment of recurrent oral-facial herpes simplex episodes (cold sores or fever blisters).

Pharmacodynamics

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 cannot, however, prevent cold sores or fever blisters from appearing.

Mechanism of action

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.

Absorption

Topical absorption has been shown to be minimal under conditions reflecting normal clinical use.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Symptoms of overdose include headache, abdominal pain, increased serum lipase, nausea, dyspepsia, dizziness, and hyperbilirubinemia.

Affected organisms

Herpes simplex virus

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Glaxosmithkline

Packagers

GlaxoSmithKline Inc.

Dosage forms

Form	Route	Strength
Cream	Topical

Prices

Unit description	Cost	Unit
Abreva 10% cream	7.57 USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Country	Patent Number	Approved	Expires (estimated)
United States	4874794	1994-04-28	2014-04-28
United States	5534554	1993-12-13	2013-12-13
Canada	2421026	2005-02-15	2022-10-15
Canada	2156063	1999-06-29	2019-06-29

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	65-72 °C	Not Available
logP	9	Not Available

Predicted Properties

Property	Value	Source
water solubility	1.96e-05 g/l	ALOGPS
logP	9.31	ALOGPS
logP	8.81	ChemAxon
logS	-7.2	ALOGPS
pKa (strongest acidic)	16.84	ChemAxon
pKa (strongest basic)	-2	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	1	ChemAxon
hydrogen donor count	1	ChemAxon
polar surface area	20.23	ChemAxon
rotatable bond count	20	ChemAxon
refractivity	104.95	ChemAxon
polarizability	47.27	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	12620
PubChem Substance	46508049
ChemSpider	12100
ChEBI	31000
ChEMBL	31000
Therapeutic Targets Database	DAP001249
PharmGKB	PA164749211
Drug Product Database	2245677
Drugs.com	http://www.drugs.com/cdi/docosanol.html
Wikipedia	http://en.wikipedia.org/wiki/Docosanol

ATC Codes

D06BB11

AHFS Codes

84:04.06

PDB Entries

Not Available

FDA label

show (622 KB)

MSDS

show (59.7 KB)

Interactions

Drug Interactions

Searched, but no interactions found.

Food Interactions

Not Available

Targets
1. Envelope glycoprotein GP340/GP220 Pharmacological action: yes Actions: intercalation Responsible for EBV binding to the CR2 receptor on human B-cells Organism class: viral UniProt ID: P03200 Gene: BLLF1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Treister NS, Woo SB: Topical n-docosanol for management of recurrent herpes labialis. Expert Opin Pharmacother. 2010 Apr;11(5):853-60. Pubmed Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. Pubmed Pope LE, Marcelletti JF, Katz LR, Lin JY, Katz DH, Parish ML, Spear PG: The anti-herpes simplex virus activity of n-docosanol includes inhibition of the viral entry process. Antiviral Res. 1998 Dec;40(1-2):85-94. Pubmed 2. Envelope glycoprotein GP340 Pharmacological action: unknown Actions: intercalation Responsible for EBV binding to the CR2 receptor on human B-cells Organism class: viral UniProt ID: P68344 Gene: BLLF1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. Pubmed

Targets

1. Envelope glycoprotein GP340/GP220

Pharmacological action: yes
Actions: intercalation

Responsible for EBV binding to the CR2 receptor on human B-cells

Organism class: viral
UniProt ID: P03200 Link_out

Gene: BLLF1
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Treister NS, Woo SB: Topical n-docosanol for management of recurrent herpes labialis. Expert Opin Pharmacother. 2010 Apr;11(5):853-60. Pubmed
Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. Pubmed
Pope LE, Marcelletti JF, Katz LR, Lin JY, Katz DH, Parish ML, Spear PG: The anti-herpes simplex virus activity of n-docosanol includes inhibition of the viral entry process. Antiviral Res. 1998 Dec;40(1-2):85-94. Pubmed

2. Envelope glycoprotein GP340

Pharmacological action: unknown
Actions: intercalation

Responsible for EBV binding to the CR2 receptor on human B-cells

Organism class: viral
UniProt ID: P68344 Link_out

Gene: BLLF1
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19