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Identification
NameDocosanol
Accession NumberDB00632  (APRD00933)
TypeSmall Molecule
GroupsApproved, Investigational
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
Thumb
Synonyms
SynonymLanguageCode
1-DocosanolNot AvailableNot Available
AbrevaNot AvailableNot Available
Behenic alcoholNot AvailableIS
Behenyl alcoholNot AvailableINCI
Docosan-1-olNot AvailableIS
DocosanolFrench/GermanINN
Docosyl alcoholNot AvailableIS
N-DocosanolNot AvailableNot Available
TadenanNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abrevacream100 mg/gtopicalGlaxo Smith Kline Consumer Healthcare Lp2010-03-19Not AvailableUs
Abrevacream10 %topicalGlaxosmithkline Consumer Healthcare Inc.Not AvailableNot AvailableCanada
International Brands
NameCompany
BlistexDDD
ErazabanHealthcare
HealipAco Hud
LafrostIncepta
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number30303-65-2
WeightAverage: 326.6
Monoisotopic: 326.354866094
Chemical FormulaC22H46O
InChI KeyNOPFSRXAKWQILS-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
IUPAC Name
docosan-1-ol
SMILES
CCCCCCCCCCCCCCCCCCCCCCO
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationFor the topical treatment of recurrent oral-facial herpes simplex episodes (cold sores or fever blisters).
PharmacodynamicsDocosanol 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 actionDocosanol 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.
AbsorptionTopical absorption has been shown to be minimal under conditions reflecting normal clinical use.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include headache, abdominal pain, increased serum lipase, nausea, dyspepsia, dizziness, and hyperbilirubinemia.
Affected organisms
  • Herpes simplex virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9947
Blood Brain Barrier+0.9579
Caco-2 permeable+0.7688
P-glycoprotein substrateNon-substrate0.618
P-glycoprotein inhibitor INon-inhibitor0.9201
P-glycoprotein inhibitor IINon-inhibitor0.9092
Renal organic cation transporterNon-inhibitor0.8735
CYP450 2C9 substrateNon-substrate0.7931
CYP450 2D6 substrateNon-substrate0.8437
CYP450 3A4 substrateNon-substrate0.7094
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 substrateNon-inhibitor0.8798
CYP450 2D6 substrateNon-inhibitor0.9262
CYP450 2C19 substrateNon-inhibitor0.933
CYP450 3A4 substrateNon-inhibitor0.9142
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8928
Ames testNon AMES toxic0.9872
CarcinogenicityNon-carcinogens0.5579
BiodegradationReady biodegradable0.8849
Rat acute toxicity1.5561 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8578
hERG inhibition (predictor II)Non-inhibitor0.7525
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
Packagers
Dosage forms
FormRouteStrength
Creamtopical10 %
Creamtopical100 mg/g
Prices
Unit descriptionCostUnit
Abreva 10% cream7.57USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada21560631999-06-292019-06-29
Canada24210262005-02-152022-10-15
United States48747941994-04-282014-04-28
United States55345541993-12-132013-12-13
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point65-72 °CNot Available
logP9Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.96e-05 mg/mLALOGPS
logP9.31ALOGPS
logP8.81ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity104.95 m3·mol-1ChemAxon
Polarizability47.27 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS1D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesD06BB11
AHFS Codes
  • 84:04.06
PDB EntriesNot Available
FDA labelDownload (622 KB)
MSDSDownload (59.7 KB)
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. Envelope glycoprotein GP350

Kind: protein

Organism: HHV-4

Pharmacological action: yes

Actions: intercalation

Components

Name UniProt ID Details
Envelope glycoprotein GP350 P03200 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Treister NS, Woo SB: Topical n-docosanol for management of recurrent herpes labialis. Expert Opin Pharmacother. 2010 Apr;11(5):853-60. Pubmed
  4. Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. Pubmed
  5. 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

Kind: protein

Organism: HHV-4

Pharmacological action: unknown

Actions: intercalation

Components

Name UniProt ID Details
Envelope glycoprotein GP340 P68344 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11