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
1-Docosanol
Behenic alcohol
Behenyl alcohol
Docosan-1-ol
Docosanol
Docosyl alcohol
N-Docosanol
External IDs IK-2 / Lanette 22
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AbrevaCream10 %TopicalGlaxosmithkline Inc2005-08-15Not applicableCanada
AbrevaCream100 mg/gTopicalGlaxo Smith Kline Consumer Healthcare Holdings (Us) Llc2010-03-19Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
BlistexDDD
ErazabanHealthcare
HealipAco Hud
LafrostIncepta
Brand mixturesNot Available
Categories
UNII9G1OE216XY
CAS number661-19-8
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
Pharmacology
Indication

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

Structured Indications
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Envelope glycoprotein GP350Proteinyes
intercalation
HHV-4P03200 details
Envelope glycoprotein GP340Proteinunknown
intercalation
HHV-4P68344 details
Related Articles
Absorption

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

Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

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

Affected organisms
  • Herpes simplex virus
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions No interactions found.
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesD06BB11 — Docosanol
AHFS Codes
  • 84:04.06
PDB EntriesNot Available
FDA labelDownload (622 KB)
MSDSDownload (59.7 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentReccurent Herpes Labialis1
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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2156063 No1999-06-292019-06-29Canada
CA2421026 No2005-02-152022-10-15Canada
US4874794 No1994-04-282014-04-28Us
US5534554 No1993-12-132013-12-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)65-72 °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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8798
CYP450 2D6 inhibitorNon-inhibitor0.9262
CYP450 2C19 inhibitorNon-inhibitor0.933
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-9404000000-07035644854a3aadee15View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0a4l-9000000000-809da2804db4c444826eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0910000000-57263f402e03ec3b6118View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0910000000-8019512337243ed50237View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0292000000-dcde24f71302487910abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03e9-0392000000-bc888101b8e5bdc1433cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a5c-9100000000-e4725e578cce9e0d56c9View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
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 ParentsPrimary alcohols / Hydrocarbon derivatives
SubstituentsFatty alcohol / Organic oxygen compound / Hydrocarbon derivative / Primary alcohol / Organooxygen compound / Alcohol / Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptorslong-chain primary fatty alcohol, fatty alcohol 22:0 (CHEBI:31000 ) / Fatty alcohols (LMFA05000008 ) / a long-chain alcohol, a primary alcohol, a fatty alcohol (CPD-7845 )

Targets

Kind
Protein
Organism
HHV-4
Pharmacological action
yes
Actions
intercalation
General Function:
Not Available
Specific Function:
Initiates virion attachment to host B-lymphocyte cell, leading to virus entry. Acts by binding to host CR2 at the surface of B-lymphocytes, facilitating the binding of viral glycoprotein gp42 to HLA class II molecules. Attachment triggers virion-host membrane fusion and invasion of the host cell.
Gene Name:
Not Available
Uniprot ID:
P03200
Molecular Weight:
94430.75 Da
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:17139284 ]
  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:17016423 ]
  3. Treister NS, Woo SB: Topical n-docosanol for management of recurrent herpes labialis. Expert Opin Pharmacother. 2010 Apr;11(5):853-60. doi: 10.1517/14656561003691847. [PubMed:20210688 ]
  4. Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. [PubMed:15571473 ]
  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:9864049 ]
Kind
Protein
Organism
HHV-4
Pharmacological action
unknown
Actions
intercalation
General Function:
Not Available
Specific Function:
Responsible for EBV binding to the CR2 receptor on human B-cells.
Gene Name:
Not Available
Uniprot ID:
P68344
Molecular Weight:
92387.715 Da
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:17139284 ]
  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:17016423 ]
  3. Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. [PubMed:15571473 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:51