Docosanol

Identification

Name
Docosanol
Accession Number
DB00632  (APRD00933)
Type
Small Molecule
Groups
Approved, 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
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AbrevaCream10 %TopicalGlaxosmithkline Inc2005-08-15Not applicableCanada
AbrevaCream100 mg/1gTopicalA-S Medication Solutions2010-03-19Not applicableUs
AbrevaCream100 mg/1gTopicalGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2010-03-19Not applicableUs
International/Other Brands
Blistex (DDD) / Erazaban (Healthcare) / Healip (Aco Hud) / Lafrost (Incepta)
Categories
UNII
9G1OE216XY
CAS number
661-19-8
Weight
Average: 326.6
Monoisotopic: 326.354866094
Chemical Formula
C22H46O
InChI Key
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
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).

Associated Conditions
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.

TargetActionsOrganism
AEnvelope glycoprotein GP350
intercalation
HHV-4
UEnvelope glycoprotein GP340
intercalation
HHV-4
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
No interactions found.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014770
PubChem Compound
12620
PubChem Substance
46508049
ChemSpider
12100
ChEBI
31000
ChEMBL
CHEMBL1200453
Therapeutic Targets Database
DAP001249
PharmGKB
PA164749211
Drugs.com
Drugs.com Drug Page
Wikipedia
Docosanol
ATC Codes
D06BB11 — Docosanol
AHFS Codes
  • 84:04.06 — Antivirals
FDA label
Download (622 KB)
MSDS
Download (59.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentReccurent Herpes Labialis1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline
Packagers
  • GlaxoSmithKline Inc.
Dosage forms
FormRouteStrength
CreamTopical10 %
CreamTopical100 mg/1g
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)
US4874794No1989-10-172014-04-28Us
US5534554No1996-07-092013-12-13Us
CA2421026No2005-02-152022-10-15Canada
CA2156063No1999-06-292019-06-29Canada

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-001i-9404000000-07035644854a3aadee15
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9000000000-809da2804db4c444826e
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-9404000000-07035644854a3aadee15
Mass Spectrum (Electron Ionization)MSsplash10-0a5c-9100000000-e4725e578cce9e0d56c9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0910000000-57263f402e03ec3b6118
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0910000000-8019512337243ed50237
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-001i-0292000000-dcde24f71302487910ab
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03e9-0392000000-bc888101b8e5bdc1433c
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty alcohols
Direct Parent
Fatty alcohols
Alternative Parents
Primary alcohols / Hydrocarbon derivatives
Substituents
Fatty alcohol / Organic oxygen compound / Hydrocarbon derivative / Primary alcohol / Organooxygen compound / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
long-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 HL...
Gene Name
Not Available
Uniprot ID
P03200
Uniprot Name
Envelope glycoprotein GP350
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
Uniprot Name
Envelope glycoprotein GP340
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 December 12, 2018 07:06