Docosanol

Identification

Summary

Docosanol is an antiviral used to treat orofacial herpes sores.

Brand Names
Abreva
Generic Name
Docosanol
DrugBank Accession Number
DB00632
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 326.6
Monoisotopic: 326.354866094
Chemical Formula
C22H46O
Synonyms
  • 1-Docosanol
  • Behenic alcohol
  • Behenyl alcohol
  • Docosan-1-ol
  • Docosanol
  • Docosyl alcohol
  • N-Docosanol
External IDs
  • IK-2
  • Lanette 22

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofCold sores••• •••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
No interactions found.
Food Interactions
No interactions found.

Products

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International/Other Brands
Blistex (DDD) / Erazaban (Healthcare) / Healip (Aco Hud) / Lafrost (Incepta)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AbrevaCream10 %TopicalGlaxosmithkline Inc2005-08-15Not applicableCanada flag
AbrevaCream100 mg/1gTopicalHaleon US Holdings LLC2010-03-19Not applicableUS flag
AbrevaCream100 mg/1gTopicalHaleon US Holdings LLC2022-03-25Not applicableUS flag
AbrevaCream100 mg/1gTopicalA-S Medication Solutions2010-03-19Not applicableUS flag
Cold Sore Fever BlisterCream100 mg/1gTopicalH E B2023-12-31Not applicableUS flag

Categories

ATC Codes
D06BB11 — Docosanol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic acyclic compound / Fatty alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Primary alcohol
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)
Affected organisms
  • Herpes simplex virus

Chemical Identifiers

UNII
9G1OE216XY
CAS number
661-19-8
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

References

General References
  1. DailyMed: docosanol cream [Link]
Human Metabolome Database
HMDB0014770
PubChem Compound
12620
PubChem Substance
46508049
ChemSpider
12100
BindingDB
50239998
RxNav
594680
ChEBI
31000
ChEMBL
CHEMBL1200453
ZINC
ZINC000006920384
Therapeutic Targets Database
DAP001249
PharmGKB
PA164749211
Drugs.com
Drugs.com Drug Page
Wikipedia
1-Docosanol
FDA label
Download (622 KB)
MSDS
Download (59.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentReccurent Herpes Labialis1
2Enrolling by InvitationTreatmentOral Herpes Simplex1
2Unknown StatusTreatmentRecurrent Herpes Labialis1

Pharmacoeconomics

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

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-MSsplash10-002g-3980000000-1de3f264f616e9cd2e99
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-5009000000-a25d4e0b6dce61883a48
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-fdf3b2c3f2e52d3f7280
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9112000000-20f399a3efffa7959846
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-e0aec90f94a3a16d263f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kxu-4293000000-f9abed6eb426b621edfb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-97ac74c2c0d76529451f
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-229.8837766
predicted
DarkChem Lite v0.1.0
[M-H]-230.3945766
predicted
DarkChem Lite v0.1.0
[M-H]-229.7367766
predicted
DarkChem Lite v0.1.0
[M-H]-180.10338
predicted
DeepCCS 1.0 (2019)
[M+H]+230.7182766
predicted
DarkChem Lite v0.1.0
[M+H]+230.6885766
predicted
DarkChem Lite v0.1.0
[M+H]+230.2759766
predicted
DarkChem Lite v0.1.0
[M+H]+183.96567
predicted
DeepCCS 1.0 (2019)
[M+Na]+230.3146766
predicted
DarkChem Lite v0.1.0
[M+Na]+229.4045766
predicted
DarkChem Lite v0.1.0
[M+Na]+230.6985766
predicted
DarkChem Lite v0.1.0
[M+Na]+192.98418
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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. [Article]
  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. [Article]
  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. [Article]
  4. Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  3. Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48