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).
Reduce drug development failure ratesBuild, train, & validate machine-learning models
with evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Cold sores ••• ••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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.
Target Actions Organism AEnvelope glycoprotein GP350 intercalationHHV-4 UEnvelope glycoprotein GP340 intercalationHHV-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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Symptoms of overdose include headache, abdominal pain, increased serum lipase, nausea, dyspepsia, dizziness, and hyperbilirubinemia.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions. - International/Other Brands
- Blistex (DDD) / Erazaban (Healthcare) / Healip (Aco Hud) / Lafrost (Incepta)
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abreva Cream 100 mg/1g Topical Haleon US Holdings LLC 2022-03-25 Not applicable US Abreva Cream 100 mg/1g Topical Haleon US Holdings LLC 2010-03-19 Not applicable US Abreva Cream 100 mg/1g Topical A-S Medication Solutions 2010-03-19 Not applicable US Abreva Cream 10 % Topical Glaxosmithkline Inc 2005-08-15 Not applicable Canada Cold Sore Fever Blister Cream 100 mg/1g Topical The Kroger Co. 2020-07-01 Not applicable US
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
- DailyMed: docosanol cream [Link]
- External Links
- Human Metabolome Database
- HMDB0014770
- PubChem Compound
- 12620
- PubChem Substance
- 46508049
- ChemSpider
- 12100
- BindingDB
- 50239998
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Unknown Status Treatment Reccurent Herpes Labialis 1 2 Enrolling by Invitation Treatment Oral Herpes Simplex 1 2 Unknown Status Treatment Recurrent Herpes Labialis 1
Pharmacoeconomics
- Manufacturers
- Glaxosmithkline
- Packagers
- GlaxoSmithKline Inc.
- Dosage Forms
Form Route Strength Cream Topical 10 % Cream Topical 100 mg/1g Cream Topical - Prices
Unit description Cost Unit Abreva 10% cream 7.57USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US4874794 No 1989-10-17 2014-04-28 US US5534554 No 1996-07-09 2013-12-13 US CA2421026 No 2005-02-15 2022-10-15 Canada CA2156063 No 1999-06-29 2019-06-29 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 65-72 °C Not Available logP 9 Not Available - Predicted Properties
Property Value Source Water Solubility 1.96e-05 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 20 Chemaxon Refractivity 104.95 m3·mol-1 Chemaxon Polarizability 47.27 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9947 Blood Brain Barrier + 0.9579 Caco-2 permeable + 0.7688 P-glycoprotein substrate Non-substrate 0.618 P-glycoprotein inhibitor I Non-inhibitor 0.9201 P-glycoprotein inhibitor II Non-inhibitor 0.9092 Renal organic cation transporter Non-inhibitor 0.8735 CYP450 2C9 substrate Non-substrate 0.7931 CYP450 2D6 substrate Non-substrate 0.8437 CYP450 3A4 substrate Non-substrate 0.7094 CYP450 1A2 substrate Non-inhibitor 0.5 CYP450 2C9 inhibitor Non-inhibitor 0.8798 CYP450 2D6 inhibitor Non-inhibitor 0.9262 CYP450 2C19 inhibitor Non-inhibitor 0.933 CYP450 3A4 inhibitor Non-inhibitor 0.9142 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8928 Ames test Non AMES toxic 0.9872 Carcinogenicity Non-carcinogens 0.5579 Biodegradation Ready biodegradable 0.8849 Rat acute toxicity 1.5561 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8578 hERG inhibition (predictor II) Non-inhibitor 0.7525
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 229.8837766 predictedDarkChem Lite v0.1.0 [M-H]- 230.3945766 predictedDarkChem Lite v0.1.0 [M-H]- 229.7367766 predictedDarkChem Lite v0.1.0 [M-H]- 180.10338 predictedDeepCCS 1.0 (2019) [M+H]+ 230.7182766 predictedDarkChem Lite v0.1.0 [M+H]+ 230.6885766 predictedDarkChem Lite v0.1.0 [M+H]+ 230.2759766 predictedDarkChem Lite v0.1.0 [M+H]+ 183.96567 predictedDeepCCS 1.0 (2019) [M+Na]+ 230.3146766 predictedDarkChem Lite v0.1.0 [M+Na]+ 229.4045766 predictedDarkChem Lite v0.1.0 [M+Na]+ 230.6985766 predictedDarkChem Lite v0.1.0 [M+Na]+ 192.98418 predictedDeepCCS 1.0 (2019)
Targets
insights and accelerate drug research.
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- Leung DT, Sacks SL: Docosanol: a topical antiviral for herpes labialis. Expert Opin Pharmacother. 2004 Dec;5(12):2567-71. [Article]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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 February 20, 2024 23:55