Docosanol

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Docosanol
Skeletal formula of docosanol
Spacefill model of docosanol
Identifiers
CAS number 661-19-8 YesY
PubChem 12620
ChemSpider 12100 YesY
UNII 9G1OE216XY YesY
EC number 211-546-6
DrugBank DB00632
KEGG D03884 YesY
MeSH docosanol
ChEBI CHEBI:31000 YesY
ChEMBL CHEMBL1200453 N
RTECS number JR1315000
ATC code D06BB11
Beilstein Reference 1770470
Jmol-3D images Image 1
Properties
Molecular formula C22H46O
Molar mass 326.60 g mol−1
Melting point 70 °C; 158 °F; 343 K
Boiling point 180 °C; 356 °F; 453 K at 29 Pa
log P 10.009
Pharmacology
Routes of
administration
Topical
Legal status


OTC(US)

Pregnancy
category
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Docosanol, also known as behenyl alcohol, is a saturated fatty alcohol used traditionally as an emollient, emulsifier, and thickener in cosmetics,[3][4][5] and nutritional supplement (as an individual entity and also as a constituent of policosanol).

More recently, docosanol has been approved by the Food and Drug Administration (FDA) as a pharmaceutical antiviral agent[6] for reducing the duration of cold sores caused by the herpes simplex virus in the OTC medication Abreva.[7]

Mechanism and history of antiviral drug usage[edit]

Docosanol is thought to act by inhibiting the fusion of the human host cell with the viral envelope of the herpes virus, thus preventing its replication. This mechanism has not been demonstrated empirically.[citation needed]

The drug was licensed as an oral herpes medicine after clinical trials by the FDA in July 2000.[8] It was shown to shorten the healing by 17.5 hours on average (95% confidence interval: 2 to 22 hours) in a placebo-controlled trial.[9] Another trial showed no effect when treating the infected backs of guinea pigs.[10]

Marketed by Avanir Pharmaceuticals, Abreva was the first but not the only over-the-counter antiviral drug approved for sale in the United States and Canada. In Europe, it is marketed by Healthcare Brands under the name Erazaban. In the UK it is known by the name "Blistex Cold Sore Cream". In March 2007 it was the subject of a US nationwide class-action suit against Avanir and GlaxoSmithKline as the claim that it cut recovery times in half was found to have been misleading in a California court, but the case was eventually settled and the "cuts healing time in half" claim had not been used in product advertising for some years.[11]

Side effects[edit]

One of the most common side effects that has been reported from docosanol is headache. Headaches caused by the drug tend to be mild and can occur in any region of the head. The intensity of the pain can, in some cases, interfere with the ability of remaining focused when working or when at school.[12]

Skin irritation may also occur at the site of application. Usually, skin irritation is mild to moderate and does not need any further treatment. It may also diminish after prolonged use of docosanol.

The most serious side effects, although rare, are allergic reactions. Some of the patients experienced the symptoms of allergic reactions, including difficulty breathing, confusion, facial swelling, fainting, dizziness, hives or chest pain.[12] Allergic reactions are medical emergencies and individuals who experience them are recommended to seek immediate medical care in order to prevent further complications.

Other side effects may include: acne, burning, dryness, itching, rash, redness, acute diarrhea, soreness, swelling.[13]

Contraindications[edit]

People who are allergic to one of the ingredients of Abreva are advised to avoid taking this medication. Also, it is not to be used by individuals who suffer from different medical conditions before consulting their health care provider. Interactions with docosanol may occur.

This topical has not been yet tested if it is safe to be used by pregnant women. Also, people who are taking other over-the-counter drugs, supplements or herbal preparations are recommended to consult their doctor prior to starting therapy. Nursing mothers are advised to avoid using this topical as it is not established if the active ingredients in the medicine pass into the breast milk. People who are allergic to docosanol or any other ingredient of the product are strongly advised not to use it.

Cosmetic products are recommended to be avoided while using docosanol mainly because they are likely to spread the unhealed infection and not because they interact with the topical. Lipstick is not contraindicated but it is recommended to be applied by using a different applicator to prevent spreading of the infection and recurrence. Cosmetics must be removed before applying the ointment. Also, it is important to know that herpes is highly contagious during outbreaks and patients are advised to avoid physical contact with other people as well as sharing the medicine.

Docosanol has not been specifically approved for treatment of children under 12[13] but is not expected to produce different side effects or problems than it does in adults. This topical is only intended for external, oral-facial use and should not be administered with the purpose of curing genital herpes or shingles.

See also[edit]

References[edit]

  1. ^ a b c d "Docosan-1-ol (CHEBI:31000)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute. 
  2. ^ a b c Chemical Book: 1-Docosanol
  3. ^ Fleur's Cosmetics Canada
  4. ^ Korres USA
  5. ^ Avalon Organics
  6. ^ Katz DH, Marcelletti JF, Khalil MH, Pope LE, Katz LR (December 1991). "Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex". Proc. Natl. Acad. Sci. U.S.A. 88 (23): 10825–9. doi:10.1073/pnas.88.23.10825. PMC 53024. PMID 1660151. 
  7. ^ mediLexicon: Docosanol
  8. ^ "Drug Name: ABREVA (docosanol) - approval". centerwatch.com. July 2000. Retrieved 2007-10-17. 
  9. ^ Sacks, SL; Thisted, RA; Jones, TM; Barbarash, RA; Mikolich, DJ; Ruoff, GE; Jorizzo, JL; Gunnill, LB et al. (2001). "Clinical efficacy of topical docosanol 10% cream for herpes simplex labialis: A multicenter, randomized, placebo-controlled trial". J Am Acad Dermatol 45 (2): 222–30. doi:10.1067/mjd.2001.116215. PMID 11464183. 
  10. ^ McKeough, M. B.; Spruance, S. L. (2001). "Comparison of new topical treatments for herpes labialis: Efficacy of penciclovir cream, acyclovir cream, and n-docosanol cream against experimental cutaneous herpes simplex virus type 1 infection". Archives of dermatology 137 (9): 1153–1158. doi:10.1001/archderm.137.9.1153 (inactive 2014-08-12). PMID 11559210.  edit
  11. ^ "California Court Upholds Settlement Of Class Action Over Cold Sore Medicationl". BNA Inc. July 2000. Archived from the original on 2008-02-05. Retrieved 2007-10-17. 
  12. ^ a b "Abreva Side Effects". Livestrong.com. Retrieved 2010-05-20. 
  13. ^ a b "Side Effects". Drugs.com. Retrieved 2010-05-20. 

External links[edit]