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Docosanol
Systematic (IUPAC) name
docosan-1-ol
Identifiers
CAS number 661-19-8
ATC code D06BB11
PubChem 12620
DrugBank APRD00933
ChemSpider 12100
Chemical data
Formula C22H46O 
Mol. mass 326.6 g/mol
SMILES eMolecules & PubChem
Synonyms 1-Docosanol, n-docosanol, docosyl alcohol, behenic alcohol, behenyl alcohol, Cachalot BE-22, Dehydag wax 22 (lanette), Emery 3304, Loxiol VPG 1451
Physical data
Melt. point 71 °C (160 °F)
Boiling point 180 °C (356 °F)
Pharmacokinetic data
Bioavailability Not absorbed
Metabolism N/A
Half life N/A
Therapeutic considerations
Pregnancy cat. B(US)
Legal status OTC (US)
Routes Topical
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Docosanol, also known as behenyl alcohol, is a saturated fatty alcohol[1] used traditionally as an emollient, emulsifier, and thickener in cosmetics[2][3][4], nutritional supplement (as an individual entity and also as a constituent of polyicosanol), and more recently, in an FDA-approved pharmaceutical, Abreva[5], approved for reducing the duration of "cold sores" caused by the herpes simplex virus (see antiviral agent).

Contents

Mechanism and history of antiviral drug usage

The presumed mechanism of action in Abreva is by inhibiting the fusion of the human host cell with the viral envelope of the herpes virus, thus preventing its replication. This mechanism has neither been directly observed nor proven, however.

Abreva was licensed as an oral herpes medicine after clinical trials by the U.S. Food and Drug Administration in July 2000.[6] 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.[7] Three other trials showed negative results, but these were not published.[8]

Marketed by Avanir Pharmaceuticals, Abreva was the first 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 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.[9]

See also

References

  1. ^ 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. PMID 1660151.& PMC 53024. http://www.pnas.org/cgi/pmidlookup?view=long&pmid=1660151. 
  2. ^ http://fleur-s-cosmetics.stalgroup.com/
  3. ^ http://www.korresusa.com/product/4820/eye-cream/skincare/category/anti-aging-
  4. ^ http://www.avalonorganics.com/?id=124&show=B
  5. ^ mediLexicon: Docosanol
  6. ^ "Drug Name: ABREVA (docosanol) - approval". centerwatch.com. July 2000. http://www.centerwatch.com/patient/drugs/dru627.html. Retrieved 2007-10-17. 
  7. ^ Sacks, SL. Clinical efficacy of topical docosanol 10% cream for herpes simplex labialis: A multicenter, randomized, placebo-controlled trial. 45. J Am Acad Dermatol. pp. 222–230. 
  8. ^ Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2008/2009
  9. ^ "California Court Upholds Settlement Of Class Action Over Cold Sore Medicationl". BNA Inc.. July 2000. http://web.archive.org/web/20080205070115/http://subscript.bna.com/SAMPLES/plp.nsf/85256269004a991e8525611300214487/29d5bb623a50fd25852572ad0074f772?OpenDocument. Retrieved 2007-10-17. 

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