Docosanol

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Docosanol
Systematic (IUPAC) name
docosan-1-ol
Identifiers
CAS number 661-19-8
ATC code D06BB11
PubChem 12620
DrugBank APRD00933
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
Excretion  ?
Therapeutic considerations
Pregnancy cat.

B(US)
Legal status

OTC(US)
Routes Topical

Docosanol, also known as behenyl alcohol, is a saturated fatty alcohol[1] used mainly as an antiviral agent, specifically for treatment of "cold sores" caused by the herpes simplex virus. It is normally administered topically in a cream containing a base and a 10% mix of the active ingredient.

Contents

[edit] Mechanism

The proposed mechanism of action is by inhibiting the fusion of the human host cell with the viral envelope of the herpes virus, thus preventing its replication.

[edit] History

Docosanol was approved for use after clinical trials by the U.S. Food and Drug Administration in July 2000.[2] 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.[3] Three other trials showed negative results, but these were not published.[4]

Marketed by Avanir Pharmaceuticals under the brand name Abreva, it 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.[5]

[edit] See also

[edit] 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. ^ "Drug Name: ABREVA (docosanol) - approval". centerwatch.com. July 2000. http://www.centerwatch.com/patient/drugs/dru627.html. Retrieved on 2007-10-17. 
  3. ^ 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. 
  4. ^ Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2008/2009
  5. ^ "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 on 2007-10-17. 

http://www.medilexicon.com/drugs/abreva.php

[edit] External links

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#WHO-EM. †Undergoing clinical trials, not FDA approved. ‡Withdrawn from market. §Development halted.
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