Docosanol

Docosanol
Systematic name Docosan-1-ol[1]
Other names Behenic alcohol[1] Behenyl alcohol[1] Cachalot BE-22[citation needed] 1-Docosanol[2] n-Docosanol[2] Docosyl alcohol[1] Emery 3304[2] Loxiol VPG 1451[citation needed]
Identifiers
CAS number	661-19-8 Y
PubChem	12620
ChemSpider	12100 Y
UNII	9G1OE216XY Y
EC number	211-546-6
DrugBank	DB00632
KEGG	D03884 Y
MeSH	docosanol
ChEBI	CHEBI:31000 Y
ChEMBL	CHEMBL1200453 N
RTECS number	JR1315000
ATC code	D06BB11
Beilstein Reference	1770470
Jmol-3D images	Image 1
SMILES CCCCCCCCCCCCCCCCCCCCCCO
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 Y Key: NOPFSRXAKWQILS-UHFFFAOYSA-N Y InChI=1/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 Key: NOPFSRXAKWQILS-UHFFFAOYAB
Properties
Molecular formula	C22H46O
Molar mass	326.6 g mol−1
Exact mass	326.354866094 g mol-1
Melting point	70 °C, 343 K, 158 °F
Boiling point	180 °C, 453 K, 356 °F (at 29 Pa)
log P	10.009
Pharmacology
Routes of administration	Topical
Legal status	OTC(US)
Pregnancy category	B(US)
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Docosanol, also known as behenyl alcohol, is a saturated fatty alcohol^[3] used traditionally as an emollient, emulsifier, and thickener in cosmetics,^[4][5][6] nutritional supplement (as an individual entity and also as a constituent of polyicosanol), and more recently, in a Food and Drug Administration (FDA) approved pharmaceutical, Abreva,^[7] approved as an antiviral agent for reducing the duration of cold sores caused by the herpes simplex virus.

Mechanism and history of antiviral drug usage

The presumed mechanism of action in docosanol 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.

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] Three other trials showed negative results, but these were not published.^[10]

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.^[11]

Side effects

Side effects from the drug, if they occur, may go away during treatment as the body adjusts to it, otherwise a physician should be consulted.^[12]

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.^[13] If headaches develop while using the ointment, one is recommended to take an over-the-counter medication such as paracetamol to alleviate the pain.

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.^[13] 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^[12]

Contraindications

As soon as side effects develop, individuals must interrupt therapy and consult their medical care provider.

People who are allergic to one of the ingredients of Abreva are recommended 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 although there are no known specific interactions at this moment. Therefore, people who are taking other drugs are recommended to first consult their physician and then start the therapy.

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^[12] 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

• Behenic acid

References

1. ^ ^{a b c d} "Docosan-1-ol (CHEBI:31000)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute. http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31000. 
2. ^ ^{a b c} Chemical Book: 1-Docosanol
3. ^ 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. http://www.pnas.org/cgi/pmidlookup?view=long&pmid=1660151. 
4. ^ Fleur's Cosmetics Canada
5. ^ Korres USA
6. ^ Avalon Organics
7. ^ mediLexicon: Docosanol
8. ^ "Drug Name: ABREVA (docosanol) - approval". centerwatch.com. July 2000. http://www.centerwatch.com/patient/drugs/dru627.html. 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. ^ Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2008/2009
11. ^ "California Court Upholds Settlement Of Class Action Over Cold Sore Medicationl". BNA Inc.. July 2000. Archived from the original on 2008-02-05. http://web.archive.org/web/20080205070115/http://subscript.bna.com/SAMPLES/plp.nsf/85256269004a991e8525611300214487/29d5bb623a50fd25852572ad0074f772?OpenDocument. Retrieved 2007-10-17. 
12. ^ ^{a b c} "Side Effects". Drugs.com. http://www.drugs.com/cons/docosanol-topical.html/. Retrieved 2010-05-20. 
13. ^ ^{a b} "Abreva Side Effects". Livestrong.com. http://www.livestrong.com/article/112151-abreva-side-effects/. Retrieved 2010-05-20. 

External links

• Abreva
• Abreva adverse events reported to the FDA