Docosanol

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

Docosanol
Names
Systematic IUPAC name
Docosan-1-ol[1]
Other names
Behenic alcohol[1]

Behenyl alcohol[1]
Cachalot BE-22
1-Docosanol[2]
n-Docosanol[2]
Docosyl alcohol[1]
Emery 3304[2]

Loxiol VPG 1451
Identifiers
3D model (JSmol)
1770470
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.498
EC Number
  • 211-546-6
KEGG
MeSH docosanol
RTECS number
  • JR1315000
UNII
Properties
C22H46O
Molar mass 326.609 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
D06BB11 (WHO)
  • US: B (No risk in non-human studies)
    Topical
    Legal status
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
    N verify (what is YN ?)
    Infobox references

    More recently, docosanol has been approved by the Food and Drug Administration (FDA) as a pharmaceutical antiviral agent[3] for reducing the duration of cold sores caused by the herpes simplex virus in the OTC medication Abreva.[4]

    Side effects

    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.[5] The intensity of the pain can, in some cases, interfere with the ability of remaining focused when working or when at school.

    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, angioedema (facial swelling), fainting, dizziness, hives or chest pain.[5] Allergic reactions are medical emergencies and individuals who experience them are advised 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.[6]

    Contraindications

    This topical has not been yet tested if it is safe to be used by pregnant women. It is not established whether the active ingredient in the medicine passes into the breast milk. Docosanol has not been specifically approved for treatment of children under 12[6] 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 not for genital herpes or shingles.

    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.

    Mechanism of action

    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.

    History

    The drug was approved as a cream for oral herpes after clinical trials by the FDA in July 2000.[7] 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.[8] Another trial showed no effect when treating the infected backs of guinea pigs.[9]

    Two experiments with n-docosanol cream failed to show statistically significant differences by any parameter between n-docosanol cream and vehicle control–treated sites or between n-docosanol and untreated infection sites.[9]

    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 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.[10]

    Society and culture

    When introduced in Canada in 2005 it sold for CA$6.12 per gram of 10% cream.[11] In the United States in 2019 this amount cost US$10.36.[12]

    gollark: That government would be a monopoly with basically the same problems.
    gollark: No, that would be really bad.
    gollark: (I know exactly 1.6km right now)
    gollark: Not as far as I know.
    gollark: No.

    See also

    References
    1. "Docosan-1-ol (CHEBI:31000)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
    2. 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): 10825–10829. doi:10.1073/pnas.88.23.10825. PMC 53024. PMID 1660151.
    4. mediLexicon: Docosanol
    5. "Abreva Side Effects". Livestrong.com. Retrieved 2010-05-20.
    6. "Side Effects". Drugs.com. Retrieved 2010-05-20.
    7. "Drug Name: ABREVA (docosanol) – approval". centerwatch.com. July 2000. Retrieved 2007-10-17.
    8. 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): 222–230. doi:10.1067/mjd.2001.116215. PMID 11464183.
    9. McKeough, MB; Spruance, SL (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. PMID 11559210.
    10. "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.
    11. "Report on New Patented Drugs - Abreva". pmprb-cepmb.gc.ca. 13 May 2014. Retrieved 25 November 2019.
    12. "Docosanol topical Prices, Coupons & Patient Assistance Programs". Drugs.com. Retrieved 25 November 2019.
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