1-Docosanol

1-Docosanol
Skeletal formula of docosanol
Spacefill model of docosanol
Names
Preferred 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
CAS Number
3D model (JSmol)
Beilstein Reference
 1770470
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 211-546-6
KEGG
MeSH docosanol
PubChem CID
RTECS number
  • JR1315000
UNII
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 checkY
    Key: NOPFSRXAKWQILS-UHFFFAOYSA-N checkY
  • 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
SMILES
  • CCCCCCCCCCCCCCCCCCCCCCO
Properties
Chemical formula
 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)
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 checkY☒N ?)
Infobox references

1-Docosanol, (Docosonal) also known as behenyl alcohol, is a saturated fatty alcohol containing 22 carbon atoms, used traditionally as an emollient, emulsifier, and thickener in cosmetics,[3] 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[4] for reducing the duration of cold sores caused by the herpes simplex virus in the OTC medication Abreva.[5] In Europe, this cream is available as Erazaban.[6]

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.[7] In clinical trials, headache occurred in 10.4% of people treated with docosanol cream and 10.7% of people treated with placebo.[6]

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.[7] 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.[8]

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[8] 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 because no interaction studies have been done.[6]

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.[6][9] 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.[10] 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.[11] Another trial showed no effect when treating the infected backs of guinea pigs.[12]

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.[12]

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.[13]

Society and culture

Cost

The medication in the U.S. has a cost of $21 (USD) for 2 grams of Docosanol topical solution[14]

  • Docosanol costs (US)
    Docosanol costs (US)
  • Docosanol prescriptions (US)
    Docosanol prescriptions (US)

See also

  • Behenic acid

References

  1. 1 2 3 4 "Docosan-1-ol (CHEBI:31000)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute. Archived from the original on 2014-08-04. Retrieved 2021-03-26.
  2. 1 2 3 "Chemical Book: 1-Docosanol". Archived from the original on 2013-06-30. Retrieved 2021-03-26.
  3. ↑ "CosIng: Behenyl alcohol". European Commission. Archived from the original on 2021-08-27. Retrieved 2021-03-14.
  4. ↑ 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. Bibcode:1991PNAS...8810825K. doi:10.1073/pnas.88.23.10825. PMC 53024. PMID 1660151. Archived from the original on 2021-08-27. Retrieved 2021-03-26.
  5. ↑ "mediLexicon: Docosanol". Archived from the original on 2013-03-10. Retrieved 2021-03-26.
  6. 1 2 3 4 Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Erazaban Creme.{{cite book}}: CS1 maint: unrecognized language (link)
  7. 1 2 "Abreva Side Effects". Livestrong.com. Archived from the original on 2010-05-23. Retrieved 2010-05-20.
  8. 1 2 "Side Effects". Drugs.com. Archived from the original on 2008-05-11. Retrieved 2010-05-20.
  9. ↑ Docosanol Monograph. Accessed 2021-03-14.
  10. ↑ "Drug Name: ABREVA (docosanol) – approval". centerwatch.com. July 2000. Archived from the original on 2008-10-06. Retrieved 2007-10-17.
  11. ↑ 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.
  12. 1 2 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.
  13. ↑ "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.
  14. ↑ "Docosanol topical Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 21 January 2021. Retrieved 28 March 2021.
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