1-Docosanol

1-Docosanol
Skeletal formula of docosanol
Spacefill model of docosanol
Names
Preferred IUPAC name
Docosan-1-ol[1]
Other names
Identifiers
3D model (JSmol)
1770470
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.498 Edit this at Wikidata
EC Number
  • 211-546-6
KEGG
MeSH docosanol
RTECS number
  • JR1315000
UNII
  • 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
  • CCCCCCCCCCCCCCCCCCCCCCO
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)
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 ?)

1-Docosanol, also known as behenyl alcohol, is a saturated fatty alcohol containing 22 carbon atoms, used traditionally as an emollient, emulsifier, and thickener in cosmetics.[6]

In July 2000, docosanol was approved for medical use in the United States as an antiviral agent for reducing the duration of cold sores.[3][4][7] It is an over-the-counter medication (OTC). It is sold under the brand name Abreva among others.[3][5][8][9]

Side effects

One of the most common side effects that has been reported from docosanol is headache. Headaches caused by the medication tend to be mild and can occur in any region of the head.[10] In clinical trials, headache occurred in 10.4% of people treated with docosanol cream and 10.7% of people treated with placebo.[8]

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.[10]

Other side effects may include: acne, burning, dryness, itching, rash, redness, acute diarrhea, soreness, swelling.[11]

Mechanism of action

Docosanol is thought to work by interfering with and stabilizing the host cell's surface phospholipids, preventing the fusion of the herpes virus's viral envelope with the human host cell. This disrupted ability of the virus to fuse with the host cell membrane prevents entry and subsequent replication.[12][8][13]

History

The drug was approved as a cream for oral herpes after clinical trials by the FDA in July 2000.[4][14] 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.[15] Another trial showed no effect when treating the infected backs of guinea pigs.[16]

Two experiments with 1-docosanol cream failed to show statistically significant differences by any parameter between 1-docosanol cream and vehicle control–treated sites or between 1-docosanol and untreated infection sites.[16]

Society and culture

Controversy

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, instead stating "clinically proven to speed healing".[17]

References

  1. ^ a b c d "Docosan-1-ol (CHEBI:31000)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute. Archived from the original on 4 August 2014. Retrieved 26 July 2011.
  2. ^ a b c "Chemical Book: *1-Docosanol". Archived from the original on 30 June 2013. Retrieved 26 July 2011.
  3. ^ a b c "Abreva- docosanol cream". DailyMed. 18 April 2022. Archived from the original on 14 October 2022. Retrieved 14 October 2022.
  4. ^ a b c "Drug Approval Package: Abreva (Docosanol) NDA #20-941". U.S. Food and Drug Administration (FDA). 21 August 2001. Archived from the original on 14 October 2022. Retrieved 13 October 2022.
  5. ^ a b "List of nationally authorised medicinal products" (PDF). ema.europa.eu. European Medicines Agency. 2 December 2021. Archived (PDF) from the original on 15 October 2022. Retrieved 23 October 2022.
  6. ^ "CosIng: Behenyl alcohol". European Commission. Archived from the original on 27 August 2021. Retrieved 14 March 2021.
  7. ^ 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.
  8. ^ a b c Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Erazaban Creme.
  9. ^ "mediLexicon: Docosanol". Archived from the original on 10 March 2013. Retrieved 2 September 2008.
  10. ^ a b "Abreva Side Effects". Livestrong.com. Archived from the original on 23 May 2010. Retrieved 20 May 2010.
  11. ^ "Side Effects". Drugs.com. Archived from the original on 11 May 2008. Retrieved 20 May 2010.
  12. ^ Sadowski LA, Upadhyay R, Greeley ZW, Margulies BJ (June 2021). "Current Drugs to Treat Infections with Herpes Simplex Viruses-1 and -2". Viruses. 13 (7): 1228. doi:10.3390/v13071228. PMC 8310346. PMID 34202050. n-Docosanol is a long-chain, 22-carbon, primary alcohol offered over the counter. It likely inhibits a broad range of enveloped viruses that uncoat at the plasma membrane of target cells. The drug appears to prevent binding and entry of HSVs by interfering directly with the cell surface phospholipids, which are required by the viruses for entry, and stabilizing them. This activity tends to work well against ACV-resistant HSVs and can even act synergistically with other anti-HSV drugs.
  13. ^ Docosanol Monograph. Accessed 14 March 2021.
  14. ^ "Drug Name: Abreva (docosanol) – approval". centerwatch.com. July 2000. Archived from the original on 6 October 2008. Retrieved 17 October 2007.
  15. ^ 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.
  16. ^ a b 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.
  17. ^ "California Court Upholds Settlement Of Class Action Over Cold Sore Medicationl". BNA Inc. July 2000. Archived from the original on 5 February 2008. Retrieved 17 October 2007.