1-Docosanol

October 2022 changed changed 419109485 Docosan-1-ol.svg skin-invert-image correct ?? 244 Skeletal formula of docosanol Docosanol-3D-vdW rotated.png bg-transparent correct ?? 244 Spacefill model of docosanol Docosan-1-ol http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31000 Docosan-1-ol (CHEBI:31000) Chemical Entities of Biological Interest (ChEBI) UK European Bioinformatics Institute 26 July 2011 4 August 2014 https://web.archive.org/web/20140804191939/http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31000 live Behenic alcohol Behenyl alcohol Cachalot BE-22 July 2011 1-Docosanolhttp://www.chemicalbook.com/ChemicalProductProperty_EN_CB6219657.htm Chemical Book: *1-Docosanol 26 July 2011 30 June 2013 https://web.archive.org/web/20130630073150/http://www.chemicalbook.com/ChemicalProductProperty_EN_CB6219657.htm live n-Docosanol Docosyl alcohol Emery 3304 Loxiol VPG 1451 July 2011 661-19-8 correct CAS 12620 12100 correct chemspider 9G1OE216XY correct FDA 211-546-6 correct drugbank DB00632 D03884 correct kegg docosanol correct EBI 31000 1200453 changed EBI JR1315000 1770470 CCCCCCCCCCCCCCCCCCCCCCO 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 correct chemspider 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 NOPFSRXAKWQILS-UHFFFAOYSA-N correct chemspider NOPFSRXAKWQILS-UHFFFAOYAB 22 46 1 343 453 at 29 Pa 10.009 D06 BB11 OTC Abreva- docosanol cream DailyMed 18 April 2022 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=bf02c8c5-af60-41f1-a202-38a97491a720 14 October 2022 14 October 2022 https://web.archive.org/web/20221014040530/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=bf02c8c5-af60-41f1-a202-38a97491a720 live Drug Approval Package: Abreva (Docosanol) NDA #20-941 U.S. Food and Drug Administration (FDA) 21 August 2001 https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-941_Abreva.cfm 13 October 2022 14 October 2022 https://web.archive.org/web/20221014040518/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-941_Abreva.cfm live Rx-only List of nationally authorised medicinal products https://www.ema.europa.eu/en/documents/psusa/docosanol-list-nationally-authorised-medicinal-products-psusa/00010092/202104_en.pdf ema.europa.eu European Medicines Agency 23 October 2022 https://web.archive.org/web/20221015233411/https://www.ema.europa.eu/en/documents/psusa/docosanol-list-nationally-authorised-medicinal-products-psusa/00010092/202104_en.pdf 15 October 2022 en 2 December 2021 live Topical 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.https://ec.europa.eu/growth/tools-databases/cosing/?fuseaction=search.details_v2&id=74589 CosIng: Behenyl alcohol European Commission 14 March 2021 27 August 2021 https://web.archive.org/web/20210827200639/https://ec.europa.eu/growth/tools-databases/cosing/?fuseaction=search.details_v2&id=74589 live In July 2000, docosanol was approved for medical use in the United States as an antiviral agent for reducing the duration of cold sores.Katz DH, Marcelletti JF, Khalil MH, Pope LE, Katz LR 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 December 1991 1660151 53024 10.1073/pnas.88.23.10825 1991PNAS...8810825K free It is an over-the-counter medication (OTC). It is sold under the brand name Abreva among others.http://www.medilexicon.com/drugs/abreva.php mediLexicon: Docosanol 2 September 2008 10 March 2013 https://web.archive.org/web/20130310114409/http://www.medilexicon.com/drugs/abreva.php dead 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.http://www.livestrong.com/article/112151-abreva-side-effects/ Livestrong.com Abreva Side Effects 20 May 2010 23 May 2010 https://web.archive.org/web/20100523015616/http://www.livestrong.com/article/112151-abreva-side-effects/ live In clinical trials, headache occurred in 10.4% of people treated with docosanol cream and 10.7% of people treated with placebo. 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. Other side effects may include: acne, burning, dryness, itching, rash, redness, acute diarrhea, soreness, swelling.https://www.drugs.com/cons/docosanol-topical.html/ Drugs.com Side Effects 2010-05-20 11 May 2008 https://web.archive.org/web/20080511134513/http://www.drugs.com/cons/docosanol-topical.html live 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.Sadowski LA, Upadhyay R, Greeley ZW, Margulies BJ Current Drugs to Treat Infections with Herpes Simplex Viruses-1 and -2 Viruses 13 7 June 2021 1228 34202050 8310346 10.3390/v13071228 free 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.Austria-Codex Haberfeld H Erazaban Creme Österreichischer Apothekerverlag Vienna 2020 GermanDocosanol monograph docosanol. Accessed 14 March 2021. History The drug was approved as a cream for oral herpes after clinical trials by the FDA in July 2000. 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.Sacks SL 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 11464183 10.1067/mjd.2001.116215 2001 Thisted RA Jones TM Barbarash RA Mikolich DJ Ruoff GE Jorizzo JL Gunnill LB Katz DH Khalil MH Morrow Phillip R. Yakatan Gerald J. Pope Laura E. Berga James E. 8 Another trial showed no effect when treating the infected backs of guinea pigs. McKeough MB Spruance SL 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 2001 11559210 10.1001/archderm.137.9.1153 free 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. 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". California Court Upholds Settlement Of Class Action Over Cold Sore Medicationl BNA Inc. July 2000 http://subscript.bna.com/SAMPLES/plp.nsf/85256269004a991e8525611300214487/29d5bb623a50fd25852572ad0074f772?OpenDocument 17 October 2007 https://web.archive.org/web/20080205070115/http://subscript.bna.com/SAMPLES/plp.nsf/85256269004a991e8525611300214487/29d5bb623a50fd25852572ad0074f772?OpenDocument 5 February 2008 References Medicine Category:Antiviral drugs Category:Fatty alcohols Category:Primary alcohols Category:Drugs developed by GSK plc Category:Alkanols Category:Over-the-counter drugs in the United States