1-Docosanol, also known as behenyl alcohol, is a saturatedfatty alcohol containing 22 carbon atoms, used traditionally as an emollient, emulsifier, and thickener in cosmetics.[6]
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]
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.[8][12]
History
The drug was approved as a cream for oral herpes after clinical trials by the FDA in July 2000.[4][13] 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.[14] Another trial showed no effect when treating the infected backs of guinea pigs.[15]
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.[15]
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.[16]
References
^ abcd"Docosan-1-ol (CHEBI:31000)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute. from the original on 4 August 2014. Retrieved 26 July 2011.
^ abc"Chemical Book: 1-Docosanol". from the original on 30 June 2013. Retrieved 26 July 2011.
^ abc"Abreva- docosanol cream". DailyMed. 18 April 2022. from the original on 14 October 2022. Retrieved 14 October 2022.
^ abc"Drug Approval Package: Abreva (Docosanol) NDA #20-941". U.S. Food and Drug Administration (FDA). 21 August 2001. from the original on 14 October 2022. Retrieved 13 October 2022.
^ ab"List of nationally authorised medicinal products" (PDF). ema.europa.eu. European Medicines Agency. 2 December 2021. (PDF) from the original on 15 October 2022. Retrieved 23 October 2022.
^"CosIng: Behenyl alcohol". European Commission. from the original on 27 August 2021. Retrieved 14 March 2021.
^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. PMC53024. PMID 1660151.
docosanol, also, known, behenyl, alcohol, saturated, fatty, alcohol, containing, carbon, atoms, used, traditionally, emollient, emulsifier, thickener, cosmetics, namespreferred, iupac, name, docosan, other, names, behenic, alcohol, behenyl, alcohol, cachalot, . 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 1 Docosanol NamesPreferred IUPAC 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 IdentifiersCAS Number 661 19 8 Y3D model JSmol Interactive imageBeilstein Reference 1770470ChEBI CHEBI 31000 YChEMBL ChEMBL1200453 NChemSpider 12100 YDrugBank DB00632 YECHA InfoCard 100 010 498EC Number 211 546 6KEGG D03884 YMeSH docosanolPubChem CID 12620RTECS number JR1315000UNII 9G1OE216XY YCompTox Dashboard EPA DTXSID4027286InChI 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 YKey NOPFSRXAKWQILS UHFFFAOYSA N YInChI 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 1H3Key NOPFSRXAKWQILS UHFFFAOYABSMILES CCCCCCCCCCCCCCCCCCCCCCOPropertiesChemical formula C 22H 46OMolar mass 326 609 g mol 1Melting point 70 C 158 F 343 KBoiling point 180 C 356 F 453 K at 29 Palog P 10 009PharmacologyATC code D06BB11 WHO Routes ofadministration TopicalLegal status US OTC 3 4 EU Rx only 5 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 Contents 1 Side effects 2 Mechanism of action 3 History 4 Society and culture 4 1 Controversy 5 References 6 External linksSide effects EditOne 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 EditDocosanol 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 8 12 History EditThe drug was approved as a cream for oral herpes after clinical trials by the FDA in July 2000 4 13 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 14 Another trial showed no effect when treating the infected backs of guinea pigs 15 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 15 Society and culture EditControversy Edit 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 16 References Edit 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 a b c Chemical Book 1 Docosanol Archived from the original on 30 June 2013 Retrieved 26 July 2011 a b c Abreva docosanol cream DailyMed 18 April 2022 Archived from the original on 14 October 2022 Retrieved 14 October 2022 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 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 CosIng Behenyl alcohol European Commission Archived from the original on 27 August 2021 Retrieved 14 March 2021 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 a b c Haberfeld H ed 2020 Austria Codex in German Vienna Osterreichischer Apothekerverlag Erazaban Creme mediLexicon Docosanol Archived from the original on 10 March 2013 Retrieved 2 September 2008 a b Abreva Side Effects Livestrong com Archived from the original on 23 May 2010 Retrieved 20 May 2010 Side Effects Drugs com Archived from the original on 11 May 2008 Retrieved 20 May 2010 Docosanol Monograph Accessed 14 March 2021 Drug Name Abreva docosanol approval centerwatch com July 2000 Archived from the original on 6 October 2008 Retrieved 17 October 2007 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 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 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 External links Edit Docosanol Drug Information Portal U S National Library of Medicine Portal Medicine Retrieved from https en wikipedia org w index php title 1 Docosanol amp oldid 1135771365, wikipedia, wiki, book, books, library,
