1-Docosanol: Difference between revisions
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{{drugbox |
{{drugbox |
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| verifiedrevid = 313188437 |
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| IUPAC_name = docosan-1-ol |
| IUPAC_name = docosan-1-ol |
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| synonyms = 1-Docosanol, ''n''-docosanol, docosyl alcohol, behenic alcohol, behenyl alcohol, Cachalot BE-22, Dehydag wax 22 (lanette), Emery 3304, Loxiol VPG 1451 |
| synonyms = 1-Docosanol, ''n''-docosanol, docosyl alcohol, behenic alcohol, behenyl alcohol, Cachalot BE-22, Dehydag wax 22 (lanette), Emery 3304, Loxiol VPG 1451 |
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| image = Docosan-1-ol.svg |
| image = Docosan-1-ol.svg |
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| CASNo_Ref = {{cascite}} |
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| CAS_number = 661-19-8 |
| CAS_number = 661-19-8 |
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| ATC_prefix = D06 |
| ATC_prefix = D06 |
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| routes_of_administration = [[Topical]] |
| routes_of_administration = [[Topical]] |
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'''Docosanol''', also known as '''behenyl alcohol''', is a [[saturation (chemistry)|saturated]] [[fatty alcohol]]<ref name="pmid1660151">{{cite journal |author=Katz DH, Marcelletti JF, Khalil MH, Pope LE, Katz LR |title=Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=88 |issue=23 |pages=10825–9 |year=1991 |month=December |pmid=1660151 |pmc=53024 |doi= |url=http://www.pnas.org/cgi/pmidlookup?view=long&pmid=1660151}}</ref> used mainly as an [[Antiviral drug|antiviral agent]], specifically for treatment of "[[Herpes simplex|cold sores]]" caused by the ''[[herpes simplex virus]]''. It is normally administered topically in a cream containing a base and a 10% mix of the active ingredient. |
'''Docosanol''', also known as ada'''behenyl alcohol''', is a [[saturation (chemistry)|saturated]] [[fatty alcohol]]<ref name="pmid1660151">{{cite journal |author=Katz DH, Marcelletti JF, Khalil MH, Pope LE, Katz LR |title=Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=88 |issue=23 |pages=10825–9 |year=1991 |month=December |pmid=1660151 |pmc=53024 |doi= |url=http://www.pnas.org/cgi/pmidlookup?view=long&pmid=1660151}}</ref> used mainly as an [[Antiviral drug|antiviral agent]], specifically for treatment of "[[Herpes simplex|cold sores]]" caused by the ''[[herpes simplex virus]]''. It is normally administered topically in a cream containing a base and a 10% mix of the active ingredient. |
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==Mechanism== |
==Mechanism== |
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Revision as of 05:12, 14 October 2009
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| Clinical data | |
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| Other names | 1-Docosanol, n-docosanol, docosyl alcohol, behenic alcohol, behenyl alcohol, Cachalot BE-22, Dehydag wax 22 (lanette), Emery 3304, Loxiol VPG 1451 |
| Routes of administration | Topical |
| ATC code | |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | Not absorbed |
| Metabolism | N/A |
| Elimination half-life | N/A |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| DrugBank | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.010.498 |
| Chemical and physical data | |
| Formula | C22H46O |
| Molar mass | 326.6 g/mol g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 71 °C (160 °F) |
| Boiling point | 180 °C (356 °F) |
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| (verify) | |
Docosanol, also known as adabehenyl alcohol, is a saturated fatty alcohol[1] used mainly as an antiviral agent, specifically for treatment of "cold sores" caused by the herpes simplex virus. It is normally administered topically in a cream containing a base and a 10% mix of the active ingredient.
Mechanism
The proposed mechanism of action is by inhibiting the fusion of the human host cell with the viral envelope of the herpes virus, thus preventing its replication.
History
Docosanol was approved for use after clinical trials by the U.S. Food and Drug Administration in July 2000.[2] 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.[3] Three other trials showed negative results, but these were not published.[4]
Marketed by Avanir Pharmaceuticals under the brand name Abreva, it 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 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.[5]
See also
References
- ^ Katz DH, Marcelletti JF, Khalil MH, Pope LE, Katz LR (1991). "Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex". Proc. Natl. Acad. Sci. U.S.A. 88 (23): 10825–9. PMC 53024. PMID 1660151.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ "Drug Name: ABREVA (docosanol) - approval". centerwatch.com. July 2000. Retrieved 2007-10-17.
- ^ Sacks, SL. "Clinical efficacy of topical docosanol 10% cream for herpes simplex labialis: A multicenter, randomized, placebo-controlled trial". 45 (2). J Am Acad Dermatol: 222–230.
{{cite journal}}: Cite journal requires|journal=(help) - ^ Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2008/2009
- ^ "California Court Upholds Settlement Of Class Action Over Cold Sore Medicationl". BNA Inc. July 2000. Retrieved 2007-10-17.
http://www.medilexicon.com/drugs/abreva.php
