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| Names | |
|---|---|
| Preferred IUPAC name Docosan-1-ol[1] | |
Other names
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| Identifiers | |
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3D model (JSmol) | |
| 1770470 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank |
|
| ECHA InfoCard | 100.010.498 |
| EC Number |
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| KEGG |
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| MeSH | docosanol |
| RTECS number |
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| UNII | |
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| 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 |
| logP | 10.009 |
| Pharmacology | |
| D06BB11 (WHO) | |
| Topical | |
| Legal status | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1-Docosanol, also known asbehenyl alcohol, is asaturatedfatty alcohol containing 22 carbon atoms, used traditionally as anemollient,emulsifier, and thickener in cosmetics.[6]
In July 2000, docosanol was approved for medical use in the United States as anantiviral agent for reducing the duration ofcold sores.[3][4][7] It is anover-the-counter medication (OTC). It is sold under the brand nameAbreva among others.[3][5][8][9]
One of the most common side effects that has been reported from docosanol isheadache. 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 withplacebo.[8]
The most serious side effects, although rare, are allergic reactions. Some of the patients experienced the symptoms of allergic reactions, includingdifficulty breathing,confusion,angioedema (facial swelling),fainting,dizziness,hives orchest pain.[10]
Other side effects may include:acne, burning, dryness,itching,rash, redness, acutediarrhea,soreness, swelling.[11]
Docosanol is thought to work by interfering with and stabilizing the host cell's surface phospholipids, preventing the fusion of the herpes virus'sviral envelope with the human host cell. This disrupted ability of the virus to fuse with the host cell membrane prevents entry and subsequentreplication.[12][8][13]
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]
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]
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.
