1. 1-docosanol
2. Abreva
3. Behenyl Alcohol
4. Ik.2
1. 1-docosanol
2. Docosan-1-ol
3. Behenyl Alcohol
4. 661-19-8
5. Behenic Alcohol
6. N-docosanol
7. Abreva
8. Docosyl Alcohol
9. Tadenan
10. Lidavol
11. Stenol 1822
12. Lanette 22
13. Docosanol [usan]
14. Lidakol
15. Stenol 1822a
16. Nacol 22-97
17. Ik 2
18. 30303-65-2
19. Naa 422
20. Nsc 8407
21. Docosanol (abreua)
22. Docosanol (abreva)
23. Docosanol (usan)
24. Nsc-8407
25. 9g1oe216xy
26. Chebi:31000
27. Ncgc00159370-02
28. Docosanol (van)
29. Erazaban
30. Herepair
31. Ik.2
32. Healip
33. Cachalot Be-22
34. Abreva (tn)
35. Hsdb 5739
36. Loxiol Vpg 1451
37. Einecs 211-546-6
38. Brn 1770470
39. Unii-9g1oe216xy
40. Ai3-36489
41. Ccris 8943
42. N-docosan-1-ol
43. C22 Alcohol
44. Docosanol-(1)
45. Mfcd00002939
46. 1-docosanol, 98%
47. Docosanol [ii]
48. Docosanol [hsdb]
49. Docosanol [vandf]
50. Dsstox_cid_7286
51. N-docosanol [mi]
52. Docosanol [mart.]
53. Ec 211-546-6
54. Docosanol [who-dd]
55. Dsstox_rid_78387
56. Dsstox_gsid_27286
57. Schembl51925
58. 4-01-00-01906 (beilstein Handbook Reference)
59. Behenyl Alcohol [inci]
60. Docosanol [orange Book]
61. Chembl1200453
62. Dtxsid4027286
63. Nsc8407
64. Hms2093p22
65. Pharmakon1600-01505729
66. Hy-b0222
67. Zinc6920384
68. Tox21_111611
69. Lmfa05000008
70. Nsc759235
71. S1637
72. Akos015902887
73. Ccg-213539
74. Db00632
75. Nsc-759235
76. Behenyl Alcohol, Ai3-36489, Behenic Alcohol, 1-docosanol, Docosyl Alcohol, Ik-2, Tadenan
77. Ncgc00159370-03
78. Ncgc00159370-04
79. Ncgc00159370-05
80. 1-docosanol, Purum, >=97.0% (gc)
81. Ac-19852
82. Cas-661-19-8
83. Sbi-0206938.p001
84. A8416
85. Am20100601
86. D0964
87. Ft-0622609
88. D03884
89. D70615
90. Ab01563123_01
91. Ab01563123_02
92. Sr-05000001915
93. Q3033497
94. Sr-05000001915-1
95. A3d72d45-625e-49b5-b0fc-394010b3485d
| Molecular Weight | 326.6 g/mol |
|---|---|
| Molecular Formula | C22H46O |
| XLogP3 | 10.5 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 20 |
| Exact Mass | 326.354866087 g/mol |
| Monoisotopic Mass | 326.354866087 g/mol |
| Topological Polar Surface Area | 20.2 Ų |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Complexity | 190 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 2 | |
|---|---|
| Drug Name | Abreva |
| PubMed Health | Docosanol (On the skin) |
| Drug Classes | Antiviral |
| Active Ingredient | Docosanol |
| Dosage Form | Cream |
| Route | Topical |
| Strength | 10% |
| Market Status | Over the Counter |
| Company | Glaxosmithkline |
| 2 of 2 | |
|---|---|
| Drug Name | Abreva |
| PubMed Health | Docosanol (On the skin) |
| Drug Classes | Antiviral |
| Active Ingredient | Docosanol |
| Dosage Form | Cream |
| Route | Topical |
| Strength | 10% |
| Market Status | Over the Counter |
| Company | Glaxosmithkline |
Topical docosanol is indicated in the treatment of recurrent oral-facial herpes simplex (fever blisters or cold sores) in adults. /Included in US product labeling/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1236
Docosanol ... has been approved by the US FDA as a 10% ever-the-counter cream for treatment of recurrent orolabial herpes. Docosanol inhibits the in vitro replication of many lipid enveloped viruses, including HSV /(herpes simplex virus)/, at millimolar concentrations. It dose not directly inactivate HSV but appears to block fusion between the cellular and viral envelope membranes and inhibit viral entry into the cell. Topical treatment beginning within 12 hr of prodromal symptoms or lesion onset reduces healing time by about 1 day and appears to be well tolerated. Treatment initiation at papular or later stages provides no benefit. /Docosanol/
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1322
Therap cat: Antiviral (topical)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 598
Adverse effects occurring in 2% or more of patients receiving docosanol include headache (incidence similar to placebo), application site reaction (e.g., burning, stinging) (incidence similar to placebo), and herpes simplex outside the treatment area (incidence similar to placebo).
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3397
Docosanol 10% cream is recommended only for use on cold sores/fever blisters.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3397
FDA Pregnancy Risk Category: B /NO EVIDENCE OF RISK IN HUMANS. Adequate, well controlled studies in pregnant women have not shown increased risk of fetal abnormalities despite adverse findings in animals, or, in the absence of adequate human studies, animal studies show no fetal risk. The chance of fetal harm is remote but remains a possibility./
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1237
For the topical treatment of recurrent oral-facial herpes simplex episodes (cold sores or fever blisters).
FDA Label
Docosanol is a saturated 22-carbon aliphatic alcohol which exhibits antiviral activity against many lipid enveloped viruses including herpes simplex virus (HSV). Docosanol speeds the healing of cold sores and fever blisters on the face or lips. It also relieves the accompanying symptoms, including tingling, pain, burning, and itching. Docosanol cannot, however, prevent cold sores or fever blisters from appearing.
Antiviral Agents
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)
D06BB11
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
D - Dermatologicals
D06 - Antibiotics and chemotherapeutics for dermatological use
D06B - Chemotherapeutics for topical use
D06BB - Antivirals
D06BB11 - Docosanol
Absorption
Topical absorption has been shown to be minimal under conditions reflecting normal clinical use.
Absorption of docosanol has been shown to be minimal under conditions reflecting normal clinical use. Of 209 plasma samples taken from ten subjects 24 hours after a multi-day test, only one had a docosanol level above the quantitation limits (19 nanograms/mL).
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1236
Long chain alcohols were detected in developing rat brain at their highest level of 0.0109% of the total lipids at the age of 10 days and decreased to 0.0036% at the age of 40 days. They consited mainly of hexadecanol, octadecanol, octadecenol, eicosanol, docosanol, and tetracosanol.
Natarajan V, Schmid HH; Lipids 12 (1): 128-30 (1977)
A mixture of cis-9[1(-14)C] octadecenol and [1(-14)C] docosanol was injected into the brains of 19-day-old rats, and incorporation of radioactivity into brain lipids was determined after 3, 12, and 24 hr. Both alcohols were metabolized by the brain but at different rates; each was oxidized to the corresponding fatty acid, but oleic acid was more readily incorporated into polar lipids. Substantial amounts of radioactivity were incorporated into 18:1 alkyl and alk-1-enyl moieties of the ethanolamine phosphoglycerides and into 18:1 alkyl moieties of the choline phosphoglycerides. Even after the disappearance of the 18:1 alcohol from the substrate mixture (12 hr), the 22:0 alcohol was not used to any measurable extent for alkyl and alk-1-enylglycerol formation.
PMID:916829 Natarajan V, Schmid HH; Lipids 12 (10): 872-5 (1977)
The 22-carbon fatty alcohol, n-docosanol, exhibits in vitro antiviral activity against several lipid-enveloped viruses including herpes simplex viruses 1 and 2 by a mechanism that interferes with normal viral entry into target cells. We previously reported that mammalian cells incorporate significant quantities of radiolabeled n-docosanol. Herein, we report that cells extensively metabolize the internalized fatty alcohol. This is evidenced by incorporation of up to 60% of cell-associated radiolabel into phospholipids that copurify with phosphatidylcholine and phosphatidylethanolamine. Analysis by chemical (Vitride) reduction suggests that a significant portion of n-docosanol is oxidized to n-docosanoic acid and then incorporated as an acyl group on polar lipids. A measurable amount of radiolabel, however, is resistant to Vitride reduction, consistent with incorporation of n-docosanol into ether lipids. The rate and extent of metabolic conversion of n-docosanol vary with the cell type and surfactant used to suspend the compound. Furthermore, the anti-HSV activity of n-docosanol is quantitatively proportional to the amount of metabolism observed. These findings suggest that the anti-HSV activity of n-docosanol involves cellular uptake and metabolism of the drug.
PMID:8906594 Pope LE et al; J Lipid Res 37 (10): 2167-78 (1996)
A mixture of cis-9[1(-14)C] octadecenol and [1(-14)C] docosanol was injected into the brains of 19-day-old rats. Both alcohols were metabolized by the brain but at different rates; each was oxidized to the corresponding fatty acid. Substantial amounts of radioactivity were incorporated into 18:1 alkyl and alk-1-enyl moieties of the ethanolamine phosphoglycerides and into 18:1 alkyl moieties of the choline phosphoglycerides.
Natarajan V, Schmid HH; Lipids 12 (10): 872-5 (1977)
Docosanol works by inhibiting fusion between the human cell plasma membrane and the herpes simplex virus (HSV) envelope, thereby preventing viral entry into cells and subsequent viral replication. Unlike other cold-sore antivirals, docosanol does not act directly on the virus, and as such it is unlikely it will produce drug resistant mutants of HSV.
n-Docosanol-treated cells resist infection by a variety of lipid-enveloped viruses including the herpesviruses. Previous studies of the mechanism of action demonstrated that n-docosanol inhibits an event prior to the expression of intermediate early gene products but subsequent to HSV attachment. The studies reported here indicate that n-docosanol inhibits fusion of the HSV envelope with the plasma membrane. Evidence suggests that antiviral activity requires a time-dependent metabolic conversion of the compound. Cellular resistance to infection declines after removal of the drug with a t1/2 of approximately 3 h. Reduced expression of viral genes in n-docosanol-treated cells was confirmed by a 70% reduction in expression of a reporter gene regulated by a constitutive promoter inserted into the viral genome. Inhibited release in treated cells of virion-associated regulatory proteins--an immediate post entry event--was indicated by a 75% reduction in the expression of beta-galactosidase in target cells carrying a stably transfected lacZ gene under control of an HSV immediate--early promoter. Finally, the fusion-dependent dequenching of a lipophilic fluorescent probe, octadecyl rhodamine B chloride, inserted into the HSV envelope was significantly inhibited in treated cells. Inhibition of fusion between the plasma membrane and the HSV envelope, and the subsequent lack of replicative events, may be the predominant mechanism for the anti-HSV activity of n-docosanol.
PMID:9864049 Pope LE et al; Antiviral Res 40 (1-2): 85-94 (1998)
Docosanol reduces viral replication and activity by effectively inhibiting the fusion between the plasma membrane and the herpes simplex virus envelope.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1236
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