Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H46O |
| Molecular Weight | 326.6 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCCCCCCCCO
InChI
InChIKey=NOPFSRXAKWQILS-UHFFFAOYSA-N
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00632Curator's Comment: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB00632
Curator's Comment: Description was created based on several sources, including
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 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. Used for the topical treatment of recurrent oral-facial herpes simplex episodes (cold sores or fever blisters).
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: HIV-1 replication |
10.0 mM [EC50] | ||
Target ID: P03200 Gene ID: 3783713.0 Gene Symbol: NA Target Organism: Epstein-Barr virus (strain B95-8) (HHV-4) (Human herpesvirus 4) Sources: http://www.drugbank.ca/drugs/DB00632 |
|||
Target ID: CHEMBL2364696 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Abreva Approved UseHerpes Labialis
Topical treatment of recurrent herpes labialis (perioral herpes, cold sores, fever blisters) Launch Date9.6439678E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.007 ng × eq/g |
25 mg/kg single, topical dose: 25 mg/kg route of administration: Topical experiment type: SINGLE co-administered: |
DOCOSANOL plasma | Oryctolagus cuniculus population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
|
318 ng/mL |
5 g single, oral dose: 5 g route of administration: Oral experiment type: SINGLE co-administered: |
DOCOSANOL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.02 μg × eq × h/g |
25 mg/kg single, topical dose: 25 mg/kg route of administration: Topical experiment type: SINGLE co-administered: |
DOCOSANOL plasma | Oryctolagus cuniculus population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
10 % 5 times / day steady, topical Recommended Dose: 10 %, 5 times / day Route: topical Route: steady Dose: 10 %, 5 times / day Sources: Page: 1 |
unhealthy, 18-77 years n = 370 Health Status: unhealthy Condition: Recurrent herpes simplex labialis Age Group: 18-77 years Sex: M+F Population Size: 370 Sources: Page: 1 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| n-Docosanol inhibits in vitro replication of HIV and other retroviruses. | 1996 Jan 1 |
|
| Clinical efficacy of topical docosanol 10% cream for herpes simplex labialis: A multicenter, randomized, placebo-controlled trial. | 2001 Aug |
|
| Herpes simplex virus: clinical presentation and treatment. | 2001 May |
|
| A review of antiviral therapy for herpes labialis. | 2001 Sep |
|
| Inhibition of type 1 and type 2 5alpha-reductase activity by free fatty acids, active ingredients of Permixon. | 2002 Oct |
|
| Constituents of Hypericum laricifolium and their cyclooxygenase (COX) enzyme activities. | 2003 Dec |
|
| Molecular transfer and transport in noncovalent microcontact printing. | 2004 Feb 3 |
|
| [Tadenan (Pygeum africanum extract) in the treatment of patients with benign prostatic hyperplasia]. | 2004 Sep-Oct |
|
| Low-dose tadenan protects the rabbit bladder from bilateral ischemia/ reperfusion-induced contractile dysfunction. | 2005 Jan |
|
| [Modern pharmacotherapy of benign prostatic hyperplasia]. | 2005 Nov |
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| Two-dimensional miscibility studies--the analysis of interaction between long-chain alcohols and semifluorinated alkanes. | 2006 Feb 23 |
|
| [Efficacy of tadenan in chronic prostatitis complicated by sterility]. | 2008 Jul-Aug |
|
| Docosanol: new drug. Herpes labialis: barely more effective than an excipient. | 2009 Jun |
|
| [Tadenan treatment of prostatic adenoma]. | 2009 Mar-Apr |
|
| Policosanol, alpha-tocopherol, and moisture content as a function of timing of harvest of Switchgrass (Panicum virgatum L.). | 2009 May 13 |
|
| [Study on the chemical constituents from Clematis brevicaudata]. | 2009 Oct |
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| Topical n-docosanol for management of recurrent herpes labialis. | 2010 Apr |
|
| Soybean metabolites regulated in root hairs in response to the symbiotic bacterium Bradyrhizobium japonicum. | 2010 Aug |
|
| An ethnobotanical survey of medicinal plants in Babungo, Northwest Region, Cameroon. | 2010 Feb 15 |
|
| Nutritional bioactive components of wheat straw as affected by genotype and environment. | 2010 Jan |
|
| A Potent, Broad-Spectrum Antiviral Agent that Targets Viral Membranes. | 2010 May |
|
| Nongenital herpes simplex virus. | 2010 Nov 1 |
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WHO-ATC |
D06BB11
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WHO-VATC |
QD06BB11
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NCI_THESAURUS |
C281
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661-19-8
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DTXSID4027286
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9G1OE216XY
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100000088244
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m4714
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DB00632
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CHEMBL1200453
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940
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C47498
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31000
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9G1OE216XY
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8407
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594680
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12620
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5739
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LL-43
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SUB21986
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DOCOSANOL
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211-546-6
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ACTIVE MOIETY
