Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H46O |
Molecular Weight | 326.6009 |
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8825621 |
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 |
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Target ID: CHEMBL2364696 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9864049 |
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 |
---|---|---|
Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex. | 1991 Dec 1 |
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n-Docosanol inhibits in vitro replication of HIV and other retroviruses. | 1996 Jan 1 |
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Clinical efficacy of topical docosanol 10% cream for herpes simplex labialis: A multicenter, randomized, placebo-controlled trial. | 2001 Aug |
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Identification of Mycobacterium xenopi by gas chromatography. | 2001 Jan |
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The antiviral drug docosanol as a treatment for Kaposi's sarcoma lesions in HIV type 1-infected patients: a pilot clinical study. | 2001 Jan 1 |
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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. | 2001 Sep |
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Effect of oral Tadenan treatment on rabbit bladder structure and function after partial outlet obstruction. | 2002 May |
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Molecular transfer and transport in noncovalent microcontact printing. | 2004 Feb 3 |
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Therapeutic options for herpes labialis, II: Topical agents. | 2004 Jul |
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Two-dimensional packing patterns of amino acid surfactant and higher alcohols in an aqueous phase and their associated packing parameters. | 2004 May 15 |
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Low-dose tadenan protects the rabbit bladder from bilateral ischemia/ reperfusion-induced contractile dysfunction. | 2005 Jan |
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[Modern pharmacotherapy of benign prostatic hyperplasia]. | 2005 Nov |
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New antiviral agents. | 2006 Apr |
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Self-assembled two-dimensional ordered arrays of tripod-type molecules on graphite. | 2006 Jul 4 |
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Management of recurrent oral herpes simplex infections. | 2007 Mar |
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Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
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Soybean metabolites regulated in root hairs in response to the symbiotic bacterium Bradyrhizobium japonicum. | 2010 Aug |
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A Potent, Broad-Spectrum Antiviral Agent that Targets Viral Membranes. | 2010 May |
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Nongenital herpes simplex virus. | 2010 Nov 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/docosanol-topical.html
Apply docosanol topical in a quantity sufficient to cover the affected lesions and immediately surrounding skin five times a day until the lesions are healed.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8825621
31 mM docosanol inhibited HIV-1 replication up to 82%
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Classification Tree | Code System | Code | ||
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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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661-19-8
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9G1OE216XY
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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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594680
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12620
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5739
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SUB21986
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DOCOSANOL
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211-546-6
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ACTIVE MOIETY