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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
Structure of DOCOSANOL

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

HIDE SMILES / InChI

Molecular Formula C22H46O
Molecular Weight 326.6
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
10.0 mM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Abreva

Cmax

ValueDoseCo-administeredAnalytePopulation
0.007 ng × eq/g
25 mg/kg single, topical
DOCOSANOL plasma
Oryctolagus cuniculus
318 ng/mL
5 g single, oral
DOCOSANOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.02 μg × eq × h/g
25 mg/kg single, topical
DOCOSANOL plasma
Oryctolagus cuniculus

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
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
31 mM docosanol inhibited HIV-1 replication up to 82%
Substance Class Chemical
Record UNII
9G1OE216XY
Record Status Validated (UNII)
Record Version