PRODUCTS

DOCOSANOL

CAS Number : 661-19-8
EC Number : 211-546-6
ECHA InfoCard : 100.010.498
PubChem CID : 12620
ChemSpider : 12100
Chemical formula : C22H46O
Molar mass   : 326.609 g·mol−1
Melting point   : 70 °C
Boiling point   : 180 °C

Preferred IUPAC name :
Docosan-1-ol

Other names :
-Behenic alcohol
-Behenyl alcohol
-Cachalot BE-22
-1-Docosanol
-n-Docosanol
-Docosyl alcohol
-Emery 3304
-Loxiol VPG 1451

Docosanol , also known as behenyl alcohol, is a saturated fatty alcohol containing 22 carbon atoms, used traditionally as an emollient, emulsifier, and thickener in cosmetics.
In July 2000, docosanol was approved for medical use in the United States as an antiviral agent for reducing the duration of cold sores.
Docosanol is an over-the-counter medication (OTC).
Docosanol is sold under the brand name Abreva among others.

Side effects of Docosanol
One of the most common side effects that has been reported from docosanol is headache.
Headaches caused by the medication tend to be mild and can occur in any region of the head.
In clinical trials, headache occurred in 10.4% of people treated with docosanol cream and 10.7% of people treated with placebo.
The most serious side effects, although rare, are allergic reactions.
Some of the patients experienced the symptoms of allergic reactions, including difficulty breathing, confusion, angioedema (facial swelling), fainting, dizziness, hives or chest pain.
Other side effects may include: acne, burning, dryness, itching, rash, redness, acute diarrhea, soreness, swelling.

Mechanism action of Docosanol
Docosanol is thought to act by inhibiting the fusion of the human host cell with the viral envelope of the herpes virus, thus preventing its replication.

History of Docosanol
The drug was approved as a cream for oral herpes after clinical trials by the FDA in July 2000.
Docosanol was shown to shorten the healing by 17.5 hours on average (95% confidence interval: 2 to 22 hours) in a placebo-controlled trial.
Another trial showed no effect when treating the infected backs of guinea pigs.
Two experiments with n-docosanol cream failed to show statistically significant differences by any parameter between n-docosanol cream and vehicle control–treated sites or between n-docosanol and untreated infection sites.

Society and culture of Docosanol
Controversy
In March 2007, Docosanol 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.

Docosanol is a saturated 22-carbon aliphatic alcohol with antiviral activity.
Docosanol has a distinct mechanism of action and inhibits fusion between the plasma membrane and the herpes simplex virus envelope, thereby preventing viral entry into cells and subsequent viral activity and replication.
Docosanol is used topically in the treatment of recurrent herpes simplex labialis episodes and relieves associated pain and may help heal sores faster.

Docosanol is a drug used for topical treatment for recurrent herpes simplex labialis episodes (episodes of cold sores or fever blisters).
A saturated 22-carbon aliphatic alcohol, docosanol exhibits antiviral activity against many lipid enveloped viruses including herpes simplex virus (HSV).
Docosanol inhibits fusion between the plasma membrane and the herpes simplex virus (HSV) envelope, thereby preventing viral entry into cells and subsequent viral replication.
Docosanol is a natural product found in Populus tremula, Hypericum laricifolium, and other organisms with data available.

Use and Manufacturing of Docosanol
Used in synthetic fibers and lubricants and as an evaporation retardant on water surfaces; [HSDB] Used to treat benign prostatic hypertrophy; [Merck Index]

Industry Uses of Docosanol
-Intermediates
-Lubricants and lubricant additives
-Paint additives and coating additives not described by other categories
-Personal Care product ingredient
-Processing aids, not otherwise listed
-Surface active agents

Consumer Uses of Docosanol
-Laundry and dishwashing products
-Paints and coatings
-Paper products
-Personal care products
-Plastic and rubber products not covered elsewhere

Household Products of Docosanol
Household & Commercial/Institutional Products
Information on 168 consumer products that contain Behenyl alcohol in the following categories is provided:
-Home Maintenance
-Personal Care

General Manufacturing Information
Industry Processing Sectors
-All other basic organic chemical manufacturing
-Paint and coating manufacturing
-Paper manufacturing
-Petroleum lubricating oil and grease manufacturing
-Plastic material and resin manufacturing
-Soap, cleaning compound, and toilet preparation manufacturing

Docosanol is used to treat "cold sores/fever blisters" (herpes labialis).
Docosanol can speed up healing of the sores and decrease symptoms (such as tingling, pain, burning, itching).
Docosanol works by blocking the virus that causes the cold sores (herpes simplex) from entering the healthy skin cells and growing in number.
This medication does not cure herpes and does not prevent passing the infection to someone else.
Docosanol does not prevent a future occurrence.Do not use this medication to treat canker sores (sores found commonly in the mouth), shingles, or genital herpes.

Docosanol belongs to the family of medicines called antivirals.
Antivirals are used to treat infections caused by viruses.
Usually they work for only one kind or group of virus infections.
Topical docosanol is used to treat the symptoms of herpes simplex virus infections around the mouth.
Although topical docosanol will not cure herpes simplex, it may help relieve the pain and discomfort and may help the sores (if any) heal faster.

Docosanol is available over the counter.
Docosanol is available in the following dosage forms:
-Cream

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.
Docosanol also relieves the accompanying symptoms, including tingling, pain, burning, and itching.
Docosanol cannot, however, prevent cold sores or fever blisters from appearing.

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.

Docosanol (n-docosanol or behenyl alcohol; Abreva) is a saturated 22-carbon aliphatic alcohol that inhibits a broad range of lipid-enveloped viruses including HSV-1 and HSV-2 at millimolar concentrations in vitro.
Docosanol is not directly virucidal, and its principal anti-HSV mechanism of action in vitro apparently relates to interference with viral fusion to host cell membranes early in replication, although other inhibitory effects may be possible.
A nonantiviral mechanism of action resulting from anti-inflammatory effects has been described.
In a guinea pig model of cutaneous HSV, topical docosanol did not show antiviral or therapeutic benefits and was less active than topical penciclovir and acyclovir.
No emergence of resistance has been described to date.

Uses of Docosanol
Docosanol is used to treat "cold sores/fever blisters" (herpes labialis).
Docosanol can speed up healing of the sores and decrease symptoms (such as tingling, pain, burning, itching).
Docosanol works by blocking the virus that causes the cold sores (herpes simplex) from entering the healthy skin cells and growing in number.
This medication does not cure herpes and does not prevent passing the infection to someone else.
Docosanol does not prevent a future occurrence.
Do not use this medication to treat canker sores (sores found commonly in the mouth), shingles, or genital herpes.

Docosanol topical (for the skin) is used to treat cold sores on the face and lips.
Docosanol may also be used for purposes not listed in this medication guide.
Use exactly as directed on the label, or as prescribed by your doctor.
Do not take by mouth.

Topical medicine is for use only on the skin.
Rinse with water if this medicine gets in your eyes or mouth.
Apply this medicine at the first sign of a cold sore, such as tingling, redness, itching, or a blister.
Wash your hands before and after applying docosanol topical.

Remove any cosmetics before applying docosanol topical.
Apply enough medicine to completely cover the cold sore. Rub in gently and completely.
Call your doctor if your symptoms do not improve within 10 days, or if they get worse.
Store at room temperature away from moisture and heat. Do not freeze.

First-aid measures of Docosanol

Eye Contact :
Rinse immediately with plenty of water, also under the eyelids, for at least 15 minutes.
Getmedical attention.

Skin Contact :
Wash off immediately with plenty of water for at least 15 minutes.
Get medical attention immediately if symptoms occur.

Inhalation :
Remove to fresh air.
Get medical attention immediately if symptoms occur.

Ingestion :
Clean mouth with water and drink afterwards plenty of water.
Get medical attention if symptoms occur.

Substance identity

EC / List no.: 211-546-6
CAS no.: 661-19-8
Mol. formula: C22H46O

Hazard classification & labelling of Docosanol
Danger! According to the classification provided by companies to ECHA in REACH registrations this substance is very toxic to aquatic life with long lasting effects, is very toxic to aquatic life, causes serious eye irritation, is a highly flammable liquid and vapour, is harmful if swallowed, is harmful in contact with skin, may cause respiratory irritation and may cause drowsiness or dizziness.

About Docosanol
Docosanol is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.
Docosanol is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses of Docosanol
Docosanol is used in the following products: biocides (e.g. disinfectants, pest control products), anti-freeze products, coating products, finger paints, lubricants and greases, polishes and waxes and cosmetics and personal care products.
Other release to the environment of Docosanol is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use, indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment) and indoor use in long-life materials with high release rate (e.g. release from fabrics, textiles during washing, removal of indoor paints).

Article service life of Docosanol
Release to the environment of Docosanol can occur from industrial use: in processing aids at industrial sites, in the production of articles and industrial abrasion processing with low release rate (e.g. cutting of textile, cutting, machining or grinding of metal).
Other release to the environment of Docosanol is likely to occur from: outdoor use, indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Docosanol can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones) and stone, plaster, cement, glass or ceramic (e.g. dishes, pots/pans, food storage containers, construction and isolation material).

Widespread uses by professional workers of Docosanol
Docosanol is used in the following products: lubricants and greases, coating products, fillers, putties, plasters, modelling clay, biocides (e.g. disinfectants, pest control products), air care products, anti-freeze products, finger paints, washing & cleaning products and welding & soldering products.
Docosanol is used in the following areas: building & construction work and agriculture, forestry and fishing.
Docosanol is used for the manufacture of: machinery and vehicles, rubber products, plastic products, mineral products (e.g. plasters, cement), furniture and fabricated metal products.
Other release to the environment of Docosanol is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Formulation or re-packing of Docosanol
Docosanol is used in the following products: pH regulators and water treatment products, laboratory chemicals and polymers.
Docosanol has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of Docosanol can occur from industrial use: formulation of mixtures, formulation in materials, as an intermediate step in further manufacturing of another substance (use of intermediates), manufacturing of the substance, in processing aids at industrial sites, in the production of articles, as processing aid, for thermoplastic manufacture, as processing aid and of substances in closed systems with minimal release.

Uses at industrial sites of Docosanol
Docosanol is used in the following products: lubricants and greases, fillers, putties, plasters, modelling clay, coating products, adhesives and sealants, non-metal-surface treatment products and pH regulators and water treatment products.
Docosanol is used in the following areas: building & construction work and mining.
Docosanol is used for the manufacture of: chemicals, mineral products (e.g. plasters, cement), machinery and vehicles, plastic products, rubber products, textile, leather or fur and pulp, paper and paper products.

Release to the environment of Docosanol can occur from industrial use: in processing aids at industrial sites, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), of substances in closed systems with minimal release and as processing aid.
Other release to the environment of Docosanol is likely to occur from: outdoor use.

Manufacture of Docosanol
Release to the environment of Docosanol can occur from industrial use: manufacturing of the substance, formulation of mixtures, formulation in materials, in processing aids at industrial sites, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, for thermoplastic manufacture, as processing aid and of substances in closed systems with minimal release.

Synonyms :
1-DOCOSANOL
docosan-1-ol
Docosanol
Behenyl alcohol
661-19-8
Behenic alcohol
n-Docosanol
Abreva
Docosyl alcohol
Tadenan
Lidavol
Stenol 1822
Lanette 22
Lidakol
Stenol 1822A
Docosanol [USAN]
Nacol 22-97
IK 2
NAA 422
30303-65-2
NSC 8407
UNII-9G1OE216XY
Docosanol (Abreua)
Docosanol (Abreva)
Docosanol (USAN)
9G1OE216XY
CHEBI:31000
NSC-8407
NCGC00159370-02
Docosanol (VAN)
Erazaban
Herepair
IK.2
Healip
Cachalot BE-22
Abreva (TN)
HSDB 5739
Loxiol VPG 1451
EINECS 211-546-6
BRN 1770470
AI3-36489
CCRIS 8943
n-Docosan-1-ol
C22 Alcohol
Docosanol-(1)
MFCD00002939
1-Docosanol, 98%
DSSTox_CID_7286
EC 211-546-6
DSSTox_RID_78387
DSSTox_GSID_27286
SCHEMBL51925
4-01-00-01906 (Beilstein Handbook Reference)
CHEMBL1200453
DTXSID4027286
NSC8407
HMS2093P22
Pharmakon1600-01505729
HY-B0222
ZINC6920384
Tox21_111611
LMFA05000008
NSC759235
s1637
AKOS015902887
CCG-213539
DB00632
NSC-759235
Behenyl alcohol, AI3-36489, Behenic alcohol, 1-Docosanol, Docosyl alcohol, IK-2, Tadenan
NCGC00159370-03
NCGC00159370-04
NCGC00159370-05
1-Docosanol, purum, >=97.0% (GC)
AC-19852
CAS-661-19-8
SBI-0206938.P001
A8416
AM20100601
D0964
FT-0622609
D03884
D70615
AB01563123_01
AB01563123_02
SR-05000001915
Q3033497
SR-05000001915-1
UNII-2C9Z9D1QFE component NOPFSRXAKWQILS-UHFFFAOYSA-N
UNII-B1K89384RJ component NOPFSRXAKWQILS-UHFFFAOYSA-N
UNII-O4M0347C6A component NOPFSRXAKWQILS-UHFFFAOYSA-N
A3D72D45-625E-49B5-B0FC-394010B3485D
Docosan-1-ol
Docosan-1-ol
docosan-1-ol
1-Docosanol
1-DOCOSANOL
1-Docosanol
Behenyl alcohol
Behenyl Alcohol
Docosan-1-ol
docosan-1-ol
Docosan-1-ol
docosan-1-ol
Nacol 22
Nafol 1822
Nafol 2024
Tenac®-C EF450
1-Docosanol
Docosan-1-ol
661-19-8
1770470 [Beilstein]
1-Docosanol [ACD/Index Name] [ACD/IUPAC Name]
1-Docosanol [German] [ACD/Index Name] [ACD/IUPAC Name]
1-Docosanol [French] [ACD/Index Name] [ACD/IUPAC Name]
211-546-6 [EINECS]
661-19-8 [RN]
9G1OE216XY
Abreva
behenic alcohol
behenyl alcohol
docosan-1-ol
Docosanol [INN] [USAN] [Wiki]
IK 2 (alcohol)
Lidakol
MFCD00002939 [MDL number]
n-docosanol
(R)-2-(1-(((9H-Fluoren-9-yl)methoxy)carbonyl)pyrrolidin-2-yl)acetic acid
4-01-00-01906 [Beilstein]
Docosanol (n-Docosanol)
Docosanol (USAN)
Docosanol|1-docosanol
docosanyl alcohol
DOCOSYL ALCOHOL
IK 2
Lanette 22
Lidavol
Nacol 22-97
Stenol 1822
Stenol 1822A
Tadenan
UNII:9G1OE216XY
UNII-9G1OE216XY