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30303-65-2 molecular structure
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docosan-1-ol

ChemBase ID: 514
Molecular Formular: C22H46O
Molecular Mass: 326.60004
Monoisotopic Mass: 326.35486609
SMILES and InChIs

SMILES:
OCCCCCCCCCCCCCCCCCCCCCC
Canonical SMILES:
CCCCCCCCCCCCCCCCCCCCCCO
InChI:
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
InChIKey:
NOPFSRXAKWQILS-UHFFFAOYSA-N

Cite this record

CBID:514 http://www.chembase.cn/molecule-514.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
docosan-1-ol
IUPAC Systematic name
Docosan-1-ol
IUPAC Traditional name
docosanol
Brand Name
Abreva
Synonyms
Behenyl alcohol
docosanol
Docosanol
BEHENYL ALCOHOL TECHNICAL GRADE
Behenic alcohol
Cachalot BE-22
n-Docosanol
Docosyl alcohol
Emery 3304
Loxiol VPG 1451
Abreva
1-Docosanol
BEHENYL ALCOHOL
1-Docosanol
Docosan-1-ol
山嵛醇
正二十二醇
CAS Number
30303-65-2
661-19-8
EC Number
211-546-6
MDL Number
MFCD00002939
Beilstein Number
1770470
PubChem SID
24867521
46508049
24850264
160963977
PubChem CID
12620
CHEBI ID
31000
ATC CODE
D06BB11
CHEMBL
1200453
Chemspider ID
12100
DrugBank ID
DB00632
KEGG ID
D03884
MeSH Name
docosanol
Unique Ingredient Identifier
9G1OE216XY
Wikipedia Title
Docosanol

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.843943  H Acceptors
H Donor LogD (pH = 5.5) 8.807558 
LogD (pH = 7.4) 8.807558  Log P 8.807558 
Molar Refractivity 104.9529 cm3 Polarizability 41.941555 Å3
Polar Surface Area 20.23 Å2 Rotatable Bonds 20 
Lipinski's Rule of Five false 
Log P 9.31  LOG S -7.22 
Solubility (Water) 1.96e-05 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Melting Point
65-72 °C(lit.) expand Show data source
69.85°C (343K) expand Show data source
70-71 °C expand Show data source
Boiling Point
179.85°C (453K) (at 29 Pa) expand Show data source
180 °C/0.22 mmHg(lit.) expand Show data source
Partition Coefficient
10.009 expand Show data source
Hydrophobicity(logP)
9 expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
JR1315000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
nwg expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Topical expand Show data source
Legal Status
OTC (US) expand Show data source
Pregnancy Category
B (US) expand Show data source
Purity
~98% expand Show data source
≥97.0% (GC) expand Show data source
80% expand Show data source
95+% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
TECHNICAL expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Linear Formula
CH3(CH2)21OH expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05204154 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 05213459 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02156476 external link
(1-Docosanol)
Purity: ∼98%
DrugBank - DB00632 external link
Item Information
Drug Groups approved; investigational
Description 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.
Indication For the topical treatment of recurrent oral-facial herpes simplex episodes (cold sores or fever blisters).
Pharmacology 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.
Toxicity Symptoms of overdose include headache, abdominal pain, increased serum lipase, nausea, dyspepsia, dizziness, and hyperbilirubinemia.
Affected Organisms
Herpes simplex virus
Absorption Topical absorption has been shown to be minimal under conditions reflecting normal clinical use.
External Links
Wikipedia
Drugs.com
Selleck Chemicals - S1637 external link
Research Area: Infection
Biological Activity:
Docosanol is a saturated fatty alcoholused traditionally as an emollient, emulsifier, and thickener in cosmetics, nutritional supplement (as an individual entity and also as a constituent of polyicosanol). [1] It 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. The ED50 of 1-docosanol is around 2.5 mg/ml for plaque inhibition and 1.7 mg/ml for inhibition of virus production for wild-type and Acv-resistant HSV-2. [2]
Sigma Aldrich - 169102 external link
Packaging
50 g in poly bottle

REFERENCES

REFERENCES

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  • • http://en.wikipedia.org/wiki/Docosanol
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PATENTS

PATENTS

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INTERNET

INTERNET

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