Dichlorobenzyl alcohol

Identification

Name
Dichlorobenzyl alcohol
Accession Number
DB13269
Type
Small Molecule
Groups
Approved
Description

Dichlorobenzyl alcohol is a mild antiseptic with a broad spectrum for bacterial and virus associated with mouth and throat infections.[3] Dichlorobenzyl alcohol is considered as an active ingredient found in several marketed OTC products by Health Canada which has categorized this agent as an anatomical therapeutic chemical.[6] On the other hand, dichlorobenzyl alcohol is categorized by the FDA in the inactive ingredient for approved drug products.[5]

Structure
Thumb
Synonyms
  • 2,4-dichlorobenzenemethanol
  • 2,4-dichlorobenzyl alcohol
External IDs
NSC-15635
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antibacterial Throat LozengesDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg)LozengeOralQuimica Canada Limited2013-03-07Not applicableCanada
Benylin Antiseptic Throat LozengesDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg)LozengeOralMcneil Consumer Healthcare Division Of Johnson & Johnson IncNot applicableNot applicableCanada
Cepacol Children's Fruity StrawberryDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg)LozengeOralReckitt Benckiser2013-08-15Not applicableCanada
Cepacol Children's Sweet Honey LemonDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg)LozengeOralReckitt Benckiser2013-08-15Not applicableCanada
Cepacol SensationsDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg)LozengeOralReckitt Benckiser2012-07-19Not applicableCanada
Cepacol Sensations CoolingDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg) + Menthol (8.0 mg)LozengeOralReckitt Benckiser2012-07-19Not applicableCanada
Cepacol Sensations Ginger FlavourDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg)LozengeOralReckitt Benckiser2015-07-01Not applicableCanada
Cepacol Sensations Sore Throat & Blocked NoseDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg) + Menthol (8.0 mg)LozengeOralReckitt Benckiser2012-07-19Not applicableCanada
Cepacol Sensations Sore Throat & CoughDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg) + Menthol (8.0 mg)LozengeOralReckitt Benckiser2012-09-04Not applicableCanada
Cepacol Sensations WarmingDichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg)LozengeOralReckitt Benckiser2012-07-19Not applicableCanada
Categories
UNII
1NKX3648J9
CAS number
1777-82-8
Weight
Average: 177.02
Monoisotopic: 175.9795702
Chemical Formula
C7H6Cl2O
InChI Key
DBHODFSFBXJZNY-UHFFFAOYSA-N
InChI
InChI=1S/C7H6Cl2O/c8-6-2-1-5(4-10)7(9)3-6/h1-3,10H,4H2
IUPAC Name
(2,4-dichlorophenyl)methanol
SMILES
OCC1=C(Cl)C=C(Cl)C=C1

Pharmacology

Indication

Dichlorobenzyl alcohol in combination with Amylmetacresol is available in over-the-counter products used for symptomatic relief of acute sore throat and postoperative sore throat.[1]

Associated Conditions
Pharmacodynamics

In vitro studies with the combination of dichlorobenzyl alcohol and amylmetacresol have shown a virucidal against a number of viruses associated with the common cold which is observed by a reduction in the viral load.[2] In clinical trials, administration of dichlorobenzyl alcohol lozenges has been shown to generate a reduced throat soreness and to provide pain relief and relief from difficulty in swallowing 5 minutes after administration. This effect can last for even 2 hours.[7] The relief effect was shown to reach a steady-state after 45 minutes.[8]

Mechanism of action

The use of dichlorobenzyl alcohol has been related to its antibacterial, antiviral and local anesthetic properties. The local anesthetic action of dichlorobenzyl alcohol is thought to be due to a reduced sodium channel blockade.[2] The antiseptic mechanism of action of dichlorobenzyl alcohol is not fully understood but it is thought to be related to a denaturation of external proteins and rearrangement of the tertiary structure proteins.[4]

TargetActionsOrganism
ASodium channel protein
antagonist
Human
Absorption

Dichlorobenzyl alcohol is released almost immediately from its formulation and reaches peak concentration after 3-4 minutes.[8] The concentration in saliva after 120 minutes represents about 50% of the administered dose.[9]

Volume of distribution

This pharmacokinetic property has not been fully studied.

Protein binding

This pharmacokinetic property has not been fully studied.

Metabolism

Dichlorobenzyl alcohol is metabolized in the liver to form hippuric acid.[10]

Route of elimination

In preclinical trials, dermal administration of dichlorobenzyl alcohol results in renal elimination of 90% of the administered dose.[8] After metabolism, dichlorobenzyl alcohol is excreted in the urine.[10]

Half life

This pharmacokinetic property has not been fully studied.

Clearance

This pharmacokinetic property has not been fully studied.

Toxicity

Fertility and mutagenicity studies do not indicate any effect driven by dichlorobenzyl alcohol.[7] Overdose studies indicate that in systemic overdose there might be a presence of a CNS transitory stimulation followed by CNS and cardiovascular. Chronic administration is not recommended as it might alter the normal microbial balance of the throat.[9] depression In rats, the reported LD50 is of about 2.7 g/kg when administered orally.[7]

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenAcetaminophen may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
AlprazolamAlprazolam may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
AmilorideAmiloride may increase the excretion rate of Dichlorobenzyl alcohol which could result in a lower serum level and potentially a reduction in efficacy.
AmlodipineAmlodipine may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
AmoxicillinAmoxicillin may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
AmphetamineAmphetamine may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
AmpicillinAmpicillin may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
AuranofinAuranofin may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
BaclofenBaclofen may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. McNally D, Shephard A, Field E: Randomised, double-blind, placebo-controlled study of a single dose of an amylmetacresol/2,4-dichlorobenzyl alcohol plus lidocaine lozenge or a hexylresorcinol lozenge for the treatment of acute sore throat due to upper respiratory tract infection. J Pharm Pharm Sci. 2012;15(2):281-94. [PubMed:22579007]
  2. Tan TW, Chen BC, Tan HL, Chang CM: Effectiveness of amylmetacresol and 2,4-dichlorobenzyl alcohol throat lozenges in patients with acute sore throat due to upper respiratory tract infection: a systematic review protocol. JBI Database System Rev Implement Rep. 2017 Apr;15(4):862-872. doi: 10.11124/JBISRIR-2016-003034. [PubMed:28398972]
  3. Oxford JS, Lambkin R, Gibb I, Balasingam S, Chan C, Catchpole A: A throat lozenge containing amyl meta cresol and dichlorobenzyl alcohol has a direct virucidal effect on respiratory syncytial virus, influenza A and SARS-CoV. Antivir Chem Chemother. 2005;16(2):129-34. doi: 10.1177/095632020501600205. [PubMed:15889535]
  4. Morokutti-Kurz M, Graf C, Prieschl-Grassauer E: Amylmetacresol/2,4-dichlorobenzyl alcohol, hexylresorcinol, or carrageenan lozenges as active treatments for sore throat. Int J Gen Med. 2017 Feb 28;10:53-60. doi: 10.2147/IJGM.S120665. eCollection 2017. [PubMed:28280379]
  5. FDA Inactive ingredient search [Link]
  6. Health Canada [Link]
  7. Strepsils [File]
  8. Netherlands Public Assessment Report [File]
  9. Product characteristics throat lonzenges [File]
  10. Strepsils + anaesthetic spray [File]
External Links
ChemSpider
14918
ChEBI
48220
ChEMBL
CHEMBL3184437
Wikipedia
2,4-Dichlorobenzyl_alcohol
ATC Codes
R02AA03 — Dichlorobenzyl alcohol
MSDS
Download (56.3 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LozengeOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)55-58 ºC'MSDS'
boiling point (°C)150 ºC'MSDS'
water solubilitySlightly SolubleNetherlands Public Assessment Report
logP2.36'MSDS'
Predicted Properties
PropertyValueSource
Water Solubility1.38 mg/mLALOGPS
logP2.51ALOGPS
logP2.41ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.48 m3·mol-1ChemAxon
Polarizability16.26 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Dichlorobenzenes
Alternative Parents
Benzyl alcohols / Aryl chlorides / Primary alcohols / Organochlorides / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,3-dichlorobenzene / Benzyl alcohol / Aryl halide / Aryl chloride / Organic oxygen compound / Hydrocarbon derivative / Aromatic alcohol / Primary alcohol / Organooxygen compound / Organochloride
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzyl alcohols, dichlorobenzene (CHEBI:48220)

Targets

Kind
Protein group
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Voltage-gated sodium channel activity
Specific Function
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...

Components:
References
  1. Tan TW, Chen BC, Tan HL, Chang CM: Effectiveness of amylmetacresol and 2,4-dichlorobenzyl alcohol throat lozenges in patients with acute sore throat due to upper respiratory tract infection: a systematic review protocol. JBI Database System Rev Implement Rep. 2017 Apr;15(4):862-872. doi: 10.11124/JBISRIR-2016-003034. [PubMed:28398972]

Drug created on June 23, 2017 14:38 / Updated on August 02, 2018 06:50