Identification
- Summary
Dichlorobenzyl alcohol is a medication used to treat a sore throat.
- Generic Name
- Dichlorobenzyl alcohol
- DrugBank Accession Number
- DB13269
- Background
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
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Dichlorobenzyl alcohol (DB13269)
- Weight
- Average: 177.02
Monoisotopic: 175.9795702 - Chemical Formula
- C7H6Cl2O
- Synonyms
- 2,4-dichlorobenzenemethanol
- 2,4-dichlorobenzyl alcohol
- Alcohol diclorobencílico
- External IDs
- NSC-15635
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
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Mouth infection Combination Product in combination with: Amylmetacresol (DB13908) •••••••••••• ••••••• Used in combination for symptomatic treatment of Throat infection Combination Product in combination with: Amylmetacresol (DB13908) •••••••••••• ••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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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
Target Actions Organism ASodium channel protein antagonistHumans - 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
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- 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.
- Adverse Effects
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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
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Dichlorobenzyl alcohol which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Dichlorobenzyl alcohol which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antibacterial Throat Lozenges Dichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg) Lozenge Oral Quimica Canada Limited 2013-03-07 Not applicable Canada 
Benylin Antiseptic Throat Lozenges Dichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg) Lozenge Oral Mcneil Consumer Healthcare Division Of Johnson & Johnson Inc Not applicable Not applicable Canada BETADINE SORE THROAT LOZENGES HONEY & LEMON Dichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg) Lozenge Oral Mundipharma Pharmaceuticals Sdn. Bhd. 2020-09-08 Not applicable Malaysia 
BETADINE SORE THROAT LOZENGES MENTHOL & EUCALYPTUS Dichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg) Lozenge Oral Mundipharma Pharmaceuticals Sdn. Bhd. 2020-09-08 Not applicable Malaysia BETADINE SORE THROAT LOZENGES ORANGE Dichlorobenzyl alcohol (1.2 mg) + Amylmetacresol (0.6 mg) Lozenge Oral Mundipharma Pharmaceuticals Sdn. Bhd. 2020-09-08 Not applicable Malaysia
Categories
- ATC Codes
- R02AA03 — Dichlorobenzyl alcohol
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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 / Alcohol / Aromatic alcohol / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzyl alcohol / Hydrocarbon derivative / Organic oxygen compound / Organochloride
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- benzyl alcohols, dichlorobenzene (CHEBI:48220)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1NKX3648J9
- CAS number
- 1777-82-8
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- FDA Inactive ingredient search [Link]
- Health Canada [Link]
- Strepsils [File]
- Netherlands Public Assessment Report [File]
- Product characteristics throat lonzenges [File]
- Strepsils + anaesthetic spray [File]
- External Links
- ChemSpider
- 14918
- 22906
- ChEBI
- 48220
- ChEMBL
- CHEMBL3184437
- ZINC
- ZINC000000157458
- Wikipedia
- 2,4-Dichlorobenzyl_alcohol
- MSDS
- Download (56.3 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Tonsillopharyngitis / Viral Respiratory Tract Infection 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Transmucosal Pastille Oral Lozenge Oral 1.2 mg Tablet Transmucosal 0.6 MG/1.2MG Mouthwash Oral 28.8 MG/120ML Spray Oral 0.6 % Tablet, orally disintegrating Oral Lozenge Oral Tablet Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 55-58 ºC 'MSDS' boiling point (°C) 150 ºC 'MSDS' water solubility Slightly Soluble Netherlands Public Assessment Report logP 2.36 'MSDS' - Predicted Properties
Property Value Source Water Solubility 1.38 mg/mL ALOGPS logP 2.51 ALOGPS logP 2.41 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 14.68 Chemaxon pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 42.48 m3·mol-1 Chemaxon Polarizability 16.26 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-0900000000-4bfb47f5ba9c8a38948b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100000000-8279d1eedf2c72746ee2 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-15547e238b873d27895f Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0900000000-93643a4134c7858e4e24 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-2900000000-d05b8a7cb3b144685481 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-0405deb3efffa2c2a076 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 120.9075756 predictedDarkChem Lite v0.1.0 [M-H]- 129.27681 predictedDeepCCS 1.0 (2019) [M+H]+ 121.7099756 predictedDarkChem Lite v0.1.0 [M+H]+ 133.10524 predictedDeepCCS 1.0 (2019) [M+Na]+ 121.2114756 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.21234 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein group
- Organism
- Humans
- 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
- 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. [Article]
Drug created at June 23, 2017 20:38 / Updated at January 09, 2021 18:41