Identification
- Summary
Amylmetacresol is an antiseptic used to treat infections in the mouth and throat.
- Generic Name
- Amylmetacresol
- DrugBank Accession Number
- DB13908
- Background
Amylmetacresol is an antiseptic available in Canada over-the-counter in a number of lozenges for the treatment of sore throat and minor mouth infections 8, 9. Amylmetacresol is often combined with dichlorobenzyl alcohol and menthol in the commonly used sore throat lozenges, known as Strepsils 13.
The acute sore throat (pharyngitis) is one of the most common conditions for which children are seen in the primary care setting. Pharyngitis is normally caused by viruses and proves benign and self-limiting. Clinically proven, over-the-counter throat lozenges offer rapid and effective relief of acute sore throat symptoms, and are increasingly important in the management of this condition 6.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Amylmetacresol (DB13908)
- Weight
- Average: 178.275
Monoisotopic: 178.1357652 - Chemical Formula
- C12H18O
- Synonyms
- 5-methyl-2-pentylphenol
- 6-amyl-m-cresol
- 6-n-amyl-m-cresol
- 6-n-pentyl-m-cresol
- 6-pentyl-m-cresol
- amilmetacresol
- Amyl metacresol
- Amylmetacresol
- amylmetacresolum
- External IDs
- BRN 2440952
Pharmacology
- Indication
Sore throat, minor mouth and throat infections 8, 9, 1.
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- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
The mixture of amylmetacresol throat lozenge medications markedly reduces the infectivity of certain infectious viruses in the throat and in cough droplets, thus reducing opportunities for person-to-person transmission 9. In addition, it relieves symptoms of sore throat/irritation of the throat 1, 2.
Amylmetacresol is thought to inhibit the inflammatory and pain mediators that are involved in the inflammation of the mouth and throat mucous membranes, as well as the sore throat 11.
- Mechanism of action
The mechanism of virucidal action is not fully elucidated, however it is suggested that denaturation of external protein spikes, a pH-induced rearrangement of the tertiary structure of attachment proteins, or a selective effect on viral lipid membranes/protein–lipid interaction is responsible for this action 4.
Amylmetacresol is an antibacterial and antiviral agent, and blocks voltage-gated Na channels in a local anesthetic-like manner 5.
Target Actions Organism USodium channel protein type 2 subunit alpha antagonistHumans - Absorption
Rapidly absorbed and eliminated 12.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Oral LD50: 1500 mg/kg (rat) MSDS
Adverse effects include hypersensitivity reactions, tongue soreness 8.
Occasionally, hypersensitivity reactions may occur, manifested by digestive problems such as nausea or dyspepsia. This is extremely rare 9.
In the case of overdose, management should be symptomatic. In cases of severe overdosage, gastric lavage may be warranted to empty the stomach contents. Saline laxatives and activated charcoal may be administered orally 8.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image MAC DUAL ACTION LOZENGES,HONEY &LEMON FLAVOUR Lozenge Oral ZIWELL MEDICAL SDN BHD 2020-09-08 Not applicable Malaysia 
Strepsils 1 - Loz Lozenge 0.6 mg Oral Knoll Pharma Inc. 1996-12-31 1997-07-31 Canada 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antibacterial Throat Lozenges Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) Lozenge Oral Quimica Canada Limited 2013-03-07 Not applicable Canada Benylin Antiseptic Throat Lozenges Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) Lozenge Oral Mcneil Consumer Healthcare Division Of Johnson & Johnson Inc Not applicable Not applicable Canada BETADINE SORE THROAT LOZENGES HONEY & LEMON Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) Lozenge Oral Mundipharma Pharmaceuticals Sdn. Bhd. 2020-09-08 Not applicable Malaysia BETADINE SORE THROAT LOZENGES MENTHOL & EUCALYPTUS Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) Lozenge Oral Mundipharma Pharmaceuticals Sdn. Bhd. 2020-09-08 Not applicable Malaysia BETADINE SORE THROAT LOZENGES ORANGE Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) Lozenge Oral Mundipharma Pharmaceuticals Sdn. Bhd. 2020-09-08 Not applicable Malaysia Cepacol Children's Fruity Strawberry Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) Lozenge Oral Rb Health (Canada) Inc. 2013-08-15 Not applicable Canada Cepacol Children's Sweet Honey Lemon Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) Lozenge Oral Reckitt Benckiser 2013-08-15 2020-07-29 Canada Cepacol Sensations Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) Lozenge Oral Rb Health (Canada) Inc. 2012-07-19 Not applicable Canada Cepacol Sensations Cool Mint Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) + Levomenthol (8 mg) Lozenge Oral Rb Health (Canada) Inc. Not applicable Not applicable Canada Cepacol Sensations Cooling Amylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) + Levomenthol (8 mg) Lozenge Oral Reckitt Benckiser 2012-07-19 2017-11-24 Canada
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Cresols
- Direct Parent
- Meta cresols
- Alternative Parents
- Toluenes / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Hydrocarbon derivative / M-cresol / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound / Toluene
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols (CHEBI:48213)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 05W904P57F
- CAS number
- 1300-94-3
- InChI Key
- CKGWFZQGEQJZIL-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H18O/c1-3-4-5-6-11-8-7-10(2)9-12(11)13/h7-9,13H,3-6H2,1-2H3
- IUPAC Name
- 5-methyl-2-pentylphenol
- SMILES
- CCCCCC1=CC=C(C)C=C1O
References
- General References
- Weckmann G, Hauptmann-Voss A, Baumeister SE, Klotzer C, Chenot JF: Efficacy of AMC/DCBA lozenges for sore throat: A systematic review and meta-analysis. Int J Clin Pract. 2017 Oct;71(10). doi: 10.1111/ijcp.13002. Epub 2017 Sep 4. [Article]
- Foadi N, de Oliveira RC, Buchholz V, Stoetzer C, Wegner F, Pilawski I, Haeseler G, Leuwer M, Ahrens J: A combination of topical antiseptics for the treatment of sore throat blocks voltage-gated neuronal sodium channels. Naunyn Schmiedebergs Arch Pharmacol. 2014 Oct;387(10):991-1000. doi: 10.1007/s00210-014-1016-y. Epub 2014 Jul 12. [Article]
- 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]
- 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]
- Buchholz V, Leuwer M, Ahrens J, Foadi N, Krampfl K, Haeseler G: Topical antiseptics for the treatment of sore throat block voltage-gated neuronal sodium channels in a local anaesthetic-like manner. Naunyn Schmiedebergs Arch Pharmacol. 2009 Aug;380(2):161-8. doi: 10.1007/s00210-009-0416-x. Epub 2009 Apr 15. [Article]
- Thompson A, Reader S, Field E, Shephard A: Open-label taste-testing study to evaluate the acceptability of both strawberry-flavored and orange-flavored amylmetacresol/2,4-dichlorobenzyl alcohol throat lozenges in healthy children. Drugs R D. 2013 Jun;13(2):101-7. doi: 10.1007/s40268-013-0012-x. [Article]
- Amylmetacresol [Link]
- Amylmetacresol, MIMS [Link]
- Bioxer Pharma, Amylmetacresol [Link]
- Amylmetacresol/2,4-dichlorobenzyl alcohol, hexylresorcinol, or carrageenan lozenges as active treatments for sore throat [Link]
- Neo agin [Link]
- A Note on the Toxicity of Amyl-meta-cresol [Link]
- Review Article: Sprays and lozenges for sore throats [Link]
- PUBLIC ASSESSMENT REPORT of the Medicines Evaluation Board in the Netherlands: Amylmetacresol and 2,4-Dichlorobenzyl alcohol [File]
- UK public assessment report: Sore Throat Relief Honey & Lemon Flavour 0.6mg Lozenges [File]
- Acute sore throat revisited: clinical and experimental evidence for the efficacy of over-the-counter AMC/DCBA throat lozenges. [File]
- External Links
- ChemSpider
- 14076
- 236248
- ChEBI
- 48213
- ChEMBL
- CHEMBL1512677
- ZINC
- ZINC000002039651
- Wikipedia
- Amylmetacresol
- MSDS
- Download (119 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Transmucosal Pastille Oral Lozenge Oral Tablet Oral Lozenge Oral 0.6 mg Lozenge Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 24 MSDS boiling point (°C) 258 MSDS water solubility not soluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.068 mg/mL ALOGPS logP 4.33 ALOGPS logP 4.47 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 10.39 Chemaxon pKa (Strongest Basic) -5.5 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 4 Chemaxon Refractivity 56.53 m3·mol-1 Chemaxon Polarizability 22.15 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes 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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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...
- Gene Name
- SCN2A
- Uniprot ID
- Q99250
- Uniprot Name
- Sodium channel protein type 2 subunit alpha
- Molecular Weight
- 227972.64 Da
References
- Buchholz V, Leuwer M, Ahrens J, Foadi N, Krampfl K, Haeseler G: Topical antiseptics for the treatment of sore throat block voltage-gated neuronal sodium channels in a local anaesthetic-like manner. Naunyn Schmiedebergs Arch Pharmacol. 2009 Aug;380(2):161-8. doi: 10.1007/s00210-009-0416-x. Epub 2009 Apr 15. [Article]
Drug created at September 18, 2017 19:49 / Updated at October 02, 2023 21:58