Identification

Name
Amylmetacresol
Accession Number
DB13908
Type
Small Molecule
Groups
Approved
Description

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].

Structure
Thumb
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
  • amylmetacresolum
External IDs
BRN 2440952
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Strepsils 1 - LozLozenge0.6 mgOralKnoll Pharma Inc.1996-12-311997-07-31Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antibacterial Throat LozengesAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg)LozengeOralQuimica Canada Limited2013-03-07Not applicableCanada
Benylin Antiseptic Throat LozengesAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg)LozengeOralMcneil Consumer Healthcare Division Of Johnson & Johnson IncNot applicableNot applicableCanada
Cepacol Children's Fruity StrawberryAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg)LozengeOralReckitt Benckiser2013-08-15Not applicableCanada
Cepacol Children's Sweet Honey LemonAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg)LozengeOralReckitt Benckiser2013-08-15Not applicableCanada
Cepacol SensationsAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg)LozengeOralReckitt Benckiser2012-07-19Not applicableCanada
Cepacol Sensations CoolingAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) + Menthol (8.0 mg)LozengeOralReckitt Benckiser2012-07-19Not applicableCanada
Cepacol Sensations Ginger FlavourAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg)LozengeOralReckitt Benckiser2015-07-01Not applicableCanada
Cepacol Sensations Sore Throat & Blocked NoseAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) + Menthol (8.0 mg)LozengeOralReckitt Benckiser2012-07-19Not applicableCanada
Cepacol Sensations Sore Throat & CoughAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg) + Menthol (8.0 mg)LozengeOralReckitt Benckiser2012-09-04Not applicableCanada
Cepacol Sensations WarmingAmylmetacresol (0.6 mg) + Dichlorobenzyl alcohol (1.2 mg)LozengeOralReckitt Benckiser2012-07-19Not applicableCanada
Categories
UNII
05W904P57F
CAS number
1300-94-3
Weight
Average: 178.275
Monoisotopic: 178.1357652
Chemical Formula
C12H18O
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

Pharmacology

Indication

Sore throat, minor mouth and throat infections [8], [9], [1].

Associated Conditions
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].

TargetActionsOrganism
UVoltage gated sodium channel
antagonist
human
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
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].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:28869700]
  2. 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. [PubMed:25012093]
  3. 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]
  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. 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. [PubMed:19367399]
  6. 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. [PubMed:23588685]
  7. Amylmetacresol [Link]
  8. Amylmetacresol, MIMS [Link]
  9. Bioxer Pharma, Amylmetacresol [Link]
  10. Amylmetacresol/2,4-dichlorobenzyl alcohol, hexylresorcinol, or carrageenan lozenges as active treatments for sore throat [Link]
  11. Neo agin [Link]
  12. A Note on the Toxicity of Amyl-meta-cresol [Link]
  13. Review Article: Sprays and lozenges for sore throats [Link]
  14. PUBLIC ASSESSMENT REPORT of the Medicines Evaluation Board in the Netherlands: Amylmetacresol and 2,4-Dichlorobenzyl alcohol [File]
  15. UK public assessment report: Sore Throat Relief Honey & Lemon Flavour 0.6mg Lozenges [File]
  16. Acute sore throat revisited: clinical and experimental evidence for the efficacy of over-the-counter AMC/DCBA throat lozenges. [File]
External Links
ChemSpider
14076
ChEBI
48213
ChEMBL
CHEMBL1512677
Wikipedia
Amylmetacresol
AHFS Codes
  • 52:04.92 — Miscellaneous Anti-infectives
MSDS
Download (119 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LozengeOral
LozengeOral0.6 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)24MSDS
boiling point (°C)258MSDS
water solubilitynot solubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.068 mg/mLALOGPS
logP4.33ALOGPS
logP4.47ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.39ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.53 m3·mol-1ChemAxon
Polarizability22.15 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 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
M-cresol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Toluene / Monocyclic benzene moiety / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols (CHEBI:48213)

Targets

1. Voltage gated sodium channel
Kind
Protein group
Organism
human
Pharmacological action
Unknown
Actions
Antagonist
References
  1. 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. [PubMed:19367399]

Drug created on September 18, 2017 13:49 / Updated on November 13, 2018 08:08