Amylmetacresol (AMC) is an
antiseptic
An antiseptic ( and ) is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection, or putrefaction. Antiseptics are generally distinguished from ''antibiotics'' by the latter's abil ...
used to treat
infection
An infection is the invasion of tissue (biology), tissues by pathogens, their multiplication, and the reaction of host (biology), host tissues to the infectious agent and the toxins they produce. An infectious disease, also known as a transmis ...
s of the
mouth
A mouth also referred to as the oral is the body orifice through which many animals ingest food and animal communication#Auditory, vocalize. The body cavity immediately behind the mouth opening, known as the oral cavity (or in Latin), is also t ...
and
throat
In vertebrate anatomy, the throat is the front part of the neck, internally positioned in front of the vertebrae. It contains the Human pharynx, pharynx and larynx. An important section of it is the epiglottis, separating the esophagus from the t ...
. It is used as an
active pharmaceutical ingredient
An active ingredient is any ingredient that provides biological activity, biologically active or other direct effect in the diagnosis, cure, mitigation, treatment, or prevention of disease or to affect the structure or any function of the body of ...
in
Strepsils
Strepsils is a brand of throat lozenges manufactured by United Kingdom, British–Netherlands, Dutch company Reckitt, Reckitt Benckiser. Strepsils throat lozenges are used to relieve discomfort caused by mouth and throat infections.
Ingredient ...
,
Cēpacol
Cepacol ( styled Cēpacol) is an American brand of personal hygiene products, as well as for relief of sore throat. It is distributed in the US by Reckitt. The brand was originally owned by J.B. Williams. Following acquisition by Combe Incorpo ...
,
Gorpils,
Cofsils and
Lorsept throat lozenges
A throat lozenge (also known as a cough drop, sore throat sweet, troche, cachou, pastille or cough sweet) is a small, typically medicated tablet intended to be dissolved slowly in the mouth to temporarily stop coughs, lubricate, and soothe irri ...
, typically in combination with
dichlorobenzyl alcohol, another antiseptic.
Medical uses
The lozenges are used to treat sore throat and minor mouth and throat infections including
pharyngitis
Pharyngitis is inflammation of the back of the throat, known as the pharynx. It typically results in a sore throat and fever. Other symptoms may include a runny nose, cough, headache, difficulty swallowing, swollen lymph nodes, and a hoarse vo ...
and
gingivitis.
A 2017
meta-analysis
Meta-analysis is a method of synthesis of quantitative data from multiple independent studies addressing a common research question. An important part of this method involves computing a combined effect size across all of the studies. As such, th ...
found that the combination of AMC with dichlorobenzyl alcohol has a modest advantage over un-medicated lozenges regarding pain relief.
Contraindications
No contraindications are known apart from
hypersensitivity
Hypersensitivity (also called hypersensitivity reaction or intolerance) is an abnormal physiological condition in which there is an undesirable and adverse immune response to an antigen. It is an abnormality in the immune system that causes Imm ...
to the substance.
Adverse effects
Amylmetacresol sometimes causes soreness of the tongue. Hypersensitivity reactions are very rare and show symptoms such as
nausea
Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat.
Over 30 d ...
or
dyspepsia
Indigestion, also known as dyspepsia or upset stomach, is a condition of impaired digestion. Symptoms may include upper abdominal fullness, heartburn, nausea, belching, or upper abdominal pain. People may also experience feeling full earlier ...
, although it is not entirely clear which side effects are caused by AMC and which by dichlorobenzyl alcohol or other ingredients of the lozenges.
AMC has a low toxicity with an
LD50 of 1500 mg/kg body weight (in rats).
Overdose
No cases of overdosing have been reported. It is not expected to cause symptoms other than
gastrointestinal
The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The tract is the largest of the body's systems, after the cardiovascular system. ...
discomfort.
Interactions
No interactions with other drugs are known.
Pharmacology
Mechanism of action
Amylmetacresol is an
antibacterial
An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention ...
and
antiviral substance. It also
blocks sodium channels in a manner similar to
local anaesthetics.
It has a
Rideal-Walker coefficient of 250.
Pharmacokinetics
The substance is rapidly absorbed. It is
oxidised to a
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
,
glucuronidated, and quickly eliminated via the kidneys.
Chemistry
AMC is a derivative of
''m''-cresol, with a
pentyl group attached to the sixth carbon atom. The pure substance melts at , and boils between at a pressure of . It is soluble in water,
ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
,
acetone
Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
,
diethylether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...
, and oil.
See also
*
2,4-Dichlorobenzyl alcohol
*
Hexylresorcinol
*
Cetylpyridinium chloride
Cetylpyridinium chloride (CPC) is a cationic quaternary ammonium compound used in some types of mouthwashes, toothpastes, lozenges, throat sprays, breath sprays, and nasal sprays. It is an antiseptic that kills bacteria and other microor ...
*
Dequalinium
References
Further reading
*
*
{{refend
Antiseptics
Alkylphenols
Pentyl compounds