Amylmetacresol (AMC) is an

antiseptic An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...

used to treat

infection An infection is the invasion of tissues by pathogens, their multiplication, and the reaction of host tissues to the infectious agent and the toxins they produce. An infectious disease, also known as a transmissible disease or communicable d ...

s of the

mouth In animal anatomy, the mouth, also known as the oral cavity, or in Latin cavum oris, is the opening through which many animals take in food and issue vocal sounds. It is also the cavity lying at the upper end of the alimentary canal, bounded on 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 pharynx and larynx. An important section of it is the epiglottis, separating the esophagus from the trachea (windpi ...

. It is used as an active pharmaceutical ingredient in Strepsils, Cēpacol, Gorpils and Lorsept throat lozenges, 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.. Accessed 20 May 2021. A 2017

meta-analysis A meta-analysis is a statistical analysis that combines the results of multiple scientific studies. Meta-analyses can be performed when there are multiple scientific studies addressing the same question, with each individual study reporting m ...

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) refers to undesirable reactions produced by the normal immune system, including allergies and autoimmunity. They are usually referred to as an over-reaction of the immune ...

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. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...

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 GI tract contains all the major organs of the digestive system, in humans and ...

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 R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyl ...

, 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 (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a h ...

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible wi ...

, diethylether, and oil.

References

External links

* * {{cite journal , vauthors=Oxford JS, Lambkin R, Gibb I, Balasingam S, Chan C, Catchpole A , date=2005 , title=A throat lozenge containing amyl meta cresol and dichlorobenzyl alcohol has a direct virucidal effect on respiratory syncytial virus, influenza A and SARS-CoV , journal=Antivir Chem Chemother , volume=16 , issue=2 , pages=129–34 , pmid=15889535 , doi=10.1177/095632020501600205, doi-access=free Antiseptics Alkylphenols