Chemistry:Amylmetacresol
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| AHFS/Drugs.com | International Drug Names |
| Routes of administration | By mouth (throat lozenges) |
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| Pharmacokinetic data | |
| Metabolism | Oxidation, glucuronidation |
| Excretion | Via kidneys |
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| Formula | C12H18O |
| Molar mass | 178.27 g·mol−1 |
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| Melting point | 24 °C (75 °F) |
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Amylmetacresol (AMC) is an antiseptic used to treat infections of the mouth and throat. It is used as an active pharmaceutical ingredient in Strepsils, Cēpacol, Gorpils and Lorsept throat lozenges, typically in combination with dichlorobenzyl alcohol, another antiseptic.[1][2]
Medical uses
The lozenges are used to treat sore throat and minor mouth and throat infections including pharyngitis and gingivitis.[1][3]
A 2017 meta-analysis found that the combination of AMC with dichlorobenzyl alcohol has a modest advantage over un-medicated lozenges regarding pain relief.[4][5]
Contraindications
No contraindications are known apart from hypersensitivity to the substance.[1][2]
Adverse effects
Amylmetacresol sometimes causes soreness of the tongue. Hypersensitivity reactions are very rare and show symptoms such as nausea or dyspepsia, although it is not entirely clear which side effects are caused by AMC and which by dichlorobenzyl alcohol or other ingredients of the lozenges.[1][3]
AMC has a low toxicity with an LD50 of 1500 mg/kg body weight (in rats).[3][6]
Overdose
No cases of overdosing have been reported. It is not expected to cause symptoms other than gastrointestinal discomfort.[1][2]
Interactions
No interactions with other drugs are known.[1][2]
Pharmacology
Mechanism of action
Amylmetacresol is an antibacterial and antiviral substance. It also blocks sodium channels in a manner similar to local anaesthetics.[3] It has a Rideal-Walker coefficient of 250.[6]
Pharmacokinetics
The substance is rapidly absorbed. It is oxidised to a carboxylic acid, glucuronidated, and quickly eliminated via the kidneys.[1][3]
Chemistry
AMC is a derivative of m-cresol, with a pentyl group attached to the sixth carbon atom. The pure substance melts at 24 °C (75 °F), and boils between 137 and 139 °C (279 and 282 °F) at a pressure of 6.7 kilopascals (50 mmHg). It is soluble in water, ethanol, acetone, diethylether, and oil.[6]
See also
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 (in German) Austria-Codex. Vienna: Österreichischer Apothekerverlag. 2020. Neo-Angin-Pastillen.
- ↑ 2.0 2.1 2.2 2.3 "Strepsils - Summary of Product Characteristics (SPC) - (eMC)" (in en). https://www.medicines.org.uk/emc/medicine/23391.
- ↑ 3.0 3.1 3.2 3.3 3.4 "Amylmetacresol". DrugBank. https://go.drugbank.com/drugs/DB13908.
- ↑ "Efficacy of AMC/DCBA lozenges for sore throat: A systematic review and meta-analysis". International Journal of Clinical Practice 71 (10): 1742–1241. October 2017. doi:10.1111/ijcp.13002. PMID 28869700.
- ↑ "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". Journal of Pharmacy & Pharmaceutical Sciences 15 (2): 281–294. 2012. doi:10.18433/j31309. PMID 22579007.
- ↑ 6.0 6.1 6.2 "Further researches on bactericidal mists and smokes". The Journal of Hygiene 42 (3): 266–283. May 1942. doi:10.1017/s0022172400035476. PMID 20475630.
Further reading
- "The disinfectant and antiseptic properties of amyl-meta-cresol.". British Journal of Experimental Pathology 12 (5): 331. October 1931.
- "A throat lozenge containing amyl meta cresol and dichlorobenzyl alcohol has a direct virucidal effect on respiratory syncytial virus, influenza A and SARS-CoV". Antiviral Chemistry & Chemotherapy 16 (2): 129–134. 2005. doi:10.1177/095632020501600205. PMID 15889535.
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