Amylmetacresol

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]

Amylmetacresol
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth (throat lozenges)
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
MetabolismOxidation, glucuronidation
ExcretionVia kidneys
Identifiers
IUPAC name
  • 5-Methyl-2-pentylphenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.013.722
Chemical and physical data
FormulaC12H18O
Molar mass178.27 g·mol−1
3D model (JSmol)
Melting point24 °C (75 °F)
SMILES
  • CCCCCC1=C(C=C(C=C1)C)O
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 Y
  • Key:CKGWFZQGEQJZIL-UHFFFAOYSA-N Y
  (verify)

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. Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Neo-Angin-Pastillen.
  2. "Strepsils - Summary of Product Characteristics (SPC) - (eMC)". Datapharm UK. Retrieved 2017-02-20.
  3. DrugBank DB13908 . Accessed 20 May 2021.
  4. Weckmann G, Hauptmann-Voß A, Baumeister SE, Klötzer C, Chenot JF (2017). "Efficacy of AMC/DCBA lozenges for sore throat: A systematic review and meta-analysis". Int J Clin Pract. 71 (10): 1742–1241. doi:10.1111/ijcp.13002. PMID 28869700. S2CID 23055607.
  5. McNally D, Shephard A, Field E (2012). "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. 15 (2): 281–94. doi:10.18433/j31309. PMID 22579007.
  6. Twort, CC; Baker, AH (1942). "Further Researches on Bactericidal Mists and Smokes". The Journal of Hygiene. 42 (3): 266–283. doi:10.1017/s0022172400035476. PMC 2199819. PMID 20475630.
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