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Amylmetacresol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
  • 5-Methyl-2-pentylphenol
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.013.722Edit this at Wikidata
Chemical and physical data
FormulaC12H18O
Molar mass178.275 g·mol−1
3D model (JSmol)
Melting point24 °C (75 °F)
  • CCCCCC1=C(C=C(C=C1)C)O
  • InChI=1S/C12H18O/c1-3-4-5-6-11-8-7-10(2)9-12(11)13/h7-9,13H,3-6H2,1-2H3 checkY
  • Key:CKGWFZQGEQJZIL-UHFFFAOYSA-N checkY
  (verify)

Amylmetacresol (AMC) is anantiseptic used to treatinfections of themouth andthroat. It is used as anactive pharmaceutical ingredient inStrepsils,Cēpacol,Gorpils,Cofsils andLorseptthroat lozenges, typically in combination withdichlorobenzyl alcohol, another antiseptic.[1][2]

Medical uses

[edit]

The lozenges are used to treat sore throat and minor mouth and throat infections includingpharyngitis andgingivitis.[1][3]

A 2017meta-analysis found that the combination of AMC with dichlorobenzyl alcohol has a modest advantage over un-medicated lozenges regarding pain relief.[4][5]

Contraindications

[edit]

No contraindications are known apart fromhypersensitivity to the substance.[1][2]

Adverse effects

[edit]

Amylmetacresol sometimes causes soreness of the tongue. Hypersensitivity reactions are very rare and show symptoms such asnausea ordyspepsia, 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 anLD50 of 1500 mg/kg body weight (in rats).[3][6]

Overdose

[edit]

No cases of overdosing have been reported. It is not expected to cause symptoms other thangastrointestinal discomfort.[1][2]

Interactions

[edit]

No interactions with other drugs are known.[1][2]

Pharmacology

[edit]

Mechanism of action

[edit]

Amylmetacresol is anantibacterial andantiviral substance. It alsoblocks sodium channels in a manner similar tolocal anaesthetics.[3] It has aRideal-Walker coefficient of 250.[6]

Pharmacokinetics

[edit]

The substance is rapidly absorbed. It isoxidised to acarboxylic acid,glucuronidated, and quickly eliminated via the kidneys.[1][3]

Chemistry

[edit]

AMC is a derivative ofm-cresol, with apentyl 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

[edit]

References

[edit]
  1. ^abcdefgHaberfeld H, ed. (2020).Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Neo-Angin-Pastillen.
  2. ^abcd"Strepsils - Summary of Product Characteristics (SPC) - (eMC)".Datapharm UK. Retrieved2017-02-20.
  3. ^abcde"Amylmetacresol".DrugBank. DB13908. Retrieved20 May 2021.
  4. ^Weckmann G, Hauptmann-Voß A, Baumeister SE, Klötzer C, Chenot JF (October 2017)."Efficacy of AMC/DCBA lozenges for sore throat: A systematic review and meta-analysis".International Journal of Clinical Practice.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".Journal of Pharmacy & Pharmaceutical Sciences.15 (2):281–294.doi:10.18433/j31309.PMID 22579007.
  6. ^abcTwort CC, Baker AH (May 1942)."Further researches on bactericidal mists and smokes".The Journal of Hygiene.42 (3):266–283.doi:10.1017/s0022172400035476.PMC 2199819.PMID 20475630.

Further reading

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