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{{Short description|Chemical compound}} |
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{{Drugbox| verifiedrevid = 415527556 |
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{{Drugbox |
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|used in strepsils |
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| verifiedrevid = 443857623 |
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|IUPAC_name = 4-hexylbenzene-1,3-diol |
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| IUPAC_name = 5-Methyl-2-pentylphenol |
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| image=Hexylresorcinol.svg |
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| image = Amylmetacresol.svg |
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| image2=Hexylresorcinol-3D-balls.png |
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| width = 175 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D04441 |
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<!--Clinical data--> |
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| InChI = 1/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3 |
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| tradename = |
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| InChIKey = WFJIVOKAWHGMBH-UHFFFAOYAH |
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| Drugs.com = {{drugs.com|international|hexylresorcinol}} |
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| smiles = Oc1cc(O)ccc1CCCCCC |
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| pregnancy_category = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 443605 |
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| legal_status = OTC |
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| routes_of_administration = ] (]s) |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| metabolism = ], ] |
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| excretion = Via kidneys |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 1300-94-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 05W904P57F |
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| ATC_prefix = None |
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| ATC_suffix = |
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| PubChem = 14759 |
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| ChEMBL = 1512677 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 14076 |
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| DrugBank = DB13908 |
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| KEGG_Ref = |
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| KEGG = |
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<!--Chemical data--> |
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| C=12 | H=18 | O=1 |
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| melting_point = 24 |
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| smiles = CCCCCC1=C(C=C(C=C1)C)O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3 |
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| StdInChI = 1S/C12H18O/c1-3-4-5-6-11-8-7-10(2)9-12(11)13/h7-9,13H,3-6H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WFJIVOKAWHGMBH-UHFFFAOYSA-N |
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| StdInChIKey = CKGWFZQGEQJZIL-UHFFFAOYSA-N |
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| CAS_number=136-77-6 |
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| ATC_prefix=R02 |
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| ATC_suffix=AA12 |
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| ATC_supplemental= |
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| UNII = R9QTB5E82N |
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| PubChem=3610 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=21106121 |
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| DrugBank= |
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| C=12 | H=18 | O=2 |
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| molecular_weight = 194.27 |
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| bioavailability= |
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| metabolism = |
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| elimination_half-life= |
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| excretion = |
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| pregnancy_category = |
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| legal_status = |
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| routes_of_administration= |
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}} |
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}} |
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'''Hexylresorcinol''' is a chemical compound with ], ] and ] properties. |
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'''Amylmetacresol''' ('''AMC''') is an ] used to treat ]s of the ] and ]. It is used as an ] in ], ], ], ] and ] ], typically in combination with ], another antiseptic.<ref name="AC">{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Neo-Angin-Pastillen|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2020|language=German}}</ref><ref name="Strepsils">{{Cite web|url=https://www.medicines.org.uk/emc/medicine/23391|title=Strepsils - Summary of Product Characteristics (SPC) - (eMC)|website=Datapharm UK|language=en|access-date=2017-02-20}}</ref> |
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It can be used topically on small ]s, or as an ingredient in ]s. |
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==Medical uses== |
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An ingredient in ] Extra (but not Strepsils Original) and, as a 0,1% solution, it is the active ingredient in S.T.37, Topical Antiseptic/Oral Pain Reliever. |
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The lozenges are used to treat sore throat and minor mouth and throat infections including ] and ].<ref name="AC" /><ref name="DrugBank">{{cite web | title = Amylmetacresol | url = https://go.drugbank.com/drugs/DB13908 | access-date = 20 May 2021 | work = DrugBank | id = DB13908 }}</ref> |
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A 2017 ] found that the combination of AMC with dichlorobenzyl alcohol has a modest advantage over un-medicated lozenges regarding pain relief.<ref>{{cite journal | vauthors = Weckmann G, Hauptmann-Voß A, Baumeister SE, Klötzer C, Chenot JF | title = Efficacy of AMC/DCBA lozenges for sore throat: A systematic review and meta-analysis | journal = International Journal of Clinical Practice | volume = 71 | issue = 10 | pages = 1742–1241 | date = October 2017 | pmid = 28869700 | doi = 10.1111/ijcp.13002 | s2cid = 23055607 | doi-access = free }}</ref><ref>{{cite journal | vauthors = McNally D, Shephard A, Field E | title = 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 = Journal of Pharmacy & Pharmaceutical Sciences | volume = 15 | issue = 2 | pages = 281–294 | date = 2012 | pmid = 22579007 | doi = 10.18433/j31309 | doi-access = free }}</ref> |
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A study published in Chemical Research in Toxicology in March 2009<ref>Chem. Res. Toxicol., 2009, 22 (1), pp 52–63</ref> shows that 4-hexylresorcinol used as a food additive (E-586) exhibits some estrogenic activity, i.e. resembles action of the female sex hormone ]. |
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==Contraindications== |
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== References == |
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No contraindications are known apart from ] to the substance.<ref name="AC" /><ref name="Strepsils" /> |
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<references /> |
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==Adverse effects== |
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{{Throat preparations}} |
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Amylmetacresol sometimes causes soreness of the tongue. Hypersensitivity reactions are very rare and show symptoms such as ] or ], although it is not entirely clear which side effects are caused by AMC and which by dichlorobenzyl alcohol or other ingredients of the lozenges.<ref name="AC" /><ref name="DrugBank" /> |
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AMC has a low toxicity with an ] of 1500 mg/kg body weight (in rats).<ref name="DrugBank" /><ref name="Twort">{{cite journal | vauthors = Twort CC, Baker AH | title = Further researches on bactericidal mists and smokes | journal = The Journal of Hygiene | volume = 42 | issue = 3 | pages = 266–283 | date = May 1942 | pmid = 20475630 | pmc = 2199819 | doi = 10.1017/s0022172400035476 }}</ref> |
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{{respiratory-system-drug-stub}} |
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{{nervous-system-drug-stub}} |
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==Overdose== |
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No cases of overdosing have been reported. It is not expected to cause symptoms other than ] discomfort.<ref name="AC" /><ref name="Strepsils" /> |
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== Interactions == |
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No interactions with other drugs are known.<ref name="AC" /><ref name="Strepsils" /> |
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==Pharmacology== |
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===Mechanism of action=== |
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Amylmetacresol is an ] and ] substance. It also ] in a manner similar to ].<ref name="DrugBank" /> It has a ] of 250.<ref name="Twort" /> |
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===Pharmacokinetics=== |
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The substance is rapidly absorbed. It is ] to a ], ], and quickly eliminated via the kidneys.<ref name="AC" /><ref name="DrugBank" /> |
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==Chemistry== |
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AMC is a derivative of ], with a ] group attached to the sixth carbon atom. The pure substance melts at {{convert|24|°C|°F}}, and boils between {{convert|137 and 139|°C|°F}} at a pressure of {{convert|6.7|kPa|mmHg}}. It is soluble in water, ], ], ], and oil.<ref name="Twort" /> |
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== See also == |
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* ] |
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* ] |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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== Further reading == |
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{{refbegin}} |
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* {{cite journal | vauthors = Coulthard CE | title = The disinfectant and antiseptic properties of amyl-meta-cresol. | journal = British Journal of Experimental Pathology | date = October 1931 | volume = 12 | issue = 5 | pages = 331 }} |
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* {{cite journal | vauthors = Oxford JS, Lambkin R, Gibb I, Balasingam S, Chan C, Catchpole A | 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 = Antiviral Chemistry & Chemotherapy | volume = 16 | issue = 2 | pages = 129–134 | date = 2005 | pmid = 15889535 | doi = 10.1177/095632020501600205 | doi-access = free }} |
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{{refend}} |
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] |
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] |
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] |