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Revision as of 14:35, 18 January 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoB← Previous edit Latest revision as of 08:13, 20 November 2024 edit undoSlothwizard (talk | contribs)Extended confirmed users1,354 editsNo edit summaryTags: Visual edit Mobile edit Mobile web edit 
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{{short description|First generation antihistamine}}
{{Use dmy dates|date=April 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 408589836
| class = ]
| verifiedrevid = 408591350
| IUPAC_name = ''N''-(4-methoxybenzyl)-''N<nowiki>'</nowiki>'',''N<nowiki>'</nowiki>''-dimethyl-''N''-pyridin-2-ylethane-1,2-diamine | IUPAC_name = ''N''-(4-methoxybenzyl)-''N<nowiki>'</nowiki>'',''N<nowiki>'</nowiki>''-dimethyl-''N''-pyridin-2-ylethane-1,2-diamine
| synonyms = <small>''N''--''N''-pyridin-2-amine</small>
| image = Mepyramine.svg | image = Mepyramine.svg

<!--Clinical data-->| tradename =
| Drugs.com = {{drugs.com|international|mepyramine}}
| MedlinePlus = a606008
| pregnancy_category =
| legal_status = OTC
| routes_of_administration = ], ]

<!--Pharmacokinetic data-->| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion = <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 91-84-9
| CAS_supplemental = <br/>{{CAS|59-33-6}} (maleate)
| ATC_prefix = R06
| ATC_suffix = AC01
| ATC_supplemental = {{ATC|D04|AA02}}
| PubChem = 4992
| IUPHAR_ligand = 1227
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB06691
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4818 | ChemSpiderID = 4818
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = HPE317O9TL | UNII = HPE317O9TL
| KEGG_Ref = {{keggcite|correct|kegg}}
| InChI = 1/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3
| KEGG = D08183
| InChIKey = YECBIJXISLIIDS-UHFFFAOYAS
| ChEBI_Ref = {{ebicite|changed|EBI}}
| smiles = O(c1ccc(cc1)CN(c2ncccc2)CCN(C)C)C
| ChEBI = 6762
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 511 | ChEMBL = 511
| synonyms = Pyrilamine; ''N''--''N''-pyridin-2-amine

<!--Chemical data-->| C = 17
| H = 23
| N = 3
| O = 1
| SMILES = O(c1ccc(cc1)CN(c2ncccc2)CCN(C)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3 | StdInChI = 1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YECBIJXISLIIDS-UHFFFAOYSA-N | StdInChIKey = YECBIJXISLIIDS-UHFFFAOYSA-N
| CAS_number = 91-84-9
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_supplemental = <br/>59-33-6 (maleate)
| ATC_prefix = R06
| ATC_suffix = AC01
| ATC_supplemental = {{ATC|D04|AA02}}
| PubChem = 4992
| IUPHAR_ligand = 1227
| IUPHAR_ligand = 1220
| DrugBank =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08183
| C=17 | H=23 | N=3 | O=1
| molecular_weight = 285.38 g/mol
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_category=
| legal_status =
| routes_of_administration =
}} }}


'''Mepyramine''', also known as '''pyrilamine''', is a ], targeting the ].<ref>{{cite journal | author = Parsons, M. E. and Ganellin, C. R. | title = Histamine and its receptors | journal = British Journal of Pharmacology | volume = 147 | pages = S127–S135 | year = 2006 | pmid = 16402096 | doi = 10.1038/sj.bjp.0706440 | pmc = 1760721}}</ref> However, it rapidly permeates the brain often causing ]. It also has ] properties. It is used in over-the-counter combination products to treat the common cold and menstrual symptoms.<ref></ref> It is also the active ingredient of the topical antihistamine cream ''Anthisan'', sold for the treatment of insect bites, stings and nettle rash. '''Mepyramine''', also known as '''pyrilamine''', is a ], targeting the ] as an ].<ref name=":0" /> Mepyramine rapidly permeates the brain, often causing ].<ref>
{{cite web
|url= https://go.drugbank.com/drugs/DB06691
|title =Mepyramine
|access-date = 8 May 2021
|website=drugbank.com
}}
</ref> It is often sold as a ] salt, '''pyrilamine maleate'''.


The medication has negligible ] activity, with 130,000-fold ] for the ] ] over the ]s (for comparison, ] had 20-fold selectivity for the H<sub>1</sub> receptor).<ref name="pmid2884340">{{cite journal | vauthors = Kubo N, Shirakawa O, Kuno T, Tanaka C | title = Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay | journal = Japanese Journal of Pharmacology | volume = 43 | issue = 3 | pages = 277–282 | date = March 1987 | pmid = 2884340 | doi = 10.1254/jjp.43.277 | doi-access = free }}</ref>
== References ==
{{Reflist|2}}


<!-- Society and culture -->
It was patented in 1943 and came into medical use in 1949.<ref name=Fis2006>{{cite book | veditors = Fischer J, Gannelin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=545 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA545 |language=en}}</ref>
It was marketed under the names Histadyl, Histalon, Neo-Antergan, Neo-Pyramine, and Nisaval.<ref name="sleepaids">{{cite journal | vauthors = Thornton WE | title = Sleep aids and sedatives | journal = ] (JACEP) | volume = 6 | issue = 9 | pages = 408–412 | date = September 1977 | pmid = 330911 | doi = 10.1016/S0361-1124(77)80006-3 }}</ref> In the 1960s and 70s it was a very common component in over-the-counter ] such as Alva-Tranquil, Dormin, Sedacaps, ], Nytol, and many others.<ref name="sleepaids"/> The US ] (FDA) included it in the list of chemicals and compounds barred from use in ] (OTC) nighttime sleep aid products in 1989.<ref>{{Federal Register|54|6826}}</ref>


It is used in over-the-counter combination products to treat the common cold and menstrual symptoms such as ].<ref>{{Cite web |url=http://midol.com/menstrual_complete_caps.html#q1 |title=Active Ingredients for Midol Complete |access-date=2009-12-08 |archive-url=https://web.archive.org/web/20091202030735/http://www.midol.com/menstrual_complete_caps.html#q1 |work=] |archive-date=2009-12-02 |url-status=dead}}</ref> It is also the active ingredient of the topical antihistamine creams Anthisan<ref>{{Cite web |url=https://www.medicines.org.uk/emc/product/1618/pil |title=Anthisan Cream - Patient Information Leaflet (PIL) |website=Medicines.org}}</ref> and Neoantergan<ref name=":0">{{cite journal | vauthors = Parsons ME, Ganellin CR | title = Histamine and its receptors | journal = British Journal of Pharmacology | volume = 147 | issue = Suppl 1 | pages = S127–S135 | date = January 2006 | pmid = 16402096 | pmc = 1760721 | doi = 10.1038/sj.bjp.0706440 | publication-date = 2009-02-02 }}</ref> sold for the treatment of insect bites, stings, and nettle rash.
{{Antipruritics}}
{{Cholinergics}}
{{Histaminergics}}


== See also ==
* ]


== References ==
{{Reflist}}


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