Chemistry:Mepyramine
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Other names | Pyrilamine; N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine |
AHFS/Drugs.com | International Drug Names |
MedlinePlus | a606008 |
Routes of administration | oral, topical, |
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Formula | C17H23N3O |
Molar mass | 285.391 g·mol−1 |
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Mepyramine, also known as pyrilamine, is a first generation antihistamine, targeting the H1 receptor as an inverse agonist.[1] Mepyramine rapidly permeates the brain, often causing drowsiness.[2] It is often sold as a maleate salt, pyrilamine maleate.
The medication has negligible anticholinergic activity, with 130,000-fold selectivity for the histamine H1 receptor over the muscarinic acetylcholine receptors (for comparison, diphenhydramine had 20-fold selectivity for the H1 receptor).[3]
It was patented in 1943 and came into medical use in 1949.[4] It was marketed under the names Histadyl, Histalon, Neo-Antergan, Neo-Pyramine, and Nisaval.[5] In the 1960s and 70s it was a very common component in over-the-counter sleep aids such as "Alva-Tranquil", "Dormin", "Sedacaps", "Sominex", "Nytol", and many others.[5]
It is used in over-the-counter combination products to treat the common cold and menstrual symptoms such as Midol Complete.[6] It is also the active ingredient of the topical antihistamine creams Anthisan[7] and Neoantergan[1] sold for the treatment of insect bites, stings, and nettle rash.
See also
- Chloropyramine (chloro instead of methoxy)
References
- ↑ 1.0 1.1 "Histamine and its receptors". British Journal of Pharmacology 147 (Suppl 1): S127–S135. January 2006. doi:10.1038/sj.bjp.0706440. PMID 16402096.
- ↑ "Mepyramine". https://go.drugbank.com/drugs/DB06691.
- ↑ "Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay". Japanese Journal of Pharmacology 43 (3): 277–282. March 1987. doi:10.1254/jjp.43.277. PMID 2884340.
- ↑ (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 545. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA545.
- ↑ 5.0 5.1 "Sleep aids and sedatives". Journal of the American College of Emergency Physicians 6 (9): 408–412. September 1977. doi:10.1016/S0361-1124(77)80006-3. PMID 330911.
- ↑ "Active Ingredients for Midol Complete". Bayer HealthCare LLC. http://midol.com/menstrual_complete_caps.html#q1.
- ↑ "Anthisan Cream - Patient Information Leaflet (PIL)". SANOFI Consumer Healthcare. https://www.medicines.org.uk/emc/product/1618/pil.
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[[Chemistry:AntihistAntihistamine]]s (R06) | |
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For topical use |
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