Phenbenzamine: Difference between revisions
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'''Phenbenzamine''', sold under the brand name '''Antergan''', is an [[antihistamine]] of the [[ethylenediamine]] class which also has [[anticholinergic]] properties.<ref>{{cite encyclopedia | title = Phenbenzamine | url = http://www.britannica.com/EBchecked/topic/455484/phenbenzamine | encyclopedia = Encyclopædia Britannica }}</ref> It was introduced in 1941 or 1942 and was the first antihistamine to be introduced for medical use.<ref name="Moncrieff2013">{{cite book | title = The Bitterest Pills | last1 = Moncrieff | first1 = Joanna | chapter = Chlorpromazine: The First Wonder Drug | date = 2013 | pages = 20–38 | publisher = Palgrave Macmillan UK | doi = 10.1057/9781137277442_2 | url = }}</ref><ref name="WilliamsFoyeLemke2002">{{cite book | author1 = David A. Williams | author2 = William O. Foye | author3 = Thomas L. Lemke | date = 2002 | title = Foye's Principles of Medicinal Chemistry | publisher = Lippincott Williams & Wilkins | pages = 799– | isbn = 978-0-683-30737-5 | url = https://books.google.com/books?id=qLJ6Bs1Qml4C&pg=PA799}}</ref><ref name="Welcome2018">{{cite book | author = Menizibeya Osain Welcome | date = 20 June 2018 | title = Gastrointestinal Physiology: Development, Principles and Mechanisms of Regulation | publisher = Springer | pages = 827– | isbn = 978-3-319-91056-7 | url = https://books.google.com/books?id=UyVhDwAAQBAJ&pg=PA827}}</ref> Soon following its introduction, phenbenzamine was replaced by another antihistamine of the same class known as [[mepyramine]] (pyrilamine).<ref name="Welcome2018" /> Following this, other antihistamines, such as [[diphenhydramine]], [[promethazine]], and [[tripelennamine]], were developed and introduced.<ref name="Welcome2018" /><ref name="LandauAchilladelisScriabine1999">{{cite book | author1 = Ralph Landau | author2 = Basil Achilladelis | author3 = Alexander Scriabine | date = 1999 | title = Pharmaceutical Innovation: Revolutionizing Human Health | publisher = Chemical Heritage Foundation | pages = 230–231 | isbn = 978-0-941901-21-5 | url = https://books.google.com/books?id=IH4lPs6S1bMC&pg=PA230}}</ref> Whereas phenbenzamine was the first clinically useful antihistamine, [[piperoxan]] was the first compound with antihistamine properties to be discovered and was synthesized in the early 1930s.<ref name="LandauAchilladelisScriabine1999" /> |
'''Phenbenzamine''', sold under the brand name '''Antergan''' and known by the former developmental code name '''RP-2339''', is an [[antihistamine]] of the [[ethylenediamine]] class which also has [[anticholinergic]] properties.<ref>{{cite encyclopedia | title = Phenbenzamine | url = http://www.britannica.com/EBchecked/topic/455484/phenbenzamine | encyclopedia = Encyclopædia Britannica }}</ref><ref name="MaxwellEckhardt2012">{{cite book | author1 = Robert A. Maxwell | author2 = Shohreh B. Eckhardt | date = 6 December 2012 | title = Drug Discovery: A Casebook and Analysis | publisher = Springer Science & Business Media | pages = 113– | isbn = 978-1-4612-0469-5 | url = https://books.google.com/books?id=35TzBwAAQBAJ&pg=PA113}}</ref> It was introduced in 1941 or 1942 and was the first antihistamine to be introduced for medical use.<ref name="Moncrieff2013">{{cite book | title = The Bitterest Pills | last1 = Moncrieff | first1 = Joanna | chapter = Chlorpromazine: The First Wonder Drug | date = 2013 | pages = 20–38 | publisher = Palgrave Macmillan UK | doi = 10.1057/9781137277442_2 | url = }}</ref><ref name="WilliamsFoyeLemke2002">{{cite book | author1 = David A. Williams | author2 = William O. Foye | author3 = Thomas L. Lemke | date = 2002 | title = Foye's Principles of Medicinal Chemistry | publisher = Lippincott Williams & Wilkins | pages = 799– | isbn = 978-0-683-30737-5 | url = https://books.google.com/books?id=qLJ6Bs1Qml4C&pg=PA799}}</ref><ref name="Welcome2018">{{cite book | author = Menizibeya Osain Welcome | date = 20 June 2018 | title = Gastrointestinal Physiology: Development, Principles and Mechanisms of Regulation | publisher = Springer | pages = 827– | isbn = 978-3-319-91056-7 | url = https://books.google.com/books?id=UyVhDwAAQBAJ&pg=PA827}}</ref> Soon following its introduction, phenbenzamine was replaced by another antihistamine of the same class known as [[mepyramine]] (pyrilamine).<ref name="Welcome2018" /> Following this, other antihistamines, such as [[diphenhydramine]], [[promethazine]], and [[tripelennamine]], were developed and introduced.<ref name="Welcome2018" /><ref name="LandauAchilladelisScriabine1999">{{cite book | author1 = Ralph Landau | author2 = Basil Achilladelis | author3 = Alexander Scriabine | date = 1999 | title = Pharmaceutical Innovation: Revolutionizing Human Health | publisher = Chemical Heritage Foundation | pages = 230–231 | isbn = 978-0-941901-21-5 | url = https://books.google.com/books?id=IH4lPs6S1bMC&pg=PA230}}</ref> Whereas phenbenzamine was the first clinically useful antihistamine, [[piperoxan]] was the first compound with antihistamine properties to be discovered and was synthesized in the early 1930s.<ref name="LandauAchilladelisScriabine1999" /> |
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==Chemistry== |
==Chemistry== |
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Revision as of 23:59, 23 November 2021
 | This article may be too technical for most readers to understand. (October 2014) |
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| Clinical data | |
|---|---|
| Trade names | Antergan |
| Other names | RP-2339 |
| Drug class | Antihistamine; H1 receptor antagonist |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C17H22N2 |
| Molar mass | 254.377 g·mol−1 |
| 3D model (JSmol) | |
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Phenbenzamine, sold under the brand name Antergan and known by the former developmental code name RP-2339, is an antihistamine of the ethylenediamine class which also has anticholinergic properties.[1][2] It was introduced in 1941 or 1942 and was the first antihistamine to be introduced for medical use.[3][4][5] Soon following its introduction, phenbenzamine was replaced by another antihistamine of the same class known as mepyramine (pyrilamine).[5] Following this, other antihistamines, such as diphenhydramine, promethazine, and tripelennamine, were developed and introduced.[5][6] Whereas phenbenzamine was the first clinically useful antihistamine, piperoxan was the first compound with antihistamine properties to be discovered and was synthesized in the early 1930s.[6]
Chemistry
Synthesis
Phenbenzamine can be prepared by the reaction of N-benzylaniline with 2-chloroethyldimethylamine.[7][8]
Phenbenzamine synthesis
References
- ^ "Phenbenzamine". Encyclopædia Britannica.
- ^ Robert A. Maxwell; Shohreh B. Eckhardt (6 December 2012). Drug Discovery: A Casebook and Analysis. Springer Science & Business Media. pp. 113–. ISBN 978-1-4612-0469-5.
- ^ Moncrieff, Joanna (2013). "Chlorpromazine: The First Wonder Drug". The Bitterest Pills. Palgrave Macmillan UK. pp. 20–38. doi:10.1057/9781137277442_2.
- ^ David A. Williams; William O. Foye; Thomas L. Lemke (2002). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 799–. ISBN 978-0-683-30737-5.
- ^ a b c Menizibeya Osain Welcome (20 June 2018). Gastrointestinal Physiology: Development, Principles and Mechanisms of Regulation. Springer. pp. 827–. ISBN 978-3-319-91056-7.
- ^ a b Ralph Landau; Basil Achilladelis; Alexander Scriabine (1999). Pharmaceutical Innovation: Revolutionizing Human Health. Chemical Heritage Foundation. pp. 230–231. ISBN 978-0-941901-21-5.
- ^ US 2634293, Kyrides LP, Zienty FB, "Process of preparing a monobasic salt of a secondary amine", issued 7 April 1953, assigned to Monsanto Chemicals
- ^ Kaye IA, Parris CL, Weiner N (1953). "A Novel N-Alkylation Reaction". Journal of the American Chemical Society. 75 (3): 744–745. doi:10.1021/ja01099a508.
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