Chemistry:Methoxamine
Methoxamine, sold under the brand names Vasoxine, Vasoxyl, and Vasylox among others, is a sympathomimetic medication used as an antihypotensive agent.[1][2][3][4] It has mostly or entirely been discontinued.[5]
The drug is an α1-adrenergic receptor agonist.[3][additional citation(s) needed]
Medical uses
The long duration of action of methoxamine has been said to have rendered it obsolete in modern clinical practice.[1]
Pharmacology
Methoxamine is an α1-adrenergic receptor agonist.[1] It is described as a long-acting α1-adrenergic receptor agonist and this is contrasted with phenylephrine which is said to be short-acting.[1] Phenylephrine is 5 to 10 times more potent than methoxamine and has a 3-fold higher maximal effect.[1]
Chemistry
Methoxamine, also known as 2,5-dimethoxy-β-hydroxy-α-methylphenethylamine or as 2,5-dimethoxy-β-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative.[2]
It is somewhat similar in chemical structure to those of desglymidodrine (3,6-dimethoxy-β-hydroxyphenethylamine), dimetofrine (3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine), 2,5-dimethoxyamphetamine (2,5-DMA), and butaxamine ((1S,2S)-3,6-dimethoxy-β-hydroxy-N-tert-butylamphetamine).
History
Methoxamine was synthesized by 1944.[2] It was marketed in the United States by 1949.[6]
Society and culture
Names
Methoxamine is the generic name of the drug and its INN and BAN, while méthoxamine is its DCF and methoxamina is its DCIT.[2][3][5] In the case of the hydrochloride salt, its generic name is methoxamine hydrochloride and this is its USAN, BANM, and JAN.[2][3][7][5] A synonym of methoxamine is methoxamedrine.[3] The drug has been sold under brand names including Idasal, Mexan, Pressomin, Vasosterol, Vasoxine, Vasoxyl, and Vasylox.[2][3][5]
Availability
Methoxamine has been marketed in Canada, the Czech Republic, Ireland, Japan, Spain, the United Kingdom, and the United States and was available in these countries in 2000.[3][5] However, it was discontinued in Canada and the United Kingdom by 2004.[7] It has also been discontinued in the United States.[6] By 2016, methoxamine appeared to remain available only in Japan.[5]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "The physiologic implications of isolated alpha(1) adrenergic stimulation". Anesth Analg 113 (2): 284–296. August 2011. doi:10.1213/ANE.0b013e3182124c0e. PMID 21519050.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 788. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA788. Retrieved 2024-09-01.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 669. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA669. Retrieved 2024-09-01.
- ↑ "5". Pharmacology. Rapid Review (Second ed.). Philadelphia, PA: Mosby-Elsevier. 2007. p. 39. ISBN 978-0-323-04550-6.
- ↑ 5.0 5.1 5.2 5.3 5.4 5.5 "Methoxamine". 20 October 2012. https://drugs.com/international/methoxamine.html.
- ↑ 6.0 6.1 "Drugs@FDA: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&varApplNo=006772.
- ↑ 7.0 7.1 Schweizerischer Apotheker-Verein (2004). Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 779. ISBN 978-3-88763-101-7. https://books.google.com/books?id=EgeuA47Ocm4C&pg=PA779. Retrieved 1 September 2024.
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