Metaraminol
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Trade names | Aramine, Metaramin, Pressonex, others |
Other names | Metaradrine; Hydroxynorephedrine; m-Hydroxypropadrine; m-Hydroxynorephedrine; meta-Hydroxynorephedrine; 3-Hydroxyphenylisopropanolamine; (1R,2S)-3,β-Dihydroxy-α-methylphenethylamine; (1R,2S)-3,β-Dihydroxyamphetamine |
AHFS/Drugs.com | International Drug Names |
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Routes of administration | Intramuscular injection, intravenous administration[1][2] |
Drug class | Norepinephrine releasing agent; Adrenergic receptor agonist; Sympathomimetic; Antihypotensive |
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Protein binding | 45%[2] |
Metabolism | Liver[2] |
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Formula | C9H13NO2 |
Molar mass | 167.208 g·mol−1 |
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Metaraminol, also known as metaradrine and sold under the brand names Aramine and Pressonex among others, is a sympathomimetic medication which is used in the prevention and treatment of hypotension (low blood pressure), particularly as a complication of anesthesia.[1][4][5] It is given by intramuscular or intravenous administration.[1][2]
Side effects of metaraminol include reflex bradycardia among others. Metaraminol is a norepinephrine releasing agent and at high doses a α1-adrenergic receptor agonist with some β-adrenergic effect.[6][7][8] It is a substituted amphetamine and is closely related to phenylpropanolamine, ephedrine, and oxilofrine.[4][5]
Metaraminol was first described and introduced for medical use by 1955.[9][10]
Medical uses
[edit]![](http://upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Metaraminol_prefilledsyringe.jpg/220px-Metaraminol_prefilledsyringe.jpg)
Metaraminol is given intravenously as either a bolus (often 0.5–1 mg doses) or as an infusion, usually via peripheral intravenous access. Metaraminol is commonly available as 10 mg in 1 mL, that requires dilution prior to administration (often made up to a 0.5 mg/mL solution), however pre-prepared syringes of metaraminol for bolus use for hypotension are also commonly available.[11][12]
Metaraminol is also used in the treatment of priapism.[13][14][15]
Pharmacology
[edit]Pharmacodynamics
[edit]The dominant mechanism of action for the vasopressor action of metaraminol is indirect,[6] with metaraminol displacing norepinephrine from neuronal vesicles in order for the noradrenaline to exert these effects.[7] Metaraminol at higher doses may have direct α-adrenergic agonist and β1-adrenergic agonist effects.[6][2] However at doses common in clinical practice, the indirect α1-adrenergic effects predominate, such that reflex bradycardia is a common side effect.
Chemistry
[edit]Metaraminol, also known as (1R,2S)-3,β-dihydroxy-α-methylphenethylamine or as (1R,2S)-3,β-dihydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative.[4][5] It is the (1R,2S)-enantiomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine).[4][5] The drug is closely related to phenylpropanolamine ((1RS,2SR)-β-hydroxyamphetamine; norephedrine), ephedrine ((1R,2S)-β-hydroxy-N-methylamphetamine), para-hydroxynorephedrine (4,β-dihydroxyamphetamine), and oxilofrine (4,β-dihydroxy-N-methylamphetamine).[4][5]
The experimental log P of metaraminol is -0.27 and its predicted log P ranges from -0.59 to 0.07.[16][2][17]
Metaraminol is used pharmaceutically as the bitartrate salt.[4][5]
History
[edit]Metaraminol was first described and introduced for medical use by 1955.[9][10][4]
Society and culture
[edit]Names
[edit]Metaraminol is the generic name of the drug and its INN and BAN , while its DCF is métaraminol and its DCIT is metaraminolo.[4][5][18] As the bitartrate salt, its generic name is metaraminol bitartrate and this is its USAN and JAN , while metaraminol tartrate is its BANM .[4][5][18] A synonym of metaraminol is metaradrine.[5][18] Brand names of metaraminol include Aramin, Aramine, and Pressonex, among others.[4][5][18]
Availability
[edit]Metaraminol appears to remain available in Argentina, Australia, Brazil, China, and Thailand.[18] It was previously marketed in many more countries, including the United States and United Kingdom, but seems to have been discontinued in these countries.[5] However, one formulation still remains available in the United States as of August 2024.[19]
References
[edit]- ^ a b c https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/009509s026lbl.pdf
- ^ a b c d e f "Metaraminol: Uses, Interactions, Mechanism of Action". DrugBank Online. 1 July 2024. Retrieved 1 September 2024.
- ^ "Injection : Aramine (Metaraminol Bitartrate)" (PDF). U.S. Food and Drug Administration (FDA). Retrieved 12 March 2022.
- ^ a b c d e f g h i j Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 62. ISBN 978-1-4757-2085-3. Retrieved 31 August 2024.
- ^ a b c d e f g h i j k Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 660. ISBN 978-3-88763-075-1. Retrieved 31 August 2024.
- ^ a b c "Metaraminol". Deranged Physiology. Retrieved 19 October 2022.
- ^ a b Harrison DC, Chidsey CA, Braunwald E (September 1963). "Studies on the Mechanism of Action of Metaraminol (Aramine)". Annals of Internal Medicine. 59 (3): 297–305. doi:10.7326/0003-4819-59-3-297. PMID 14065947.
- ^ Kee VR (August 2003). "Hemodynamic pharmacology of intravenous vasopressors". Crit Care Nurse. 23 (4): 79–82. doi:10.4037/ccn2003.23.4.79. PMID 12961786.
- ^ a b Weil MH, Spink WW (June 1955). "Clinical studies on a vasopressor agent: metaraminol (aramine). I. Observations in normotensive subjects". Am J Med Sci. 229 (6): 661–669. doi:10.1097/00000441-195506000-00008. PMID 14376394.
- ^ a b Weil MH (October 1955). "Clinical studies on a vasopressor agent: metaraminol (aramine). II. Observations on its use in the management of shock". Am J Med Sci. 230 (4): 357–369. doi:10.1097/00000441-195510000-00001. PMID 13258566.
- ^ "Metaraminol 0.5 mg/ml, Solution for Injection in pre-filled syringe - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 19 October 2022.
- ^ Goodrick N, Wentrup T, Messer G, Gleeson P, Culwick M, Goulding G (21 August 2020). "Pre-filled emergency drugs: The introduction of pre-filled metaraminol and ephedrine syringes into the main operating theatres of a major metropolitan centre". Australasian Anaesthesia (2013): 127–134.
- ^ McDonald M, Santucci R (2004). "Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol". Int Braz J Urol. 30 (2): 121–122. doi:10.1590/S1677-55382004000200007. PMID 15703094.
- ^ Koga S, Shiraishi K, Saito Y (1990). "Post-traumatic priapism treated with metaraminol bitartrate: case report". J Trauma. 30 (12): 1591–3. doi:10.1097/00005373-199012000-00029. PMID 2258979.
- ^ Block T, Sturm W, Ernst G, Staehler G, Schmiedt E (1988). "[Metaraminol in therapy of various forms of priapism]". Urologe A. 27 (4): 225–9. PMID 3140463.
- ^ "Metaraminol". PubChem. Retrieved 1 September 2024.
- ^ "Metaraminol". ChemSpider. 1 September 2024. Retrieved 1 September 2024.
- ^ a b c d e https://web.archive.org/web/20160303210434/https://www.drugs.com/international/metaraminol.html
- ^ "Drugs@FDA: FDA-Approved Drugs". accessdata.fda.gov. Retrieved 1 September 2024.
External links
[edit]- "Metaraminol". Drug Information Portal. U.S. National Library of Medicine.
- "Metaraminol bitartrate". Drug Information Portal. U.S. National Library of Medicine.