Chemistry:Metaraminol
Metaraminol, also known as metaradrine and sold under the brand name Aramine 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][2][3] It is given by intramuscular or intravenous administration.[1]
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.[4][5][6] It is a substituted amphetamine and is closely related to phenylpropanolamine, ephedrine, and oxilofrine.[2][3]
Metaraminol was approved for medical use in the United States in September 1954.[7][8][9]
Medical uses
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.[10][11]
Metaraminol is also used in the treatment of priapism.[12][13][14]
Pharmacology
Pharmacodynamics
The dominant mechanism of action for the vasopressor action of metaraminol is indirect,[4] with metaraminol displacing norepinephrine from neuronal vesicles in order for the noradrenaline to exert these effects.[5] Metaraminol at higher doses may have direct α-adrenergic agonist and β1-adrenergic agonist effects.[4] However at doses common in clinical practice, the indirect α1-adrenergic effects predominate, such that reflex bradycardia is a common side effect.
Chemistry
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.[2][3] It is the (1R,2S)-enantiomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine).[2][3] 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).[2][3]
The experimental log P of metaraminol is -0.27 and its predicted log P ranges from -0.59 to 0.07.[15][16]
Metaraminol is used pharmaceutically as the bitartrate salt.[2][3]
History
Metaraminol was approved for medical use in the United States in September 1954.[7][8][9][2]
Society and culture
Names
Metaraminol is the generic name of the medication and its INN and BAN, while its DCF is métaraminol and its DCIT is metaraminolo.[2][3][17] As the bitartrate salt, its generic name is metaraminol bitartrate and this is its USAN and JAN, while metaraminol tartrate is its BANM.[2][3][17] A synonym of metaraminol is metaradrine.[3][17] Brand names of metaraminol include Aramin, Aramine, and Pressonex, among others.[2][3][17]
References
- ↑ 1.0 1.1 Cite error: Invalid
<ref>tag; no text was provided for refs namedFDA Label - ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 62. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA62. Retrieved 31 August 2024.
- ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 660. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA660. Retrieved 31 August 2024.
- ↑ 4.0 4.1 4.2 "Metaraminol" (in en). Deranged Physiology. https://derangedphysiology.com/main/cicm-primary-exam/required-reading/cardiovascular-system/Chapter%20979/metaraminol.
- ↑ 5.0 5.1 "Studies on the Mechanism of Action of Metaraminol (Aramine)". Annals of Internal Medicine 59 (3): 297–305. September 1963. doi:10.7326/0003-4819-59-3-297. PMID 14065947.
- ↑ "Hemodynamic pharmacology of intravenous vasopressors". Crit Care Nurse 23 (4): 79–82. Aug 2003. doi:10.4037/ccn2003.23.4.79. PMID 12961786. http://ccn.aacnjournals.org/content/23/4/79.long.
- ↑ 7.0 7.1 "Aaramine: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=009509.
- ↑ 8.0 8.1 "Clinical studies on a vasopressor agent: metaraminol (aramine). I. Observations in normotensive subjects". Am J Med Sci 229 (6): 661–669. June 1955. doi:10.1097/00000441-195506000-00008. PMID 14376394.
- ↑ 9.0 9.1 "Clinical studies on a vasopressor agent: metaraminol (aramine). II. Observations on its use in the management of shock". The American Journal of the Medical Sciences 230 (4): 357–369. October 1955. 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)". https://www.medicines.org.uk/emc/product/11698/smpc.
- ↑ "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. 21 August 2020. https://search.informit.org/doi/abs/10.3316/INFORMIT.477021141406775.
- ↑ "Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol.". Int Braz J Urol 30 (2): 121–122. 2004. doi:10.1590/S1677-55382004000200007. PMID 15703094.
- ↑ "Post-traumatic priapism treated with metaraminol bitartrate: case report.". J Trauma 30 (12): 1591–3. 1990. doi:10.1097/00005373-199012000-00029. PMID 2258979.
- ↑ "[Metaraminol in therapy of various forms of priapism]". Urologe A 27 (4): 225–9. 1988. PMID 3140463.
- ↑ "Metaraminol". https://pubchem.ncbi.nlm.nih.gov/compound/5906.
- ↑ "Metaraminol". 1 September 2024. https://www.chemspider.com/Chemical-Structure.5695.html.
- ↑ 17.0 17.1 17.2 17.3 "Metaraminol - Drugs.com". https://www.drugs.com/international/metaraminol.html.
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