Metaraminol
Antihypotensive medication
From Wikipedia, the free encyclopedia
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][3][4] It is given by intramuscular or intravenous administration.[1]
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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 |
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| Routes of administration | Intramuscular injection, intravenous administration[1] |
| Drug class | Norepinephrine releasing agent; Adrenergic receptor agonist; Sympathomimetic; Antihypotensive |
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| Protein binding | 45% |
| Metabolism | Liver |
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| Formula | C9H13NO2 |
| Molar mass | 167.208 g·mol−1 |
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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.[5][6][7] It is a substituted amphetamine and is closely related to phenylpropanolamine, ephedrine, and oxilofrine.[3][4]
Metaraminol was approved for medical use in the United States in September 1954.[8][9][10]
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.[11][12]
Metaraminol is also used in the treatment of priapism.[13][14][15]
Pharmacology
Pharmacodynamics
The dominant mechanism of action for the vasopressor action of metaraminol is indirect,[5] with metaraminol displacing norepinephrine from neuronal vesicles in order for the noradrenaline to exert these effects.[6] Metaraminol at higher doses may have direct α-adrenergic agonist and β1-adrenergic agonist effects.[5] 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.[3][4] It is the (1R,2S)-enantiomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine).[3][4] 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).[3][4]
The experimental log P of metaraminol is -0.27 and its predicted log P ranges from -0.59 to 0.07.[16][17]
Metaraminol is used pharmaceutically as the bitartrate salt.[3][4]
History
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.[3][4][18] As the bitartrate salt, its generic name is metaraminol bitartrate and this is its USAN and JAN, while metaraminol tartrate is its BANM.[3][4][18] A synonym of metaraminol is metaradrine.[4][18] Brand names of metaraminol include Aramin, Aramine, and Pressonex, among others.[3][4][18]
