Metaraminol

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Metaraminol
Metaraminol Structural Formulae.png
Clinical data
Trade names Aramine, Metaramin, Pressonex, others
Other namesMetaradrine; 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
License data
Pregnancy
category
  • AU:C
Routes of
administration
Intramuscular injection, intravenous administration [1] [2]
Drug class Norepinephrine releasing agent; Adrenergic receptor agonist; Sympathomimetic; Antihypotensive
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 45% [2]
Metabolism Liver [2]
Identifiers
  • (1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C9H13NO2
Molar mass 167.208 g·mol−1
3D model (JSmol)
  • O[C@H](c1cc(O)ccc1)[C@@H](N)C
  • InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1 Yes check.svgY
  • Key:WXFIGDLSSYIKKV-RCOVLWMOSA-N Yes check.svgY
   (verify)

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]

Contents

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

A commercially prepared pre-filled syringe of metaraminol for bolus use during anaesthesia, made up as 0.5 mg/mL (2.5 mg in 5 mL). Metaraminol prefilledsyringe.jpg
A commercially prepared pre-filled syringe of metaraminol for bolus use during anaesthesia, made up as 0.5 mg/mL (2.5 mg in 5 mL).

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, [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

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

Metaraminol was first described and introduced for medical use by 1955. [9] [10] [4]

Society and culture

Names

Metaraminol is the generic name of the drug and its INN Tooltip International Nonproprietary Name and BAN Tooltip British Approved Name, while its DCF Tooltip Dénomination Commune Française is métaraminol and its DCIT Tooltip Denominazione Comune Italiana is metaraminolo. [4] [5] [18] As the bitartrate salt, its generic name is metaraminol bitartrate and this is its USAN Tooltip United States Adopted Name and JAN Tooltip Japanese Accepted Name, while metaraminol tartrate is its BANM Tooltip British Approved Name. [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

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]

Related Research Articles

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<span class="mw-page-title-main">Ephedrine</span> Medication and stimulant

Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection, it lasts about an hour, and when taken by mouth, it can last up to four hours.

<span class="mw-page-title-main">Phenylpropanolamine</span> Sympathomimetic agent

Phenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was previously commonly used in prescription and over-the-counter cough and cold preparations. The medication is taken by mouth.

<span class="mw-page-title-main">Atenolol</span> Beta blocker medication

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<span class="mw-page-title-main">Sympathomimetic drug</span> Substance that mimics effects of catecholamines

Sympathomimetic drugs are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in heart rate, force of cardiac contraction, and blood pressure. The primary endogenous agonists of the sympathetic nervous system are the catecholamines, which function as both neurotransmitters and hormones. Sympathomimetic drugs are used to treat cardiac arrest and low blood pressure, or even delay premature labor, among other things.

<span class="mw-page-title-main">Phenylephrine</span> Decongestant medication

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Beta<sub>2</sub>-adrenergic agonist Compounds that bind to and activate adrenergic beta-2 receptors

Beta2-adrenergic agonists, also known as adrenergic β2 receptor agonists, are a class of drugs that act on the β2 adrenergic receptor. Like other β adrenergic agonists, they cause smooth muscle relaxation. β2 adrenergic agonists' effects on smooth muscle cause dilation of bronchial passages, vasodilation in muscle and liver, relaxation of uterine muscle, and release of insulin. They are primarily used to treat asthma and other pulmonary disorders. Bronchodilators are considered an important treatment regime for chronic obstructive pulmonary disease (COPD) and are usually used in combination with short acting medications and long acting medications in a combined inhaler.

<span class="mw-page-title-main">Alpha-adrenergic agonist</span> Class of drugs

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<span class="mw-page-title-main">Norfenefrine</span> Sympathomimetic drug

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<i>meta</i>-Hydroxynorephedrine Chemical compound

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References

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