Clinical data | |
---|---|
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 |
License data |
|
Pregnancy category |
|
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 | |
| |
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) | |
| |
| |
(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]
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]
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]
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.
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]
Metaraminol was first described and introduced for medical use by 1955. [9] [10] [4]
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]
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]
Pseudoephedrine, sold under the brand name Sudafed among others, is a sympathomimetic medication which is used as a decongestant to treat nasal congestion. It has also been used off-label for certain other indications, like treatment of low blood pressure. At higher doses, it may produce various additional effects, including psychostimulant, appetite suppressant, and performance-enhancing effects. In relation to this, non-medical use of pseudoephedrine has been encountered. The medication is taken by mouth.
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.
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.
Atenolol is a beta blocker medication primarily used to treat high blood pressure and heart-associated chest pain. Although used to treat high blood pressure, it does not seem to improve mortality in those with the condition. Other uses include the prevention of migraines and treatment of certain irregular heart beats. It is taken orally or by intravenous injection. It can also be used with other blood pressure medications.
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.
Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among numerous others, is a medication used as a decongestant for uncomplicated nasal congestion, used to dilate the pupil, used to increase blood pressure, and used to relieve hemorrhoids. It can be taken by mouth, as a nasal spray, given by injection into a vein or muscle, applied to the skin, or as a rectal suppository.
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.
Alpha-adrenergic agonists are a class of sympathomimetic agents that selectively stimulates alpha adrenergic receptors. The alpha-adrenergic receptor has two subclasses α1 and α2. Alpha 2 receptors are associated with sympatholytic properties. Alpha-adrenergic agonists have the opposite function of alpha blockers. Alpha adrenoreceptor ligands mimic the action of epinephrine and norepinephrine signaling in the heart, smooth muscle and central nervous system, with norepinephrine being the highest affinity. The activation of α1 stimulates the membrane bound enzyme phospholipase C, and activation of α2 inhibits the enzyme adenylate cyclase. Inactivation of adenylate cyclase in turn leads to the inactivation of the secondary messenger cyclic adenosine monophosphate and induces smooth muscle and blood vessel constriction.
Methoxamine, sold under the brand names Vasoxine, Vasoxyl, and Vasylox among others, is a sympathomimetic medication used as an antihypotensive agent. It has mostly or entirely been discontinued.
Norfenefrine, also known as meta-octopamine or norphenylephrine and sold under the brand name Novadral among others, is a sympathomimetic medication which is used in the treatment of hypotension. Along with its structural isomer p-octopamine and the tyramines, norfenefrine is a naturally occurring endogenous trace amine and plays a role as a minor neurotransmitter in the brain.
Etilefrine, sold under the brand name Effortil among others, is a sympathomimetic medication used as an antihypotensive agent to treat orthostatic hypotension. It is usually used by mouth, but is also available as an injectable.
Phenylethanolamine, or β-hydroxyphenethylamine, is a trace amine with a structure similar to those of other trace phenethylamines as well as the catecholamine neurotransmitters dopamine, norepinephrine, and epinephrine. As an organic compound, phenylethanolamine is a β-hydroxylated phenethylamine that is also structurally related to a number of synthetic drugs in the substituted phenethylamine class. In common with these compounds, phenylethanolamine has strong cardiovascular activity and, under the name Apophedrin, has been used as a drug to produce topical vasoconstriction.
Oxilofrine, sold under the brand names Carnigen and Suprifen among others, is a sympathomimetic medication which has been used as an antihypotensive agent and cough suppressant. It is taken by mouth.
Methylephedrine, sold under the brand name Metheph among others, is a sympathomimetic medication described as an antiasthmatic agent and used to treat coughing and nasal congestion. It is reported to be used in various over-the-counter cough and cold preparations throughout the world, including Japan.
meta-Hydroxynorephedrine or 3-hydroxynorephedrine, also known as 3,β-dihydroxyamphetamine, is an adrenergic drug of the amphetamine class which was patented as a vasopressor and nasal decongestant but was never marketed. It is the racemic form of the sympathomimetic drug metaraminol.
Norepinephrine, also known as noradrenaline and sold under the brand name Levophed among others, is a medication used to treat people with very low blood pressure. It is the typical medication used in sepsis if low blood pressure does not improve following intravenous fluids. It is the same molecule as the hormone and neurotransmitter norepinephrine. It is given by slow injection into a vein.
Angiotensin II is a medication that is used to treat hypotension resulting from septic shock or other distributive shock. It is a synthetic vasoconstrictor peptide that is identical to human hormone angiotensin II and is marketed under the brand name Giapreza. The Food and Drug Administration approved the use of angiotensin II in December 2017 to treat low blood pressure resulting from septic shock.
Hydroxymethylamphetamine, or hydroxymethamphetamine, also known as phenylpropanolmethylamine, may refer to:
Substituted β-hydroxyamphetamines, also known as substituted phenylisopropanolamines, substituted phenylpropanolamines, substituted norephedrines, or substituted cathinols, are derivatives of β-hydroxyamphetamine with one or more chemical substituents. They are substituted phenethylamines, phenylethanolamines (β-hydroxyphenethylamines), and amphetamines (α-methylphenethylamines), and are closely related to but distinct from the substituted cathinones (β-ketoamphetamines). Examples of β-hydroxyamphetamines include the β-hydroxyamphetamine stereoisomers phenylpropanolamine and cathine and the stereospecific N-methylated β-hydroxyamphetamine derivatives ephedrine and pseudoephedrine, among many others.
Trecadrine is a drug that was originally developed as an anti-ulcer agent but was found to act as a β3-adrenergic receptor agonist with potential anti-obesity and anti-diabetic properties. It is selective for the β3-adrenergic receptor, lacking activity at the β1- and β2-adrenergic receptors. The drug is orally active. Structurally, trecadrine is a substituted β-hydroxyamphetamine and derivative of β-hydroxy-N-methylamphetamine with a tricyclic moiety attached at the amine.