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Clinical data | |
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Trade names | Ildamen, Modacor, Myofedrin |
Other names | Oxyfedrin; Oxyphedrine; Oxyphedrin; Oxifedrine; Oxifedrin; Oxiphedrine; Oxiphedrin |
AHFS/Drugs.com | International Drug Names |
Routes of administration | Oral, intravenous [1] |
Drug class | Sympathomimetic; Coronary vasodilator; β-Adrenergic receptor partial agonist; Norepinephrine releasing agent |
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Pharmacokinetic data | |
Bioavailability | Oral: 85% [1] |
Protein binding | Almost 100% [1] |
Metabolites | • Norephedrine [2] |
Elimination half-life | 4.2 hours [1] |
Excretion | Urine (active metabolites 90%) [1] |
Identifiers | |
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Chemical and physical data | |
Formula | C19H23NO3 |
Molar mass | 313.397 g·mol−1 |
3D model (JSmol) | |
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Oxyfedrine, sold under the brand names Ildamen and Myofedrin among others, is a sympathomimetic agent and coronary vasodilator which is used in the treatment of coronary heart disease, angina pectoris, and acute myocardial infarction. [1] [3] [4] [5] [6] [7] It is taken by mouth or intravenously. [1]
The drug acts as a β-adrenergic receptor partial agonist. [1] [7] It may also act as a norepinephrine releasing agent via its major active metabolite norephedrine. [2] Oxyfedrine is a phenethylamine and amphetamine derivative. [6] [7]
Oxyfedrine has been marketed in Europe, Hong Kong, India, Central America, and elsewhere. [4] [8] [9] It appears to remain marketed only in India. [9]
Oxyfedrine is a β-adrenergic receptor partial agonist. [1] [7] It appears to be non-selective for the β1- and β2-adrenergic receptors. [7] It is selective for the β-adrenergic receptors over the α-adrenergic receptors. [7] However, it has also been reported to interact with the α-adrenergic receptors at high concentrations, acting as a partial agonist or antagonist of these receptors. [7] Norephedrine, a norepinephrine releasing agent, is a major active metabolite of oxyfedrine, and hence oxyfedrine may additionally act as an indirectly acting sympathomimetic. [2]
It has been found to depress the tonicity of coronary vessels, improve myocardial metabolism (so that heart can sustain hypoxia better) and also exert a positive chronotropic and inotropic effects, [1] thereby not precipitating angina pectoris. The latter property (positive chronotropic and inotropic effects) is particularly important, because other vasodilators used in angina may be counter productive causing coronary steal phenomenon.[ additional citation(s) needed ]
The drug is chemically and pharmacologically unrelated to any other antianginal drugs. [1]
Oxyfedrine's oral bioavailability is 85%. [1] The plasma protein binding is almost 100%. [1] Its elimination half-life is 4.2 hours. [1] Norephedrine is a major active metabolite of oxyfedrine. [2] The excretion of the active metabolites of oxyfedrine is 90% in urine. [1] About 75 to 100% of oxyfedrine is excreted as norephedrine. [2]
Oxyfedrine is a substituted phenethylamine and amphetamine derivative. [7] It is l-norephedrine with a bulky and lipophilic 3-methoxypropiophenone substituent at the nitrogen atom. [7]
Mannich condensation of phenylpropanolamine (1) with formaldehyde and m-acetanisole (3-acetylanisole) (2) yields oxyfedrine (3). [10]
Synergistic effects of oxyfedrine with antibiotics against bacteria have been suggested. [11]
An antianginal is a drug used in the treatment of angina pectoris, a symptom of ischaemic heart disease.
Beta blockers, also spelled β-blockers, are a class of medications that are predominantly used to manage abnormal heart rhythms (arrhythmia), and to protect the heart from a second heart attack after a first heart attack. They are also widely used to treat high blood pressure, although they are no longer the first choice for initial treatment of most patients.
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.
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.
Isoprenaline, also known as isoproterenol and sold under the brand name Isuprel among others, is a sympathomimetic medication which is used in the treatment of acute bradycardia, heart block, and rarely for asthma, among other indications. It is used by injection into a vein, muscle, fat, or the heart, by inhalation, and in the past under the tongue or into the rectum.
Dobutamine is a medication used in the treatment of cardiogenic shock and severe heart failure. It may also be used in certain types of cardiac stress tests. It is given by IV only, as an injection into a vein or intraosseous as a continuous infusion. The amount of medication needs to be adjusted to the desired effect. Onset of effects is generally seen within 2 minutes. It has a half-life of two minutes. This drug is generally only administered short term, although it may be used for longer periods to relieve symptoms of heart failure in patients awaiting heart transplantation.
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, particularly as a complication of anesthesia. It is given by intramuscular or intravenous administration.
Corbadrine, sold under the brand name Neo-Cobefrine and also known as levonordefrin and α-methylnorepinephrine, is a catecholamine sympathomimetic used as a topical nasal decongestant and vasoconstrictor in dentistry in the United States. It is usually used in a pre-mixed solution with local anesthetics, such as mepivacaine.
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.
Prenalterol, sold under the brand name Hyprenan, is a sympathomimetic agent and cardiac stimulant which acts as a β1-adrenergic receptor partial agonist and is used in the treatment of heart failure. It has selectivity for the β1-adrenergic receptor. Its partial agonist activity or intrinsic sympathomimetic activity is about 60%. It is said to have much greater impact on myocardial contractility than on heart rate. The drug has been marketed in Denmark, Norway, and Sweden.
Mephentermine, sold under the brand name Wyamine among others, is a sympathomimetic medication which was previously used in the treatment of low blood pressure but is mostly no longer marketed. It is used by injection into a vein or muscle, by inhalation, and by mouth.
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.
A cardiac stimulant is a drug which acts as a stimulant of the heart – e.g., via positive chronotropic action and/or inotropic action. They increase cardiac output.
Beta adrenergic agonists or beta agonists are medications that relax muscles of the airways, causing widening of the airways and resulting in easier breathing. They are a class of sympathomimetic agents, each acting upon the beta adrenoceptors. In general, pure beta-adrenergic agonists have the opposite function of beta blockers: beta-adrenoreceptor agonist ligands mimic the actions of both epinephrine- and norepinephrine- signaling, in the heart and lungs, and in smooth muscle tissue; epinephrine expresses the higher affinity. The activation of β1, β2 and β3 activates the enzyme, adenylate cyclase. This, in turn, leads to the activation of the secondary messenger cyclic adenosine monophosphate (cAMP); cAMP then activates protein kinase A (PKA) which phosphorylates target proteins, ultimately inducing smooth muscle relaxation and contraction of the cardiac tissue.
β1-Adrenergic receptor agonists, also known as beta-1 agonists, are a class of drugs that bind selectively to the β1-adrenergic receptor. As a result, they act more selectively upon the heart. β-Adrenoceptors typically bind to norepinephrine release by sympathetic adrenergic nerves and to circulating epinephrine. The effect of β-adrenoceptors is cardiac stimulation, such as increased heart rate, heart contractility, heart conduction velocity, and heart relaxation.
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.
Peripherally selective drugs have their primary mechanism of action outside of the central nervous system (CNS), usually because they are excluded from the CNS by the blood–brain barrier. By being excluded from the CNS, drugs may act on the rest of the body without producing side-effects related to their effects on the brain or spinal cord. For example, most opioids cause sedation when given at a sufficiently high dose, but peripherally selective opioids can act on the rest of the body without entering the brain and are less likely to cause sedation. These peripherally selective opioids can be used as antidiarrheals, for instance loperamide (Imodium).
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.