Isoetarine
Encyclopedia
Isoetarine or isoetharine (USAN
), trade names Bronkosol and Bronkometer, is a selective beta2-adrenergic receptor agonist
. It can be called the "granddaughter of adrenalin" in the line of beta-two antagonists that gave quick relief for brochospasm and asthma. Adrenalin or epinephrine was the first of these, and next came Isuprel. Isoetharine was the third drug in this line, thus the third generation or granddaughter of the original.
In the western US it was the drug of choice in the late 1970s and early 1980s for nebulization ("breathing treatment") to relieve airway spasm. It generally gave sharp relief of shortness of breath, starting within two to five minutes after the patient began breathing the nebulized mist. This rapid onset is not as clearly present in later drugs.
All of the early beta-two agonist catecholamines used for bronchospasm had strong side effects, with increase in heart rate as the most common and most problematic. This came because its "beta-two effect" was not quite as selective as might be hoped. Beta-one receptors appeared to also be stimulated in some patients, causing cardiac and other CNS side effects. With Bronkosol this effect tended to be transient and usually went away within a matter of minutes after the end of the treatment. Increase in blood pressure also occurred in a small but significant percentage of cases, but also was almost invariably transient.
By the late 1980s isoetharine was largely replaced in the marketplace by Alupent/metaproterenol, which seemed to have slightly less cardiac side effect and lasted a couple of hours longer. Alupent in turn was replaced by albuterol. Some practitioners still believe that these later aerosolized bronchodilators never gave quite as quick of relief from asthmatic shortness of breath as did Bronkosol. Thus they see a continued specialty role in treatment of severe shortness of breath that does not improve in the first five minutes of albuterol treatment.
in the presence of an additional ethyl group in the ethylamino side chain—and is synthesized by bromination of 3,4-dibenzyloxybutyrophenone and the subsequent reaction of the resulting bromo derivative with isopropylamine
. The product undergoes reduction by hydrogen using a palladium catalyst, during which the carbonyl
group is simultaneously reduced and the benzyl
-protecting group
s are cleaved forming isoetharine.
United States Adopted Name
United States Adopted Names are unique nonproprietary names assigned to pharmaceuticals marketed in the United States. Each name is assigned by the USAN Council, which is co-sponsored by the American Medical Association , the United States Pharmacopeial Convention , and the American Pharmacists...
), trade names Bronkosol and Bronkometer, is a selective beta2-adrenergic receptor agonist
Beta2-adrenergic receptor agonist
β2-adrenergic agonists, also known as β2-adrenergic receptor agonists, are a class of drugs used to treat asthma and other pulmonary disease states.-Uses:...
. It can be called the "granddaughter of adrenalin" in the line of beta-two antagonists that gave quick relief for brochospasm and asthma. Adrenalin or epinephrine was the first of these, and next came Isuprel. Isoetharine was the third drug in this line, thus the third generation or granddaughter of the original.
In the western US it was the drug of choice in the late 1970s and early 1980s for nebulization ("breathing treatment") to relieve airway spasm. It generally gave sharp relief of shortness of breath, starting within two to five minutes after the patient began breathing the nebulized mist. This rapid onset is not as clearly present in later drugs.
All of the early beta-two agonist catecholamines used for bronchospasm had strong side effects, with increase in heart rate as the most common and most problematic. This came because its "beta-two effect" was not quite as selective as might be hoped. Beta-one receptors appeared to also be stimulated in some patients, causing cardiac and other CNS side effects. With Bronkosol this effect tended to be transient and usually went away within a matter of minutes after the end of the treatment. Increase in blood pressure also occurred in a small but significant percentage of cases, but also was almost invariably transient.
By the late 1980s isoetharine was largely replaced in the marketplace by Alupent/metaproterenol, which seemed to have slightly less cardiac side effect and lasted a couple of hours longer. Alupent in turn was replaced by albuterol. Some practitioners still believe that these later aerosolized bronchodilators never gave quite as quick of relief from asthmatic shortness of breath as did Bronkosol. Thus they see a continued specialty role in treatment of severe shortness of breath that does not improve in the first five minutes of albuterol treatment.
Chemistry
Isoetharine, 3,4-dihydroxy-α-[1-(iso-propylamino)propyl]benzylic alcohol, differs from isoproterenolIsoproterenol
Isoprenaline or isoproterenol is a medication used for the treatment of bradycardia , heart block, and rarely for asthma...
in the presence of an additional ethyl group in the ethylamino side chain—and is synthesized by bromination of 3,4-dibenzyloxybutyrophenone and the subsequent reaction of the resulting bromo derivative with isopropylamine
Isopropylamine
Isopropylamine, also called 2-aminopropane, 2-propanamine, monoisopropylamine, and MIPA, is an organic compound, an amine. It is a base, as typical for amines. It is a hygroscopic colorless liquid with ammonia-like odor. Its melting point is −95.2 °C and its boiling point is 32.4 °C. It is miscible...
. The product undergoes reduction by hydrogen using a palladium catalyst, during which the carbonyl
Carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups....
group is simultaneously reduced and the benzyl
Benzyl
In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-. Benzyl features a benzene ring attached to a CH2 group.-Nomenclature:...
-protecting group
Protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction...
s are cleaved forming isoetharine.
- G. Ehrhart, L. Stein, (1936).