| Candidate ID: | R0389 |
| Source ID: | DB01064 |
| Source Type: | approved; investigational |
| Compound Type: |
small molecule
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| Compound Name: |
Isoprenaline
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| Synonyms: |
(±)-isoprenaline; (±)-isoproterenol; 1-(3,4-dihydroxyphenyl)-2-(isopropylamino)ethanol; 1-(3,4-dihydroxyphenyl)-2-isopropylaminoethanol; 3,4-dihydroxy-α-[(isopropylamino)methyl]benzyl alcohol; Isoprenaline; Isopropyl noradrenaline; Isoproterenol; N-isopropyl-β-dihydroxyphenyl-β-hydroxyethylamine; N-Isopropylnoradrenaline; N-Isopropylnorepinephrine; α-(isopropylaminomethyl)protocatechuyl alcohol
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| Molecular Formula: |
C11H17NO3
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| SMILES: |
CC(C)NCC(O)C1=CC(O)=C(O)C=C1
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| Structure: |
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| DrugBank Description: |
Isoprenaline is a non-selective beta adrenergic receptor agonist indicated to treat heart block, Adams-Stokes attacks, bronchospasm in anesthesia, cadiac arrest, hypovolemic shocks, septic shock, hypoperfusion, congestive hear failure, and cardiogenic shock.
Isoprenaline research in the 1940s found that this isopropyl analog of epinephrine dilated the bronchi, as well as raising the heart rate and cardiac output, without vasoconstriction. The US patent from 1943 states that this compound had a wider therapeutic index and a stronger action than .
Isoprenaline was granted FDA approval on 19 February 1948.
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| CAS Number: |
7683-59-2
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| Molecular Weight: |
211.2576
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| DrugBank Indication: |
Isoprenaline is indicated to treat mild or transient episodes of heart block not requiring electric shock or pacemakers, serious episodes of heart block and Adams-Stokes attacks not caused by ventricular tachycardia or fibrillation, and bronchospasm during anesthesia. Isoprenaline is also indicated for cases of cardiac arrest until preferable treatments like electric shock and pacemakers are available. Isoprenaline is also indicated as an adjunct therapy to fluid and electrolyte replacement therapy in hypovolemic shock, septic shock, hypoperfusion, congestive heart failure, and cardiogenic shock.
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| DrugBank Pharmacology: |
Isoprenaline is a non-selective beta adrenergic receptor agonist used in a number of indications for the heart, as well as bronchospasm in anesthesia. Isoprenaline has a short duration of action as it is rapidly cleared, and a wide therapeutic index. Patients should be counselled regarding the risks of isoprenaline in the treatment of cardiogenic shock following myocardial infarction, paradoxical worsening of heart block, or precipitation of Adams-Stokes attacks.
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| DrugBank MoA: |
Isoprenaline is a non-selective beta adrenergic receptor agonist. Agonism of beta-1 and beta-2 adrenergic receptors causes the alpha subunit of G-protein coupled receptors to exchange GMP for GTP, activating them, and allowing the alpha subunit to dissociate from the beta and gamma subunits. Dissociation of the alpha subunit activates adenylate cyclase, converting ATP to cyclic AMP. Cyclic AMP activates protein kinase A (PKA), which phosphorylates cardiac L-type calcium channels such as Ca<sub>v</sub>1.2. These channels depolarize cells by inward active transport of calcium ions.
Agonism of beta-1 adrenergic receptors lead to increased strength of contractility, conduction of nerve impulses, speed of relaxation, and rate in the heart.
Agonism of beta-2 adrenergic receptors leads to glycogenolysis in the liver, glucagon release from the pancreas, and activation of the renin-angiotensin-aldosterone system.
In the alveoli, agonism of beta-2 adrenergic receptors, activates similar pathways to the heart, however the end result is regulation of sodium channels, the cystic fibrosis transmembrane conductance regulator (CFTR), and sodium potassium ATPase. PKA phosphorylates scaffolding proteins and sodium channels, increasing the number of sodium channels on the apical side of alveolar cells and increasing active transport of sodium ions into cells. Agonism of beta-2 adrenergic receptors can also increase chloride ion transport across CFTR. Together, these actions lead to passive transport of water out of the alveoli, and the clearance of alveolar fluid.
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| Targets: |
Beta-1 adrenergic receptor agonist; Beta-2 adrenergic receptor agonist&binder; Beta-3 adrenergic receptor agonist; Superoxide dismutase [Cu-Zn] stabilization
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| Inclusion Criteria: |
Therapeutic strategy associated
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