Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H17NO3 |
Molecular Weight | 211.2576 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NCC(O)C1=CC=C(O)C(O)=C1
InChI
InChIKey=JWZZKOKVBUJMES-UHFFFAOYSA-N
InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugs.com/cdi/isoproterenol.html | https://www.ncbi.nlm.nih.gov/pubmed/209581 | https://www.ncbi.nlm.nih.gov/pubmed/22073124 | https://www.ncbi.nlm.nih.gov/pubmed/11723224
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/cdi/isoproterenol.html | https://www.ncbi.nlm.nih.gov/pubmed/209581 | https://www.ncbi.nlm.nih.gov/pubmed/22073124 | https://www.ncbi.nlm.nih.gov/pubmed/11723224
Isoproterenol (trade names Medihaler-Iso and Isuprel) is a medication used for the treatment of bradycardia (slow heart rate), heart block, and rarely for asthma. Isoproterenol is a non-selective β adrenoreceptor agonist and TAAR1 agonist that is the isopropylaminomethyl analog of epinephrine. Isoprenaline's effects on the cardiovascular system (non-selective) relate to its actions on cardiac β1 receptors and β2 receptors on smooth muscle within the tunica media of arterioles. Isoprenaline has positive inotropic and chronotropic effects on the heart. β2 adrenoceptor stimulation in arteriolar smooth muscle induces vasodilation. Its inotropic and chronotropic effects elevate systolic blood pressure, while its vasodilatory effects tend to lower diastolic blood pressure. The overall effect is to decrease mean arterial pressure due to the β2 receptors' vasodilation. The adverse effects of isoprenaline are also related to the drug's cardiovascular effects. Isoprenaline can produce tachycardia (an elevated heart rate), which predisposes patients to cardiac arrhythmias.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22073124 |
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Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22182578 |
240.0 nM [EC50] | ||
Target ID: CHEMBL246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26125514 |
86.0 nM [IC50] | ||
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19581100 |
12.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ISOPROTERENOL HYDROCHLORIDE Approved UseIsoproterenol hydrochloride injection is indicated: For mild or transient episodes of heart block that do not require electric shock or pacemaker therapy. For serious episodes of heart block and Adams-Stokes attacks (except when caused by ventricular tachycardia or fibrillation). (See CONTRAINDICATIONS.) For use in cardiac arrest until electric shock or pacemaker therapy, the treatments of choice, is available. (See CONTRAINDICATIONS.) For bronchospasm occurring during anesthesia. As an adjunct to fluid and electrolyte replacement therapy and the use of other drugs and procedures in the treatment of hypovolemic and septic shock, low cardiac output (hypoperfusion) states, congestive heart failure, and cardiogenic shock. (See WARNINGS.) Launch Date-4.35974406E11 |
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Primary | ISOPROTERENOL HYDROCHLORIDE Approved UseIsoproterenol hydrochloride injection is indicated: For mild or transient episodes of heart block that do not require electric shock or pacemaker therapy. For serious episodes of heart block and Adams-Stokes attacks (except when caused by ventricular tachycardia or fibrillation). (See CONTRAINDICATIONS.) For use in cardiac arrest until electric shock or pacemaker therapy, the treatments of choice, is available. (See CONTRAINDICATIONS.) For bronchospasm occurring during anesthesia. As an adjunct to fluid and electrolyte replacement therapy and the use of other drugs and procedures in the treatment of hypovolemic and septic shock, low cardiac output (hypoperfusion) states, congestive heart failure, and cardiogenic shock. (See WARNINGS.) Launch Date-4.35974406E11 |
|||
Primary | ISOPROTERENOL HYDROCHLORIDE Approved UseIsoproterenol hydrochloride injection is indicated: For mild or transient episodes of heart block that do not require electric shock or pacemaker therapy. For serious episodes of heart block and Adams-Stokes attacks (except when caused by ventricular tachycardia or fibrillation). (See CONTRAINDICATIONS.) For use in cardiac arrest until electric shock or pacemaker therapy, the treatments of choice, is available. (See CONTRAINDICATIONS.) For bronchospasm occurring during anesthesia. As an adjunct to fluid and electrolyte replacement therapy and the use of other drugs and procedures in the treatment of hypovolemic and septic shock, low cardiac output (hypoperfusion) states, congestive heart failure, and cardiogenic shock. (See WARNINGS.) Launch Date-4.35974406E11 |
|||
Primary | ISOPROTERENOL HYDROCHLORIDE Approved UseIsoproterenol hydrochloride injection is indicated: For mild or transient episodes of heart block that do not require electric shock or pacemaker therapy. For serious episodes of heart block and Adams-Stokes attacks (except when caused by ventricular tachycardia or fibrillation). (See CONTRAINDICATIONS.) For use in cardiac arrest until electric shock or pacemaker therapy, the treatments of choice, is available. (See CONTRAINDICATIONS.) For bronchospasm occurring during anesthesia. As an adjunct to fluid and electrolyte replacement therapy and the use of other drugs and procedures in the treatment of hypovolemic and septic shock, low cardiac output (hypoperfusion) states, congestive heart failure, and cardiogenic shock. (See WARNINGS.) Launch Date-4.35974406E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7422709 |
0.3 mg/kg single, subcutaneous dose: 0.3 mg/kg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
ISOPROTERENOL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
15 mg 1 times / day multiple, respiratory (max) Studied dose Dose: 15 mg, 1 times / day Route: respiratory Route: multiple Dose: 15 mg, 1 times / day Sources: Page: p.642 |
unhealthy, 27 - 67 n = 12 Health Status: unhealthy Condition: Bronchial asthma Age Group: 27 - 67 Sex: M+F Population Size: 12 Sources: Page: p.642 |
Other AEs: Tachycardia, Premature ventricular contractions... Other AEs: Tachycardia (66.7%) Sources: Page: p.642Premature ventricular contractions (8.3%) |
0.2 mg multiple, intravenous (max) Recommended Dose: 0.2 mg Route: intravenous Route: multiple Dose: 0.2 mg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Heart block|Adams-Stokes attacks|Cardiac arrest Sources: Page: p.2 |
Disc. AE: Block heart, Adams-Stokes syndrome... AEs leading to discontinuation/dose reduction: Block heart Sources: Page: p.2Adams-Stokes syndrome |
1 mg multiple, intramuscular (max) Recommended Dose: 1 mg Route: intramuscular Route: multiple Dose: 1 mg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Heart block|Adams-Stokes attacks|Cardiac arrest Sources: Page: p.2 |
Disc. AE: Block heart, Adams-Stokes syndrome... AEs leading to discontinuation/dose reduction: Block heart Sources: Page: p.2Adams-Stokes syndrome |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Tachycardia | 66.7% | 15 mg 1 times / day multiple, respiratory (max) Studied dose Dose: 15 mg, 1 times / day Route: respiratory Route: multiple Dose: 15 mg, 1 times / day Sources: Page: p.642 |
unhealthy, 27 - 67 n = 12 Health Status: unhealthy Condition: Bronchial asthma Age Group: 27 - 67 Sex: M+F Population Size: 12 Sources: Page: p.642 |
Premature ventricular contractions | 8.3% | 15 mg 1 times / day multiple, respiratory (max) Studied dose Dose: 15 mg, 1 times / day Route: respiratory Route: multiple Dose: 15 mg, 1 times / day Sources: Page: p.642 |
unhealthy, 27 - 67 n = 12 Health Status: unhealthy Condition: Bronchial asthma Age Group: 27 - 67 Sex: M+F Population Size: 12 Sources: Page: p.642 |
Adams-Stokes syndrome | Disc. AE | 0.2 mg multiple, intravenous (max) Recommended Dose: 0.2 mg Route: intravenous Route: multiple Dose: 0.2 mg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Heart block|Adams-Stokes attacks|Cardiac arrest Sources: Page: p.2 |
Block heart | Disc. AE | 0.2 mg multiple, intravenous (max) Recommended Dose: 0.2 mg Route: intravenous Route: multiple Dose: 0.2 mg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Heart block|Adams-Stokes attacks|Cardiac arrest Sources: Page: p.2 |
Adams-Stokes syndrome | Disc. AE | 1 mg multiple, intramuscular (max) Recommended Dose: 1 mg Route: intramuscular Route: multiple Dose: 1 mg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Heart block|Adams-Stokes attacks|Cardiac arrest Sources: Page: p.2 |
Block heart | Disc. AE | 1 mg multiple, intramuscular (max) Recommended Dose: 1 mg Route: intramuscular Route: multiple Dose: 1 mg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Heart block|Adams-Stokes attacks|Cardiac arrest Sources: Page: p.2 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18725507/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18725507/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18725507/ |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[Myocardial DNA and cell count following isoproterenol-induced myocardial necrosis in the rat]. | 1975 |
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Method for the production of severe ventricular dysrhythmias in small laboratory animals. | 1975 |
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Membrane phospholipid metabolism in the isoproterenol-induced cardiomyopathy of the rat. | 1975 |
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Metabolic response after isoproterenol-induced myocardial infarction in arteriosclerotic breeder vs nonarteriosclerotic virgin intact and gonadectomized male rats. | 1975 Apr |
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Serum prolactin levels in rats following isoproterenol-induced myocardial infarction. | 1975 Dec |
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[Pharmacology of acebutolol in animals]. | 1975 Dec 31 |
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Prolyl hydroxylase and collagen metabolism after experimental mycardial infarction. | 1975 Jan |
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Effects of prindolol on isoproterenol-induced subendocardial ischaemia in dogs with multiple chronic coronary artery occlusion. | 1975 Jul |
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The use of practolol in supraventricular arrhythmias associated with acute illnesses. | 1975 May |
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Metabolic responses following isoproterenol-induced myocardial infarction in arteriosclerotic breeder vs. non-arteriosclerotic virgin and ovariectomized female rats. | 1975 May-Jun |
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[Prevention of isoproterenol-induced lesions in the rat myocardium by prenylamine]. | 1975 Sep-Oct |
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Decreased SOD activity and increased nitrates level in rat heart with left ventricular hypertrophy induced by isoproterenol. | 1999 Jul-Dec |
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Recurrent asystoles associated with vasovagal reaction during venipuncture. | 2000 Dec |
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Pharmacological effects of an aldehyde type alpha/beta-adrenoceptor blocking agent with vasodilating properties. | 2000 Jun |
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[Effects of isoprenaline on apoptosis related gene expression in rat myocardium cells]. | 2000 Nov |
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Lipopolysaccharide-induced tumor necrosis factor-alpha release is controlled by the central nervous system. | 2001 |
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Evidence that ranolazine behaves as a weak beta1- and beta2-adrenoceptor antagonist in the rat [correction of cat] cardiovascular system. | 2001 Apr |
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Elevated parasympathetic nerve tone in isoproterenol-induced neurally mediated syncope during head-up tilt testing. | 2001 Apr |
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A comparison of effects measured with isotonic and isometric recording: II. Concentration-effect curves for physiological antagonists. | 2001 Aug |
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Effects of alpha- and beta-adrenergic stimulation on free magnesium concentrations in platelets from healthy and obese individuals. | 2001 Dec |
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Differential effects of atropine and isoproterenol on inducibility of atrioventricular nodal reentrant tachycardia. | 2001 Dec |
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Isoproterenol-induced cardiac hypertrophy: role of circulatory versus cardiac renin-angiotensin system. | 2001 Dec |
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Paroxysmal tachycardia in children and teenagers with normal sinus rhythm and without heart disease. | 2001 Jan |
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Interaction of calcitonin gene-related peptide (CGRP), substance P (SP) and conventional autonomic agonists in rat submandibular salivary peroxidase release in vitro. | 2001 Jan 14 |
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Activation of mitochondrial oxidative phosphorylation during (+/-)-isoproterenol-induced cell injury of myocardium. | 2001 Jan-Mar |
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[Functional characterization of myocardial hypertrophy induced by isoproterenol and its regression]. | 2001 Jul |
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Different mechanisms of isoproterenol-induced and nitroglycerin-induced syncope during head-up tilt in patients with unexplained syncope: important role of epinephrine in nitroglycerin-induced syncope. | 2001 Jul |
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A new aspect of view in synthesizing new type beta-adrenoceptor blockers with ancillary antioxidant activities. | 2001 Jul |
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Catecholamines stimulate interleukin-6 synthesis in rat cardiac fibroblasts. | 2001 Jul |
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Alterative and plastic insufficiency of cardiomyocytes: isoproterenol-induced damage to myocardium during anthracycline cardiomyopathy. | 2001 Jun |
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beta-Adrenergic and endothelin receptor interaction in dilated human cardiomyopathic myocardium. | 2001 Jun |
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Report of a life-threatening arrhythmia after hospital discharge in a liver transplant recipient with previously unknown congenital long QT syndrome. | 2001 Jun-Jul |
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In vivo regulation of Na/Ca exchanger expression by adrenergic effectors. | 2001 Mar |
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Targeted inhibition of calcineurin attenuates cardiac hypertrophy in vivo. | 2001 Mar 13 |
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Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal. | 2001 Mar 2 |
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Cardioprotective effects of Picrorrhiza kurroa against isoproterenol-induced myocardial stress in rats. | 2001 May |
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PKC-beta is not necessary for cardiac hypertrophy. | 2001 May |
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In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV. | 2001 Nov |
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Spironolactone and captopril attenuates isoproterenol-induced cardiac remodelling in rats. | 2001 Oct |
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Calcineurin-GATA4 pathway is involved in beta-adrenergic agonist-responsive endothelin-1 transcription in cardiac myocytes. | 2001 Sep 14 |
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Impaired intracellular signal transduction via cyclic AMP contributes to cerebral vasospasm in rats with subarachnoid hemorrhage. | 2002 Apr |
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Expression of human angiotensinogen-renin in rat: effects on transcription and heart function. | 2002 Feb |
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The regulation of human vascular smooth muscle extracellular matrix protein production by alpha- and beta-adrenoceptor stimulation. | 2002 Feb |
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Effect of an orally active Na+/H+ exchange inhibitor, SMP-300, on experimental angina and myocardial infarction models in rats. | 2002 Feb |
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99mTc-glucarate for detection of isoproterenol-induced myocardial infarction in rats. | 2002 Feb 21 |
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Synergistic effect of nicorandil and amlodipine on mitochondrial function during isoproterenol-induced myocardial infarction in rats. | 2002 Jan |
|
Allosteric modulation of beta2-adrenergic receptor by Zn(2+). | 2002 Jan |
|
Bone marrow-derived regenerated cardiomyocytes (CMG Cells) express functional adrenergic and muscarinic receptors. | 2002 Jan 22 |
|
Glucose uptake via SGLT-1 is stimulated by beta(2)-adrenoceptors in the ruminal epithelium of sheep. | 2002 Jun |
|
Vanillylamide-based propanolamine derivative displays alpha/beta-adrenoceptor blocking and vasodilating properties. | 2002 Jun |
Patents
Sample Use Guides
Bolus intravenous injection: 0.02 mg to 0.06 mg; Intravenous infusion: 5 mcg/min; Intramuscular 0.2 mg; Subcutaneous 0.2 mg; Intracardiac 0.02 mg;
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22073124
Human embryonic kidney cells (HEK293) were cultured in Minimum Essential Medium (MEM) Earle’s (Biochrom AG) supplemented with 10% FBS (PAA Laboratories GmbH), 100 U/ml penicillin, and 100 mg/ml streptomycin (Biochrom AG) and 2 mM L-glutamine (Invitrogen) at 37C with 5% CO2. 48 well plates were coated with Poly-L-Lysine (Biochrom) and HEK293 cells were seeded with 37,500 cells per well. Transient transfection in triplicates with 84 ng DNA/well using metafectene according to manufactures instructions (Biontex, Munich, Germany) was performed 28 hours later. 40 hours after transfection cells were pre-incubated for 5 minutes with stimulation buffer containing of MEM Earle’s media and 1 mM 3-isobutyl-1-methylxanthine (IBMX, Sigma). This stimulation buffer was used for all further steps. For ligand competition experiments cells were incubated with tyramine, 2-phenylethylamine or octopamine ranging from 6.7 nM to 6700 nM, diluted in stimulation buffer for 15 minutes followed by a stimulation with isoprenaline in concentrations ranging from 1 nM to 10000 nM for 30 minutes. All reactions were performed at 37C with 5% CO2 saturated air and stopped by aspirating medium.
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WHO-VATC |
QC01CA02
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C319
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C01CA02
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R03AK02
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NDF-RT |
N0000175555
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N0000000245
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R03CB01
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R03AB02
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QR03AB02
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QR03CB01
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QR03AK02
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QR03CB51
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R03CB51
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CHEMBL434
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D007545
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)