Details
Stereochemistry | RACEMIC |
Molecular Formula | 2C11H17NO3.H2O4S |
Molecular Weight | 520.594 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.CC(C)NCC(O)C1=CC=C(O)C(O)=C1.CC(C)NCC(O)C2=CC=C(O)C(O)=C2
InChI
InChIKey=ZOLBALGTFCCTJF-UHFFFAOYSA-N
InChI=1S/2C11H17NO3.H2O4S/c2*1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8;1-5(2,3)4/h2*3-5,7,11-15H,6H2,1-2H3;(H2,1,2,3,4)
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 Date1956 |
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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 Date1956 |
|||
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 Date1956 |
|||
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 Date1956 |
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 |
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[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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Metabolic response after isoproterenol-induced myocardial infarction in arteriosclerotic breeder vs nonarteriosclerotic virgin intact and gonadectomized male rats. | 1975 Apr |
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[Pharmacology of acebutolol in animals]. | 1975 Dec 31 |
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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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[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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Increased JNK, AP-1 and NF-kappa B DNA binding activities in isoproterenol-induced cardiac remodeling. | 1999 Nov |
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Inhibition of adipocyte lipolysis by papaverine: papaverine can inhibit the redistribution of hormone-sensitive lipase. | 2000 |
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Influences of catecholamines on the sudden death induced in dogs by an antifungal agent, D0870. | 2000 Apr |
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Images in cardiovascular medicine. Labile repolarization from "cell to bedside". | 2000 Aug 15 |
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Recurrent asystoles associated with vasovagal reaction during venipuncture. | 2000 Dec |
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Low catecholamine concentrations protect adult rat ventricular myocytes against apoptosis through cAMP-dependent extracellular signal-regulated kinase activation. | 2000 Dec |
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beta-adrenergic stimulation restores rat lung ability to clear edema in ventilator-associated lung injury. | 2000 Jul |
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The influence of indomethacin on the acth secretion induced by central stimulation of adrenergic receptors. | 2000 Jun |
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Requirement of activation of the extracellular signal-regulated kinase cascade in myocardial cell hypertrophy. | 2000 Jun |
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Isoproterenol-induced myocardial injury resulting in altered S100A4 and S100A11 protein expression in the rat. | 2000 Jun |
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Hypersensitivity of cerebral artery response to catecholamine in patients with neurally mediated syncope induced by isoproterenol. | 2000 Jun 1 |
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Mitochondrial oligomycin-sensitive ATPase during isoproterenol-induced cell injury of myocardium. | 2000 Mar-Apr |
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Norepinephrine induces vascular endothelial growth factor gene expression in brown adipocytes through a beta -adrenoreceptor/cAMP/protein kinase A pathway involving Src but independently of Erk1/2. | 2000 May 5 |
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Effect of SMP-300, a new Na+/H+ exchange inhibitor, on myocardial ischemia and experimental angina models in rats. | 2000 Oct |
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Attenuation of isoproterenol-mediated myocardial injury in rat by an inhibitor of polyamine synthesis. | 2000 Sep-Oct |
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Lipopolysaccharide-induced tumor necrosis factor-alpha release is controlled by the central nervous system. | 2001 |
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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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Effects of alpha- and beta-adrenergic stimulation on free magnesium concentrations in platelets from healthy and obese individuals. | 2001 Dec |
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Isoproterenol-induced cardiac hypertrophy: role of circulatory versus cardiac renin-angiotensin system. | 2001 Dec |
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Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
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Paroxysmal tachycardia in children and teenagers with normal sinus rhythm and without heart disease. | 2001 Jan |
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Relationships between lipolysis induced by various lipolytic agents and hormone-sensitive lipase in rat fat cells. | 2001 Jan |
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beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice. | 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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cAMP mediated upregulation of CYP2A5 in mouse hepatocytes. | 2001 Jan 26 |
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Activation of mitochondrial oxidative phosphorylation during (+/-)-isoproterenol-induced cell injury of myocardium. | 2001 Jan-Mar |
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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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beta-Adrenergic and endothelin receptor interaction in dilated human cardiomyopathic myocardium. | 2001 Jun |
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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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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 |
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Allosteric modulation of beta2-adrenergic receptor by Zn(2+). | 2002 Jan |
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Bone marrow-derived regenerated cardiomyocytes (CMG Cells) express functional adrenergic and muscarinic receptors. | 2002 Jan 22 |
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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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299-95-6
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ACTIVE MOIETY
SUBSTANCE RECORD