Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H17NO3 |
Molecular Weight | 211.258 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NCC(c1ccc(c(c1)O)O)O
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
Molecular Formula | C11H17NO3 |
Molecular Weight | 211.258 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
|
Method for the production of severe ventricular dysrhythmias in small laboratory animals. | 1975 |
|
Membrane phospholipid metabolism in the isoproterenol-induced cardiomyopathy of the rat. | 1975 |
|
Metabolic response after isoproterenol-induced myocardial infarction in arteriosclerotic breeder vs nonarteriosclerotic virgin intact and gonadectomized male rats. | 1975 Apr |
|
Serum prolactin levels in rats following isoproterenol-induced myocardial infarction. | 1975 Dec |
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Electrophysiologic studies in the denervated transplanted human heart. II. Response to norepinephrine, isoproterenol and propranolol. | 1975 Dec |
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[Pharmacology of acebutolol in animals]. | 1975 Dec 31 |
|
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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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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Activity of Na+/K+-ATPase and of Ca++-ATPase under the action of adenosine triphosphate in experimental myocardial hypertrophy. | 1998 Jul-Dec |
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Overexpression of insulin-like growth factor-I in hearts of rats with isoproterenol-induced cardiac hypertrophy. | 1999 Nov |
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Effects of beta-receptor blockade and angiotensin II type I receptor antagonism in isoproterenol-induced heart failure in the rat. | 1999 Nov-Dec |
|
Effect of beta(2)-adrenoceptor activation and angiotensin II on tumour necrosis factor and interleukin 6 gene transcription in the rat renal resident macrophage cells. | 1999 Oct |
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In vivo evidence that isoproterenol may increase heart rate in the rat by mechanisms in addition to activation of cardiac beta(1)- or beta(2)-adrenoceptors. | 1999 Oct 15 |
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Inhibition of adipocyte lipolysis by papaverine: papaverine can inhibit the redistribution of hormone-sensitive lipase. | 2000 |
|
Influences of catecholamines on the sudden death induced in dogs by an antifungal agent, D0870. | 2000 Apr |
|
Recurrent asystoles associated with vasovagal reaction during venipuncture. | 2000 Dec |
|
Viral-mediated gene delivery of constitutively activated G alpha s alters vasoreactivity. | 2000 Jan-Feb |
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Pharmacological effects of an aldehyde type alpha/beta-adrenoceptor blocking agent with vasodilating properties. | 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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Isoproterenol-induced hypertrophy may result in distinct left ventricular changes. | 2000 May-Jun |
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[Effects of isoprenaline on apoptosis related gene expression in rat myocardium cells]. | 2000 Nov |
|
Catecholamines suppress leptin release from in vitro differentiated subcutaneous human adipocytes in primary culture via beta1- and beta2-adrenergic receptors. | 2000 Sep |
|
Coronary microvascular endothelial cells cosecrete angiotensin II and endothelin-1 via a regulated pathway. | 2000 Sep |
|
Hemodynamic and antiadrenergic effects of dronedarone and amiodarone in animals with a healed myocardial infarction. | 2000 Sep |
|
Lipopolysaccharide-induced tumor necrosis factor-alpha release is controlled by the central nervous system. | 2001 |
|
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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A comparison of effects measured with isotonic and isometric recording: II. Concentration-effect curves for physiological antagonists. | 2001 Aug |
|
Isoproterenol-induced cardiac hypertrophy: role of circulatory versus cardiac renin-angiotensin system. | 2001 Dec |
|
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 |
|
cAMP mediated upregulation of CYP2A5 in mouse hepatocytes. | 2001 Jan 26 |
|
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 |
|
Catecholamines stimulate interleukin-6 synthesis in rat cardiac fibroblasts. | 2001 Jul |
|
Alterative and plastic insufficiency of cardiomyocytes: isoproterenol-induced damage to myocardium during anthracycline cardiomyopathy. | 2001 Jun |
|
Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal. | 2001 Mar 2 |
|
PKC-beta is not necessary for cardiac hypertrophy. | 2001 May |
|
In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV. | 2001 Nov |
|
Calcineurin-GATA4 pathway is involved in beta-adrenergic agonist-responsive endothelin-1 transcription in cardiac myocytes. | 2001 Sep 14 |
|
Impaired intracellular signal transduction via cyclic AMP contributes to cerebral vasospasm in rats with subarachnoid hemorrhage. | 2002 Apr |
|
Expression of human angiotensinogen-renin in rat: effects on transcription and heart function. | 2002 Feb |
|
The regulation of human vascular smooth muscle extracellular matrix protein production by alpha- and beta-adrenoceptor stimulation. | 2002 Feb |
|
99mTc-glucarate for detection of isoproterenol-induced myocardial infarction in rats. | 2002 Feb 21 |
|
Synergistic effect of nicorandil and amlodipine on mitochondrial function during isoproterenol-induced myocardial infarction in rats. | 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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 10:00:52 UTC 2021
by
admin
on
Sat Jun 26 10:00:52 UTC 2021
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Record UNII |
L628TT009W
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QC01CA02
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NCI_THESAURUS |
C319
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WHO-ATC |
C01CA02
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WHO-ATC |
R03AK02
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NDF-RT |
N0000175555
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NDF-RT |
N0000000245
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WHO-ATC |
R03CB01
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WHO-ATC |
R03AB02
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WHO-VATC |
QR03AB02
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WHO-VATC |
QR03CB01
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WHO-VATC |
QR03AK02
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WHO-VATC |
QR03CB51
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WHO-ATC |
R03CB51
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Code System | Code | Type | Description | ||
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CHEMBL434
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D007545
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1499
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ISOPRENALINE
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7683-59-2
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DB01064
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3779
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M6533
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L628TT009W
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6054
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536
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SUB08330MIG
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7683-59-2
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M6533
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231-687-7
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C62041
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4201
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
SHORT-ACTING
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TARGET -> AGONIST | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
SHORT-ACTING
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |