Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H23NO3.ClH |
Molecular Weight | 337.8417 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(CCc1ccc(cc1)O)NCCc2ccc(c(c2)O)O.Cl
InChI
InChIKey=BQKADKWNRWCIJL-UHFFFAOYSA-N
InChI=1S/C18H23NO3.ClH/c1-13(2-3-14-4-7-16(20)8-5-14)19-11-10-15-6-9-17(21)18(22)12-15;/h4-9,12-13,19-22H,2-3,10-11H2,1H3;1H
Molecular Formula | ClH |
Molecular Weight | 36.4609 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H23NO3 |
Molecular Weight | 301.3808 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Dobutamine is a sympathomimetic drug used in the treatment of heart failure and cardiogenic shock. Dobutamine hydrochloride is a direct-acting inotropic agent whose primary activity results from stimulation of the ß-receptors of the heart while producing comparatively mild chronotropic, hypertensive, arrhythmogenic, and vasodilative effects. It does not
cause the release of endogenous norepinephrine, as does dopamine. Dobutamine directly stimulates beta-1 receptors of the heart to increase myocardial contractility and stroke volume, resulting in increased cardiac output. Dobutamine Injection, USP is indicated when parenteral therapy is necessary for inotropic support in the short-term treatment of adults with cardiac decompensation due to depressed contractility resulting either from organic heart disease or from cardiac surgical procedures.
Originator
Sources: http://www.drugsupdate.com/generic/view/814/Dobutamine | https://www.ncbi.nlm.nih.gov/pubmed/234805
Curator's Comment:: Dobutamine was developed in the 1970s by Drs. Ronald Tuttle and Jack Mills at Eli Lilly and Company, as a structural analogue of isoprenaline.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
3.2 µM [Ki] | |||
1.4 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Dobutamine hydrochloride Approved UseDobutamine in 5% Dextrose Injection is indicated when parenteral therapy is necessary for inotropic support in the short-term treatment of patients with cardiac decompensation due to depressed contractility resulting either from organic heart disease or from cardiac surgical procedures. Experience with intravenous dobutamine in controlled trials does not extend beyond 48 hours of repeated boluses and/or continuous infusions. Whether given orally, continuously intravenously, or intermittently intravenously, neither dobutamine nor any other cyclic-AMP-dependent inotrope has been shown in controlled trials to be safe or effective in the long-term treatment of congestive heart failure. In controlled trials of chronic oral therapy with various such agents, symptoms were not consistently alleviated, and the cyclic-AMP-dependent inotropes were consistently associated with increased risks of hospitalization and death. Patients with NYHA Class IV symptoms appeared to be at particular risk. Launch Date2.69568E11 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/699477/ |
2.5 μg/kg/min other, intravenous dose: 2.5 μg/kg/min route of administration: Intravenous experiment type: OTHER co-administered: |
DOBUTAMINE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.37 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/699477/ |
2.5 μg/kg/min other, intravenous dose: 2.5 μg/kg/min route of administration: Intravenous experiment type: OTHER co-administered: |
DOBUTAMINE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
40 ug/kg/min multiple, intravenous Highest studied dose Dose: 40 ug/kg/min Route: intravenous Route: multiple Dose: 40 ug/kg/min Sources: |
unhealthy, 43 years (ranhe: 20-72 years) n = 6 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 6 Sources: |
Other AEs: Adverse event... |
30 ug/kg/min multiple, intravenous Dose: 30 ug/kg/min Route: intravenous Route: multiple Dose: 30 ug/kg/min Sources: |
unhealthy, 43 years (ranhe: 20-72 years) n = 5 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 5 Sources: |
Disc. AE: Angina, Arrhythmia... AEs leading to discontinuation/dose reduction: Angina (5 patients) Sources: Arrhythmia (5 patients) Hypertension (severe, 5 patients) |
2 ug/kg/min multiple, intravenous Dose: 2 ug/kg/min Route: intravenous Route: multiple Dose: 2 ug/kg/min Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Age Group: 46 years Sex: M Population Size: 1 Sources: |
Disc. AE: Eosinophilia... AEs leading to discontinuation/dose reduction: Eosinophilia (1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Adverse event | 40 ug/kg/min multiple, intravenous Highest studied dose Dose: 40 ug/kg/min Route: intravenous Route: multiple Dose: 40 ug/kg/min Sources: |
unhealthy, 43 years (ranhe: 20-72 years) n = 6 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 6 Sources: |
|
Angina | 5 patients Disc. AE |
30 ug/kg/min multiple, intravenous Dose: 30 ug/kg/min Route: intravenous Route: multiple Dose: 30 ug/kg/min Sources: |
unhealthy, 43 years (ranhe: 20-72 years) n = 5 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 5 Sources: |
Arrhythmia | 5 patients Disc. AE |
30 ug/kg/min multiple, intravenous Dose: 30 ug/kg/min Route: intravenous Route: multiple Dose: 30 ug/kg/min Sources: |
unhealthy, 43 years (ranhe: 20-72 years) n = 5 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 5 Sources: |
Hypertension | severe, 5 patients Disc. AE |
30 ug/kg/min multiple, intravenous Dose: 30 ug/kg/min Route: intravenous Route: multiple Dose: 30 ug/kg/min Sources: |
unhealthy, 43 years (ranhe: 20-72 years) n = 5 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 5 Sources: |
Eosinophilia | 1 patient Disc. AE |
2 ug/kg/min multiple, intravenous Dose: 2 ug/kg/min Route: intravenous Route: multiple Dose: 2 ug/kg/min Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Age Group: 46 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Modulation of inotropic therapy by venodilation in acute heart failure: a randomised comparison of four inotropic agents, alone and combined with isosorbide dinitrate. | 1992 Jan |
|
Cimetidine-dobutamine interaction? | 1992 Nov |
|
Enhanced responsiveness of the myocardial beta-adrenoceptor-adenylate cyclase system in the perfused rat heart (I). | 1998 Oct |
|
Disruption of myoglobin in mice induces multiple compensatory mechanisms. | 1999 Aug 31 |
|
The relationship between modified pulse wave transit time and cardiovascular changes in isoflurane anesthetized dogs. | 1999 Dec |
|
Torsade de pointes ventricular tachycardia during low dose intermittent dobutamine treatment in a patient with dilated cardiomyopathy and congestive heart failure. | 1999 Feb |
|
Changes in endothelium-derived vascular regulatory factors during dobutamine-stress-induced silent myocardial ischemia in patients with Kawasaki disease. | 1999 Jul |
|
Transmural metabolic heterogeneity at high cardiac work states. | 1999 Jul |
|
The clinical impact of dynamic intraventricular obstruction during dobutamine stress echocardiography. | 1999 Jul 31 |
|
Dobutamine-induced hypotension is an independent predictor for mortality in patients with left ventricular dysfunction following myocardial infarction. | 1999 Mar 15 |
|
Relation between the extent of coronary artery disease and tachyarrhythmias during dobutamine stress echocardiography. | 1999 Mar 15 |
|
Hypertensive encephalopathy as a complication of hyperdynamic therapy for vasospasm: report of two cases. | 1999 May |
|
Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists. | 1999 Nov |
|
Fatal ventricular fibrillation during a low-dose dobutamine stress test. | 2000 Mar |
|
Prolonged left ventricular dysfunction occurs in patients with coronary artery disease after both dobutamine and exercise induced myocardial ischaemia. | 2000 Mar |
|
Prognostic value of pharmacologic stress echocardiography in patients with left bundle branch block. | 2001 Apr 1 |
|
[Complications of stress echocardiography]. | 2001 Aug |
|
Milrinone versus dobutamine in heart failure subjects treated chronically with carvedilol. | 2001 Dec |
|
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
The Arg 389 Gly beta1-adrenergic receptor gene polymorphism and human fat cell lipolysis. | 2001 Nov |
|
Attenuation of lung inflammation by adrenergic agonists in murine acute lung injury. | 2001 Oct |
|
Dobutamine stress cine-MRI of cardiac function in the hearts of adult cardiomyocyte-specific VEGF knockout mice. | 2001 Oct |
|
[Reversible cardiomyopathy secondary to interferon-alpha in chronic myelogenous leukemia]. | 2002 Feb |
|
Long-term treatment with perindopril ameliorates dobutamine-induced myocardial ischemia in patients with coronary artery disease. | 2002 Jan |
|
Cardiac myocyte-specific excision of the beta1 integrin gene results in myocardial fibrosis and cardiac failure. | 2002 Mar 8 |
|
Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography. | 2003 Apr |
|
Dobutamine-induced ST-segment elevation associated with a biphasic response of wall motion in patients with a recent myocardial infarction is caused by myocardial ischaemia and is abolished by revascularization of the infarct-related artery. | 2003 Dec |
|
Comparison of late outcome in patients with versus without angina pectoris having reversible perfusion abnormalities during dobutamine stress technetium-99m sestamibi single-photon emission computed tomography. | 2003 Feb 1 |
|
Dobutamine modulates lipopolysaccharide-induced macrophage inflammatory protein-1alpha and interleukin-8 production in human monocytes. | 2003 Jul |
|
Dobutamine inhibits monocyte chemoattractant protein-1 production and chemotaxis in human monocytes. | 2003 Jul |
|
Heme oxygenase-1 gene expression in pericentral hepatocytes through beta1-adrenoceptor stimulation. | 2004 Apr |
|
Myocardial ischemia and induction of sustained ventricular tachyarrhythmias: evaluation using dobutamine stress echocardiography-electrophysiologic testing. | 2004 Aug |
|
Protein kinase Cepsilon overexpression alters myofilament properties and composition during the progression of heart failure. | 2004 Aug 20 |
|
Effects of growth hormone on the function of beta-adrenoceptor subtypes in rat adipocytes. | 2004 Feb |
|
Hypersensitivity myocarditis complicating hypertrophic cardiomyopathy heart. | 2004 Jul |
|
Prognostic value of dobutamine stress echocardiography in patients with normal left ventricular systolic function. | 2004 Jul |
|
Eosinophilic myocarditis in patients awaiting heart transplantation. | 2004 Mar |
|
Chronic beta-adrenoreceptor stimulation in vivo decreased Bcl-2 and increased Bax expression but did not activate apoptotic pathways in mouse heart. | 2004 Mar |
|
Chronic phospholamban inhibition prevents progressive cardiac dysfunction and pathological remodeling after infarction in rats. | 2004 Mar |
|
Dobutamine-induced myoclonia in severe renal failure. | 2004 May |
|
Synergistic contributions of the functional groups of epinephrine to its affinity and efficacy at the beta2 adrenergic receptor. | 2004 May |
|
Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro. | 2004 Nov |
|
Dobutamine stress MRI. Part I. Safety and feasibility of dobutamine cardiovascular magnetic resonance in patients suspected of myocardial ischemia. | 2004 Oct |
|
Overexpression of the catalytic subunit of protein phosphatase 2A impairs cardiac function. | 2004 Sep 24 |
|
Dobutamine induced severe midventricular obstruction and mitral regurgitation in left ventricular apical ballooning syndrome. | 2005 Mar |
|
Treatment of cardiogenic shock with levosimendan in combination with beta-adrenergic antagonists. | 2005 Nov |
|
Upstream transcription factor-1 gene polymorphism is associated with increased adipocyte lipolysis. | 2005 Sep |
|
Clinical and prognostic implications of angina pectoris developing during dobutamine stress echocardiography in the absence of inducible wall motion abnormalities. | 2005 Sep 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/dobutamine.html
Usual Adult Dose for Congestive Heart Failure
Initial dose: 0.5 to 1 mcg/kg/min IV infusion
Maintenance dose: 2 to 20 mcg/kg/min IV infusion
Maximum dose: 40 mcg/kg/min IV infusion
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3022421
Dobutamine (10(-5)-10(-4) M), a relatively specific beta 1-adrenoceptor agonist caused a small but significant relaxant response in in rabbit urinary bladder trigonal muscle but no change in detrusor.
Substance Class |
Chemical
Created
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Edited
Fri Jun 25 20:52:43 UTC 2021
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Record UNII |
0WR771DJXV
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Record Status |
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Record Version |
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C48149
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1224507
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256-464-1
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C28997
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DBSALT000711
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CHEMBL926
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M4710
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65324
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SUPERSEDED |
Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |