Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H23NO3 |
Molecular Weight | 301.3808 |
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
InChI
InChIKey=JRWZLRBJNMZMFE-UHFFFAOYSA-N
InChI=1S/C18H23NO3/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
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 |
---|---|---|
Influence of dobutamine on regional myocardial blood flow and ventricular performance during acute and chronic myocardial ischemia in dogs. | 1976 May |
|
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 |
|
Clinical significance of abrupt vasodepression during dobutamine stress echocardiography. | 1992 Jun 1 |
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The relationship between modified pulse wave transit time and cardiovascular changes in isoflurane anesthetized dogs. | 1999 Dec |
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Hypotension with dobutamine: beta-adrenergic antagonist selectivity at low doses of carvedilol. | 1999 Dec |
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Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists. | 1999 Nov |
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[Distributive shock and it's therapy by cardio-vascular acting drugs]. | 1999 Oct |
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Fibroblast growth factor-2 mediates pressure-induced hypertrophic response. | 1999 Sep |
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Dobutamine stress echocardiography: safety in diagnosing coronary artery disease. | 2000 Apr |
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Acute cardiac rupture during dobutamine-atropine echocardiography stress test. | 2000 Feb |
|
Acute infarction of a previously stented coronary artery precipitated by dobutamine stress echocardiography. | 2000 Feb |
|
Severe dynamic obstruction of the left ventricular outflow tract induced by dobutamine. | 2000 Jan |
|
Incidence and significance of profound hypotension during dobutamine stress echocardiography. | 2000 Jan |
|
Myocardial ischemia due to coronary artery spasm during dobutamine stress echocardiography. | 2000 Jan 1 |
|
Safety, hemodynamic profile, and feasibility of dobutamine stress technetium myocardial perfusion single-photon emission CT imaging for evaluation of coronary artery disease in the elderly. | 2000 Mar |
|
Catecholamines suppress leptin release from in vitro differentiated subcutaneous human adipocytes in primary culture via beta1- and beta2-adrenergic receptors. | 2000 Sep |
|
[Complications of stress echocardiography]. | 2001 Aug |
|
Increased inducible nitric oxide synthase expression contributes to myocardial dysfunction and higher mortality after myocardial infarction in mice. | 2001 Aug 7 |
|
Milrinone versus dobutamine in heart failure subjects treated chronically with carvedilol. | 2001 Dec |
|
Hypotension and functional left ventricular obstruction during dobutamine stress echocardiography--two case reports. | 2001 Jul |
|
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 |
|
[Safety of stress echocardiography with dobutamine used in patients with aortic stenosis and left ventricular dysfunction]. | 2002 |
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Dobutamine stress myocardial perfusion imaging in coronary artery disease. | 2002 Dec |
|
[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 |
|
Multifocal myoclonus due to verapamil overdose. | 2002 Mar 26 |
|
Cardiac myocyte-specific excision of the beta1 integrin gene results in myocardial fibrosis and cardiac failure. | 2002 Mar 8 |
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Kallikrein gene delivery improves cardiac reserve and attenuates remodeling after myocardial infarction. | 2002 Nov |
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Controlled expression of cardiac-directed adenylylcyclase type VI provides increased contractile function. | 2002 Nov |
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Real-time MR image acquisition during high-dose dobutamine hydrochloride stress for detecting left ventricular wall-motion abnormalities in patients with coronary arterial disease. | 2002 Sep |
|
Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography. | 2003 Apr |
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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 |
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Impaired cardiac contraction and relaxation and decreased expression of sarcoplasmic Ca2+-ATPase in mice lacking the CREM gene. | 2003 Jan |
|
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 |
|
Levosimendan: a new dual-action drug in the treatment of acute heart failure. | 2003 Jun |
|
Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system. | 2003 Jun |
|
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 |
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Effects of growth hormone on the function of beta-adrenoceptor subtypes in rat adipocytes. | 2004 Feb |
|
Hypersensitivity myocarditis complicating hypertrophic cardiomyopathy heart. | 2004 Jul |
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Chronic phospholamban inhibition prevents progressive cardiac dysfunction and pathological remodeling after infarction in rats. | 2004 Mar |
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Overexpression of the catalytic subunit of protein phosphatase 2A impairs cardiac function. | 2004 Sep 24 |
|
[Levosimendan, a revolution in the world of inotropic agents?]. | 2005 May 25 |
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Myocardial stiffness, cardiac remodeling, and diastolic dysfunction in calcification-prone fetuin-A-deficient mice. | 2005 Nov |
|
Clinical and prognostic implications of angina pectoris developing during dobutamine stress echocardiography in the absence of inducible wall motion abnormalities. | 2005 Sep 15 |
|
Adenoviral gene transfer of Akt enhances myocardial contractility and intracellular calcium handling. | 2006 Jan |
|
Beneficial effects of high doses of growth hormone in the introduction and optimization of medical treatment in decompensated congestive heart failure. | 2006 Jun 28 |
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.
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NDF-RT |
N0000000245
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WHO-ATC |
C01CA07
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WHO-VATC |
QC01CA07
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NDF-RT |
N0000175555
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C61733
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CHEMBL926
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SUB06343MIG
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DB00841
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3616
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36811
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937
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3S12J47372
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34368-04-2
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M4710
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Dobutamine
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34368-04-2
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D004280
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DOBUTAMINE
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535
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67230-43-7
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3340
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ACTIVE MOIETY
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