U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H23NO3.BrH
Molecular Weight 382.2923
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOBUTAMINE HYDROBROMIDE

SMILES

CC(CCc1ccc(cc1)O)NCCc2ccc(c(c2)O)O.Br

InChI

InChIKey=QMCDOYGKCFLHBO-UHFFFAOYSA-N
InChI=1S/C18H23NO3.BrH/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

HIDE SMILES / InChI

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 ( + / - )

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Dobutamine hydrochloride

Approved Use

Dobutamine 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 Date

2.69568E11
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2.37 min
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

Doses

DosePopulationAdverse 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...
Other AEs:
Adverse event
Sources:
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)
Arrhythmia (5 patients)
Hypertension (severe, 5 patients)
Sources:
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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
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
Long-term dobutamine therapy for refractory congestive heart failure.
1992 Jul
Clinical significance of abrupt vasodepression during dobutamine stress echocardiography.
1992 Jun 1
The relationship between modified pulse wave transit time and cardiovascular changes in isoflurane anesthetized dogs.
1999 Dec
[Safety of stress echocardiography with dobutamine used in patients with aortic stenosis and left ventricular dysfunction].
2002
Dobutamine stress myocardial perfusion imaging in coronary artery disease.
2002 Dec
Effects of norepinephrine on rat cultured microglial cells that express alpha1, alpha2, beta1 and beta2 adrenergic receptors.
2002 Nov
Generalized tetany: an unusual complication during dobutamine stress echocardiography.
2002 Nov
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
Dopamine stabilizes milrinone-induced changes in heart rate and arterial pressure during anaesthesia with isoflurane.
2003 Feb
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
Catecholamine-induced T-wave lability in congenital long QT syndrome: a novel phenomenon associated with syncope and cardiac arrest.
2003 Jan
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
[Left ventricular hypertrophy: a marker for patients at risk of arterial hypotension during stress echocardiography with dobutamine?].
2003 Jun
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
Gene therapy in cardiac surgery: intramyocardial injection of naked plasmid DNA for chronic myocardial ischemia.
2003 Nov
Beta 1-adrenergic receptor polymorphisms confer differential function and predisposition to heart failure.
2003 Oct
Electrical storm: case series and review of management.
2003 Sep
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
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
The Arg389Gly beta1-adrenoceptor gene polymorphism determines contractile response to catecholamines.
2004 Nov
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
Detrimental effects after dobutamine infusion on rat left ventricular function: mechanical work and energetics.
2005 Jul
Dobutamine-induced bradycardia in a dog.
2005 Mar
Dobutamine induced severe midventricular obstruction and mitral regurgitation in left ventricular apical ballooning syndrome.
2005 Mar
[Levosimendan, a revolution in the world of inotropic agents?].
2005 May 25
Myocardial stiffness, cardiac remodeling, and diastolic dysfunction in calcification-prone fetuin-A-deficient mice.
2005 Nov
Treatment of cardiogenic shock with levosimendan in combination with beta-adrenergic antagonists.
2005 Nov
A Dobutamine paradox: eosinophilic myocarditis in the explanted heart of a 9-year-old girl undergoing cardiac transplantation.
2005 Oct
Polymorphism of the AHSG gene is associated with increased adipocyte beta2-adrenoceptor function.
2005 Oct
Sustained ventricular tachycardia induced by dobutamine stress echocardiography: a prospective study.
2005 Sep
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
Adenoviral gene transfer of Akt enhances myocardial contractility and intracellular calcium handling.
2006 Jan
Atrial fibrillation in dobutamine stress echocardiography.
2006 Jul 28
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

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
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
by admin
on Sat Jun 26 04:54:54 UTC 2021
Edited
by admin
on Sat Jun 26 04:54:54 UTC 2021
Record UNII
27T771FEOY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOBUTAMINE HYDROBROMIDE
Common Name English
1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROBROMIDE
Systematic Name English
1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROBROMIDE (1:1)
Systematic Name English
1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROBROMIDE, (+/-)-
Systematic Name English
Code System Code Type Description
CAS
82473-35-6
Created by admin on Sat Jun 26 04:54:54 UTC 2021 , Edited by admin on Sat Jun 26 04:54:54 UTC 2021
SUPERSEDED
FDA UNII
27T771FEOY
Created by admin on Sat Jun 26 04:54:54 UTC 2021 , Edited by admin on Sat Jun 26 04:54:54 UTC 2021
PRIMARY
CAS
74753-15-4
Created by admin on Sat Jun 26 04:54:54 UTC 2021 , Edited by admin on Sat Jun 26 04:54:54 UTC 2021
PRIMARY
ECHA (EC/EINECS)
277-982-4
Created by admin on Sat Jun 26 04:54:54 UTC 2021 , Edited by admin on Sat Jun 26 04:54:54 UTC 2021
PRIMARY
PUBCHEM
20205114
Created by admin on Sat Jun 26 04:54:54 UTC 2021 , Edited by admin on Sat Jun 26 04:54:54 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE