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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
Structure of DOBUTAMINE

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

HIDE SMILES / InChI
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
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
Hypotension with dobutamine: beta-adrenergic antagonist selectivity at low doses of carvedilol.
1999 Dec
Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists.
1999 Nov
[Distributive shock and it's therapy by cardio-vascular acting drugs].
1999 Oct
Fibroblast growth factor-2 mediates pressure-induced hypertrophic response.
1999 Sep
Dobutamine stress echocardiography: safety in diagnosing coronary artery disease.
2000 Apr
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
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
Kallikrein gene delivery improves cardiac reserve and attenuates remodeling after myocardial infarction.
2002 Nov
Controlled expression of cardiac-directed adenylylcyclase type VI provides increased contractile function.
2002 Nov
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
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
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
Effects of growth hormone on the function of beta-adrenoceptor subtypes in rat adipocytes.
2004 Feb
Hypersensitivity myocarditis complicating hypertrophic cardiomyopathy heart.
2004 Jul
Chronic phospholamban inhibition prevents progressive cardiac dysfunction and pathological remodeling after infarction in rats.
2004 Mar
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
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

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.
Name Type Language
DOBUTAMINE
INN   MI   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
DL-DOBUTAMINE
Common Name English
COMPOUND-81929
Code English
DOBUTAMINE [USP]
Common Name English
(+/-)-DOBUTAMINE
Common Name English
DOBUTAMINE [USAN]
Common Name English
DOBUTAMINE [VANDF]
Common Name English
1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-
Systematic Name English
RACEMIC DOBUTAMINE
Common Name English
DOBUTAMINE [MI]
Common Name English
1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, (+/-)-
Systematic Name English
4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-1,2-BENZENEDIOL
Systematic Name English
DOBUTAMINE [WHO-DD]
Common Name English
DOBUTAMINE [INN]
Common Name English
(+/-)-4-(2-((3-(P-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)PYROCATECHOL
Common Name English
COMPOUND 81929
Code English
Classification Tree Code System Code
NDF-RT N0000000245
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
WHO-ATC C01CA07
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
WHO-VATC QC01CA07
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
NDF-RT N0000175555
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C61733
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL926
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
EVMPD
SUB06343MIG
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
DRUG BANK
DB00841
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
RXCUI
3616
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY RxNorm
PUBCHEM
36811
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
DRUG CENTRAL
937
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
FDA UNII
3S12J47372
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
EPA CompTox
34368-04-2
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
MERCK INDEX
M4710
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY Merck Index
LACTMED
Dobutamine
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
CAS
34368-04-2
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
MESH
D004280
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
WIKIPEDIA
DOBUTAMINE
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
IUPHAR
535
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY
CAS
67230-43-7
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
SUPERSEDED
INN
3340
Created by admin on Sat Jun 26 10:11:22 UTC 2021 , Edited by admin on Sat Jun 26 10:11:22 UTC 2021
PRIMARY