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Details

Stereochemistry RACEMIC
Molecular Formula C18H23NO3
Molecular Weight 301.3801
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOBUTAMINE

SMILES

CC(CCC1=CC=C(O)C=C1)NCCC2=CC(O)=C(O)C=C2

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
Cimetidine-dobutamine interaction?
1992 Nov
Hypotension with dobutamine: beta-adrenergic antagonist selectivity at low doses of carvedilol.
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
Transmural metabolic heterogeneity at high cardiac work states.
1999 Jul
Dobutamine-induced hypotension is an independent predictor for mortality in patients with left ventricular dysfunction following myocardial infarction.
1999 Mar 15
Hypertensive encephalopathy as a complication of hyperdynamic therapy for vasospasm: report of two cases.
1999 May
Enhanced contractility and decreased beta-adrenergic receptor kinase-1 in mice lacking endogenous norepinephrine and epinephrine.
1999 May 25
[Distributive shock and it's therapy by cardio-vascular acting drugs].
1999 Oct
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
Effect of intravenous metoprolol or intravenous metoprolol plus glucagon on dobutamine-induced myocardial ischemia.
2000 Nov
[Prognostic value of cardiac perfusion scintigraphy associated with the dobutamine test in acute coronary syndromes].
2001 Apr
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
Normal coronary angiogram and dobutamine-induced left ventricular obstruction during stress echocardiography: a higher hemodynamic responsiveness to dobutamine.
2001 May
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 myocardial perfusion imaging in coronary artery disease.
2002 Dec
Therapeutic angiogenesis in the ischemic canine heart induced by myocardial injection of naked complementary DNA plasmid encoding hepatocyte growth factor.
2002 Dec
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
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
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
Dobutamine modulates lipopolysaccharide-induced macrophage inflammatory protein-1alpha and interleukin-8 production in human monocytes.
2003 Jul
[Left ventricular hypertrophy: a marker for patients at risk of arterial hypotension during stress echocardiography with dobutamine?].
2003 Jun
Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system.
2003 Jun
Effects of growth hormone on the function of beta-adrenoceptor subtypes in rat adipocytes.
2004 Feb
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
Detrimental effects after dobutamine infusion on rat left ventricular function: mechanical work and energetics.
2005 Jul
Dobutamine-induced bradycardia in a dog.
2005 Mar
[Levosimendan, a revolution in the world of inotropic agents?].
2005 May 25
Sustained ventricular tachycardia induced by dobutamine stress echocardiography: a prospective study.
2005 Sep
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
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 [INN]
Common Name English
(±)-4-(2-((3-(P-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)PYROCATECHOL
Common Name English
COMPOUND 81929
Code English
Dobutamine [WHO-DD]
Common Name English
DOBUTAMINE [USP IMPURITY]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000245
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
WHO-ATC C01CA07
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
WHO-VATC QC01CA07
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
NDF-RT N0000175555
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
Code System Code Type Description
DAILYMED
3S12J47372
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
NCI_THESAURUS
C61733
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
SMS_ID
100000081844
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL926
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
EVMPD
SUB06343MIG
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
DRUG BANK
DB00841
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
RXCUI
3616
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY RxNorm
PUBCHEM
36811
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
DRUG CENTRAL
937
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
FDA UNII
3S12J47372
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID3022958
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
CHEBI
4670
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
MERCK INDEX
M4710
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY Merck Index
LACTMED
Dobutamine
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
CAS
34368-04-2
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
MESH
D004280
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
WIKIPEDIA
DOBUTAMINE
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
IUPHAR
535
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY
CAS
67230-43-7
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
SUPERSEDED
INN
3340
Created by admin on Wed Jul 05 23:53:45 UTC 2023 , Edited by admin on Wed Jul 05 23:53:45 UTC 2023
PRIMARY