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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

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

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
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
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
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
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
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
Prognostic value of pharmacologic stress echocardiography in patients with left bundle branch block.
2001 Apr 1
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
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
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
Effects of fluid and dobutamine treatment on renal function during partial superior mesenteric artery occlusion and reperfusion.
2002 Feb
[Coronary Spasm after Administration of Propranolol during Dobutamine Stress Echocardiography].
2002 Jul
Multifocal myoclonus due to verapamil overdose.
2002 Mar 26
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
[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
Levosimendan in patients with low-output heart failure: lessons from the LIDO trial.
2003 May
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
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 phospholamban inhibition prevents progressive cardiac dysfunction and pathological remodeling after infarction in rats.
2004 Mar
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
[Levosimendan, a revolution in the world of inotropic agents?].
2005 May 25
Treatment of cardiogenic shock with levosimendan in combination with beta-adrenergic antagonists.
2005 Nov
Polymorphism of the AHSG gene is associated with increased adipocyte beta2-adrenoceptor function.
2005 Oct
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

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 10:11:21 UTC 2021
Edited
by admin
on Sat Jun 26 10:11:21 UTC 2021
Record UNII
3S12J47372
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
SALT/SOLVATE -> PARENT
NON-LABELED -> LABELED
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY