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Details

Stereochemistry RACEMIC
Molecular Formula C18H23NO3.ClH
Molecular Weight 337.8417
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOBUTAMINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=BQKADKWNRWCIJL-UHFFFAOYSA-N
InChI=1S/C18H23NO3.ClH/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 ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Disruption of myoglobin in mice induces multiple compensatory mechanisms.
1999 Aug 31
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
Changes in endothelium-derived vascular regulatory factors during dobutamine-stress-induced silent myocardial ischemia in patients with Kawasaki disease.
1999 Jul
Transmural metabolic heterogeneity at high cardiac work states.
1999 Jul
The clinical impact of dynamic intraventricular obstruction during dobutamine stress echocardiography.
1999 Jul 31
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
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
Prognostic value of pharmacologic stress echocardiography in patients with left bundle branch block.
2001 Apr 1
[Complications of stress echocardiography].
2001 Aug
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
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
[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
Cardiac myocyte-specific excision of the beta1 integrin gene results in myocardial fibrosis and cardiac failure.
2002 Mar 8
Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography.
2003 Apr
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
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
Dobutamine inhibits monocyte chemoattractant protein-1 production and chemotaxis in human monocytes.
2003 Jul
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
Effects of growth hormone on the function of beta-adrenoceptor subtypes in rat adipocytes.
2004 Feb
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
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
Dobutamine induced severe midventricular obstruction and mitral regurgitation in left ventricular apical ballooning syndrome.
2005 Mar
Treatment of cardiogenic shock with levosimendan in combination with beta-adrenergic antagonists.
2005 Nov
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
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 Fri Jun 25 20:52:43 UTC 2021
Edited
by admin
on Fri Jun 25 20:52:43 UTC 2021
Record UNII
0WR771DJXV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOBUTAMINE HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
DOBUTAMINE HYDROCHLORIDE [USAN]
Common Name English
DOBUTAMINE HYDROCHLORIDE [JAN]
Common Name English
DL-DOBUTAMINE HYDROCHLORIDE
Common Name English
DOBUTAMINE HYDROCHLORIDE [MART.]
Common Name English
DOBUTAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
DOBUTAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROCHLORIDE, (+/-)-
Systematic Name English
DOBUTAMINE HYDROCHLORIDE [WHO-DD]
Common Name English
46236
Code English
DOBUTAMINE HYDROCHLORIDE [EP]
Common Name English
DOBUTAMINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
DOBUTAMINE HYDROCHLORIDE [USP]
Common Name English
1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
DOBUTREX
Brand Name English
(+/-)-4-(2-((3-(P-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)PYROCATECHOL HYDROCHLORIDE
Common Name English
INOTREX
Brand Name English
NSC-299583
Code English
DOBUTAMINE HCL
Common Name English
DOBUTAMINE HYDROCHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
Code System Code Type Description
USP_CATALOG
1224507
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
256-464-1
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY
NCI_THESAURUS
C28997
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY
FDA UNII
0WR771DJXV
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY
CAS
49745-95-1
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY
DRUG BANK
DBSALT000711
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY
ChEMBL
CHEMBL926
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY
MERCK INDEX
M4710
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY Merck Index
PUBCHEM
65324
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY
RXCUI
203121
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY RxNorm
EVMPD
SUB01803MIG
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
PRIMARY
CAS
52663-81-7
Created by admin on Fri Jun 25 20:52:43 UTC 2021 , Edited by admin on Fri Jun 25 20:52:43 UTC 2021
SUPERSEDED
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PARENT -> SALT/SOLVATE
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