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

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 ( + / - )

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

269568000000
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)
Health Status: unhealthy
Age Group: 43 years (ranhe: 20-72 years)
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)
Health Status: unhealthy
Age Group: 43 years (ranhe: 20-72 years)
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
Health Status: unhealthy
Age Group: 46 years
Sex: M
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)
Health Status: unhealthy
Age Group: 43 years (ranhe: 20-72 years)
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)
Health Status: unhealthy
Age Group: 43 years (ranhe: 20-72 years)
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)
Health Status: unhealthy
Age Group: 43 years (ranhe: 20-72 years)
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)
Health Status: unhealthy
Age Group: 43 years (ranhe: 20-72 years)
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
Health Status: unhealthy
Age Group: 46 years
Sex: M
Sources:
PubMed

PubMed

TitleDatePubMed
Long-term dobutamine therapy for refractory congestive heart failure.
1992 Jul
Clinical significance of abrupt vasodepression during dobutamine stress echocardiography.
1992 Jun 1
Fatal cardiac ischaemia associated with prolonged desflurane anaesthesia and administration of exogenous catecholamines.
1998 Dec
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
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
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
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
Fibroblast growth factor-2 mediates pressure-induced hypertrophic response.
1999 Sep
Dobutamine stress echocardiography: safety in diagnosing coronary artery disease.
2000 Apr
Severe dynamic obstruction of the left ventricular outflow tract induced by dobutamine.
2000 Jan
Effect of intravenous metoprolol or intravenous metoprolol plus glucagon on dobutamine-induced myocardial ischemia.
2000 Nov
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
[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
Hypotension and functional left ventricular obstruction during dobutamine stress echocardiography--two case reports.
2001 Jul
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
Long-term treatment with perindopril ameliorates dobutamine-induced myocardial ischemia in patients with coronary artery disease.
2002 Jan
[Coronary Spasm after Administration of Propranolol during Dobutamine Stress Echocardiography].
2002 Jul
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
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
[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
Beta 1-adrenergic receptor polymorphisms confer differential function and predisposition to heart failure.
2003 Oct
Heme oxygenase-1 gene expression in pericentral hepatocytes through beta1-adrenoceptor stimulation.
2004 Apr
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
The Arg389Gly beta1-adrenoceptor gene polymorphism determines contractile response to catecholamines.
2004 Nov
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
Myocardial stiffness, cardiac remodeling, and diastolic dysfunction in calcification-prone fetuin-A-deficient mice.
2005 Nov
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
Patents

Sample Use Guides

Usual Adult Dose for Congestive Heart Failure
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
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
ENANTIOMER -> RACEMATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY