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Details

Stereochemistry RACEMIC
Molecular Formula C18H23NO3.ClH
Molecular Weight 337.841
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOBUTAMINE HYDROCHLORIDE

SMILES

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

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 C18H23NO3
Molecular Weight 301.3801
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1978
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
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
Long-term dobutamine therapy for refractory congestive heart failure.
1992 Jul
Fatal cardiac ischaemia associated with prolonged desflurane anaesthesia and administration of exogenous catecholamines.
1998 Dec
The clinical impact of dynamic intraventricular obstruction during dobutamine stress echocardiography.
1999 Jul 31
Severe dynamic obstruction of the left ventricular outflow tract induced by dobutamine.
2000 Jan
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
Dobutamine stress cine-MRI of cardiac function in the hearts of adult cardiomyocyte-specific VEGF knockout mice.
2001 Oct
Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography.
2003 Apr
Catecholamine-induced T-wave lability in congenital long QT syndrome: a novel phenomenon associated with syncope and cardiac arrest.
2003 Jan
Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system.
2003 Jun
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
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 Mon Mar 31 18:47:25 GMT 2025
Edited
by admin
on Mon Mar 31 18:47:25 GMT 2025
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
DOBUTREX
Preferred 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 [EP IMPURITY]
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
46236
Code English
DOBUTAMINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
Dobutamine hydrochloride [WHO-DD]
Common Name English
DOBUTAMINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROCHLORIDE (1:1)
Systematic 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 Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
Code System Code Type Description
CHEBI
4671
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
ECHA (EC/EINECS)
256-464-1
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID30964383
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
NCI_THESAURUS
C28997
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
FDA UNII
0WR771DJXV
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
CAS
49745-95-1
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
DRUG BANK
DBSALT000711
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
ChEMBL
CHEMBL926
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
MERCK INDEX
m4710
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY Merck Index
PUBCHEM
65324
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
RS_ITEM_NUM
1224507
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
DAILYMED
0WR771DJXV
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
RXCUI
203121
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY RxNorm
NSC
299583
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
SMS_ID
100000087521
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
EVMPD
SUB01803MIG
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
PRIMARY
CAS
52663-81-7
Created by admin on Mon Mar 31 18:47:25 GMT 2025 , Edited by admin on Mon Mar 31 18:47:25 GMT 2025
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
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CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
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IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY