DOBUTAMINE HYDROCHLORIDE

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/3310640

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 163 Target ID: CHEMBL213 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10531390	Agonist 2752		3.2 µM [Ki]
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10531390	Agonist 2752		1.4 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart diseases 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020201s036lbl.pdf	Primary		Approved 8583	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

Value	Dose	Co-administered	Analyte	Population
14 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/699477/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.37 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/699477/	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/7671905	unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: https://pubmed.ncbi.nlm.nih.gov/7671905	Other AEs: Adverse event... Other AEs: Adverse event Sources: https://pubmed.ncbi.nlm.nih.gov/7671905
30 ug/kg/min multiple, intravenous Dose: 30 ug/kg/min Route: intravenous Route: multiple Dose: 30 ug/kg/min Sources: https://pubmed.ncbi.nlm.nih.gov/7671905	unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: https://pubmed.ncbi.nlm.nih.gov/7671905	Disc. AE: Angina, Arrhythmia... AEs leading to discontinuation/dose reduction: Angina (5 patients) Arrhythmia (5 patients) Hypertension (severe, 5 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/7671905
2 ug/kg/min multiple, intravenous Dose: 2 ug/kg/min Route: intravenous Route: multiple Dose: 2 ug/kg/min Sources: https://pubmed.ncbi.nlm.nih.gov/15081466	unhealthy, 46 years Health Status: unhealthy Age Group: 46 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15081466	Disc. AE: Eosinophilia... AEs leading to discontinuation/dose reduction: Eosinophilia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15081466

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/7671905	unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: https://pubmed.ncbi.nlm.nih.gov/7671905
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: https://pubmed.ncbi.nlm.nih.gov/7671905	unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: https://pubmed.ncbi.nlm.nih.gov/7671905
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: https://pubmed.ncbi.nlm.nih.gov/7671905	unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: https://pubmed.ncbi.nlm.nih.gov/7671905
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: https://pubmed.ncbi.nlm.nih.gov/7671905	unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: https://pubmed.ncbi.nlm.nih.gov/7671905
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: https://pubmed.ncbi.nlm.nih.gov/15081466	unhealthy, 46 years Health Status: unhealthy Age Group: 46 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15081466

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4670	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4670
ChemicalBook	CB5274062	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5274062
MolPort	MolPort-006-167-641	https://www.molport.com/shop/molecule-link/MolPort-006-167-641

PubMed

Title	Date	PubMed
Atrial fibrillation in dobutamine stress echocardiography.	2006-07-28	16054714
Beneficial effects of high doses of growth hormone in the introduction and optimization of medical treatment in decompensated congestive heart failure.	2006-06-28	16099518
Adenoviral gene transfer of Akt enhances myocardial contractility and intracellular calcium handling.	2006-01	16094411
Myocardial stiffness, cardiac remodeling, and diastolic dysfunction in calcification-prone fetuin-A-deficient mice.	2005-11	16177000
Treatment of cardiogenic shock with levosimendan in combination with beta-adrenergic antagonists.	2005-11	16143579
A Dobutamine paradox: eosinophilic myocarditis in the explanted heart of a 9-year-old girl undergoing cardiac transplantation.	2005-10	16164793
Polymorphism of the AHSG gene is associated with increased adipocyte beta2-adrenoceptor function.	2005-10	16024912
Clinical and prognostic implications of angina pectoris developing during dobutamine stress echocardiography in the absence of inducible wall motion abnormalities.	2005-09-15	16169362
Sustained ventricular tachycardia induced by dobutamine stress echocardiography: a prospective study.	2005-09	16087106
Upstream transcription factor-1 gene polymorphism is associated with increased adipocyte lipolysis.	2005-09	15985485
Detrimental effects after dobutamine infusion on rat left ventricular function: mechanical work and energetics.	2005-07	15849228
[Levosimendan, a revolution in the world of inotropic agents?].	2005-05-25	15997981
Dobutamine-induced bradycardia in a dog.	2005-03	15762916
Dobutamine induced severe midventricular obstruction and mitral regurgitation in left ventricular apical ballooning syndrome.	2005-03	15710718
The Arg389Gly beta1-adrenoceptor gene polymorphism determines contractile response to catecholamines.	2004-11	15564877
Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro.	2004-11	15502056
Dobutamine stress MRI. Part I. Safety and feasibility of dobutamine cardiovascular magnetic resonance in patients suspected of myocardial ischemia.	2004-10	15278415
Overexpression of the catalytic subunit of protein phosphatase 2A impairs cardiac function.	2004-09-24	15247211
Protein kinase Cepsilon overexpression alters myofilament properties and composition during the progression of heart failure.	2004-08-20	15242976
Myocardial ischemia and induction of sustained ventricular tachyarrhythmias: evaluation using dobutamine stress echocardiography-electrophysiologic testing.	2004-08	15333083
Hypersensitivity myocarditis complicating hypertrophic cardiomyopathy heart.	2004-07	15266362
Prognostic value of dobutamine stress echocardiography in patients with normal left ventricular systolic function.	2004-07	15220898
Dobutamine-induced myoclonia in severe renal failure.	2004-05	15102987
Synergistic contributions of the functional groups of epinephrine to its affinity and efficacy at the beta2 adrenergic receptor.	2004-05	15102946
Heme oxygenase-1 gene expression in pericentral hepatocytes through beta1-adrenoceptor stimulation.	2004-04	15179140
Eosinophilic myocarditis in patients awaiting heart transplantation.	2004-03	15090952
Chronic beta-adrenoreceptor stimulation in vivo decreased Bcl-2 and increased Bax expression but did not activate apoptotic pathways in mouse heart.	2004-03	15052282
Chronic phospholamban inhibition prevents progressive cardiac dysfunction and pathological remodeling after infarction in rats.	2004-03	14991071
Effects of growth hormone on the function of beta-adrenoceptor subtypes in rat adipocytes.	2004-02	14981226
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.	2003-12	14713178
Gene therapy in cardiac surgery: intramyocardial injection of naked plasmid DNA for chronic myocardial ischemia.	2003-11	14583313
Beta 1-adrenergic receptor polymorphisms confer differential function and predisposition to heart failure.	2003-10	14502278
Electrical storm: case series and review of management.	2003-09	14506549
Dobutamine modulates lipopolysaccharide-induced macrophage inflammatory protein-1alpha and interleukin-8 production in human monocytes.	2003-07	12818968
Dobutamine inhibits monocyte chemoattractant protein-1 production and chemotaxis in human monocytes.	2003-07	12818967
[Left ventricular hypertrophy: a marker for patients at risk of arterial hypotension during stress echocardiography with dobutamine?].	2003-06	12868343
Levosimendan: a new dual-action drug in the treatment of acute heart failure.	2003-06	12846347
Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system.	2003-06	12736183
Levosimendan in patients with low-output heart failure: lessons from the LIDO trial.	2003-05	14635368
Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography.	2003-04	12655162
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.	2003-02-01	12565080
Dopamine stabilizes milrinone-induced changes in heart rate and arterial pressure during anaesthesia with isoflurane.	2003-02	12622495
Catecholamine-induced T-wave lability in congenital long QT syndrome: a novel phenomenon associated with syncope and cardiac arrest.	2003-01	12528876
[Safety of stress echocardiography with dobutamine used in patients with aortic stenosis and left ventricular dysfunction].	2002	12638346
The relationship between modified pulse wave transit time and cardiovascular changes in isoflurane anesthetized dogs.	1999-12	12578047
Cimetidine-dobutamine interaction?	1992-11	1466438
Long-term dobutamine therapy for refractory congestive heart failure.	1992-07	1617912
Clinical significance of abrupt vasodepression during dobutamine stress echocardiography.	1992-06-01	1590241
Modulation of inotropic therapy by venodilation in acute heart failure: a randomised comparison of four inotropic agents, alone and combined with isosorbide dinitrate.	1992-01	1375684
Influence of dobutamine on regional myocardial blood flow and ventricular performance during acute and chronic myocardial ischemia in dogs.	1976-05	1260986

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

DOBUTAMINE HYDROCHLORIDE

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