DOBUTAMINE

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 Search

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

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 157 Target ID: CHEMBL213 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10531390	Agonist 2451		3.2 µM [Ki]
Beta-2 adrenergic receptor 197 Target ID: CHEMBL210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10531390	Agonist 2451		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 7968	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

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) n = 6 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 6 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) n = 5 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 5 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 n = 1 Health Status: unhealthy Age Group: 46 years Sex: M Population Size: 1 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) n = 6 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 6 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) n = 5 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 5 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) n = 5 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 5 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) n = 5 Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Population Size: 5 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 n = 1 Health Status: unhealthy Age Group: 46 years Sex: M Population Size: 1 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
Influence of dobutamine on regional myocardial blood flow and ventricular performance during acute and chronic myocardial ischemia in dogs.	1976 May	1260986
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	1375684
Clinical significance of abrupt vasodepression during dobutamine stress echocardiography.	1992 Jun 1	1590241
The relationship between modified pulse wave transit time and cardiovascular changes in isoflurane anesthetized dogs.	1999 Dec	12578047
Hypotension with dobutamine: beta-adrenergic antagonist selectivity at low doses of carvedilol.	1999 Dec	10630826
Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists.	1999 Nov	10531390
[Distributive shock and it's therapy by cardio-vascular acting drugs].	1999 Oct	10570779
Fibroblast growth factor-2 mediates pressure-induced hypertrophic response.	1999 Sep	10491406
Dobutamine stress echocardiography: safety in diagnosing coronary artery disease.	2000 Apr	10789822
Acute cardiac rupture during dobutamine-atropine echocardiography stress test.	2000 Feb	10668020
Acute infarction of a previously stented coronary artery precipitated by dobutamine stress echocardiography.	2000 Feb	10668019
Severe dynamic obstruction of the left ventricular outflow tract induced by dobutamine.	2000 Jan	10978957
Incidence and significance of profound hypotension during dobutamine stress echocardiography.	2000 Jan	10680029
Myocardial ischemia due to coronary artery spasm during dobutamine stress echocardiography.	2000 Jan 1	11078231
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	10712987
Catecholamines suppress leptin release from in vitro differentiated subcutaneous human adipocytes in primary culture via beta1- and beta2-adrenergic receptors.	2000 Sep	11022189
[Complications of stress echocardiography].	2001 Aug	11525112
Increased inducible nitric oxide synthase expression contributes to myocardial dysfunction and higher mortality after myocardial infarction in mice.	2001 Aug 7	11489778
Milrinone versus dobutamine in heart failure subjects treated chronically with carvedilol.	2001 Dec	11744130
Hypotension and functional left ventricular obstruction during dobutamine stress echocardiography--two case reports.	2001 Jul	11515989
The Arg 389 Gly beta1-adrenergic receptor gene polymorphism and human fat cell lipolysis.	2001 Nov	11753577
Attenuation of lung inflammation by adrenergic agonists in murine acute lung injury.	2001 Oct	11605937
Dobutamine stress cine-MRI of cardiac function in the hearts of adult cardiomyocyte-specific VEGF knockout mice.	2001 Oct	11599061
[Safety of stress echocardiography with dobutamine used in patients with aortic stenosis and left ventricular dysfunction].	2002	12638346
Dobutamine stress myocardial perfusion imaging in coronary artery disease.	2002 Dec	12468513
[Reversible cardiomyopathy secondary to interferon-alpha in chronic myelogenous leukemia].	2002 Feb	11865642
Long-term treatment with perindopril ameliorates dobutamine-induced myocardial ischemia in patients with coronary artery disease.	2002 Jan	11855668
Multifocal myoclonus due to verapamil overdose.	2002 Mar 26	11914425
Cardiac myocyte-specific excision of the beta1 integrin gene results in myocardial fibrosis and cardiac failure.	2002 Mar 8	11884376
Kallikrein gene delivery improves cardiac reserve and attenuates remodeling after myocardial infarction.	2002 Nov	12411458
Controlled expression of cardiac-directed adenylylcyclase type VI provides increased contractile function.	2002 Nov	12393090
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	12202724
Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography.	2003 Apr	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 Feb 1	12565080
Impaired cardiac contraction and relaxation and decreased expression of sarcoplasmic Ca2+-ATPase in mice lacking the CREM gene.	2003 Jan	12475904
Dobutamine modulates lipopolysaccharide-induced macrophage inflammatory protein-1alpha and interleukin-8 production in human monocytes.	2003 Jul	12818968
Dobutamine inhibits monocyte chemoattractant protein-1 production and chemotaxis in human monocytes.	2003 Jul	12818967
Levosimendan: a new dual-action drug in the treatment of acute heart failure.	2003 Jun	12846347
Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system.	2003 Jun	12736183
Myocardial ischemia and induction of sustained ventricular tachyarrhythmias: evaluation using dobutamine stress echocardiography-electrophysiologic testing.	2004 Aug	15333083
Protein kinase Cepsilon overexpression alters myofilament properties and composition during the progression of heart failure.	2004 Aug 20	15242976
Effects of growth hormone on the function of beta-adrenoceptor subtypes in rat adipocytes.	2004 Feb	14981226
Hypersensitivity myocarditis complicating hypertrophic cardiomyopathy heart.	2004 Jul	15266362
Chronic phospholamban inhibition prevents progressive cardiac dysfunction and pathological remodeling after infarction in rats.	2004 Mar	14991071
Overexpression of the catalytic subunit of protein phosphatase 2A impairs cardiac function.	2004 Sep 24	15247211
[Levosimendan, a revolution in the world of inotropic agents?].	2005 May 25	15997981
Myocardial stiffness, cardiac remodeling, and diastolic dysfunction in calcification-prone fetuin-A-deficient mice.	2005 Nov	16177000
Clinical and prognostic implications of angina pectoris developing during dobutamine stress echocardiography in the absence of inducible wall motion abnormalities.	2005 Sep 15	16169362
Adenoviral gene transfer of Akt enhances myocardial contractility and intracellular calcium handling.	2006 Jan	16094411
Beneficial effects of high doses of growth hormone in the introduction and optimization of medical treatment in decompensated congestive heart failure.	2006 Jun 28	16099518

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.

Name

Type

Language

DOBUTAMINE

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