DOBUTAMINE HYDROBROMIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H23NO3.BrH
Molecular Weight	382.292
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=QMCDOYGKCFLHBO-UHFFFAOYSA-N

InChI=1S/C18H23NO3.BrH/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	BrH
Molecular Weight	80.912
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 158 Target ID: CHEMBL213 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10531390	Agonist 2662		3.2 µM [Ki]
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10531390	Agonist 2662		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 8360	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
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
Long-term dobutamine therapy for refractory congestive heart failure.	1992 Jul	1617912
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
Changes in endothelium-derived vascular regulatory factors during dobutamine-stress-induced silent myocardial ischemia in patients with Kawasaki disease.	1999 Jul	10462014
Transmural metabolic heterogeneity at high cardiac work states.	1999 Jul	10409202
The clinical impact of dynamic intraventricular obstruction during dobutamine stress echocardiography.	1999 Jul 31	10454307
[Distributive shock and it's therapy by cardio-vascular acting drugs].	1999 Oct	10570779
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
Fatal ventricular fibrillation during a low-dose dobutamine stress test.	2000 Mar	11014735
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
Prolonged left ventricular dysfunction occurs in patients with coronary artery disease after both dobutamine and exercise induced myocardial ischaemia.	2000 Mar	10677406
Catecholamines suppress leptin release from in vitro differentiated subcutaneous human adipocytes in primary culture via beta1- and beta2-adrenergic receptors.	2000 Sep	11022189
[Prognostic value of cardiac perfusion scintigraphy associated with the dobutamine test in acute coronary syndromes].	2001 Apr	11333816
Milrinone versus dobutamine in heart failure subjects treated chronically with carvedilol.	2001 Dec	11744130
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.	2001 Feb	11160877
Attenuation of lung inflammation by adrenergic agonists in murine acute lung injury.	2001 Oct	11605937
Effects of fluid and dobutamine treatment on renal function during partial superior mesenteric artery occlusion and reperfusion.	2002 Feb	12002358
[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
Generalized tetany: an unusual complication during dobutamine stress echocardiography.	2002 Nov	12415240
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	14713178
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
Heme oxygenase-1 gene expression in pericentral hepatocytes through beta1-adrenoceptor stimulation.	2004 Apr	15179140
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
Chronic beta-adrenoreceptor stimulation in vivo decreased Bcl-2 and increased Bax expression but did not activate apoptotic pathways in mouse heart.	2004 Mar	15052282
The Arg389Gly beta1-adrenoceptor gene polymorphism determines contractile response to catecholamines.	2004 Nov	15564877
Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro.	2004 Nov	15502056
Dobutamine stress MRI. Part I. Safety and feasibility of dobutamine cardiovascular magnetic resonance in patients suspected of myocardial ischemia.	2004 Oct	15278415
Overexpression of the catalytic subunit of protein phosphatase 2A impairs cardiac function.	2004 Sep 24	15247211
Detrimental effects after dobutamine infusion on rat left ventricular function: mechanical work and energetics.	2005 Jul	15849228
Dobutamine-induced bradycardia in a dog.	2005 Mar	15762916
Dobutamine induced severe midventricular obstruction and mitral regurgitation in left ventricular apical ballooning syndrome.	2005 Mar	15710718
[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
Treatment of cardiogenic shock with levosimendan in combination with beta-adrenergic antagonists.	2005 Nov	16143579
A Dobutamine paradox: eosinophilic myocarditis in the explanted heart of a 9-year-old girl undergoing cardiac transplantation.	2005 Oct	16164793
Polymorphism of the AHSG gene is associated with increased adipocyte beta2-adrenoceptor function.	2005 Oct	16024912
Sustained ventricular tachycardia induced by dobutamine stress echocardiography: a prospective study.	2005 Sep	16087106
Upstream transcription factor-1 gene polymorphism is associated with increased adipocyte lipolysis.	2005 Sep	15985485
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
Atrial fibrillation in dobutamine stress echocardiography.	2006 Jul 28	16054714
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.

Substance Class	Chemical Created by `admin` on `Thu Jul 06 16:49:09 UTC 2023` Edited by `admin` on `Thu Jul 06 16:49:09 UTC 2023`
Record UNII	27T771FEOY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOBUTAMINE HYDROBROMIDE

Common Name

English

1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROBROMIDE

Systematic Name

English

1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROBROMIDE (1:1)

Systematic Name

English

1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROBROMIDE, (±)-

Systematic Name

English

Code System Code Type Description

CAS

82473-35-6