DOBUTAMINE D-TARTRATE

Details

Stereochemistry	EPIMERIC
Molecular Formula	C18H23NO3.C4H6O6
Molecular Weight	451.467
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H]([C@H](O)C(O)=O)C(O)=O.CC(CCC1=CC=C(O)C=C1)NCCC2=CC(O)=C(O)C=C2

InChI

InChIKey=WZIUXGZIVZDXIG-WUUYCOTASA-N

InChI=1S/C18H23NO3.C4H6O6/c1-13(2-3-14-4-7-16(20)8-5-14)19-11-10-15-6-9-17(21)18(22)12-15;5-1(3(7)8)2(6)4(9)10/h4-9,12-13,19-22H,2-3,10-11H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.0/s1

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 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 2678		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 2678		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 8429	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) 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
Long-term dobutamine therapy for refractory congestive heart failure.	1992 Jul	1617912
Effect of intravenous metoprolol or intravenous metoprolol plus glucagon on dobutamine-induced myocardial ischemia.	2000 Nov	11079278
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
Prognostic value of pharmacologic stress echocardiography in patients with left bundle branch block.	2001 Apr 1	11286950
[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
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.	2001 Feb	11160877
Normal coronary angiogram and dobutamine-induced left ventricular obstruction during stress echocardiography: a higher hemodynamic responsiveness to dobutamine.	2001 May	11415497
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
Therapeutic angiogenesis in the ischemic canine heart induced by myocardial injection of naked complementary DNA plasmid encoding hepatocyte growth factor.	2002 Dec	12447174
Effects of fluid and dobutamine treatment on renal function during partial superior mesenteric artery occlusion and reperfusion.	2002 Feb	12002358
Long-term treatment with perindopril ameliorates dobutamine-induced myocardial ischemia in patients with coronary artery disease.	2002 Jan	11855668
[Coronary Spasm after Administration of Propranolol during Dobutamine Stress Echocardiography].	2002 Jul	12113709
Multifocal myoclonus due to verapamil overdose.	2002 Mar 26	11914425
Effects of norepinephrine on rat cultured microglial cells that express alpha1, alpha2, beta1 and beta2 adrenergic receptors.	2002 Nov	12423672
Generalized tetany: an unusual complication during dobutamine stress echocardiography.	2002 Nov	12415240
Kallikrein gene delivery improves cardiac reserve and attenuates remodeling after myocardial infarction.	2002 Nov	12411458
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
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
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
Gene therapy in cardiac surgery: intramyocardial injection of naked plasmid DNA for chronic myocardial ischemia.	2003 Nov	14583313
Beta 1-adrenergic receptor polymorphisms confer differential function and predisposition to heart failure.	2003 Oct	14502278
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
Prognostic value of dobutamine stress echocardiography in patients with normal left ventricular systolic function.	2004 Jul	15220898
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
Chronic phospholamban inhibition prevents progressive cardiac dysfunction and pathological remodeling after infarction in rats.	2004 Mar	14991071
Dobutamine-induced myoclonia in severe renal failure.	2004 May	15102987
Synergistic contributions of the functional groups of epinephrine to its affinity and efficacy at the beta2 adrenergic receptor.	2004 May	15102946
The Arg389Gly beta1-adrenoceptor gene polymorphism determines contractile response to catecholamines.	2004 Nov	15564877
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
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.

Name

Type

Language

DOBUTAMINE D-TARTRATE

Common Name

English

LY174008

Code

English

DOBUTAMINE TARTRATE [USAN]

Common Name

English

LY-174008

Code

English

DOBUTAMINE TARTRATE

Official Name

English

DOBUTAMINE (-)-TARTRATE

Common Name

English

(±)-4-(2-((3-(P-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)PYROCATECHOL D-TARTRATE (1:1) (SALT)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149