DOBUTAMINE HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H23NO3.ClH
Molecular Weight	337.8417
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.Cl

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	ClH
Molecular Weight	36.4609
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H23NO3
Molecular Weight	301.3808
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 153 Target ID: CHEMBL213 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10531390	Agonist 2470		3.2 µM [Ki]
Beta-2 adrenergic receptor 194 Target ID: CHEMBL210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020255s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10531390	Agonist 2470		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 8043	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
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
Cimetidine-dobutamine interaction?	1992 Nov	1466438
Enhanced responsiveness of the myocardial beta-adrenoceptor-adenylate cyclase system in the perfused rat heart (I).	1998 Oct	10192281
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
The clinical impact of dynamic intraventricular obstruction during dobutamine stress echocardiography.	1999 Jul 31	10454307
Dobutamine-induced hypotension is an independent predictor for mortality in patients with left ventricular dysfunction following myocardial infarction.	1999 Mar 15	10213281
Hypertensive encephalopathy as a complication of hyperdynamic therapy for vasospasm: report of two cases.	1999 May	10232545
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
Myocardial ischemia due to coronary artery spasm during dobutamine stress echocardiography.	2000 Jan 1	11078231
Fatal ventricular fibrillation during a low-dose dobutamine stress test.	2000 Mar	11014735
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
The Arg 389 Gly beta1-adrenergic receptor gene polymorphism and human fat cell lipolysis.	2001 Nov	11753577
[Safety of stress echocardiography with dobutamine used in patients with aortic stenosis and left ventricular dysfunction].	2002	12638346
[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
[Coronary Spasm after Administration of Propranolol during Dobutamine Stress Echocardiography].	2002 Jul	12113709
Effects of norepinephrine on rat cultured microglial cells that express alpha1, alpha2, beta1 and beta2 adrenergic receptors.	2002 Nov	12423672
Kallikrein gene delivery improves cardiac reserve and attenuates remodeling after myocardial infarction.	2002 Nov	12411458
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
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
[Left ventricular hypertrophy: a marker for patients at risk of arterial hypotension during stress echocardiography with dobutamine?].	2003 Jun	12868343
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
Levosimendan in patients with low-output heart failure: lessons from the LIDO trial.	2003 May	14635368
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
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
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 `Fri Jun 25 20:52:43 UTC 2021` Edited by `admin` on `Fri Jun 25 20:52:43 UTC 2021`
Record UNII	0WR771DJXV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOBUTAMINE HYDROCHLORIDE

Official 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 [ORANGE BOOK]

Common Name

English

1,2-BENZENEDIOL, 4-(2-((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)ETHYL)-, HYDROCHLORIDE, (+/-)-

Systematic Name

English

DOBUTAMINE HYDROCHLORIDE [WHO-DD]

Common Name

English

46236

Code

English

DOBUTAMINE HYDROCHLORIDE [EP]

Common Name

English

DOBUTAMINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

DOBUTAMINE HYDROCHLORIDE [USP]

Common Name

English

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

Systematic Name

English

DOBUTREX

Brand 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