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
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
Fatal cardiac ischaemia associated with prolonged desflurane anaesthesia and administration of exogenous catecholamines.	1998 Dec	10051940
The clinical impact of dynamic intraventricular obstruction during dobutamine stress echocardiography.	1999 Jul 31	10454307
Severe dynamic obstruction of the left ventricular outflow tract induced by dobutamine.	2000 Jan	10978957
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.	2001 Feb	11160877
Dobutamine stress cine-MRI of cardiac function in the hearts of adult cardiomyocyte-specific VEGF knockout mice.	2001 Oct	11599061
Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography.	2003 Apr	12655162
Catecholamine-induced T-wave lability in congenital long QT syndrome: a novel phenomenon associated with syncope and cardiac arrest.	2003 Jan	12528876
Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system.	2003 Jun	12736183
Protein kinase Cepsilon overexpression alters myofilament properties and composition during the progression of heart failure.	2004 Aug 20	15242976
Hypersensitivity myocarditis complicating hypertrophic cardiomyopathy heart.	2004 Jul	15266362

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

Download

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