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
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
| 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 | ( + / - ) |
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
Sources: http://www.drugsupdate.com/generic/view/814/Dobutamine | https://www.ncbi.nlm.nih.gov/pubmed/234805
Curator's Comment:: Dobutamine was developed in the 1970s by Drs. Ronald Tuttle and Jack Mills at Eli Lilly and Company, as a structural analogue of isoprenaline.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 3.20000000000000018 µM [Ki] | |||
| 1.39999999999999991 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Dobutamine hydrochloride Approved UseDobutamine 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 Date269568000000 |
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 |
T1/2
| 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: |
unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: |
Other AEs: Adverse event... |
30 ug/kg/min multiple, intravenous Dose: 30 ug/kg/min Route: intravenous Route: multiple Dose: 30 ug/kg/min Sources: |
unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: |
Disc. AE: Angina, Arrhythmia... AEs leading to discontinuation/dose reduction: Angina (5 patients) Sources: Arrhythmia (5 patients) Hypertension (severe, 5 patients) |
2 ug/kg/min multiple, intravenous Dose: 2 ug/kg/min Route: intravenous Route: multiple Dose: 2 ug/kg/min Sources: |
unhealthy, 46 years |
Disc. AE: Eosinophilia... AEs leading to discontinuation/dose reduction: Eosinophilia (1 patient) Sources: |
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: |
unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: |
|
| 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: |
unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: |
| 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: |
unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: |
| 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: |
unhealthy, 43 years (ranhe: 20-72 years) Health Status: unhealthy Age Group: 43 years (ranhe: 20-72 years) Sources: |
| 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: |
unhealthy, 46 years |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Long-term dobutamine therapy for refractory congestive heart failure. | 1992 Jul |
|
| Clinical significance of abrupt vasodepression during dobutamine stress echocardiography. | 1992 Jun 1 |
|
| Fatal cardiac ischaemia associated with prolonged desflurane anaesthesia and administration of exogenous catecholamines. | 1998 Dec |
|
| Enhanced responsiveness of the myocardial beta-adrenoceptor-adenylate cyclase system in the perfused rat heart (I). | 1998 Oct |
|
| Disruption of myoglobin in mice induces multiple compensatory mechanisms. | 1999 Aug 31 |
|
| Hypotension with dobutamine: beta-adrenergic antagonist selectivity at low doses of carvedilol. | 1999 Dec |
|
| Torsade de pointes ventricular tachycardia during low dose intermittent dobutamine treatment in a patient with dilated cardiomyopathy and congestive heart failure. | 1999 Feb |
|
| The clinical impact of dynamic intraventricular obstruction during dobutamine stress echocardiography. | 1999 Jul 31 |
|
| Dobutamine-induced hypotension is an independent predictor for mortality in patients with left ventricular dysfunction following myocardial infarction. | 1999 Mar 15 |
|
| Hypertensive encephalopathy as a complication of hyperdynamic therapy for vasospasm: report of two cases. | 1999 May |
|
| Enhanced contractility and decreased beta-adrenergic receptor kinase-1 in mice lacking endogenous norepinephrine and epinephrine. | 1999 May 25 |
|
| Fibroblast growth factor-2 mediates pressure-induced hypertrophic response. | 1999 Sep |
|
| Dobutamine stress echocardiography: safety in diagnosing coronary artery disease. | 2000 Apr |
|
| Severe dynamic obstruction of the left ventricular outflow tract induced by dobutamine. | 2000 Jan |
|
| Effect of intravenous metoprolol or intravenous metoprolol plus glucagon on dobutamine-induced myocardial ischemia. | 2000 Nov |
|
| Catecholamines suppress leptin release from in vitro differentiated subcutaneous human adipocytes in primary culture via beta1- and beta2-adrenergic receptors. | 2000 Sep |
|
| Prognostic value of pharmacologic stress echocardiography in patients with left bundle branch block. | 2001 Apr 1 |
|
| [Complications of stress echocardiography]. | 2001 Aug |
|
| Milrinone versus dobutamine in heart failure subjects treated chronically with carvedilol. | 2001 Dec |
|
| Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
| Hypotension and functional left ventricular obstruction during dobutamine stress echocardiography--two case reports. | 2001 Jul |
|
| Dobutamine stress myocardial perfusion imaging in coronary artery disease. | 2002 Dec |
|
| Therapeutic angiogenesis in the ischemic canine heart induced by myocardial injection of naked complementary DNA plasmid encoding hepatocyte growth factor. | 2002 Dec |
|
| Long-term treatment with perindopril ameliorates dobutamine-induced myocardial ischemia in patients with coronary artery disease. | 2002 Jan |
|
| [Coronary Spasm after Administration of Propranolol during Dobutamine Stress Echocardiography]. | 2002 Jul |
|
| Cardiac myocyte-specific excision of the beta1 integrin gene results in myocardial fibrosis and cardiac failure. | 2002 Mar 8 |
|
| Kallikrein gene delivery improves cardiac reserve and attenuates remodeling after myocardial infarction. | 2002 Nov |
|
| Controlled expression of cardiac-directed adenylylcyclase type VI provides increased contractile function. | 2002 Nov |
|
| 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 |
|
| Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography. | 2003 Apr |
|
| 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 |
|
| Catecholamine-induced T-wave lability in congenital long QT syndrome: a novel phenomenon associated with syncope and cardiac arrest. | 2003 Jan |
|
| Impaired cardiac contraction and relaxation and decreased expression of sarcoplasmic Ca2+-ATPase in mice lacking the CREM gene. | 2003 Jan |
|
| Dobutamine modulates lipopolysaccharide-induced macrophage inflammatory protein-1alpha and interleukin-8 production in human monocytes. | 2003 Jul |
|
| [Left ventricular hypertrophy: a marker for patients at risk of arterial hypotension during stress echocardiography with dobutamine?]. | 2003 Jun |
|
| Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system. | 2003 Jun |
|
| Beta 1-adrenergic receptor polymorphisms confer differential function and predisposition to heart failure. | 2003 Oct |
|
| Heme oxygenase-1 gene expression in pericentral hepatocytes through beta1-adrenoceptor stimulation. | 2004 Apr |
|
| Protein kinase Cepsilon overexpression alters myofilament properties and composition during the progression of heart failure. | 2004 Aug 20 |
|
| Hypersensitivity myocarditis complicating hypertrophic cardiomyopathy heart. | 2004 Jul |
|
| The Arg389Gly beta1-adrenoceptor gene polymorphism determines contractile response to catecholamines. | 2004 Nov |
|
| Overexpression of the catalytic subunit of protein phosphatase 2A impairs cardiac function. | 2004 Sep 24 |
|
| Detrimental effects after dobutamine infusion on rat left ventricular function: mechanical work and energetics. | 2005 Jul |
|
| Dobutamine-induced bradycardia in a dog. | 2005 Mar |
|
| Dobutamine induced severe midventricular obstruction and mitral regurgitation in left ventricular apical ballooning syndrome. | 2005 Mar |
|
| Myocardial stiffness, cardiac remodeling, and diastolic dysfunction in calcification-prone fetuin-A-deficient mice. | 2005 Nov |
|
| Polymorphism of the AHSG gene is associated with increased adipocyte beta2-adrenoceptor function. | 2005 Oct |
|
| Sustained ventricular tachycardia induced by dobutamine stress echocardiography: a prospective study. | 2005 Sep |
|
| Upstream transcription factor-1 gene polymorphism is associated with increased adipocyte lipolysis. | 2005 Sep |
Patents
Sample Use Guides
| Substance Class |
Chemical
Created
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| Record UNII |
0WR771DJXV
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Validated (UNII)
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C48149
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1224507
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256-464-1
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C28997
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0WR771DJXV
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49745-95-1
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DBSALT000711
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CHEMBL926
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M4710
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65324
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203121
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SUB01803MIG
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52663-81-7
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SUPERSEDED |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
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|
|
ENANTIOMER -> RACEMATE | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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||
|
|
ENANTIOMER -> RACEMATE | |||
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |