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
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
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 |
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
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 |
---|---|---|---|
3.2 µM [Ki] | |||
1.4 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 Date1978 |
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 |
---|---|---|
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 |
|
Long-term dobutamine therapy for refractory congestive heart failure. | 1992 Jul |
|
Fatal cardiac ischaemia associated with prolonged desflurane anaesthesia and administration of exogenous catecholamines. | 1998 Dec |
|
The clinical impact of dynamic intraventricular obstruction during dobutamine stress echocardiography. | 1999 Jul 31 |
|
Severe dynamic obstruction of the left ventricular outflow tract induced by dobutamine. | 2000 Jan |
|
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
Dobutamine stress cine-MRI of cardiac function in the hearts of adult cardiomyocyte-specific VEGF knockout mice. | 2001 Oct |
|
Sensitive method of detecting myocardial ischemia during dobutamine stress echocardiography. | 2003 Apr |
|
Catecholamine-induced T-wave lability in congenital long QT syndrome: a novel phenomenon associated with syncope and cardiac arrest. | 2003 Jan |
|
Expression of glycerokinase in brown adipose tissue is stimulated by the sympathetic nervous system. | 2003 Jun |
|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/dobutamine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3022421
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
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0WR771DJXV
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C48149
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SUPERSEDED |
Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |