Dobutamine

Dobutamine
Systematic (IUPAC) name
(RS)-4-(2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682861
Pregnancy cat. B
Legal status  ?
Routes Intravenous
Pharmacokinetic data
Half-life 2 minutes
Identifiers
CAS number 34368-04-2 YesY
ATC code C01CA07
PubChem CID 36811
IUPHAR ligand 535
DrugBank APRD00122
ChemSpider 33786 YesY
UNII 0WR771DJXV YesY
KEGG D03879 YesY
ChEBI CHEBI:4670 YesY
ChEMBL CHEMBL926 YesY
Synonyms Dobutrex, Inotrex
Chemical data
Formula C18H23NO3 
Mol. mass 301.38 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Dobutamine is a sympathomimetic drug used in the treatment of heart failure and cardiogenic shock. Its primary mechanism is direct stimulation of β1 receptors of the sympathetic nervous system. Dobutamine was developed by a laboratory led by Drs. Ronald Tuttle and Jack Mills at Eli Lilly and Company, as a structural analogue of isoprenaline.[1]

Contents

Clinical uses

Dobutamine is used to treat acute but potentially reversible heart failure, such as which occurs during cardiac surgery or in cases of septic or cardiogenic shock, on the basis of its positive inotropic action.[2]

Dobutamine can be used in cases of congestive heart failure to increase cardiac output. It is indicated when parenteral therapy is necessary for inotropic support in the short-term treatment of patients with cardiac decompensation due to depressed contractility, which could be the result of either organic heart disease or cardiac surgical procedures. It is not useful in ischemic heart disease because it increases heart rate and thus increases myocardial oxygen demand.

The drug is also commonly used in the hospital setting as a pharmacologic stress testing agent to identify coronary artery disease.

Adverse effects

Primary side effects include those commonly seen for β1 active sympathomimetics, such as hypertension, angina, arrhythmia, and tachycardia. Used with caution in atrial fibrillation as it has the effect of increasing the atriovenrticular (AV) conduction.[3]

The most dangerous side effect of dobutamine is increased risk of arrhythmia, including fatal arrhythmias. Studies suggest that while this medication can improve symptoms in chronic CHF, it actually shortens a patient's lifespan.

Pharmacology

Dobutamine is a direct-acting agent whose primary activity results from stimulation of the β1-adrenoceptors of the heart, increasing contractility and cardiac output. Since it does not act on dopamine receptors to induce the release of norepinephrine (another α1 agonist), dobutamine is less prone to induce hypertension than is dopamine.

Dobutamine is predominantly a β1-adrenergic agonist, with weak β2 activity, and α1 selective activity, although it is used clinically in cases of cardiogenic shock for its β1 inotropic effect in increasing heart contractility and cardiac output. Dobutamine is administered as a racemic mixture consisting of both (+) and (−) isomers; the (+) isomer is a potent β1 agonist and α1 antagonist, while the (−) isomer is an α1 agonist.[4] The administration of the racemate results in the overall β1 agonism responsible for its activity. (+)-Dobutamine also has mild β2 agonist activity, which makes it useful as a vasodilator.[5]

Chemistry

It is synthesized by the reaction of 2-(3,4-dimethoxyphenyl)ethanamine and 1-(4-methoxyphenyl)-3-butanone with a simultaneous reduction of formed imine. The methoxyl-protecting groups of this intermediate are cleaved by hydrogen bromide giving dobutamine. Dobutamine synthesis.png

References

  1. ^ Tuttle RR, Mills J (January 1975). "Dobutamine: development of a new catecholamine to selectively increase cardiac contractility". Circ Res 36 (1): 185–96. doi:10.1161/01.RES.36.1.185. PMID 234805. http://circres.ahajournals.org/cgi/reprint/36/1/185. 
  2. ^ Rang HP, Dale MM, Ritter JM, Flower RJ. Rang and Dale's Pharmacology. 
  3. ^ Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 6. ISBN 1-59541-101-1. 
  4. ^ Parker K, Brunton L, Goodman LS, Blumenthal D, Buxton I (2008). Goodman & Gilman's manual of pharmacology and therapeutics. McGraw-Hill Medical. pp. 159. ISBN 0-07-144343-6. 
  5. ^ Tibayan FA, Chesnutt AN, Folkesson HG, Eandi J, Matthay MA (1997). "Dobutamine increases alveolar liquid clearance in ventilated rats by beta-2 receptor stimulation". Am. J. Respir. Crit. Care Med. 156 (2 Pt 1): 438–44. PMID 9279221. 

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  • dobutamine — n. a sympathomimetic drug (a beta agonist) used to increase the force of contraction of the ventricles and improve the heart output, for example in patients who have had a myocardial infarction or in cases of shock. It is given by intravenous… …   The new mediacal dictionary

  • dobutamine hydrochloride — the hydrochloride salt of dobutamine, having the same actions as the base; used in the treatment of cardiac decompensation in congestive heart failure or depressed contractility secondary to cardiac surgery; administered intravenously …   Medical dictionary

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  • Dob — • dobutamine …   Dictionary of medical acronyms & abbreviations

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  • DSE — dobutamine stress echocardiography; Doctor of Sanitary Engineering …   Medical dictionary

  • ДОБУТАМИН — (dobutamine) симпатомимстический лекарственный препарат, способствующий уменьшению сердечной недостаточности. Повышает сократительную способность желудочков и увеличивает сердечный выброс крови; может назначаться для длительного лечения… …   Толковый словарь по медицине

  • DbE — • dobutamine echocardiography …   Dictionary of medical acronyms & abbreviations


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