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Identification
Name Dobutamine
Accession Number DB00841 (APRD00122)
Type small molecule
Groups approved
Description

A beta-2 agonist catecholamine that has cardiac stimulant action without evoking vasoconstriction or tachycardia. It is proposed as a cardiotonic after myocardial infarction or open heart surgery. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Dobutamina [INN-Spanish]
Dobutamine [Usan:Ban:Inn]
Dobutamine [Usan]
Dobutamine Hcl
Dobutamine Hcl in Dextrose 5%
Dobutamine Hydrochloride
Dobutaminum [INN-Latin]
Dobutrex
Inotrex
Racemic-Dobutamine
Brand mixtures Not Available
Categories
  • Sympathomimetics
  • Adrenergic beta-Agonists
  • Cardiotonic Agents
  • Sympathomimetic
CAS number 34368-04-2
Weight Average: 301.3801
Monoisotopic: 301.167793607
Chemical Formula C18H23NO3
InChI Key InChIKey=JRWZLRBJNMZMFE-UHFFFAOYSA-N
InChI
InChI=1S/C18H23NO3/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
Plain Text
IUPAC Name
4-(2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol
SMILES
CC(CCC1=CC=C(O)C=C1)NCCC1=CC(O)=C(O)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Phenylpropylamines
  • Catecholamines and Derivatives
Substructures
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Catechols
  • Phenethylamines
  • Aromatic compounds
  • Phenylpropylamines
  • Phenyl Esters
  • Catecholamines and Derivatives
Pharmacology
Indication 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
Pharmacodynamics Dobutamine is a direct-acting inotropic agent whose primary activity results from stimulation of the beta-adrenoceptors of the heart while producing comparatively mild chronotropic, hypertensive, arrhythmogenic, and vasodilative effects. Dobutamine acts primarily on beta-1 adrenergic receptors, with little effect on beta-2 or alpha receptors. It does not cause the release of endogenous norepinephrine, as does dopamine. Dobutamine 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.
Mechanism of action Dobutamine directly stimulates beta-1 receptors of the heart to increase myocardial contractility and stroke volume, resulting in increased cardiac output.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination In human urine, the major excretion products are the conjugates of dobutamine and 3-O-methyl dobutamine.
Half life 2 minutes
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Astrazeneca lp
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Marsam pharmaceuticals llc
  • Teva parenteral medicines inc
  • Watson laboratories inc
  • Baxter healthcare corp
  • Eli lilly and co
Packagers
Dosage forms
Form Route Strength
Liquid Intravenous
Solution Intravenous
Prices
Unit description Cost Unit
Dobutamine 12.5 mg/ml vial 0.18 USD ml
Dobutamine 250 mg-d5w 500 ml 0.09 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 3.6 Not Available
Predicted Properties
Property Value Source
water solubility 1.37e-02 g/l ALOGPS
logP 2.97 ALOGPS
logP 2.62 ChemAxon
logS -4.3 ALOGPS
pKa (strongest acidic) 10.14 ChemAxon
pKa (strongest basic) 9.27 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 72.72 ChemAxon
rotatable bond count 7 ChemAxon
refractivity 88.39 ChemAxon
polarizability 34.44 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D03879 Link_out
KEGG Compound C06967 Link_out
PubChem Compound 36811 Link_out
PubChem Substance 46505241 Link_out
ChemSpider 33786 Link_out
BindingDB 50028971 Link_out
ChEBI 4670 Link_out
ChEMBL 4670 Link_out
Therapeutic Targets Database DAP000245 Link_out
PharmGKB PA449381 Link_out
IUPHAR 535 Link_out
Guide to Pharmacology 535 Link_out
Drug Product Database 2242010 Link_out
RxList http://www.rxlist.com/cgi/generic3/dobutamine.htm Link_out
Drugs.com http://www.drugs.com/cdi/dobutamine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Dobutamine Link_out
ATC Codes
  • C01CA07
AHFS Codes
  • 12:12.08.08
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Amitriptyline The tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect, dobutamine.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of dobutamine.
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of dobutamine.
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of dobutamine.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of dobutamine.
Entacapone Entacapone increases the effect and toxicity of the sympathomimetic, dobutamine.
Guanethidine Dobutamine may decrease the effect of guanethidine.
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of dobutamine.
Isocarboxazid Increased arterial pressure
Linezolid Possible increase of arterial pressure
Methyldopa Increased arterial pressure
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect of dobutamine.
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of dobutamine.
Phenelzine Increased arterial pressure
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Food Interactions Not Available
Targets

1. Beta-1 adrenergic receptor

Pharmacological action: yes
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Junker V, Becker A, Huhne R, Zembatov M, Ravati A, Culmsee C, Krieglstein J: Stimulation of beta-adrenoceptors activates astrocytes and provides neuroprotection. Eur J Pharmacol. 2002 Jun 20;446(1-3):25-36. Pubmed
  2. La Rosee K, Huntgeburth M, Rosenkranz S, Bohm M, Schnabel P: The Arg389Gly beta1-adrenoceptor gene polymorphism determines contractile response to catecholamines. Pharmacogenetics. 2004 Nov;14(11):711-6. Pubmed
  3. Bruck H, Leineweber K, Temme T, Weber M, Heusch G, Philipp T, Brodde OE: The Arg389Gly beta1-adrenoceptor polymorphism and catecholamine effects on plasma-renin activity. J Am Coll Cardiol. 2005 Dec 6;46(11):2111-5. Epub 2005 Nov 4. Pubmed
  4. Raddatz A, Kubulus D, Winning J, Bauer I, Pradarutti S, Wolf B, Kreuer S, Rensing H: Dobutamine improves liver function after hemorrhagic shock through induction of heme oxygenase-1. Am J Respir Crit Care Med. 2006 Jul 15;174(2):198-207. Epub 2006 Apr 20. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-2 adrenergic receptor

Pharmacological action: unknown
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Tibayan FA, Chesnutt AN, Folkesson HG, Eandi J, Matthay MA: Dobutamine increases alveolar liquid clearance in ventilated rats by beta-2 receptor stimulation. Am J Respir Crit Care Med. 1997 Aug;156(2 Pt 1):438-44. Pubmed
Enzymes

1. Catechol O-methyltransferase

Actions: substrate

Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol

UniProt ID: P21964 Link_out
Gene: COMT Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Raxworthy MJ, Youde IR, Gulliver PA: Catechol-O-methyltransferase: substrate-specificity and stereoselectivity for beta-adrenoceptor agents. Xenobiotica. 1986 Jan;16(1):47-52. Pubmed
  2. Yan M, Webster LT Jr, Blumer JL: Kinetic interactions of dopamine and dobutamine with human catechol-O-methyltransferase and monoamine oxidase in vitro. J Pharmacol Exp Ther. 2002 Apr;301(1):315-21. Pubmed
  3. Yan M, Webster LT Jr, Blumer JL: Kinetic interactions of dopamine and dobutamine with human catechol-O-methyltransferase and monoamine oxidase in vitro. J Pharmacol Exp Ther. 2002 Apr;301(1):315-21. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19