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Identification
NameDobutamine
Accession NumberDB00841  (APRD00122)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
DobutaminGermanINN
DobutaminaSpanishINN
DobutamineFrenchDCF
DobutaminumLatinINN
Salts
Name/CAS Structure Properties
Dobutamine hydrochloride
Thumb
  • InChI Key: BQKADKWNRWCIJL-UHFFFAOYNA-N
  • Monoisotopic Mass: 337.144471346
  • Average Mass: 337.841
DBSALT000711
Brand names
NameCompany
DobujectBayer
DobusafeClaris
DobutaminSandoz
DobutanDemo
DobutelNovell
DobutilMeizler
DobutrexLilly
DopminMylan Seiyaku
InotrexLilly
Brand mixturesNot Available
Categories
CAS number34368-04-2
WeightAverage: 301.3801
Monoisotopic: 301.167793607
Chemical FormulaC18H23NO3
InChI KeyInChIKey=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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentCatecholamines and Derivatives
Alternative parentsPhenylpropylamines; Phenethylamines; Polyols; Polyamines; Enols; Dialkylamines
Substituentsphenethylamine; polyol; secondary amine; secondary aliphatic amine; enol; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
Pharmacology
IndicationFor 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
PharmacodynamicsDobutamine 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 actionDobutamine directly stimulates beta-1 receptors of the heart to increase myocardial contractility and stroke volume, resulting in increased cardiac output.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationIn human urine, the major excretion products are the conjugates of dobutamine and 3-O-methyl dobutamine.
Half life2 minutes
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9937
Blood Brain Barrier - 0.7448
Caco-2 permeable + 0.5305
P-glycoprotein substrate Substrate 0.7571
P-glycoprotein inhibitor I Non-inhibitor 0.8782
P-glycoprotein inhibitor II Non-inhibitor 0.8383
Renal organic cation transporter Non-inhibitor 0.6336
CYP450 2C9 substrate Non-substrate 0.7235
CYP450 2D6 substrate Substrate 0.6265
CYP450 3A4 substrate Non-substrate 0.5296
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8231
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8827
Ames test Non AMES toxic 0.7215
Carcinogenicity Non-carcinogens 0.9306
Biodegradation Not ready biodegradable 0.9256
Rat acute toxicity 2.2261 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.828
hERG inhibition (predictor II) Inhibitor 0.8367
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
FormRouteStrength
LiquidIntravenous
SolutionIntravenous
Prices
Unit descriptionCostUnit
Dobutamine 12.5 mg/ml vial0.18USDml
Dobutamine 250 mg-d5w 500 ml0.09USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP3.6Not Available
Predicted Properties
PropertyValueSource
water solubility1.37e-02 g/lALOGPS
logP2.97ALOGPS
logP2.62ChemAxon
logS-4.3ALOGPS
pKa (strongest acidic)10.14ChemAxon
pKa (strongest basic)9.27ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count4ChemAxon
polar surface area72.72ChemAxon
rotatable bond count7ChemAxon
refractivity88.39ChemAxon
polarizability34.44ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Paulus F. C. van der Meij, Paulus P. G. de Jong, “Production of dobutamine compounds.” U.S. Patent US5442120, issued April, 1975.

US5442120
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD03879
KEGG CompoundC06967
PubChem Compound36811
PubChem Substance46505241
ChemSpider33786
BindingDB50028971
ChEBI4670
ChEMBLCHEMBL926
Therapeutic Targets DatabaseDAP000245
PharmGKBPA449381
IUPHAR535
Guide to Pharmacology535
Drug Product Database2242010
RxListhttp://www.rxlist.com/cgi/generic3/dobutamine.htm
Drugs.comhttp://www.drugs.com/cdi/dobutamine.html
WikipediaDobutamine
ATC CodesC01CA07
AHFS Codes
  • 12:12.08.08
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmitriptylineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect, dobutamine.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of dobutamine.
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of dobutamine.
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of dobutamine.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of dobutamine.
EntacaponeEntacapone increases the effect and toxicity of the sympathomimetic, dobutamine.
GuanethidineDobutamine may decrease the effect of guanethidine.
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of dobutamine.
IsocarboxazidIncreased arterial pressure
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of dobutamine.
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of dobutamine.
PhenelzineIncreased arterial pressure
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
Food InteractionsNot Available

1. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

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

1. Catechol O-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Catechol O-methyltransferase P21964 Details

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 September 16, 2013 17:12