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Identification
NameDobutamine
Accession NumberDB00841  (APRD00122)
TypeSmall Molecule
GroupsApproved
Description

A beta-1 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.

Structure
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Synonyms
SynonymLanguageCode
(+-)-4-(2-((3-(P-Hydroxyphenyl)-1-methylpropyl)amino)ethyl)pyrocatecholNot AvailableNot Available
3,4-Dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamineNot AvailableNot Available
4-{2-[3-(4-hydroxy-phenyl)-1-methyl-propylamino]-ethyl}-benzene-1,2-diolNot AvailableNot Available
DL-DobutamineNot AvailableNot Available
DobutaminGermanINN
DobutaminaSpanishINN
DobutamineFrenchDCF
DobutaminumLatinINN
rac-DobutamineNot AvailableNot Available
Racemic-dobutamineNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dobutamine Hydrochlorideinjection, solution400 mg/100mLintravenousPhysicians Total Care, Inc.2007-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dobutamineinjection, solution12.5 mg/mLintravenousHospira, Inc.1995-02-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dobutamine Hydrochlorideinjection, solution, concentrate12.5 mg/mLintravenousHospira, Inc.1993-11-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dobutamineinjection, solution12.5 mg/mLintravenousGENERAL INJECTABLES AND VACCINES, INC.2014-11-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dobutamine Hydrochlorideinjection, powder, lyophilized, for solution12.5 mg/mLintravenousGeneral Injectables & Vaccines, Inc2010-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dobutamineinjection, solution12.5 mg/mLintravenousPhysicians Total Care, Inc.2006-12-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
DobujectBayer
DobusafeClaris
DobutaminSandoz
DobutanDemo
DobutelNovell
DobutilMeizler
DobutrexLilly
DopminMylan Seiyaku
InotrexLilly
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Dobutamine hydrochloride
Thumb
  • InChI Key: BQKADKWNRWCIJL-UHFFFAOYNA-N
  • Monoisotopic Mass: 337.144471346
  • Average Mass: 337.841
DBSALT000711
Categories
CAS number34368-04-2
WeightAverage: 301.3801
Monoisotopic: 301.167793607
Chemical FormulaC18H23NO3
InChI KeyJRWZLRBJNMZMFE-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Phenylpropylamine
  • Phenethylamine
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
Pathways
PathwayCategorySMPDB ID
Dobutamine Action PathwayDrug actionSMP00662
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9937
Blood Brain Barrier-0.7448
Caco-2 permeable+0.5305
P-glycoprotein substrateSubstrate0.7571
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.6336
CYP450 2C9 substrateNon-substrate0.7235
CYP450 2D6 substrateSubstrate0.6265
CYP450 3A4 substrateNon-substrate0.5296
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8231
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8827
Ames testNon AMES toxic0.7215
CarcinogenicityNon-carcinogens0.9306
BiodegradationNot ready biodegradable0.9256
Rat acute toxicity2.2261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.828
hERG inhibition (predictor II)Inhibitor0.8367
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
Injection, powder, lyophilized, for solutionintravenous12.5 mg/mL
Injection, solutionintravenous12.5 mg/mL
Injection, solutionintravenous400 mg/100mL
Injection, solution, concentrateintravenous12.5 mg/mL
Prices
Unit descriptionCostUnit
Dobutamine 12.5 mg/ml vial0.18USD ml
Dobutamine 250 mg-d5w 500 ml0.09USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point184-186J. Mills, R. R. Tuttle, U.S. Patent 3,987,200 (1976).
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0137 mg/mLALOGPS
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 Area72.72 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity88.39 m3·mol-1ChemAxon
Polarizability34.44 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

R. R. Tuttle, J. Mills, DE 2317710 (1973).
J. Mills, R. R. Tuttle, U.S. Patent 3,987,200 (1976).

US5442120
General ReferenceNot Available
External Links
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

Targets

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

Enzymes

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

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Drug created on June 13, 2005 07:24 / Updated on December 05, 2014 11:54